Alex: Visiting a big city with kids can feel overwhelming at first, but in reality, it’s one of the easier trips to do and so much fun. Listen in as we share what it’s like to visit Chicago and New York City with kids on points.

Welcome to Points Talk®. We are three moms who’ve discovered how to leverage credit card welcome offers to get hundreds of thousands of dollars of travel expenses for nearly free. We’ve used credit card points and miles to take vacations to places like Hawaii, Paris, Greece, Maldives, Japan, and so much more. And the best part? We each still have 800 plus credit scores. Imagine being able to take the vacation of your dreams for nearly free. It’s totally possible, and we’re here to show you how.

Alex: Hey, I’m Alex.

Jess: And I’m Jess. Let’s talk points. Alex and Pam recently returned from a trip to New York City with Alex’s 10-year-old son, and I’ve recently returned from Chicago with Ted, Molly, and one of Molly’s friends. Today, we’re sharing tips for visiting each of these cities with kids, plus how to make it happen on points.

So first, we’re going to kick it off with how these trips came about. So Alex, tell us about how your New York City extravaganza came about. 

Alex: All right. So first of all, you guys noticed it’s just Jess and I here today. My mom was on this trip with us, but she is currently in Arizona and where she’s at, she has no internet service. So she was on a hotspot and we’re like, “I don’t think this is going to work very good. Your internet isn’t super stable.” So we’ll just do, we’ll just call it and we’ll just do this one without you. But just know she was on this trip and she’s here in spirit.

So when each of my kids turn 10, my mom and I take them on a trip just them and the two of us. So this was my son Kai, his 10th birthday. It was actually in January, but he, for a while has wanted to do New York City, and we were thinking, “Okay, January, we don’t know necessarily if we want to go to New York City in January, but let’s go in March.” So we just postponed it a little bit. And yeah, it worked out great. So that’s how it came about. Jess, what about yours?

Jess: Yeah, so this was just a spring break trip for Molly. She has, she gets a week off in February and a week off in March. I don’t understand it.

Alex: That’s crazy.

Jess: I mean, it kind of works out great for us because you get, you know, the February break is usually we get some off-peak travel in and she doesn’t have to miss school.

Alex: That’s really nice. Yeah.

Jess: But we did our Tanzania safari for her February break, and so I was like, we, I want to go somewhere, but I do not want to go anywhere international. I don’t want to go anywhere more than like a couple hour flight away. And so we landed on Chicago. She really wanted to go back to Chicago and do more touristy things. Ted is from there and we often go visit family, but we don’t stay downtown or do any of the touristy things. And so we decided we were going to do a little combination of both.

And then Ted and I each have a Companion Pass® and so she was able to invite a friend. So that was really fun for her. So we got to do the touristy things and we got to see Ella and Olivia, and we got to see Ted’s mom and his sister, and so, you know, we did a combo trip.

Alex: Nice. All right, so we’re just going to share quickly how we used points to get to our destinations. Of course, for either New York City or Chicago, there are a plethora of ways to get there. So this is just how we did it. So I flew Southwest to LaGuardia. We had a layover in Denver, and my mom was able to join us on that flight. 

Like kind of the way it is now, my mom and Ted were both not fans of Southwest, but they are now with assigned seating and being able to upgrade those flights or those seats, depending on the credit card you have. So I paid 14,000 points there, and then Kai is my companion, my companion on my Companion Pass. So his was just the $5.60 each way.

And then I have some LUV vouchers and flight credits. I don’t even remember. I think I got the LUV voucher for some delay issues and flight time changes and I’d reached out to Southwest via the X app and let them know the situation and asked if there’s anything they could do and they sent me a LUV voucher, which was really nice. And then I had some flight credits as well. So that’s how I paid for my flight home. Once again, was able to add Kai as my companion.

I have the Southwest Performance Business card, so I was able to select my seats at booking and then 48 hours before, I was able to upgrade to extra leg room. I, I could have done it on the LaGuardia or the Denver-LaGuardia leg, but I really like having an aisle seat and the aisle seats were gone. I don’t even know if there was two seats right next to each other and I didn’t want to separate Kai and I. And we were in like row nine or something. We were really close to the front anyway.

So, but from the Denver to Salt Lake, Salt Lake City legs, I was able to upgrade to extra leg room for both of those 48 hours before. I think even one of them I did at like 24 hours before because I forgot. So, but that for me, I’m like, okay, I am keeping this credit card because those extra leg room seats, they can be kind of spendy if you were just going to buy them. So to be able to get those, and I have like pretty lowly status with Delta, but it’s enough status where I can get upgraded to Delta Comfort or whatever they call theirs. And I very rarely get that. And so to be able to get it so easily with the Southwest® Performance Business. Mitch and I also did, we were able to upgrade to extra leg room on our flight from Maui to Oakland. That is amazing. We were able to upgrade to that 48 hours before.

And we were able to do the seats. You know, on Southwest, how they have some seats where it’s just the two seats in the exit row, and there’s no one next to you?

Jess: Yeah.

Alex: So, no, wait, we didn’t do that one. We did the one where there’s three, but there’s no seat in front of you. So Mitch had, and he’s pretty tall. And so he had that whole section. So I was like, all right, this card I’m, I’m sold on this card. 

Jess: What boarding group did you have?

Alex: We had, I think we had boarding group one, and then another time we had boarding group two. But then when I didn’t…

Jess: Yeah, we had boarding group two.

Alex: Yeah. And then one time, then when we didn’t have the extra leg room seats, we were boarding group five.

Jess: Okay.

Alex: Yeah.

Jess: Yeah, we had group two, and I was happy with that. I was like, “Man, I really like flying Southwest now.” I have this Southwest Performance Business, and so does Ted. And I, one of us will, well, one of us would be me because I fly more than he does, but I will, that is a keeper card for me from now on. That alone is 100% keeper. 

So, similar to you, we also flew Southwest. We flew from Houston Hobby to Midway in Chicago. And starting, it says as of June 4th, Southwest is not going to fly into O’Hare anymore at all. So if you want to fly Southwest, you’re going to have to fly into Midway.

Our flights were 29,000 points each round trip. So we each booked one and then we each have a Companion Pass currently. So I was able to add Molly as my companion. Ted added her friend as his companion. And so we paid just $5.60 each way for both of them, which was great. Like I said, I loved the assigned seating now. I was I was able to get extra leg room seats for us, and so that was great.

And I didn’t know this, but after I shared our trip in stories, someone replied and was like, “Did you know you get, um, a a premium drink if you’re in an extra leg room seat?” And I was like, “I didn’t know that.” So I could have been, I could have been partying it up on the Southwest flight.

And you also get pistachios, which is so random, and I remember the flight attendant coming around being like, “Would you like pistachios?” And I was like, “No, I’m good.” And I said, “No, thank you.” And in my head I was like, “That’s random. I’ve never seen them offer pistachios.” I guess that’s considered a “premium” snack.

Alex: It is. Yes. I kind of wish they had more selection for their premium snacks. That’s my only thing. It’s like, I take them and I eat them and they’re fine, but I’m not like, “Wow, I’m really loving these pistachios.”

Jess: Wow, I’m really going to pay extra for this extra leg room seat because of the pistachios.

Alex: And I don’t even drink, so I’m not even excited about their premium drink. I’m like, I’ll just stick to my ginger ale. I don’t know. Maybe they know what they need to get. They need to get a soda bar where you can get some pumps of coconut and some coconut cream and some fresh lime. Then I’d be on board with Southwest premium drinks.

Jess: Okay, well, I’m sure there are some Southwest executives listening to this episode and they’re going to go report that back right now.

Okay, next, we are going to talk about where we stayed. So I booked us at the Park Hyatt Chicago. I have always wanted to stay at the Park Hyatt and we just never have because we usually stay out in the burbs. But I was like, “No, we’re making it happen.” And then Hyatt announced that they were going to be changing up their award chart and potentially devaluing things. And I was like, “We got to stay here before we can’t afford to stay here anymore, even on points.”

So I paid 88,000 Hyatt points for four nights, and I used a Suite Upgrade Award to upgrade us to a Chicago Avenue Suite. And then when I went to the app the day of to check in, it was like, “You’ve been upgraded.” And they had upgraded us to a Lake Michigan suite, which I think is the same layout. It’s just a different view. But that one’s considered a premium suite. So I was like, “Great, I’ll take it,” you know.

The really nice thing about, okay, one of my favorite perks, my favorite milestone reward of Hyatt is the Suite Upgrade Awards, because when you’re traveling with a family, it is so nice to have the extra room. And in this case, we had an entire other full bathroom. And so the kids, the the sofa folded out into a queen-sized bed. The kids slept there and then they had their own bathroom to shower and get ready in the morning and we had our own bathroom.

We had our own bedroom with a door that closed. And so, especially when they are teenagers, they are adult-sized people. You know, we’re not talking traveling with like a three and a four-year-old. We’re talking about people the same size as me. It’s too much to share one bathroom. Yeah, it gets old after a while.

Alex: Oh, two bathrooms is a game changer.

Jess: I mean, it’s do, I mean, okay, would I, could I do it? Yes.

Alex: And do you do it often? Yes, you do it a lot because a lot of times you are, like if it’s just you, Molly, and Ted, you’re getting one room and you’re sharing a room, I mean, I guess that’s one less person, but it’s still sharing a bathroom with a teenager.

Jess: Yeah. But the ability to, you know, use the same amount of points and apply this award and get a whole other bedroom area and bathroom.

Alex: And that’s a, that seems like a really good price to me to stay at the Park Hyatt.

Jess: Yeah. I thought it was a really good price. And so yeah, those sweet upgrade awards just come in clutch for our family. I’ve also stayed at the Thompson in Chicago, which I really like. So the Park Hyatt currently is a category six. The Thompson is a category five, still a great location. We stayed in a suite there. It was big. I prefer the Park Hyatt between the two, but I don’t think you can really go wrong with either one. And there are so many Hyatts in Chicago. So there is no shortage of them. There is actually the Hyatt Regency Chicago and the Hyatt Centric Magnificent Mile. We’ve had really good reviews of both of those in our Facebook group and they’re both category fours. And so that would be a great use of a category one to four free night certificate.

Again, this could all change in May when they update everything. But as of now, there’s also, Alex, I feel like this is where your fam might stay if you all wanted to stay in one room. There’s a Hyatt Place Chicago River North. That one’s also a category four, and they have rooms with two queens and a sofa bed. So if you are a family of five or six, that could be a great option if you want to, you know, save your points and all be in one room together.

Alex: Yeah, that is nice.

Jess: And then I also, so we got a welcome email from the Park Hyatt a few days before our stay, and I replied to it using Pam’s template. I didn’t ask for an upgrade because I already was in a suite with my Suite Upgrade Award. So I was like, I’m fine with that. I don’t want anything more. But I did just mention like, “Hey, we’re bringing our daughter and her friend. This is her friend’s first time visiting Chicago. We’re really excited to stay at your hotel.” And so they wrote back and they said, “What is your daughter’s name? What’s her friend’s name? How old are they?” And so I gave them that information.

And then when we got there, they had left like a little thing of cake pops for them and a handwritten note welcoming them to Chicago. And so I thought that was just like a really cute touch. And I’m just someone who, if you do something nice for me, obviously, I appreciate it. But if you do something nice for my kid, I’m like, okay, you have a fan for life, you know?

Alex: 100% agree. 

Jess: And so, yeah, we just had a really, really great stay there. The rooms were huge, the service was amazing. And we are staying there, Alex and I are actually both staying there together.

Alex: And Pam.

Jess:  And Pam this summer. And so I’m really excited. I’m excited that we locked that in and that I get to go back.

Alex: Yeah. Yeah. All right, we stayed, we did a little hotel hopping, as Pam likes to do. No, this is actually my idea to hotel hop this time. So I had a category one through seven free night certificate from Hyatt that I had earned as a milestone reward after hitting 60 elite nights. And I was originally going to use that at the Alila Maldives, but when that trip got canceled, I was like, “Oh, I have this free night that I need to use and it expires at the end of April. When am I going to be able to use this?”

So I had originally had the Park Hyatt booked for four nights. And I was like, “Wait a minute. The Thompson’s right across the street and it’s a category six. I am going to use that there and we’ll just hotel hop.” I got 40,000 points back. So I was like, dang, this, this free night saved me 40,000 points. So I was pretty happy about the use of that.

I, so I also got an email from both hotels before we came, and I did this same thing. I sent, I let them know, “Hey, I’m here celebrating my son’s 10th birthday. This is his first time in the city.” You know, everything that email template says to do, I did. And they both replied back to me and were like, “Oh, great, we’ll have something ready for him.” The Park Hyatt asked me his name and asked if he had any dietary restrictions.

And what’s interesting is I had stayed at the Thompson in November on a girl’s trip with friends, and they had emailed me and I sent them an email back like, “Hey, I’m going with some girlfriends as a mom’s getaway. This is their first time coming to New York.” I got no reply from my email after I sent that one. Like just asking like if we could get any upgrade would be greatly appreciated, or anything you can do to make our trip more special. They were, I mean, the service was great, but I was like, is it? Do they just do better replying to kids? Are they like, “Oh, we’re going to help the kids. We don’t care about the moms.” Or maybe it was just like a different person working or maybe they didn’t see my reply. You know, things happen.

But so I wasn’t fully expecting a reply from the Thompson, but we got there in our room, there were two slices of New York-style cheesecake with strawberries on them. Like, so nice and a little card for him. He was super excited. And that’s the thing, like it’s just exciting when you get some little recognition, and you’re like, “Oh, I got a little treat.” Sometimes it doesn’t even matter what it is. You’re just like, “Oh, we got something.” 

And then the Park Hyatt had a little birthday cake, a really a little small one with some fruit on it and a little card as well. And then for me, they had chocolate-covered strawberries. I’m assuming since I’m a Globalist as a welcome gift to thank me for my loyalty. So the chocolate silver strawberries were really good and very much appreciated.

So at the Thompson, we were upgraded to their upper stories rooms. And and those upper story rooms include lounge access. So we actually didn’t use the lounge. We didn’t even go in it because we were only there for one night. And we are, we already got free breakfast with my Globalist status.

The nice thing is that either the Thompson or the Park Hyatt, your, if you have Globalist status, the breakfast, you can do room service. So that’s a really nice option. Same with, same with the Park Hyatt, Chicago. So that was really nice and kind of fun to just order our breakfast and have it delivered and eat in bed. It’s kind of fun to spoil your kids with those sorts of experiences and getting to live the high life for a bit.

The crazy thing is at the Park Hyatt, our breakfast bill, I took a video of this and I shared about it on Instagram, but you guys, the first day, it was $251. And it looks like there’s hardly any food on our table. My mom and I were dying. Like we would never have spent that. We would have been walking down the street and picking up a bagel somewhere. But like it’s just… 

Jess: And there were only three of you. It was two adults and one child.

Alex: There were three of us. Yes. And they, but they told me at check-in, they’re like, “Yeah, for breakfast, you have about $100 per person that you can spend per day that’s covered with your status.” I was like, “Holy cow.” That was wild.

Jess: Marriott could never. Let me just say, Marriott could never.

Alex: No. No. Nobody else could ever. I think.

Jess: With their $10 food and beverage credit or whatever they have.

Alex: In Hilton, too. Yeah, that’s how Hilton is in the in States as well, or domestically. Anyway, another option, we actually met somebody from the Points Talk Squad community at Harry Potter and the Cursed Child. So we saw that while we were there. And as we were leaving, this lady walked back, and she’s like, “Wait, are you guys the Points? Are you guys Points Talk? The Points Talk people?” I was like, “Yeah, we are. Nice to meet you.” So we talked to her for a minute. And she was staying on points at one of the Hyatt Places in New York. So that could be a good option for a family as well.

Jess: I love how she didn’t say, she’s like, the Points Talk because she’s probably like, what is your name again? Because you’ve changed it five times.

Alex: What is your name again? Who are you guys? Yeah. Well, I always wonder, or it seems like when people run into us, sometimes they’re confused on, are you Pam? Are you Alex? Are you…? And people mix Jess and I up all the time. it’s pretty funny, but anyway, if you see us in the wild, always say hi.

There was a girl who actually sent us a DM that was like, “I just saw Alex on the subway in New York, but I was too nervous to say hi.” And we’re like, “Oh, just say hi next time.” Especially my mom. You guys, if you see her in the wild, she thrives off of meeting you all in the wild. It makes her day. When she’ll be like, “Oh, I flew through Denver today, and I didn’t see anybody. I haven’t seen anybody in the Capital One lounge in a really long time.” So it’s pretty funny.

So anyway, Jess is going to tell us about getting around in Chicago, how she did that.

Jess: Yeah. So we rented a car. You absolutely do not need to rent a car if you’re just staying downtown and doing the touristy things. Chicago has a robust public transportation system. We were going to be visiting family out in the burbs, and so renting a car was just easier for us.

If you do want to rent a car, we rented through Costco Travel, and that’s who I always go through. I know AutoSlash is another really popular option. I think it was $200, around $250 for our four nights. I thought that was pretty reasonable. If you are staying downtown, I really think that either Midway or O’Hare are equally convenient. You can take public transportation from either one. They, Midway is much smaller, and O’Hare is really, really big. And so I would just go with whichever one has the better deal flying into. I don’t think that there’s like one wins over the other.

There’s also, obviously, Uber, Lyft, all those car services, if you want to do something like that. The Park Hyatt has an amazing location. It’s literally right off Michigan Avenue. And so when we were doing the touristy things, we just walked everywhere. We didn’t even take the L. That’s what they call their train. We didn’t even take the L at all. We walked everywhere we wanted to go, and then we just got our car out when we were going to visit family.

So, yeah, it’s actually, someone, it’s funny when I posted my stories, someone replied and was like, “I never thought about bringing my family to Chicago, but it seems really family-friendly.” And I’m like, “What? Chicago is like one of the most family-friendly cities.” And part of that is the public transportation because I know when Molly was little, like when she was in a car seat, I did not want to go anywhere I had to bring my car seat with me, you know? And so finding a place to go where we could just hop on public transportation was so nice. So Chicago is definitely one of those places.

Alex: Yeah. All right, we, like getting to and from the hotel in the airport, we just take Lyft or Uber, always trying to use those credits we have from our various credit cards. We’ve also used the black lane credit before from the Citi Strata Elite. That was really nice because the car’s waiting for you. It’s a little bit of a nicer car. So if you had the Citi Strata Elite, New York City is a really good place to use that credit.

And then once we’re there, we mostly, like you did, we did a ton of walking. The location of the Park Hyatt and the Thompson, first of all, with those two hotels, what’s really nice, I don’t know if there’s a better hotels to hotel hop between because the Thompson and the Park Hyatt, I remember seeing them one time be like, “Oh, they’re just so close.” And then last time I was there, I was like, “Wait, where’s Park Hyatt? I couldn’t find it.”

But how it works is there’s the front entrance of the Thompson, and then you go through and there’s a restaurant and there’s a back entrance to the restaurant. So to get to the Park Hyatt, you just go out the back entrance through the restaurant, and then the Park Hyatt is literally across the street. So it was like the easiest transfer we’ve ever done between hotels.

Jess: I meant to ask you this when you were talking about them, though. Did you have a preference between the Thompson and the Park Hyatt?

Alex: Um, Park Hyatt. I mean, here’s the thing. The Thompson is fantastic. It feels high-end, it smells good, it’s got a nice vibe to it. The rooms are nice, the bathrooms are really small. And to me, Park Hyatt, the bathrooms are really big. And when you’re sharing a bathroom with someone, it’s really nice having more space. And Park Hyatt has a separate, they have a soaking tub, and then the shower is huge and super nice. Our room had, it was just a small shower, was it? There’s no, there was no tub.

Jess: This was at the Thompson?

Alex: Yeah, at the Thompson, there was no tub. And so I, I could see maybe someone could like maybe the vibe of the Thompson more. It’s a little more moody and the Park Hyatt is just a little more like classic kind of luxury feel to it. The Thompson’s got like a darker, I feel like, that’s where I guess where the moody comes in. But the Park Hyatt is a little more brighter, I would say. A little more natural light, at least in the room that we had. So I like the Park Hyatt because I really like having a bigger bathroom, and the room is just a little bigger too.

But if you’re wanting to save points, Thompson is fantastic and it is much cheaper than the Park Hyatt. Park Hyatt is a splurge. The other thing too, Park Hyatt has a pool. Thompson does not. And so if you’re going with kids that maybe would love to have some downtime and swimming, then the Park Hyatt is probably going to be a better option.

Jess: And it’s an indoor pool. So we’re not talking swimming while it’s snowing outside. 

Alex: Yeah, and there’s a hot tub, and there’s a sauna. We went one day for just like an hour. We didn’t have a ton of time. But it was actually pretty busy. I expected to walk in and not really see anybody there, but there was a lot of people. And I don’t know, I know a lot of people were on spring break, so that could have been the reason.

We did also use the subway in New York. I find the subway there very easy to use. You just tap in and tap out with your credit card. If you’re going to any big city and you’re using public transportation, I highly recommend the Citymapper app. I would plug in, we’d be at our hotel and I’d say, “Hey, we’re going to Chelsea Market,” and it tells me how to what metro station or whatever to walk to, and then what line to take, when, how many stops till I need to get off, then what one to take next, and then also will give me the rest of the walking directions to get to where I need to go. And it’ll tell you time too. Okay, this train will be here in three minutes, and, you know, and it just makes it so easy.

Even Kai was able to start figuring out how the public transportation worked. I’d be like, “Okay, what are we doing next?” Like, look here at the app and, you know, figure out where we’re going to go. And so if he can do it, all of you can do it. I think it’s one of those things that public transportation at first can feel very overwhelming when you haven’t done very much of it or when you are somewhere new. And it’s, I think it’s easier than we think it’s going to be, but I will say every time I do it and I’m successful, I feel really proud of myself. I feel like so good, like, “Oh, I’m so good at this,” you know. But it’s actually not that hard. Anybody can do it. So, don’t be scared of public transportation.

So, now we’re going to talk about some of the things we did on this trip. So if you’re visiting either Chicago or New York, hopefully some of these ideas will help you plan your trip. 

Jess: All right, so Chicago has an amazing museum scene. And the things I’m going to list are not an exclusive list. There are so many things to do in Chicago with or without kids, but we went to the Museum of Science and Industry. This is a favorite of ours. We’ve been before. They actually through September 6th, the beginning of September, they have an exhibit that’s included with general admission and it’s the costumes of Paul Tazewell. He designs costumes for a lot of different things, including Wicked, including Hamilton. And so we got to see all of the costumes that were used in these shows. That was really amazing. There’s also the Field Museum. That’s the Museum of Natural History. We did not go to that one this time, but it is named after me. No, it is actually not.

Alex: After you? That’s not even, that’s your married name.

Jess: They named it after me. They named it after me after I got married. Okay?

Alex: Okay, okay.

Jess: There’s also Shedd Aquarium, which is amazing. If you want to do that, I didn’t do that this time, but that’s a really great one too. Those are just a few. There is Millennium Park. That is where The Bean is located. That is fun and free to walk around. Magnificent Mile, tons of shops. There’s an American Girl store. There’s every store. There’s the Starbucks Reserve Roastery, which is my personal favorite. We went to this, it’s basically a slime museum. It’s called the Sloomoo Institute. And it was disgusting, but Molly liked it.

Alex: I honestly, I saw your videos. If you guys want to see it, I don’t know, did you make a story highlight of Chicago on Instagram? 

Jess: I will. Yeah, I should. I guess.

Alex: I saw these videos and I was actually could not believe you let her do that because I know you’re a germaphobe. I guess maybe afterwards, you’re washing your hands like crazy.

Jess: Well, the other thing we did is we got there. We you have to buy a ticket and you have to reserve a time. And I reserved the first time of the day, and we were the first ones in there. So I was like, there’s no other kids today that have put their hands in this, but I don’t know about, I didn’t even share all my videos. Okay, so it’s basically these huge vats of slime, different types of slime with different textures and different add-ins. And you can go around and put your hands in them and feel the slime. Okay? Then there’s a part where you can take your shoes off and there’s like kiddie pools of slime, and you can like run around in them. I was horrified. 

Alex: I am horrified just hearing about it.

Jess: But Molly and her friend loved this museum. 

Alex: No, my kids would love that. They would love it. I have a question, though. Did they tell you, is there any information about how they keep this sanitary?

Jess: So they have wipes. They have, they have wipes that you’re supposed to use before you put your hands in any of the slime, you’re supposed to wipe your hands off before you go in the one with the feet. There’s wipes for you to wipe your feet off. The thing is, we know that these kids are not all doing this. There’s no one enforcing it. Okay? 

Alex: Got you. And that’s what they need. They need, like, how when you go on a Disney cruise, and they have the people watching you wash your hands before you go to the buffet or watching the kids stick their hands in those little hand washers, they need that.

Jess: Yeah. So, um, if you want to do that, it is there for you to do. The kids loved it. At the end, you do get to like make your own slime. So you get to choose the texture you want, you get to add a color, you get to add a scent, you get to add some charms to it. And so that was cute. That was fun to do. But I did not partake in any of the feet in anything or the hands in anything. I didn’t do any of that.

Alex: You know what, my kids would love that though. Like, I guess if you want to score parent points, do that.

Jess: We also saw Hamilton. There’s a good like, touring Broadway show scene in Chicago. Hamilton was in town when we were there. Some other things that we didn’t do, but that would be great for kids, and we’ve done in the past is Navy Pier, Lincoln Park Zoo. There is a Willis Tower Skydeck. It’s kind of like the observation decks that they have in New York, but it’s Chicago. That’s really fun. Architecture cruises on the Chicago River are always really fun. And then also like see a Cubs game, see a White Sox game, if they’re in town while you’re there. That’s always fun to do with the kids, too. So, basically, and this is, this is my shortened list. Okay? So there is no shortage of things to do with kids in Chicago.

Alex: Yeah. All right, well, that all sounds really fun. And I’m I’m like, oh, maybe I need to take my kids to Chicago sometime. I think there’s just something fun of doing something different and going to a city and seeing, I don’t know, having more like cultural experience of learning and educational and not just going to the beach all the time. So, I think that sounds fun.

All right, New York City. Like I said before, the location of the Park Hyatt and the Thompson is really, really great. just, I don’t know, maybe 10-minute walk to Rockefeller Center and a lots of shopping around there. So we went down there. We went to FAO Schwarz. Kai, I’m getting all my kids mixed up. Loved that. So fun. They have the giant piano like they do on Big. So he was like, you’re able to get in a line, take your shoes off and walk across the piano. So that was fun for him. 

We were able to walk to all of, you can walk to Times Square from there. So we saw some Broadway shows and we were able to walk to those. We kind of did a lot. So my original plan was, we’re going to go see Harry Potter and the Cursed Child because he has been very into Harry Potter for the last few years. Like two years ago, he was Harry Potter for Halloween. So my thoughts were always like, he wants to go to New York for his 10th birthday. We’re going to see Harry Potter and the Cursed Child. And so we, I bought the tickets ahead of time.

We all loved it. This was my first time seeing a play on Broadway, and there were some times where both my mom and I were like, “Oh, we were waiting for them to break out in song on that part.” But it was really, really cute, really well done. We all really enjoyed that. 

But then, a few, I don’t know, around the time when Stranger Things the last season came out, my family, my kids and I, we got very into Stranger Things at my house. Don’t judge me that I let my 10-year-old watch Stranger Things. I blame it on his cousins that are older because one time we were on vacation and they just started watching it and I told them, “You’re not allowed to.” But nobody listened to me. And you know what though? It didn’t scare him. He he’s, he loved it.

And so once we were going to New York and we had just finished watching the fifth season, I was like, “Oh, they have a play there called Stranger Things: The First Shadow,” and it’s the story of Henry Creel. If you watch Stranger Things, you know who that is. And it, so I was like, “Hey, should we, I was thinking of maybe going to two shows.” But I was originally like, let’s go to Lion King. He’ll love that. It’s a great age for that. It’ll be so fun. I was like, “Hey, we could either see another play because s is a play as well. We could see Stranger Things First Shadow or we could see Lion King.” He was like, “Oh, Stranger Things for sure.” So I was like, “Okay, I guess we’re doing it.”

I wanted to see it too because, like I said, we were all up in the Stranger Things hype at this time. So we saw that as well. We both really enjoyed that. There are some jump scares, which was fun, and the effects were incredible. Like how they’re able to do these things on stage for with both shows with Harry Potter and the Cursed Child and Stranger Things. You’re like, how in the world do they do this? Like this is just so, so cool.

Jess: Yeah, it is.

Alex: Well, then we were having some FOMO about Lion King. And I was just like, “I’m going to New York and I’m not seeing a musical.” Like I love musicals. So we did end up buying tickets to a matinee show to go see Lion King as well.

But that’s the really cool part about when you just take one kid on a solo trip. I don’t have to pay for three other kids and my husband. There’s just two of us instead of six. Okay, we can see three shows for the price that it would take six of us to go to one. So that was really fun. He really enjoyed all of them.

I will say he said his favorite was Stranger Things. And then Harry Potter and then Lion King. But his, here’s his reasoning. That he liked the other two more than Lion King is because he knew the story of Lion King, which and he still loved it. But like Harry Potter and the Cursed Child, he didn’t know what was going to happen. He didn’t know what was going to happen in Stranger Things. These were new stories that haven’t been told before. So that was, that was really fun for him.

We also went to Chelsea Market and we always go here and eat at Los Tacos Number One. They are so good. I will say I forgot how spicy they were. So if you don’t like the spice, don’t get the salsa or be like me and I just kind of like push the salsa out with the chip so it wasn’t so spicy, but they’re so good.

We also went to Summit One Vanderbilt. This is like an observation-type deck as well. In New York, there’s a variety of them. I’ve done the Top of the Rock, that’s the top of Rockefeller Center and Summit One Vanderbilt. I personally don’t want to go to the top of, why am I blanking on it? The Empire State Building, because I want to see the Empire State Building.

Jess: Exactly. 

Alex: But I know it’s popular and a lot of people will go to the top of the Empire State Building. I’m like, but don’t you want to see it? So I did Summit One Vanderbilt when I went with my friends in November, and I know Jess has done that one as well. And I like Summit One much more than Top of the Rock because Summit One, there’s more things to do. It’s a more immersive experience. Also, you’re inside, so if it’s cold, that’s really nice. You don’t have to deal.

Jess: It’s cold or windy or raining, then it’s… yeah, I agree with you. Summit One, hands down.

Alex: Yeah, the views are so good. It’s so like clear. We bought tickets ahead of time. You can buy them there, but you just might run into the issue of they’re sold out for your time, so you have to come back like two hours later. So we bought them just the day before online, and we really liked that. He really liked the room. There’s a small room that has these big silver, basically like beach balls, and they kind of float around in the air, and you can kind of toss them around. So that was really fun. So yeah, hands down, that’s my recommendation to Summit One Vanderbilt over the other observation things. 

One thing, just with kids, is they’re going to want to take things a little slower. This was not the same pace that I went with my friends when we were there in November. It’s a little slower, which was fine. And that was kind of the nice part about staying somewhere like the Park Hyatt was, okay, the hotel’s part of the experience here. We’re going to have our slow mornings. We’re going to order room service. We’re going to check out the pool and enjoy all of that versus go, go, go, go, go.

It was kind of funny because on our last full day, that’s when we saw The Lion King, and I gave him a few options. I said, “Hey, we could go take the Staten Island, the ferry out to Staten Island.” This is a great idea. Like, if anybody wants to do this, I did this with my friends. You take it at Whitehall Terminal, and it’s free, and it takes you right, great views of the Statue of Liberty. You get off the ferry and then you just get right back on to go back into Manhattan. And I showed him, I said, “Hey, this is what my friends and I did.” And I showed him the video. He’s like, “Well, I just saw your videos, so I think I’m good. I think I’ve seen it.” I’m like, oh my gosh, you’re so funny.

Jess: Oh my gosh, that is hilarious.

Alex: I know. Like you know the things where it’s like, have you seen the reels where people just walk up to the famous thing, and they’re like, “Oh, okay, I saw it,” and then they walk away?

Jess: Okay, I saw it. Yeah. Yeah, yeah, yeah. 

Alex: He was like, “I don’t even need to do that. I just saw your video.” So then the whole time, we did actually see the Statue of Liberty from the top of Summit One Vanderbilt, but it was very, very small. So, but that’s a fun idea to do is take the ferry out to Staten Island. I also asked him if he wanted to rent bikes and ride bikes through Central Park. And he was like, “Well, we could just ride bikes at home. We can just ride bikes anywhere.”

Jess: Kai’s very practical, it sounds like.

Alex: He’s very practical. And the other thing too is like, Central Park is not was not in its prime while we were there. The trees are still dead. This is the end of March. Nothing’s blooming yet. So we’re like, okay, it isn’t the prettiest right now. This would be better if it was, if it was prettier, I would have been like, “No, we’re doing it, Kai. We’re going on a bike ride.”

But, so that’s pretty much what we did. We went to some of those stores. We went to the Nintendo store. We basically just followed him wherever he wanted to go. We kind of let him take the reins. I gave him ideas, and then we let him run with it.

We did, I will say we did terrible at food because it was, he doesn’t care about fancy food. So it was like we walked by Chick-fil-A, we got Chick-fil-A for lunch. We went to a pizza place where they just make your own pizza that was just by the hotel. We had our room service breakfast. This wasn’t a, we’re going to New York and eating all the fun food kind of trip. It’s we’re going to New York and eating kid food. But I have no problem with kid food. I was happy with that. My mom didn’t actually go with us to see Stranger Things. She, because she’s never watched the show, but I was like, “You should maybe watch it.” It’s a little, I don’t know, I love it. Have you, you’ve never watched it, right, Jess? 

Jess: I watched the first two or three seasons, but I just, it just got, it just got like too weird for me.

Alex: Do you know what? It did for me too. And after I didn’t watch the, I think it was maybe the fourth season I didn’t watch, third or fourth, I don’t remember. There’s one season where it started off and the first episode was really too gruesome, and I was like, I can’t watch this. And I didn’t watch it. And then the last season was coming out, and my kids were so into it. I was like, I got to watch this. And it was actually the best season that they ever had. So you just got to stick with it.

Jess: Okay, maybe I’ll just watch the last season. 

Alex: Give it a try. No, you got to watch the second-to-last season. You got to watch the last two seasons. That’s all you need to watch. But, so anyway, my mom didn’t go with us to that show. She went and saw Chess and she said she loved it. Like so, so good. So if anyone’s looking for a good recommendation, that’s not a kid show, go see Chess because she loved it.

Anyway, like Jess mentioned with Chicago, this is not an exhaustive list. You, there are so, so many things to do in New York. We didn’t even go to any museums. We thought about going to the Natural History Museum, but that didn’t happen. Is there anything, I know Jess, you have been to New York many times, and Molly has been to New York. Is there anything that you want to add that you would recommend that people do with their kids when they go to New York? 

Jess: We love Central Park. We love Central Park Zoo, but like you said, that’s kind of going to be dependent on the weather. We, Molly really wants to go to the Jellycat experience in New York. And so I’m going to have to…

Alex: It is so cute. And it’s in FAO Schwartz.

Jess: Yeah, so I’m going to have to figure out how to make that happen. I’m trying to think of other, if you, if you or your child are Swifties, we do have a Swifties Guide to New York City that I will link in the show notes. And that kind of has,

Alex: And your Instagram stories all about it, too, that are saved.

Jess: So that would be a super fun, you know, mother-daughter trip if you, if you have kids that are or son, mother son, if you have sons or daughters that are into Taylor Swift. 

Alex: Yeah, that would be fun. All right, well, we had a great time visiting New York and it sounds like Jess’s trip to Chicago was equally as great. And we hope you enjoyed this episode and that it gave you some ideas and suggestions, maybe some new trips to take with your kids. So if you enjoyed this episode, please leave us a rating and review. Thanks so much.

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