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Check availability on Hillside Family-Friendly Hotels

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 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, (1008)
"Nice place to stay"
United States
Roque
The price is ₹8,369
₹9,372 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 ₹8,236
₹9,223 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 ₹6,803
₹7,618 total
includes taxes & fees
11 Dec - 12 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, (2627)
"The room was spotless and the staff where great!"
United States
Maria
The price is ₹5,556
₹8,107 total
includes taxes & fees
7 Jan - 8 Jan 2026
Freehand Chicago
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (364)
"love this place definitely coming back !"
United States
Dayanara
The price is ₹5,782
₹6,787 total
includes taxes & fees
5 Jan - 6 Jan 2026
FOUND Hotel Chicago River North
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2999)
"Very beautiful place to stay"
United States
FaithBrenda
The price is ₹10,257
₹14,682 total
includes taxes & fees
1 Jan - 2 Jan 2026
Swissotel - Chicago
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3149)
"Amazing and will be staying again!"
United States
Angie
The price is ₹8,423
₹9,888 total
includes taxes & fees
7 Jan - 8 Jan 2026
Eurostars Magnificent Mile
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2747)
"Great food clean room friendly staff"
United States
MARINA
The price is ₹7,559
₹11,515 total
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (3006)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is ₹6,119
₹9,825 total
includes taxes & fees
4 Jan - 5 Jan 2026
Warwick Allerton - Chicago
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, (1741)
"Staff was courteous, room was clean, convenient location for us. Price was good as well."
United States
Jamie
The price is ₹6,407
₹7,522 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Yes"
Albin 2-night trip
Posted 2 days ago
Hilton Chicago

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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.