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Check availability on Hillside Luxury Hotels

Our top choices for Hillside luxury hotels

Interior
Viceroy Chicago

Viceroy Chicago

4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1137)
" Great trip, hotel and location was very nice. Lots of stores and restaurants near by, walkable. "
United States
Julyana
The price is ₹19,367
₹25,380 total
includes taxes & fees
4 Jan - 5 Jan 2026
Viceroy Chicago
Meeting facility
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1577)
"Great room size and location "
United States
tilden
The price is ₹13,422
₹18,458 total
includes taxes & fees
21 Dec - 22 Dec
Sheraton Grand Chicago Riverwalk
Breakfast, lunch, dinner served; American cuisine
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2011)
"Great accommodation!"
Canada
James
The price is ₹15,289
₹20,586 total
includes taxes & fees
14 Dec - 15 Dec
Fairmont Chicago at Millennium Park
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers
Nobu Hotel Chicago

Nobu Hotel Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (757)
"Great location, amenities and staff. "
United States
Nicholas
The price is ₹28,713
₹33,706 total
includes taxes & fees
4 Jan - 5 Jan 2026
Nobu Hotel Chicago
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3348)
"I loved the location."
United States
Laura
The price is ₹12,696
₹14,904 total
includes taxes & fees
1 Jan - 2 Jan 2026
L7 Chicago by LOTTE
Premium bedding, down duvets, pillow-top beds, in-room safe
The Wade

The Wade

4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1507)
"Great location, walkable to so many area attractions. Would definitely stay here again. "
United States
Debbie
The price is ₹9,078
₹10,657 total
includes taxes & fees
14 Dec - 15 Dec
The Wade
Bar (on property)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1777)
"Amazing hotel, location, staff, and food!!"
United States
Wendy
The price is ₹24,907
₹29,238 total
includes taxes & fees
4 Jan - 5 Jan 2026
Trump International Hotel & Tower Chicago
American cuisine, al fresco dining
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1919)
"Good value, great cleaning staff "
United Kingdom
farzana
The price is ₹8,576
₹12,182 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Godfrey Hotel Chicago
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1790)
"Friendly staff and good location to all of the city"
United States
Mark
The price is ₹12,577
₹17,101 total
includes taxes & fees
23 Dec - 24 Dec
Radisson Blu Aqua Hotel Chicago
Bar (on property)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1635)
"Great place to stay "
United States
Juliet
The price is ₹16,463
₹21,965 total
includes taxes & fees
14 Dec - 15 Dec
Omni Chicago Hotel
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.
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Top Hillside Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Very nice hotel stay. Would definitely go back "
Rahul 6-night trip
Posted 2 days ago
The Whitehall Hotel, BW Premier Collection

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Frequently asked questions

Are you searching for a great accommodation for your luxury getaway to Hillside?
Expedia can help you get a flight to Chicago O'Hare International Airport (ORD) airport or Chicago Midway Airport (MDW) airport, and then you can select from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Hillside offers. During your visit, you might want to enjoy the restaurants which Hillside is known for.
When can I expect good weather in Hillside?
Planning for the weather is an important factor for making your trip to Hillside a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillside are January, November, February and December, with each month seeing an average of 13 cm of snowfall.
What's there to see and do in Hillside?
When you're in Hillside, enjoy exploring the sights and attractions here including Fresh Meadow Golf Club, Wrigley Field and Michigan Avenue. If you have extra time while you're in the area, you might want to stop by United Center and Soldier Field.