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Check availability on Hillside Family-Friendly Hotels

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Hillside Family-Friendly Hotels

Free continental breakfast on weekdays
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

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

2.5 star property
Hillside
7.0 out of 10, Good, (1004)
"Nice place to stay"
United States
Roque
The price is 2.452.503 ₫
2.746.313 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
Lobby sitting area
Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside

3.0 star property
Hillside
7.6 out of 10, Good, (1004)
"Great Hotel"
Canada
Noor
The price is 2.413.474 ₫
2.702.609 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Best Western Plus Chicago Hillside
Exterior
MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside

2.5 star property
Hillside
6.2 out of 10, (1000)
"Quiet floor and clean room "
United States
sephora
The price is 1.993.648 ₫
2.232.487 ₫ total
includes taxes & fees
8 Dec - 9 Dec
MainStay Suites Chicago Hillside
Premium Private Quadruple Room, 4 Twin Beds | Premium bedding, in-room safe, blackout curtains, iron/ironing board
Freehand Chicago

Freehand Chicago

4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2620)
"Accommodation and great customer serbice!"
United States
Haidee
The price is 1.692.355 ₫
2.451.044 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Freehand Chicago
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2991)
"Great stay"
Canada
Lorrington Ashford
The price is 3.005.767 ₫
4.302.429 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Swissotel - Chicago
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1045)
"Great Hotel!"
United States
Wendy
The price is 2.577.765 ₫
3.800.028 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3134)
"Amazing and will be staying again!"
United States
Angie
The price is 2.278.454 ₫
2.674.676 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Eurostars Magnificent Mile
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2117)
"Loved and enjoyed our stay"
United States
Luis
The price is 2.703.028 ₫
3.832.360 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1735)
"Staff was courteous, room was clean, convenient location for us. Price was good as well."
United States
Jamie
The price is 1.877.758 ₫
2.203.992 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2994)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is 1.793.228 ₫
2.879.186 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Warwick Allerton - Chicago
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

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Frequently asked questions

What's Hillside like for family-friendly holidays?
The relaxing destination of Hillside is a great choice if you've been considering a holiday with the children. The entertainment, forests and restaurants are just a few things that make this an attractive spot for a family holiday. Fly into Chicago O'Hare International Airport (ORD), which is the closest airport, or Chicago Midway Airport (MDW), which is located 10.4 mi (16.7 km) from the city centre.
When's the best time to book a family-friendly holiday in Hillside?
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 with your family in Hillside?
While you are holidaying in Hillside, you and the family may want to see some interesting spots such as Wrigley Field and Michigan Avenue. Make sure that you have plenty of time to take in activities in the area such as United Center, Soldier Field and Navy Pier.