Find Hotels with a Pool in Streeterville, IL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Streeterville Hotels with a Pool

Our top choices for Streeterville hotels with a pool

Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,242 reviews)
"Great hotel "
United States
Jeffrey
The price is AED 313
AED 368 total
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Chicago - Magnificent Mile
View from room

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,722 reviews)
"Great stay!!!"
United States
Lorenzo Martrel
The price is AED 295
AED 346 total
includes taxes & fees
25 Jan - 26 Jan
Hilton Chicago/Magnificent Mile Suites
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,041 reviews)
"All around a nice stay for the holiday "
United States
Alec
The price is AED 278
AED 326 total
includes taxes & fees
25 Jan - 26 Jan
Aloft Chicago Mag Mile
Indoor pool

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,068 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is AED 360
AED 530 total
includes taxes & fees
25 Jan - 26 Jan
Hyatt Centric Chicago Magnificent Mile
Indoor pool

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,661 reviews)
"Would definitely stay again…location was perfect "
United States
Ashley
The price is AED 372
AED 436 total
includes taxes & fees
5 Feb - 6 Feb
Courtyard by Marriott Chicago Magnificent Mile
Indoor pool

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1,607 reviews)
"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is AED 400
AED 470 total
includes taxes & fees
18 Jan - 19 Jan
The Wade
Seasonal outdoor pool, sun loungers

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (337 reviews)
"Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!"
United States
Mariana
The price is AED 505
AED 593 total
includes taxes & fees
11 Feb - 12 Feb
Hilton Grand Vacations Club Chicago Magnificent Mile
Indoor pool

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2,789 reviews)
"Great hotel staff and location. "
United States
Jacqueline
The price is AED 388
AED 563 total
includes taxes & fees
22 Jan - 23 Jan
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Fitness facility

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,582 reviews)
"Clean room, pleasant staff, breakfast was good but expensive "
United States
Jacob
The price is AED 621
AED 858 total
includes taxes & fees
25 Jan - 26 Jan
Sheraton Grand Chicago Riverwalk
Indoor pool

The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,002 reviews)
"Loved the location!"
United States
Mark
The price is AED 1,745
AED 2,048 total
includes taxes & fees
1 Feb - 2 Feb
The Peninsula Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Streeterville

Breakfast included
4 stars

Top Streeterville Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"The room was great nice and clean "
Peter 1-night trip
Posted 2 days ago
Hilton Chicago/Magnificent Mile Suites

Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Streeterville?
If laying by the pool is your idea of the perfect getaway, you may want to consider lively Streeterville, which offers 11 places to stay with pools. While you're here, you can explore sights such as Michigan Avenue and Wrigley Field, and then relax poolside at one of the accommodations in Streeterville that guests like for their pools.
What are some hotels with pools in Streeterville?
Hyatt Centric Chicago Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. The Ritz-Carlton, Chicago: Hotel, 2-minute walk from Michigan Avenue. Offers a full-service spa, a pool, and Smart TVs.
How many pool hotels will I find in Streeterville?
Expedia has 11 hotels in Streeterville for your poolside break.
What is there to see and do in Streeterville?
Explore places like Michigan Avenue, Navy Pier, and Lake Michigan while you're in Streeterville. Make a point to visit attractions like Ohio Street Beach and Chicago Children's Museum. Streeterville appeals to visitors with its beautiful lakeside setting, major shopping area, and array of dining options.
When is the best time to book a hotel with a pool in Streeterville?
You may want to think about a place to stay with an outdoor swimming pool if you're planning to visit in the warmest months of July, August, or June when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temperature is 31°F.