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Featured Chicago Hotels with an Outdoor Pool

See all 1,568 Properties in Chicago

Estimated price for 1 night/2 adults

Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5.0 221 N Columbus Dr, Chicago, IL
Free Cancellation
4.5/5 (2,038 reviews)
$186/ night for 2 guests

The room and services available were wonderful. We enjoyed the view/the fact that the hotel was within walking distance of all that we planned to do in Chicago. Bed/pillows were very comfortable, separate thermostats in the main bedroom and bathroom were fabulous. We also love the restaurant and ...

Reviewed on Apr 19, 2019
InterContinental Chicago Magnificent Mile
InterContinental Chicago Magnificent Mile
4.5 out of 5.0 505 N Michigan Ave, Chicago, IL
4.2/5 (2,507 reviews)
$189/ night for 2 guests

It is conveniently located to everything. There is a Starbucks in the lobby. The pool is beautiful and the room was perfect. We enjoyed our stay and the staff was so friendly. The breakfast buffet is definitely worth every penny. They had a vast selection of food with healthy options loaded with ...

Reviewed on Apr 3, 2019
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
3.5 out of 5.0 300 E Ohio St, Chicago, IL
Free Cancellation
4.2/5 (4,781 reviews)
$84/ night for 2 guests

Good value for money. For location in downtown Chicago, good room size.

Reviewed on Apr 15, 2019
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
3.0 out of 5.0 777 East Grand Avenue, Bensenville, IL
Free Cancellation
3.7/5 (3,122 reviews)
$80/ night for 2 guests

Bathrooms are very run down in rooms... peeling paint, cracked drywall and smells like cigarette smoke

Reviewed on Apr 11, 2019
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5.0 323 E Wacker Dr, Chicago, IL
Free Cancellation
4.4/5 (4,260 reviews)
$151/ night for 2 guests

It was elegant and spacious. Staff were great. Did not like their mandatory amenities fee.

Reviewed on Apr 7, 2019
Radisson Hotel Schaumburg
Radisson Hotel Schaumburg
3.5 out of 5.0 1998 North Roselle Road, Schaumburg, IL
Free Cancellation
4.4/5 (1,080 reviews)
$76/ night for 2 guests

Hotel was very clean & new. No problems with mold or dust, dirty linens, etc. Only odd thing, in our opinion was the half glass shower. There was only half a glass that covered the shower area...not sure why designers thought that was a good idea. Basically one half of the shower was useless and ...

Reviewed on Apr 18, 2019
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Hilton Chicago/Oak Brook Hills Resort & Conference Center
4.0 out of 5.0 3500 Midwest Road, Oak Brook, IL
Free Cancellation
4.3/5 (1,127 reviews)
$74/ night for 2 guests

Always an awesome place to stay. Great staff and great amenities.

Reviewed on Apr 7, 2019
Hampton Inn Chicago Downtown/Magnificent Mile
Hampton Inn Chicago Downtown/Magnificent Mile
2.5 out of 5.0 160 E Huron Street, Chicago, IL
Free Cancellation
4.2/5 (3,725 reviews)
$98/ night for 2 guests

Staff was very friendly, breakfast was great as well.

Reviewed on Apr 19, 2019
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago, IL
4.2/5 (11,840 reviews)
$128/ night for 2 guests

Loved the charm and history. Check in was a bit slow. Internet was a bit slow. Shower took a good 3-4 minutes to get warm.

Reviewed on Apr 18, 2019
Hilton Chicago- Michigan Ave Cultural Mile
Hilton Chicago- Michigan Ave Cultural Mile
4.0 out of 5.0 720 S Michigan Ave, Chicago, IL
Free Cancellation
4.2/5 (5,429 reviews)
$133/ night for 2 guests

Right across from park area and constant access to cabs.

Reviewed on Apr 20, 2019
Country Inn & Suites by Radisson, Schaumburg, IL
Country Inn & Suites by Radisson, Schaumburg, IL
3.0 out of 5.0 1401 North Roselle Road, Schaumburg, IL
Free Cancellation
4.5/5 (1,467 reviews)
$93/ night for 2 guests

Great location. great staff. Great breakfast. only thing i can complain about is the pillows. too soft for my liking. otherwise wonderful stay.

Reviewed on Apr 20, 2019
Holiday Inn Chicago North Shore
Holiday Inn Chicago North Shore
3.0 out of 5.0 5300 West Touhy Ave, Skokie, IL
3.6/5 (14 reviews)
$101/ night for 2 guests

Much cheaper compared to Hampton Inn and Double Tree by Hilton by Old Orchard in Skokie. Also, it is a much nicer property than the Holiday Inn Express by Old Orchard in Skokie, Great value for the price and best value in Skokie. You can walk to multiple places to eat breakfast, lunch, and dinner. ...

Reviewed on Apr 18, 2019
Comfort Suites Chicago Schaumburg
Comfort Suites Chicago Schaumburg
2.5 out of 5.0 1100 East Higgins Road, Schaumburg, IL
Free Cancellation
4.3/5 (1,527 reviews)
$99/ night for 2 guests

Perfect location for several attractions suites safe a good size for more than 2 people

Reviewed on Apr 17, 2019
Hampton Inn & Suites Rosemont Chicago O'Hare
Hampton Inn & Suites Rosemont Chicago O'Hare
2.5 out of 5.0 9480 W Higgins Road, Rosemont, IL
Free Cancellation
4.7/5 (747 reviews)
$118/ night for 2 guests

Nice to have a bar. No gluten free apps at all....even one... How about real silverware not wasteful plastic? Room was nice and jobby/bar seating good. Glad for the availability of a good cider!!

Reviewed on Apr 16, 2019
Embassy Suites Chicago Downtown Magnificent Mile
Embassy Suites Chicago Downtown Magnificent Mile
4.0 out of 5.0 511 North Columbus Drive, Chicago, IL
Free Cancellation
4.4/5 (6,037 reviews)
$148/ night for 2 guests

This hotel is in a great location. Close to sight-seeing attractions, wonderful shopping, & restaurants. The breakfast buffet and cocktail reception were great! There's a Whole Foods right across the street, which was very convenient. Will be staying here again in the future.

Reviewed on Apr 18, 2019
La Quinta by Wyndham Chicago Gurnee
La Quinta by Wyndham Chicago Gurnee
2.5 out of 5.0 5688 Northridge Drive, Gurnee, IL
Free Cancellation
3.9/5 (1,420 reviews)
$50/ night for 2 guests

The staff was amazing. Especially the housekeepers. They were so nice when i ended uo stranded there because of snow.

Reviewed on Apr 16, 2019
Hyatt Place Chicago/Downtown - The Loop
Hyatt Place Chicago/Downtown - The Loop
3.0 out of 5.0 28 North Franklin Street, Chicago, IL
4.5/5 (1,444 reviews)
$179/ night for 2 guests

It wasn’t easy to find parking information on the website.

Reviewed on Mar 30, 2019
Embassy Suites Chicago Downtown
Embassy Suites Chicago Downtown
4.0 out of 5.0 600 N State St, Chicago, IL
4.4/5 (4,036 reviews)
$135/ night for 2 guests

Property, Furniture extremely outdated. No breakfast room service oh, that's a problem. The thermostat wouldn't work the entire time I was there. Not sure if would return

Reviewed on Apr 17, 2019
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Hotels with an Outdoor Pool: Our travelers loved these

Estimated price for 1 night/2 adults

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