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
Oct 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Hillside family-friendly hotels

1. 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$3,619
NT$4,052 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

2. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$3,533
NT$3,956 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Chicago Hillside

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,650
NT$2,968 total
includes taxes & fees
Nov 22 - Nov 23
MainStay Suites Chicago Hillside

4. 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$3,990
NT$4,429 total
includes taxes & fees
Oct 26 - Oct 27
Carleton of Oak Park

5. Hotel 505 River North

Hotel 505 River North
Downtown Chicago
NT$5,184
NT$7,206 total
includes taxes & fees
Nov 22 - Nov 23
Hotel 505 River North

6. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
NT$5,226
NT$6,213 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Vacation Club Hotel Blake Chicago

7. Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago
Rosemont
NT$4,683
NT$5,338 total
includes taxes & fees
Nov 22 - Nov 23
Hyatt Regency O'Hare Chicago

8. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
Des Plaines
  • Family-friendly hotel offers indoor pool for kids and fitness facilities for parents near Allstate Arena.
NT$3,749
NT$4,423 total
includes taxes & fees
Nov 24 - Nov 25
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

9. 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$2,909
NT$3,229 total
includes taxes & fees
Oct 26 - Oct 27
SureStay Plus Hotel by Best Western Chicago Lombard

10. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
NT$4,683
NT$6,537 total
includes taxes & fees
Nov 22 - Nov 23
LondonHouse Chicago, Curio 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

River Hotel

River Hotel

10/10 Excellent
"Best location possible. Loved the river and night skyline."
cynthia 4-night trip
Posted 4 hours ago
River Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"unfriendly staffs other then that was good"
MYEONGKU 4-night trip
Posted 4 hours ago
The Chicago Hotel Collection - Magnificent Mile
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

8/10 Good
"There was an issue with check in. The staff did try to make it right. We appreciate that. The room was spectacular and the multiple views were wonderful. There were many restaurants in a walkable distance. I would stay here again and recommend it to others."
Tericka 6-night trip
Posted 5 hours ago
LondonHouse Chicago, Curio Collection by Hilton
Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Nice rooms and great location"
Gabriela 4-night trip
Posted 9 hours ago
Eurostars Magnificent Mile
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"St. Clair hotel lists the room as premium, even though the two windows in the room had no view. Both windows faced the building outter exterior brick walls from all sides. Dim lightning with no direct sunlight, very depressing to look out. The room should have been listened and offered as standard, at best, not premium."
Don E. 2-night trip
Posted 11 hours ago
Hotel Saint Clair- Magnificent Mile
Warwick Allerton - Chicago

Warwick Allerton - Chicago

10/10 Excellent
"The mattress was a little uncomfortable and pillows to high and small, but otherwise good."
Vivian 1-night trip
Posted 1 day ago
Warwick Allerton - Chicago

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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