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 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
Next weekend
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$2,714
NT$3,039 total
includes taxes & fees
Sep 7 - Sep 8
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$3,641
NT$4,077 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$2,553
NT$2,859 total
includes taxes & fees
Sep 3 - Sep 4
MainStay Suites Chicago Hillside

4. 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$4,726
NT$5,619 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Chicago/Magnificent Mile Suites

5. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
NT$3,642
NT$5,268 total
includes taxes & fees
Sep 7 - Sep 8
Claridge House Chicago, Tapestry Collection by Hilton

6. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NT$4,566
NT$5,429 total
includes taxes & fees
Aug 30 - Aug 31
The Chicago Hotel Collection Ambassador Gold Coast

7. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
NT$3,896
NT$4,632 total
includes taxes & fees
Aug 23 - Aug 24
Central Loop Hotel

8. River Hotel

River Hotel
Downtown Chicago
NT$4,127
NT$4,907 total
includes taxes & fees
Aug 23 - Aug 24
River Hotel

9. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Downtown Chicago
NT$4,316
NT$5,132 total
includes taxes & fees
Aug 30 - Aug 31
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

10. FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
Downtown Chicago
NT$4,567
NT$5,361 total
includes taxes & fees
Aug 30 - Aug 31
FOUND Hotels, Chicago, Series by Marriott
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

River Hotel

River Hotel

10/10 Excellent
"Our stay at the River Hotel was fantastic! Check-in was easy and fast, the staff was friendly and welcoming, and the location was perfect. It’s within walking distance of so many great places, which made exploring the area incredibly convenient. Overall, we had a wonderful stay and would definitely come back!"
Maria 4-night trip
Posted 1 hour ago
River Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Great experience in the high Room suite which had a pull out sofa bed."
Carol 1-night trip
Posted 1 hour ago
Crowne Plaza Chicago West Loop by IHG
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Property was clean, staff was helpful and breakfast was perfect. Great for solo traveling and being in a location close to everything."
Lydia 3-night trip
Posted 2 hours ago
The Royal Sonesta Chicago Downtown
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Excellent"
Harry 1-night trip
Posted 2 hours ago
Hyatt Regency O'Hare Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Great location, great value for money"
Girivasan 2-night trip
Posted 3 hours ago
L7 Chicago by LOTTE
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Spacious, clean room with nice city view. Comfortable beds, loved to have a couch. Very friendly staff during check-in. Great location, block from RiverWalk and London House, where we had dinner. Great stay all together. Highly recommend."
Bella 1-night trip
Posted 3 hours ago
Fairmont Chicago at Millennium Park
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Room was nice and the hotel overall was great. Will def stay here again."
TaShandra 1-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Nice"
Karisma 2-night trip
Posted 18 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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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