Chicago Hotels With Pools: The Best Hotels for a Swim

Last Updated on August 14, 2026 by Ioana

If you’re looking for Chicago hotels with pools, you have a surprisingly good selection, especially if you want to stay downtown. I’ve narrowed it down to a few of the best options, from family-friendly hotels with a beautiful indoor swimming pool to luxury stays with impressive city views.

I’d focus on River North, the Magnificent Mile, and downtown Chicago if this is your first trip. That way, you can combine a pool day with easy access to Millennium Park, Navy Pier, the Art Institute of Chicago, and the Chicago River. This blog post contains affiliate links. When you make a purchase I may get a small commission at no extra cost to you. Find out more here.

The Best Chicago Hotels With Pools at a Glance

If you don’t want to read through every option, these are the hotels I’d consider first:

• Sheraton Grand Chicago Riverwalk: Best for families and a great location
• Radisson Blu Aqua Hotel: Best for a rooftop pool and skyline views
• Hilton Chicago: Best for a historic luxury stay near Millennium Park in the heart of Chicago
• Embassy Suites by Hilton Chicago Downtown River North: Best for families who want spacious rooms
• Homewood Suites by Hilton Chicago Downtown/Magnificent Mile: Best for longer stays

If you’re currently planning your trip, check out my Chicago itinerary for inspiration.

Sheraton Grand Chicago Riverwalk: Best for Families

⭐️⭐️⭐️⭐️ • 8.2/10 (841 reviews)
💲 Mid-range • 👉 Check current prices here

The Sheraton Grand Chicago Riverwalk is one of my favorite choices if your priority is finding a hotel with a pool while still being in the middle of everything.

The location is excellent, right along the Chicago River and within a few minutes’ walk to several of the city’s most popular attractions. You’re close to Navy Pier, Millennium Park, the Magnificent Mile, and the Riverwalk, so you don’t have to spend much time getting around.

The hotel has a large indoor swimming pool, making it particularly useful for families visiting Chicago when the weather isn’t cooperating. Chicago winters are obviously not ideal for an outdoor pool, so having an indoor option is a big plus.

There’s also a fitness center, plenty of public areas, and restaurants on-site.

Another reason I like this option is that you can easily turn the pool into a break during a busy sightseeing day. Spend the morning exploring downtown Chicago, walk along the river, have lunch, and then come back for a refreshing dip.

If you’re visiting Chicago alone, check out my guide on the best things to do solo in Chicago to plan your days.

Best for: Families, first-time visitors, and anyone who wants a central location with an indoor pool.

Radisson Blu Aqua Hotel: Best for a Rooftop Pool

⭐️⭐️⭐️⭐️ • 7.8/10 (1,519 reviews)
💲 Mid-range • 👉 Check current prices here

The Radisson Blu Aqua Hotel Chicago is one of the more interesting Chicago hotels with pools because of its impressive outdoor pool area.

It’s in the Aqua building, one of the most recognizable pieces of contemporary architecture in downtown Chicago. The hotel is right in the heart of the city, close to Millennium Park and within walking distance of the Chicago River.

The outdoor pool is seasonal, so this is the hotel I’d choose during the summer months rather than during a winter trip.

The pool area also gives you a completely different perspective of the city. You’re surrounded by skyscrapers rather than sitting at some generic resort pool, which makes it feel particularly Chicago.

The hotel also has a fitness center and plenty of other amenities, and the location makes it easy to explore the city on foot.

If you’re looking for a hotel where the pool itself is part of the experience, this is one of my top picks.

Best for: Couples, summer trips, and travelers who want a pool with city views.

Hilton Chicago: Best for a Historic Luxury Stay

⭐️⭐️⭐️ • 7.8/10 (1,013 reviews)
💲 Mid-range • 👉 Check current prices here

If you’d rather have a more traditional hotel, the Hilton Chicago is a great choice.

This is a historic hotel on Michigan Avenue overlooking Grant Park, and it’s an especially convenient option for sightseeing. Millennium Park, the Art Institute of Chicago, and the lakefront are all within walking distance.

The hotel has an indoor pool, so you can use it regardless of the season.

I also like the location because you’re not completely surrounded by the busiest tourist streets. You’re still right downtown, but Grant Park and Lake Michigan are immediately outside, giving you a little more breathing room.

The hotel has spacious public areas, a fitness center, restaurants, and plenty of room options.

It’s also a good choice if you’re combining sightseeing with a special occasion. You get the historic Chicago atmosphere without giving up modern amenities.

Best for: Couples and anyone who wants a historic hotel with an indoor pool.

Embassy Suites: Best for Families and Spacious Rooms

⭐️⭐️⭐️ • 8.3/10 (3,501 reviews)
💲 Mid-range • 👉 Check current prices here

For families, I would seriously consider Embassy Suites by Hilton Chicago Downtown River North.

The biggest advantage is the room setup. Instead of staying in a tiny standard hotel room, Embassy Suites gives you spacious suites, which can make a huge difference when you’re traveling with kids or staying for several nights.

You’re also in River North, one of the best areas to stay in Chicago for first-time visitors. There are restaurants everywhere, and you can walk to the Magnificent Mile, Chicago River, and plenty of downtown attractions.

The indoor pool gives families somewhere to relax after a long day of sightseeing.

And because Embassy Suites typically includes breakfast, it can also be a good way to get more value out of your stay, particularly when Chicago hotel prices are high.

Best for: Families, groups, and travelers who want more space.

Homewood Suites: Best for Longer Stays

⭐️⭐️⭐️ • 7.6/10 (894 reviews)
💲 Mid-range • 👉 Check current prices here

If you’re staying in Chicago for a week or more, I’d look at Homewood Suites by Hilton Chicago Downtown.

The main advantage is that these aren’t just traditional hotel rooms. The suites are designed with longer stays in mind, making them a good option if you want a little more space and some of the conveniences of an apartment.

You’re also in a fantastic location near the Magnificent Mile, with easy access to restaurants, shops, public transportation, and downtown attractions.

The hotel has an indoor pool, fitness center, and other amenities that make it feel more practical than a traditional city hotel.

If you’re visiting Chicago for a longer trip, having a room where you don’t feel like you’re living out of a suitcase can make the experience much more comfortable.

Best for: Longer stays, families, and travelers who want apartment-style amenities.

What to Consider When Booking a Chicago Hotel With a Pool

Not all hotel pools are equal, so I’d check a few things before booking.

Indoor vs. outdoor pool

This is probably the biggest consideration.

If you’re visiting Chicago in the summer, an outdoor pool can be fantastic. But if you’re traveling during the colder months, you’ll want an indoor swimming pool.

Some hotels only operate their outdoor pools seasonally, so always check the current availability for your exact dates.

Check whether the pool is actually open year-round

Hotel pools can occasionally close for renovations, maintenance, or private events. I’d check the hotel’s current information rather than assuming the pool will be available just because it’s listed on a booking site.

Look for additional fees

Some Chicago hotels charge additional fees for certain amenities, parking, or resort-style facilities. The room rate isn’t necessarily the final price you’ll pay.

This is especially important if you’re comparing a seemingly cheap hotel with a more expensive one. Look at the total cost for your exact dates.

Think about location

A pool is nice, but I wouldn’t sacrifice location just to get one.

If you’re visiting Chicago for the first time, staying near River North, the Loop, or the Magnificent Mile will make your trip much easier. You’ll have easy access to public transportation and many attractions will be within walking distance.

There’s not much point staying somewhere far outside downtown just to save money on a hotel with a pool if you’re then spending an hour commuting every day. Check out my guide on the best areas to stay in Chicago so you can pick the right one for you.