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7 Best Chicago Hotels with Pools

7 Best Chicago Hotels with Pools Leave a comment

As a freelance writer, I have been creating content and writing blogs for over a decade. Not only do I love writing about traveling, but I also have experience in many other fields. I have been a guest writer on many popular blogs, as well as ghostwritten novels. When I’m not writing, you can find me with my family, reading a book, or working on an art project! Not to mention traveling around the globe!

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Updated Nov 8, 2021

The Windy City is known for a lot of different reasons. Chicago is a wonderful place for deep dish pizza, taking in the lakefront views, as well as enjoying a White Sox, or Cubs game. However, when planning your vacation to this Midwestern marvel, finding the right place with a pool is always a plus. The best Chicago hotels with pools are as diverse and luxurious as this amazing city. 

When it comes to finding the right hotel for your Chicago vacation needs, you won’t have to look farther than these fabulous selections. Here is our list of the seven best Chicago Hotels with Pools:

  • Four Seasons Chicago
  • Viceroy Chicago
  • Hilton Chicago Magnificent Mile
  • Loews Chicago
  • The Robey
  • Palmer House
  • InterContinental Chicago, Magnificent Mile

Finding your poolside pleasure at one of these amazing Chicago hotels will be an easy experience with this helpful guide. Chicago truly is one of the best places in North America to find Midwestern hospitality. Not to mention amazing Lake Michigan views, mouth watering deep dish pizza, and the best Chicago hotels with pools. 

However, sometimes a lot of information at once can be overwhelming. Take a look at the following breakdown so you can get a better idea of what to expect from our hotel selections. 

The Best Chicago Hotels with Pools for Your Vacation

Hotels are known for having both indoor and outdoor pools. Though the summer weather in Chicago can be incredibly delightful, a midwestern summer doesn’t last very long. All in all, finding a great hotel with a good location and an amazing pool doesn’t have to be difficult. Our list is made up of both incredible outdoor pools, as well as unique and wonderful indoor pools. 

Here is a brief breakdown of what you will find at these seven hotels: 

HotelPool DetailsAmenitiesCost
Four Seasons ChicagoIndoor Pool and WhirlpoolPet Friendly, Laundry, Spa, Gym, Bar, Room Service, Beach Bar, Restaurant, Children’s play area$$$$$
Viceroy ChicagoAll Seasons PoolPet Friendly up to 50 lbs, Pool, Nearby Restaurants, Bar, Lounge, Fitness Center with AIRE Ancient Baths$$$
Hilton Grand Vacations, Magnificent MileAll Seasons Outdoor PoolPool, Restaurant, Bar, Dry Cleaning, Fitness Center, Business Center$$
Loews ChicagoIndoor Lap PoolBar, Pet Friendly, Sauna, Valet Parking, Fitness Center, Restaurant, Business Center, Rooftop Bar$$$$
The RobeyAll Seasons Pool

Restaurant, Rooftop Terrace, Pool, Tech-Friendly Rooms, Complimentary Bikes

Palmer HouseIndoor Heated Pool and Lounge AreaSpa, Restaurant, Laundry, Gym, Pet Friendly, Bar, Fitness Center$$$
InterContinental Chicago, Magnificent MileJunior Olympic Pool

Fitness Center, Pet Friendly, Bar, Lounge, Dry Cleaning, Laundry


Once you know what amenities, locations, as well as what kind of pool will fit your vacation best, it is easy to start planning. The hotels on the following list are incredibly different from one another. They not only vary as far as affordability, but they also are different in style and taste. Read on to find out more details about these remarkable hotels in Chicago!

Four Seasons Chicago

Starting off our list is the peak of luxury in downtown Chicago. Not only does the Four Seasons Chicago offer a top of the line indoor pool, but it also includes a whirlpool. However, the indoor pool isn’t the only way to relax at this fantastic hotel. The Spa allows you to purchase on-site packages that include manicures, pedicures, as well as massage and facials. 

The Four Seasons Chicago is also incredibly close to a lot of downtown Chicago destinations. Here are just a few of nearby shopping and entertainment options: 

  • The Museum of Contemporary Art
  • Shedd Aquarium
  • Northwestern University
  • American Girl Place Chicago
  • Washington Square Park
  • Oak Street Beach
  • Navy Pier
  • Cloud Gate
  • Millenial Park
  • River Walk

Not only are all of these iconic Chicago landmarks nearby, but the hotel also offers inclusive discounts for the Shedd Aquarium and the Field Museum of Chicago. The Four seasons is not only a luxury hotel in the heart of Chicago, but it is also family friendly and all inclusive! You can have the kids play in the hotel play area, completely stocked with the latest toys and kid favorites. Have a fun photo scavenger hunt in Chicago, then let the kids play at the hotel!

Viceroy Chicago

The Viceroy Chicago is an Art Moderne turn into the past. Not only are there fantastic design elements throughout the hotel, but also an impressive all seasons pool on the 18th floor. The pool offers stunning views of the city, Lake Michigan, as well as a bar and lounge called the Devereaux. You can get a cocktail and enjoy delicious food all while hanging out poolside. 

The Viceroy Chicago has its beginnings from the 1920’s era hotel the Cedar Hotel. The brick facade of the Cedar makes up the base of the Viceroy. It also includes the delectable seasonal American cuisine of the Somerset Restaurant. Not to mention a lot of local nightlife locations nearby and at the on-site bar. 

However, if you’re not up for a night out on the town, then you can enjoy Viceroy’s AIRE Ancient Baths. This unique bath house takes the tradition of ancient Greece and Rome and puts it into practice in Modern Chicago. With the bath house, and the incredible decor, you will feel like you have stepped into a different, more relaxing time. All in all, if you’re looking for a truly breathtaking experience, then the Viceroy Chicago is for you. 

Hilton Grand Vacations, Magnificent Mile

The Hilton Grand Vacation is a wonderful hotel for those looking for a Magnificent Mile experience, without the large price tag. However, just because it is more affordable, doesn’t mean it is lacking in beauty or amenities. The Hilton Grand Vacations has an outdoor all seasons pool with absolutely stunning Chicago views. This hotel is made up primarily of suites and studios for both long-term and short-term guests. 

When you stay here, whether on pleasure or business, there are so many things nearby your head may spin. Not only will you have Navy Pier just up the street, but also the Shops at North Bridge, Millennium Park, and a variety of fine dining and entertainment options close as well. You won’t have to look far for a great place to eat while you’re traveling. Not to mention you won’t run out of fun things to do while you stay at the Hilton Grand Vacations Chicago.

Loews Chicago

Loews Chicago

The Loews Chicago is a great place for relaxation, beautiful surroundings, as well as a fantastic poolside experience! This stylish hotel is great for business, pleasure, as well as family travel needs. The location is great for river walks and finding entertainment for all ages nearby. The Loews Chicago has a wide variety of dining and social venues on site. Not to mention they offer amazing deals.

This Chicago hotel holds the bar pretty high for modern, comfortable design. They have fully embraced the idea of classic lines, rich marble accents, as well as charming looking rooms and furniture. Because why not sleep on something comfortable and beautiful?

The packages that Loews Chicago offers for military members, family packages, as well as their “Park and Play Package” makes staying here definitely worth it. All you have to do to take advantage of these incredible deals is to book directly through the hotel. All things considered, you can get a great rate and spend the night at one of the best Chicago hotels with pools! 

The Robey

The Robey is a unique, boutique experience near Wicker Park. Furthermore, it is a modern, trendy take on the Art Deco style. It fits right in with the local eateries, pubs, as well as the overall experience of Wicker Park. The pool is outdoors, and located in the stunning outdoor terrace space. 

Because the Robey has a rich history, you’ll find that the modern furniture and the delightful food and cocktails really bring every part of Chicago together. Chicago really is a city with a past they stay connected to, and the Robey is a stunning example of that. The Robey is not only unique for it’s architecture, but also because it offers hotel rooms of such an incredible variety.

Here are just a few of the room designs you can choose from: 

  • Queen and Two Bunk Beds Room
  • Queen Room with a Twin Sized Loft Bed
  • Two Queen Loft Beds
  • Traditional Queen and King Suites and rooms

All in all, the Robey is a charming hotel with rooms that can fit the whole family comfortably. The kids can enjoy the modern style bunk beds, while parents rest easy nearby. The Wicker park location, as well as the stylish interior make the Robey a great choice for one of the best Chicago hotels with pools. 

Palmer House

Palmer House has a decadent turn-of-the-Century style that exudes glamour. Not only is this an affordable luxury hotel, but it offers an extensive fitness center on the 8th floor. All in all, the pool, the group fitness classes, and the wide variety of fitness equipment can be accessed by guests. Not to mention you can also purchase a membership to have access to these amazing facilities year round. 

The Health Club isn’t the only thing that brings people to the Palmer House. The incredible location, as well as the romantic history and atmosphere make staying here a unique experience. The rooms rates are extremely affordable for how exotic and charming you will find this hotel. With such an expansive history, as well as opulent decor, it is no wonder people flock to the Palmer House.

InterContinental Chicago, Magnificent Mile

When it comes to having a classic hotel on the list of the best Chicago hotels with pools, you definitely need to include the InterContinental on the Magnificent Mile. Not only do they have an astounding pool, but they also have wonderful dining options. Because who wouldn’t want to eat at Micheal Jordan’s Steak House while they are in Chicago, home of the Bulls? Not to mention there are plenty of options for wining and dining on-site.

There is a three-level fitness facility within this remarkable hotel. Because it was once the Medinah Athletic Club, the pool is a remnant of this building’s glittery past. The 14th floor junior olympic pool is surrounded by beautiful Spanish Majolica tiles. Not only that, but it is also supported by the same engineering used on railroad bridges! Built in 1929 and still used today, this is the oldest indoor pool in all of Chicago. 

The fitness levels also include an amazing spa. All in all, the InterContinental can book you a complete spa package and you never have to leave the hotel. You can book anything from relaxing in the two Finnish hot steam saunas, to having an aloe body wrap. Get a message alone, as well as invite a group to a relaxing spa treatment at this best Chicago hotels with pools selection!

The Absolute Best Chicago Hotels with Pools Just for You!

Chicago is a place where midwestern American niceties meets the clamoring bustle of a big city. There are so many inspiring historical, artistic, and entertaining things to see and do. Because the Windy City has so much to offer, it can be overwhelming. That’s why we created this list of the best Chicago hotels with pools to help you easily find just the right hotel for your Chicago vacation. 

Whether you’re in town to see the Bulls, or to walk down the shores of Lake Michigan, Chicago truly has something for everyone. Find your way to Navy Pier and Cloud Gate when you stay at the Palmer House, or enjoy the hip and trendy atmosphere of Wicker Park when you stay at the Robey. There are so many options to fit all of your vacations needs with this list of the seven best Chicago hotels with pools. 

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As a freelance writer, I have been creating content and writing blogs for over a decade. Not only do I love writing about traveling, but I also have experience in many other fields. I have been a guest writer on many popular blogs, as well as ghostwritten novels. When I’m not writing, you can find me with my family, reading a book, or working on an art project! Not to mention traveling around the globe!

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