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 10 - Aug 11
Tomorrow
Aug 11 - Aug 12
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$2,745
NT$3,074 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$3,812
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$2,566
NT$2,873 total
includes taxes & fees
Sep 7 - Sep 8
MainStay Suites Chicago Hillside

4. Freehand Chicago

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

5. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
NT$3,707
NT$4,407 total
includes taxes & fees
Sep 8 - Sep 9
Congress Plaza Hotel

6. 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$4,623
NT$6,072 total
includes taxes & fees
Sep 8 - Sep 9
La Quinta Inn & Suites by Wyndham Chicago Downtown

7. 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

8. 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$3,592
NT$4,271 total
includes taxes & fees
Aug 30 - Aug 31
Travelodge by Wyndham Downtown Chicago

9. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NT$4,619
NT$5,491 total
includes taxes & fees
Aug 30 - Aug 31
The Chicago Hotel Collection Ambassador Gold Coast

10. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
  • Splash into a family adventure at this Chicago hotel where kids enjoy a supervised pool and free cribs, just steps from Willis Tower.
NT$4,652
NT$5,918 total
includes taxes & fees
Sep 8 - Sep 9
Holiday Inn & Suites Chicago - Downtown by IHG
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"The staff is great, it’s very upscale hotel which is great if you are going for that experience."
Ryan 7-night trip
Posted less than an hour ago
Eurostars Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Breakfast is top notch"
Robert 1-night trip
Posted 1 hour ago
Hyatt Regency O'Hare Chicago
Omni Chicago Hotel

Omni Chicago Hotel

10/10 Excellent
"We had a wonderful suite; the staff was very accommodating and friendly - from check in through to the doormen who were very helpful with directions, etc. when we exited the hotel for our daily adventures. Great menu in the dining room (breakfast and afternoon snacks) - and friendly bar. HIGHLY RECOMMEND."
Sharon 4-night trip
Posted 1 hour ago
Omni Chicago Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

8/10 Good
"Clean, having to take 2 different elevators is annoying. Outlets in bathroom did not fit my irons cord..was very loose"
Teresa 2-night trip
Posted 2 hours ago
Holiday Inn Chicago Dwtn - The Mart by IHG
River Hotel

River Hotel

8/10 Good
"Está bien aceptable y muy bien ubicado si.."
Diana 2-night trip
Posted 3 hours ago
River Hotel
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

8/10 Good
"Stayed here for Lollapalooza. Love the location and the hotel room itself is nicely furnished and pretty clean. The shower could be cleaner. I'm not sure if hotels can really do much about mold."
Kristine 3-night trip
Posted 3 hours ago
Fairmont Chicago at Millennium Park
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Very friendly and helpful staff!"
Jessica Ann 1-night trip
Posted 3 hours ago
Hilton Chicago
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

8/10 Good
"Great place but not a value. There was a concert and two weddings happening on the day I was staying. It was very busy! Long elevator waits. Long waits for coffee. The lobby was so crowded all the time. I suppose these are the signs of a successful business? I never felt like a “guest” more like a consumer. One K lighter for two days and a meal. The cost of big city living put the squeeze on this country mouse."
Aaro 2-night trip
Posted 6 hours ago
InterContinental Chicago Magnificent Mile by IHG
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

8/10 Good
"Check in Staff was great and welcoming, we were allowed to check in early. Room was nice and clean."
Jason 2-night trip
Posted 9 hours ago
Hyatt Regency McCormick Place 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 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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