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 15 - Aug 16
Tomorrow
Aug 16 - Aug 17
Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

Our top choices for Hillside family-friendly hotels

1. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$2,722
NT$3,048 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$3,652
NT$4,089 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$2,583
NT$2,892 total
includes taxes & fees
Sep 1 - Sep 2
MainStay Suites Chicago Hillside

4. Freehand Chicago

Freehand Chicago
Downtown Chicago
NT$2,083
NT$4,000 total
includes taxes & fees
Aug 31 - Sep 1
Freehand Chicago

5. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
Downtown Chicago
  • Kids enjoy premium TV while steps from Millennium Park, creating unforgettable family adventures with breakfast included.
NT$4,584
NT$6,021 total
includes taxes & fees
Sep 8 - Sep 9
La Quinta Inn & Suites by Wyndham Chicago Downtown

6. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
NT$3,676
NT$4,370 total
includes taxes & fees
Sep 8 - Sep 9
Congress Plaza Hotel

7. 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$4,602
NT$5,471 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Chicago/Magnificent Mile Suites

8. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
NT$3,651
NT$5,281 total
includes taxes & fees
Sep 7 - Sep 8
Claridge House Chicago, Tapestry Collection by Hilton

9. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
Downtown Chicago
  • Discover a family-friendly oasis in downtown Chicago with premium amenities, a cozy atmosphere, and easy access to Millennium Park.
NT$3,460
NT$4,113 total
includes taxes & fees
Aug 30 - Aug 31
Travelodge by Wyndham Downtown Chicago

10. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NT$4,580
NT$5,445 total
includes taxes & fees
Aug 17 - Aug 18
The Chicago Hotel Collection Ambassador Gold Coast
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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

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

10/10 Excellent
"Nice stay…good restaurant…small bathrooms, but clean"
Steven 1-night trip
Posted 1 hour ago
Hilton Chicago O'Hare Airport
River Hotel

River Hotel

10/10 Excellent
"Nice room. Ability to get filtered water. Friendly staff. Beautiful old building."
Kathryn 5-night trip
Posted 3 hours ago
River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Great location"
Marileidy 2-night trip
Posted 4 hours ago
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"n/a"
Kristin 2-night trip
Posted 5 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"The location was good the breakfast bar was good."
Janey 1-night trip
Posted 5 hours ago
The Chicago Hotel Collection - Magnificent Mile

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 Soldier Field, Navy Pier, and Michigan Avenue.

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