Beginning of main content

Search over 895,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Check prices on hotels in Chicago

Best deal Best deal Dec 28 - Dec 30
Tonight Nov 14 - Nov 15
This weekend Nov 16 - Nov 18
Next weekend Nov 23 - Nov 25

Featured Chicago Hotels with an Outdoor Pool

See all 1,283 Properties in Chicago
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5.0 221 N Columbus Dr, Chicago
Free Cancellation
4.5/5 (1,733 reviews)
$139/ nightfor 2 guests

Great hotel. The facilities, coffee bar and restaurant were top notch. Great location. Central to all the places you might want to visit.The staff were very good, doormen especially friendly. Would recommend to anyone.

Reviewed on Nov 13, 2018
InterContinental Chicago Magnificent Mile
InterContinental Chicago Magnificent Mile
4.5 out of 5.0 505 N Michigan Ave, Chicago
4.2/5 (2,257 reviews)
$142/ nightfor 2 guests

Convenient location right on magnificent mile, close to shops, bars, restaurants & not too far to walk to theater district. Have stayed here before & will definitely stay again! Enjoyed wine bar & loved the view from our room on 33rd floor...!!

Reviewed on Nov 12, 2018
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
3.5 out of 5.0 300 E Ohio St, Chicago
Free Cancellation
4.2/5 (4,501 reviews)
$78/ nightfor 2 guests

Lovely hotel and you can't beat warm Doubletree cookies at check in!

Reviewed on Nov 12, 2018
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
Free Cancellation
3.7/5 (2,856 reviews)
$69/ nightfor 2 guests

Everything was clean, staff was kind, very close to the airport, I will return in my next visit!

Reviewed on Nov 12, 2018
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5.0 323 E Wacker Dr, Chicago
Free Cancellation
4.4/5 (4,024 reviews)
$85/ nightfor 2 guests

Comfortable beds, spacious rooms, quiet, clean and the softest towels I’ve ever had in Chicago. Underground Pedway System with shops & restaurants made it so quick & easy to get to the Metra Train & also over to the State Street Macy’s. Elevator was slow our first day but must have been addressed ...

Reviewed on Nov 13, 2018
Radisson Hotel Schaumburg
Radisson Hotel Schaumburg
3.5 out of 5.0 1998 North Roselle Road, Schaumburg
Free Cancellation
4.5/5 (958 reviews)
$84/ nightfor 2 guests

All day long 5 star , one of the best hotel specially compared to price

Reviewed on Nov 11, 2018
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
Free Cancellation
4.3/5 (990 reviews)
$93/ nightfor 2 guests

Absolutely wonderful! Great place, fantastic staff comfortable beds. A slam dunk!!

Reviewed on Nov 11, 2018
Hampton Inn Chicago Downtown/Magnificent Mile
Hampton Inn Chicago Downtown/Magnificent Mile
2.5 out of 5.0 160 E Huron Street, Chicago
Free Cancellation
4.2/5 (3,361 reviews)
$85/ nightfor 2 guests

Very clean room. Excellent attention to detail. Multiple caffeinated coffee packets, bed linens were tight to the bed. Nice!

Reviewed on Nov 14, 2018
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago
Free Cancellation
4.2/5 (11,013 reviews)
$90/ nightfor 2 guests

Beautiful historic hotel! The lobby is breathtaking. The breakfast buffet included with my booking was definitely worth it, with a gorgeous setting to look at! The room was small but very nice; the only age it showed was the paint on the trim & doors. Definitely recommend & we would stay at the Palmer ...

Reviewed on Nov 13, 2018
Hilton Chicago- Michigan Ave Cultural Mile
Hilton Chicago- Michigan Ave Cultural Mile
4.0 out of 5.0 720 S Michigan Ave, Chicago
Free Cancellation
4.2/5 (5,084 reviews)
$114/ nightfor 2 guests

This is the 2nd time we stayed at Hilton on Michigan Ave, am pleased with the accommodations. It was a bit busy when we stayed, due to a fundraiser and FBLA, but it was overall ...... good.

Reviewed on Nov 10, 2018
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
Free Cancellation
4.5/5 (1,326 reviews)
$84/ nightfor 2 guests

Very nice hotel in a perfect location for our tour of Chicago area bridal salons.

Reviewed on Nov 12, 2018
Holiday Inn Chicago North Shore
Holiday Inn Chicago North Shore
3.0 out of 5.0 5300 West Touhy Ave, Skokie
3.6/5 (1,105 reviews)
$80/ nightfor 2 guests

Close to malls.it is very near McDonalds and Walmart whichnare places our grandkids like to meet us at.

Reviewed on Nov 10, 2018
Comfort Suites Chicago Schaumburg
Comfort Suites Chicago Schaumburg
2.5 out of 5.0 1100 East Higgins Road, Schaumburg
Free Cancellation
4.3/5 (1,449 reviews)
$93/ nightfor 2 guests

Had originally requested a 2 Queen Size Beds, but it was not available upon arrival. The Staff on shift was very nice and found a room to accommodate our stay for the night. The breakfast was okay.

Reviewed on Nov 12, 2018
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
4.8/5 (601 reviews)
$97/ nightfor 2 guests

This hotel was on the doorstep of the building where my conference/workshop was held. In addition it was fifteen minutes from the airport and offered a shuttle service. I would have given an excellent rating but the shower door screeched annoyingly! Therefore I'll give a very good.

Reviewed on Nov 13, 2018
Embassy Suites Chicago Downtown Magnificent Mile
Embassy Suites Chicago Downtown Magnificent Mile
4.0 out of 5.0 511 North Columbus Drive, Chicago
4.4/5 (5,647 reviews)
$95/ nightfor 2 guests

wonderful surprise to have the evening cocktails and snacks. breakfast was excellent great location

Reviewed on Nov 8, 2018
La Quinta Inn & Suites Chicago Gurnee
La Quinta Inn & Suites Chicago Gurnee
2.5 out of 5.0 5688 Northridge Drive, Gurnee
Free Cancellation
3.9/5 (1,313 reviews)
$59/ nightfor 2 guests

Nice stop before Chicago! A very quite Hotel and easy to get to.

Reviewed on Nov 12, 2018
Hyatt Place Chicago/Downtown - The Loop
Hyatt Place Chicago/Downtown - The Loop
3.0 out of 5.0 28 North Franklin Street, Chicago
4.5/5 (1,294 reviews)
$98/ nightfor 2 guests

Great staff and good breakfast. Really nice and clean.

Reviewed on Nov 13, 2018
Embassy Suites Chicago Downtown
Embassy Suites Chicago Downtown
4.0 out of 5.0 600 N State St, Chicago
4.4/5 (3,680 reviews)
$103/ nightfor 2 guests

Good location. Comfortable rooms. Enjoyed social hour

Reviewed on Nov 13, 2018

Travelers loved these Hotels with an Outdoor Pool

Map

Recently booked Hotels with an Outdoor Pool in Chicago

Comfort Suites Michigan Avenue Loop
3.0 out of 5.0
Last booking: 3 minutes ago
Residence Inn by Marriott O'Hare
3.0 out of 5.0
Last booking: 7 minutes ago
Palmer House a Hilton Hotel
4.0 out of 5.0
Last booking: 11 minutes ago
Hilton Lisle/Naperville
3.5 out of 5.0
Last booking: 13 minutes ago
SpringHill Suites by Marriott Chicago Waukegan/Gurnee
3.0 out of 5.0
Last booking: 20 minutes ago
Chicago Marriott Suites Downers Grove
3.5 out of 5.0
Last booking: 22 minutes ago
Extended Stay America Chicago - Skokie
2.5 out of 5.0
Last booking: 33 minutes ago