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 14 - Aug 15
Tomorrow
Aug 15 - Aug 16
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

Our top choices for Hillside family-friendly hotels

1. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$2,733
NT$3,060 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$3,666
NT$4,106 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$2,600
NT$2,911 total
includes taxes & fees
Sep 9 - Sep 10
MainStay Suites Chicago Hillside

4. Freehand Chicago

Freehand Chicago
Downtown Chicago
NT$2,091
NT$4,016 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$4,615
NT$6,062 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$3,690
NT$4,387 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$4,633
NT$5,508 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$3,666
NT$5,302 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$3,525
NT$4,191 total
includes taxes & fees
Aug 31 - Sep 1
Travelodge by Wyndham Downtown Chicago

10. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NT$4,611
NT$5,482 total
includes taxes & fees
Aug 30 - Aug 31
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Clean room staff is very nice, friendly and helpful enjoyed the visit 👍"
Tamer 3-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Everything you need restaurant , rentals car in same place make so easy to do ,discount in dinner was great."
Tamarra 2-night trip
Posted less than an hour ago
Hyatt Regency Chicago
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"View from room."
Matthew 1-night trip
Posted 1 hour ago
Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Beautiful hotel with an amazing pool! Spa services are fantastic!"
Elizabeth 1-night trip
Posted 6 hours ago
InterContinental Chicago Magnificent Mile by IHG
Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Very clean room. Good location. Close to metro. Welcoming staff. "
Maryann 4-night trip
Posted 9 hours ago
Eurostars Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"The complimentary breakfast was hot with multiple items to choose from and the night bar was very accommodating. The staff was pleasant and helpful. "
Delano 4-night trip
Posted 19 hours ago
The Chicago Hotel Collection - Magnificent Mile
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

8/10 Good
"Needed better cleaning of rooms"
Candice 5-night trip
Posted 23 hours ago
Holiday Inn & Suites Chicago - Downtown 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 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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