If Chicago is on your bucket list, then this post has everything you need to book an unforgettable vacation using points and miles. Chicago is so much more than meets the eye; the city is full of artsy boutique stays, incredible food, and a never-ending list of activities. Let’s build your Windy City escape the Points Talk Squad way: equal parts savvy, stylish, and booked on points.

Chicago is one of those rare cities that refuses to be one thing. It has architecture and attitude, Michelin-starred restaurants and hot dogs, lakefront serenity and rooftop chaos, all rolled into one city. And when it comes to hotels? We have options at every price point, just for you.

 

Budget-Friendly Stays

Let’s set the record straight before we go any further. Budget does not mean boring in Chicago. 

Hyatt Place Chicago/Downtown – The Loop

12,000 to 20,000 Hyatt points per night

 

 

This hotel is in one of the best sweet spots in Chicago. You are within walking distance of Millennium Park and in the heart of the Theater District, making it easy to catch a Broadway show at the nearby Cadillac Palace or Goodman Theatre. Plus, you will only be a few blocks from the iconic Willis Tower, where you can head up to the Skydeck for bird’s-eye views of the entire city. What’s even better, you can snag this hotel for very few points, even with the newest changes to the Hyatt award chart. We love Hyatt Place hotels because you always get breakfast for free. Plus, these hotels are perfect for large families, as each room can accommodate up to six people.

 

Holiday Inn Express Chicago – Magnificent Mile

20,000 to 45,000 IHG points per night

 

If you are looking for a reliable, high-value stay that puts you steps away from world-class shopping, the Holiday Inn Express is a secret weapon for your trip to Chicago. Located just off the Magnificent Mile, you are perfectly positioned to explore the shops at North Bridge or take a quick walk to the historic Water Tower. We love this property for families because, in true Holiday Inn Express fashion, you get free breakfast every morning. This hotel is practical, clean, and a surprisingly stylish base for anyone who wants to use as few points as possible.

 

Hotel Lincoln 

8,000 to 20,000 Hyatt points per night

 

The Hotel Lincoln is a wonderful boutique property with rooftop views and serious personality—and one of the highest-value redemptions in the city. This hotel is full of vintage charm and lakefront energy without draining your entire points stash. Situated directly across from the sprawling Lincoln Park, you’re just steps away from the Lincoln Zoo and the serene nature boardwalk. You will be able to enjoy a short walk to the lakefront trail, providing immediate access to North Avenue Beach and scenic paths for a morning stroll or bike ride. 

 

Mid-Tier Magical Point Stays

The mid-tier point redemptions are where Chicago really starts to shine. These hotel stays are perfect for people looking for unique and fun hotel stays.

 

The Wade Hotel by Marriott 

35,000 to 60,000 Marriott points per night

 

The Wade is where historic Chicago architecture meets modern Marriott luxury. This property is a fantastic option if you have a 35,000 to 50,000-point Marriott free-night certificate, as this hotel is a sweet spot for that! Situated in a prime location that bridges the gap between the business hustle of the Loop and the refined energy of the Near North Side, it offers a more intimate, boutique feel than some of Chicago’s larger Marriott properties. The sleek rooms make this a perfect choice for your stay in the Windy City.

 

Chicago Athletic Association Hotel

15,000 to 25,000 Hyatt points per night

 

This hotel is a stunner that was once a private club in the 1890s, and now it is one of the best Hyatt redemptions in the city. Inside this glorious hotel, you will find the best rooftop views, a bocce ball court, and just enough old-school drama to make it fun. Our favorite part is the location of this amazing hotel: it sits directly across Michigan Avenue from Millennium Park, giving you instant access to Cloud Gate (“the Bean”) and the Jay Pritzker Pavilion. Its central location places you within walking distance of the Maggie Daley Park skating ribbon and the luxury shopping along the Magnificent Mile.

 

Luxury Stays Giving Main Character Energy

If you want to book a bougie full skyline fantasy, look no further than Chicago’s top-rated hotels bookable on points.

Kimpton Gray Hotel

48,000 to 105,000 IHG points per night

 

We love a boutique hotel stay, especially one that is the best point redemptions in all of Chicago. The Kimpton Gray Hotel is one of the best upscale IHG properties in downtown Chicago. The best part is that it doesn’t feel like a corporate conference room in disguise. This hotel is full of charm, and the location is nearly unmatched. Located in the financial district, you are perfectly positioned near the Chicago Board of Trade and just a short walk from the upscale dining and shops of State Street. The Kimpton is also conveniently close to the Chicago Riverwalk, where you can explore riverside cafes, boat tours, and stunning architectural views.

 

The Ritz-Carlton, Chicago

49,000 to 85,000 Marriott points per night

 

This is arguably one of Chicago’s crown jewels. Perched atop Water Tower Place, the hotel puts you directly on the Magnificent Mile with easy access to world-class shopping and dining. You are also just a short stroll from the Museum of Contemporary Art and the 360 Chicago observation deck, offering some of the best views and culture the city has to offer. Don’t want to leave the hotel? No problem! The Ritz has multiple dining options, a spa, and classic luxury vibes; it’s one of the best ways to use Marriott points in the city.

 

The Gwen, a Luxury Collection Hotel

40,000 to 72,000 Marriott points per night

 

This hotel is a masterclass in Art Deco glamour, drawing inspiration from the 1930s heritage of its namesake, sculptress Gwen Lux. The interior is so striking. A major highlight is the rooftop at the Gwen, which offers a year-round terrace experience. The Gwen’s location is practically unrivaled for shoppers and urban explorers, as it is literally connected to the Shops at North Bridge. This means you have access to high-end retailers without ever having to step outside, which is a massive perk during Chicago’s colder months. You are also perfectly positioned just off Michigan Avenue, within a five-minute walk of the Tribune Tower and the scenic Chicago Riverwalk, making it an ideal base for a weekend of sightseeing. 

 

Park Hyatt Chicago

20,000 to 35,000 Hyatt points per night

 

This is a sophisticated sanctuary right in the heart of the city’s most bustling district. Recently renovated, the hotel blends contemporary residential design with museum-quality art, offering a calm, refined atmosphere reminiscent of a private residence. One of the major highlights of this hotel is the iconic NoMI restaurant, which features a beautiful open-air terrace overlooking the Water Tower. If you are looking for a peaceful escape that doesn’t sacrifice luxury, this is one of the premier spots to use your World of Hyatt points.

The location is also unbeatable for those who want to be in the center of it all. Situated on North Michigan Avenue, you are directly across from the historic Chicago Water Tower and steps away from the Magnificent Mile. You are also perfectly positioned for a short walk to Oak Street Beach.

 

Flying on Points to the Windy City

Flights to Chicago are one of the easiest wins in the points world, thanks to two major airports and many nonstop routes from basically everywhere. Chicago O’Hare International Airport and Chicago Midway International Airport act like the ultimate travel magnets, pulling in flights from all over the country. You also don’t need a large stash of 50,000 points. All you need is a little strategy, a flexible date or two, and the confidence to hit “book” when you see a deal. 

American Airlines

Since we are all playing the points game strategically, I know we all have points to use with American Airlines, right? AA is quietly one of the best options for domestic economy flights. These miles have actually gotten more valuable for domestic economy routes, making them one of the best options for quick getaways.

Typical Cost: 

Fly for as few as 8,000 American Advantage miles one-way.

Example Flights:

Charlotte (CLT) to Chicago (ORD)

New York (LGA) to Chicago (ORD)

Nashville (BNA) to Chicago (ORD)

 

United Airlines

United Airlines is a Chicago hub airline, which means there are tons of nonstop options and ample award availability. If you have transferable points, you can sometimes book United flights cheaper through partner airlines like Aeroplan for as little as 6,000 points one-way.

Typical Cost:

Flights are available from 11,400 to 15,000 miles one-way.

Example Flights:

Orlando (MCO) to Chicago (ORD)

Denver (DEN) to Chicago (ORD)

Newark (EWR) to Chicago (ORD)

Southwest® Airlines

Southwest® Airlines flies into Midway, and these options offer flexibility. Southwest® Rapid Rewards are tied to the cash price, so the real flex is booking when fares drop and possibly even rebooking when they drop further. We love Southwest® for family travel, especially when you book using the coveted Companion Pass.

Typical Cost: 

6,000 to 15,000 Rapid Rewards points one-way.

Example Routes:

Atlanta (ATL) to Chicago Midway (MDW)

Dallas (DAL) to Chicago Midway (MDW)

 

Baltimore (BWI) to Chicago Midway (MDW)

Final Thoughts

Chicago is the kind of city that lets you choose your own adventure, and at your own price tag. You can sip rooftop cocktails like you own the place or grab a lakefront coffee. You can drop 40,000 points on a luxe stay or stretch 9,000 points like a budgeting genius who still has impeccable taste. And the best part? There is no wrong way to visit Chicago.

So whether you are flying in for a deep dish pizza, dazzling views, or the best weekend away. Just remember, the real flex is how many points you spend and how well you play the points game. So get going and book that trip. Chicago is waiting! 

 

Related Posts

Review of Park Hyatt Chicago

Thompson Chicago Review

Podcast 178. Visiting New York City and Chicago with Kids on Points