Hillside Hotels with Pool, Chicago: Hillside Hotel Guide

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 Hillside Hotels with Pool

Tonight

30 May - 31 May

Tomorrow

Next weekend

In two weeks

12 Jun - 14 Jun

Our top choices for Hillside hotels with a pool

Indoor pool

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

Hillside

Splash into comfort at this O'Hare-area hotel with an indoor pool, perfect for all-season swims after airport arrivals.

includes taxes & fees

8 Jun - 9 Jun

Indoor pool

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

includes taxes & fees

28 Jun - 29 Jun

Indoor pool, open 7:00 AM to 10:00 PM, pool loungers

Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.

includes taxes & fees

28 Jun - 29 Jun

Indoor pool

Courtyard by Marriott Chicago Downtown River North

Downtown Chicago

Refreshing plunges await at this city centre Chicago hotel with an indoor pool open from dawn to dusk.

includes taxes & fees

1 Jul - 2 Jul

Indoor pool

The Royal Sonesta Chicago River North

Downtown Chicago

Stylish indoor pool retreat in city centre Chicago makes luxury laps a breeze after sightseeing.

includes taxes & fees

28 Jun - 29 Jun

Indoor pool, open 5:00 AM to 11:00 PM, pool loungers

voco Chicago Downtown - Riverwalk by IHG

Downtown Chicago

Dive into the Chicago city centre hotel's refreshing indoor pool and sauna for ultimate relaxation.

includes taxes & fees

14 Jun - 15 Jun

Indoor pool

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, hot tub haven, and 24-hour fitness centre.

includes taxes & fees

1 Jul - 2 Jul

Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.

includes taxes & fees

29 Jun - 30 Jun

View all properties

Choose what matters most at hotels with a pool in Hillside

Breakfast included

Hot tub

Top Hillside Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"The hotel and staff were amazing helpful. Very knowledgeable about their surroundings for their guests. The bellman was extremely friendly like a family hug."

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent

"Wonderful building, strategically well located in a very beautiful Chicago area, staff is super friendly and accommodating, I got there early and they had no problem assigning my room inmediatly, I booked a panoramic room, the view was breathtaking!! The restaurant service is also great, I had a delicious breakfast and they have a very appealing brunch package. I will be coming back every time I have to work in Chicago!"

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

6/10 Okay

"We had reserved a king bed, but since we checked in later in the evening, I guess none were available and my wife and I ended up with twin beds instead. Overall, our experience with the front desk staff was mixed — some were very friendly and helpful, while others were not."

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent

"We really enjoyed our stay at the Hyatt Regency O’Hare. The rooms were comfortable, clean and well fitted out. The two restaurants where we dined were very nice as well. The food was delicious at both. Everywhere in the hotel the service was just top notch. Everyone was so kind and helpful. Thanks!"

Frequently asked questions

What are some accommodation options with pools in Hillside?

Congress Plaza Hotel: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool and a sauna. Hotel Riu Plaza Chicago: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. The Chicago Hotel Collection - Magnificent Mile: Hotel, 2-minute walk from Michigan Avenue. Features flat-screen televisions and an indoor pool. River Hotel: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool and flat-screen televisions. Hotel Felix River North/Magnificent Mile: Hotel, 5-minute walk from Michigan Avenue. Provides a rooftop terrace, a seasonal outdoor pool and LED televisions.

What is there to see and do in Hillside?

Explore places such as Wrigley Field, Michigan Avenue and Soldier Field while you're in the area. Take a walk along the waterfront at North Avenue Beach and Oak Street Beach. Travellers 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 with an outdoor swimming pool if you'll be visiting Hillside in the hottest months of July, August or June, when the average temperature is 22°C. Accommodation with 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 -1°C.

d5687a62-f995-45d1-9907-7242d0df3eef83c74858-1bf5-4d97-aab8-a05c37aa24a0