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 7 - Aug 8
Tomorrow
Aug 8 - Aug 9
This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

Our top choices for Hillside family-friendly hotels

1. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$2,970
NT$3,326 total
includes taxes & fees
Aug 23 - Aug 24
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$3,812
NT$4,269 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,527
NT$2,830 total
includes taxes & fees
Sep 7 - Sep 8
MainStay Suites Chicago Hillside

4. SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard
Highland Hills
  • Chicago's family escape with free breakfast and premium entertainment includes free parking and Netflix streaming.
NT$2,985
NT$3,312 total
includes taxes & fees
Aug 29 - Aug 30
SureStay Plus Hotel by Best Western Chicago Lombard

5. Carleton of Oak Park

Carleton of Oak Park
Oak Park
  • Family fun awaits at this boutique Oak Park hotel with kitchenettes, premium TV, and easy access to the conservatory.
NT$3,947
NT$4,381 total
includes taxes & fees
Aug 10 - Aug 11
Carleton of Oak Park

6. Freehand Chicago

Freehand Chicago
Downtown Chicago
NT$2,101
NT$4,034 total
includes taxes & fees
Aug 31 - Sep 1
Freehand Chicago

7. River Hotel

River Hotel
Downtown Chicago
NT$3,874
NT$4,605 total
includes taxes & fees
Aug 9 - Aug 10
River Hotel

8. Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport
Schiller Park
  • Family escapes with arcade games and free airport shuttle at O'Hare's welcoming destination for all generations.
NT$3,268
NT$3,757 total
includes taxes & fees
Sep 1 - Sep 2
Comfort Suites Chicago O'Hare Airport

9. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
NT$3,848
NT$4,575 total
includes taxes & fees
Aug 9 - Aug 10
Club Quarters Hotel, Central Loop, Chicago

10. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
NT$3,682
NT$5,326 total
includes taxes & fees
Sep 7 - Sep 8
Claridge House Chicago, Tapestry Collection by Hilton
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Choose what matters most at family-friendly hotels in Hillside

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Hillside Hotel Reviews

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Nice clean hotel Great staff! Easy walk to numerous restaurants and trains"
Glen 3-night trip
Posted less than an hour ago
Holiday Inn Chicago Dwtn - The Mart by IHG
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

8/10 Good
"Was fine for a two night stay. Probably wouldn’t have booked if I had known the bathroom door was see through though. Not everyone is staying alone or sharing a room with someone they are comfortable with seeing almost everything through the door. So would not book again."
Emma 2-night trip
Posted 4 hours ago
Club Quarters Hotel, Central Loop, Chicago
Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"The hotel was great and in a perfect spot to everything in walking distance, the only issue was my key kept not working for the room but they did gladly switched it out for a new one."
RaKima 3-night trip
Posted 4 hours ago
Eurostars Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Really nice place to stay! Everything is near by and within walking distance!"
andy 5-night trip
Posted 10 hours ago
The Chicago Hotel Collection - Magnificent Mile
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"good"
Alex 3-night trip
Posted 3 days ago
The Allegro Royal Sonesta Hotel Chicago Loop

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 United Center and Wrigley Field. Make sure you have plenty of time to take in activities in the area like Michigan Avenue, Soldier Field, and Navy Pier.

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