Photo by Off The Beaten Track

Hotels with Swimming Pool in Hillside, Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Hillside Hotels with Swimming Pool

Tonight
Aug 3 - Aug 4
Tomorrow
Aug 4 - Aug 5
Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Top Hillside Hotels with Swimming Pool

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
Relax by the calm pool with a tiled edge, surrounded by lounge chairs and lush greenery.

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

2.5 star property
6.8 out of 10, (1005)
"Good Place."
The price is P6,107
P6,839 total
includes taxes & fees
Aug 10 - Aug 11
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
The Wade
Enjoy a sea view from the large window, with a comfortable seating area and unique artwork on display.

The Wade

4.5 star property
8.2 out of 10, Very Good, (1147)
"It was a very relaxing stay and amazing view!"
The price is P6,922
P8,125 total
includes taxes & fees
Sep 1 - Sep 2
The Wade
Hyatt Regency McCormick Place Chicago
Experience the vibrant city atmosphere with stunning views of the bustling metropolis and its unique architectural landmarks.

Hyatt Regency McCormick Place Chicago

4.0 star property
9.0 out of 10, Wonderful, (1004)
"Great place to stay especially with the price! "
The price is P10,993
P14,270 total
includes taxes & fees
Aug 20 - Aug 21
Hyatt Regency McCormick Place Chicago
Sheraton Grand Chicago Riverwalk
Enjoy a scenic view of the river from this balcony, which features a treadmill and stationary bike for a workout.

Sheraton Grand Chicago Riverwalk

4.0 star property
8.4 out of 10, Very Good, (1410)
" Great stay, helpful staff, perfectly located. "
The price is P11,816
P15,616 total
includes taxes & fees
Aug 24 - Aug 25
Sheraton Grand Chicago Riverwalk
Loews Chicago Hotel
Relax by the pool surrounded by lush greenery and a vibrant mural.

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1510)
"This is a nice hotel in a great neighborhood. "
The price is P11,575
P15,432 total
includes taxes & fees
Sep 1 - Sep 2
Loews Chicago Hotel
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Relax by the rectangular pool surrounded by lounge chairs and tables.

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (2717)
"Wonderful place to stay definitely will return"
The price is P10,417
P13,683 total
includes taxes & fees
Aug 24 - Aug 25
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Relax by the pool surrounded by lounge chairs and umbrellas, taking in the city skyline views.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1953)
"Very pleasant stay!"
The price is P9,260
P10,870 total
includes taxes & fees
Sep 1 - Sep 2
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Relax by the rectangular pool with marked lanes, surrounded by sun loungers and a seating area.

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very Good, (1571)
"Lovely hotel and in the most convenient location"
The price is P10,698
P14,333 total
includes taxes & fees
Aug 17 - Aug 18
Radisson Blu Aqua Hotel Chicago
Aloft Chicago Mag Mile
Relax by the pool surrounded by comfortable seating and lush greenery.

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2778)
"We love our stay here !"
The price is P7,102
P8,337 total
includes taxes & fees
Aug 10 - Aug 11
Aloft Chicago Mag Mile
Hyatt Centric Chicago Magnificent Mile
Indoor pool

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1024)
"Best place we have stayed in Chicago in a long time. "
The price is P9,248
P12,563 total
includes taxes & fees
Aug 24 - Aug 25
Hyatt Centric Chicago Magnificent Mile
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.

Top Hillside Hotel Reviews

The Wade

The Wade

10/10 Excellent
"Property is great and very nice location. Beautiful views of lakefront. Only downside is coffee service ends at 10. You can ask for a coffee maker for room but not the same. "
Jennifer 1-night trip
Posted 14 hours ago
The Wade

Frequently asked questions

What are some accommodations with pools in Hillside?
Congress Plaza Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a steam room. InterContinental Chicago Magnificent Mile by IHG: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel, 4-minute walk from Michigan Avenue. Features complimentary wired internet access, an indoor pool, and LCD televisions. Crowne Plaza Chicago West Loop by IHG: Hotel, 3-minute walk from Merchandise Mart. Provides 2 restaurants, an indoor pool, and complimentary wireless internet access. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions.
What is there to see and do in Hillside?
Explore places like Wrigley Field, Michigan Avenue, and Navy Pier while you're in the area. Take a walk along the waterfront at North Avenue Beach and Oak Street Beach. Travelers love Hillside for its array of dining options.
When is the best time to book a hotel with a pool in Hillside?
You may want to consider a place to stay that offers an outdoor pool if you will be visiting Hillside in the hottest months of July, August, or June when the average temperature is 71°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 30°F.