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$2,593
NT$2,903 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$3,690
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$4,620
NT$5,492 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$3,460
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$4,598
NT$5,466 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

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

10/10 Excellent
"👍"
Arianna 1-night trip
Posted 1 hour ago
Holiday Inn & Suites Chicago - Downtown by IHG
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"We were on the 8th floor. The room was very spacious and very nice. It came with a mini fridge and coffeemaker. The bathroom was very small. When you used the toilet your knees touched the bath tub. There was rust in the bottom of the tub but that didnt bother us at all seeing as how we didnt take a bath just showers. The staff was very helpful and very nice. We did order doordash and we had to walk down to the security office to pick it up which didnt bother us. The only thing I wish they had was free parking. We had to pay $125.00 for parking near the hotel."
Alisha 2-night trip
Posted 1 hour ago
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Our stay was fantastic: breakfast was great, onsite gym was great, enjoyed time at the bar. Our room was very clean and comfortable, had everything we needed."
Susan 2-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

8/10 Good
"Parking like everywhere else in Chicago was expensive. Guests have limited spaces in the parking garage and it costs 57$ a night. One night we did not have guest parking available and had to pay 62$ with out being able to come and go or else be charged another 62$."
Nelson 2-night trip
Posted 2 hours ago
Crowne Plaza Chicago West Loop by IHG
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Thank you for a quick wonderful experience over a busy weekend. Totally my stay every time I’m in town. Brian,"
Brian 1-night trip
Posted 2 hours ago
Hilton Chicago
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"A grand old dame of a hotel, with emphasis on the grand. Although I would skip the in-house restaurants entirely, the place is well-maintained, well-run, with strong service and with a marvelous pool the likes of which one rarely sees. The location is two blocks from the Chicago river. The building itself is part of the Chicago skyline, and architectural gem."
Richard 3-night trip
Posted 6 hours ago
InterContinental Chicago Magnificent Mile 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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