A lush green valley with a winding road, steep mountains, and a misty atmosphere.

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Check availability on Hillside Family Hotels

Tonight
Aug 22 - Aug 23
Tomorrow
Aug 23 - Aug 24
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

Our top choices for Hillside family-friendly hotels

1. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$2,934
NT$3,286 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Plus Chicago Hillside

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

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
Hillside
NT$3,632
NT$4,067 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,545
NT$2,850 total
includes taxes & fees
Sep 8 - Sep 9
MainStay Suites Chicago Hillside

4. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
  • Chicago family suites near Michigan Avenue offer spacious, kid-friendly accommodations just minutes from beach fun.
NT$4,805
NT$5,713 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Chicago/Magnificent Mile Suites

5. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
NT$3,640
NT$5,265 total
includes taxes & fees
Sep 7 - Sep 8
Claridge House Chicago, Tapestry Collection by Hilton

6. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NT$4,555
NT$5,415 total
includes taxes & fees
Aug 30 - Aug 31
The Chicago Hotel Collection Ambassador Gold Coast

7. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
NT$3,887
NT$4,621 total
includes taxes & fees
Aug 30 - Aug 31
Central Loop Hotel

8. River Hotel

River Hotel
Downtown Chicago
NT$4,191
NT$4,983 total
includes taxes & fees
Aug 23 - Aug 24
River Hotel

9. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Downtown Chicago
NT$4,035
NT$4,797 total
includes taxes & fees
Aug 30 - Aug 31
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

10. FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
Downtown Chicago
NT$4,556
NT$5,348 total
includes taxes & fees
Aug 30 - Aug 31
FOUND Hotels, Chicago, Series by Marriott
View all properties

Choose what matters most at family-friendly hotels in Hillside

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Hillside Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"This is an amazing hotel in the heart of Chicago. Highly recommended. I got an upgrade for a huge room apartment style with river and downtown view. Room was quiet and clean. The staff is very friendly and helpful. The hotel is conveniently located close to many attractions within walking distance. And public transportation is nearby. I did not need a rental or a taxi."
Jos 3-night trip
Posted 3 hours ago
The Royal Sonesta Chicago Downtown
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Very clean room and confidently located near the millennium park."
Anup 1-night trip
Posted 5 hours ago
Fairmont Chicago at Millennium Park
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Great place in a central location"
Oliver 1-night trip
Posted 6 hours ago
L7 Chicago by LOTTE
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Very nice staff. Terrific location. Comfortable room"
Charles 1-night trip
Posted 7 hours ago
InterContinental Chicago Magnificent Mile by IHG
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Very nice hotel. We had a King size bed overlooking Buckingham fountain. Booking a park view room is highly recommended. The shower/bathroom is on the smaller end, however, knowing the history of the hotel, it comes at no surprise. The hotel itself has so much history and has quite a few famous guests throughout it's time. We are already planning our next trip back to Chicago and will likely stay here again! Highly recommend staying here!"
Alexandra 1-night trip
Posted 11 hours ago
Congress Plaza Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Staff were wonderful! Personable and helpful. Facilities were clean."
MAYPAHOU 2-night trip
Posted 11 hours ago
Holiday Inn Chicago Dwtn - The Mart by IHG

Frequently asked questions

What's Hillside like for family-friendly vacations?
The relaxing destination of Hillside is a great choice if you've been considering a vacation with the kids. The entertainment, forests, and restaurants are just a few things that make this an attractive spot for a family vacation. Fly into Chicago O'Hare Intl. Airport (ORD), which is the closest airport, or Chicago Midway Airport (MDW), which is located 10.4 mi (16.7 km) from the city center.
When's the best time to book a family-friendly vacation in Hillside?
The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Hillside are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What's there to see and do with your family in Hillside?
While you are vacationing in Hillside, you and the family might want to see interesting spots such as Wrigley Field and Soldier Field. Make sure you have plenty of time to take in activities in the area like Navy Pier, United Center, and Michigan Avenue.

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