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
Sep 14 - Sep 15
Tomorrow
Sep 15 - Sep 16
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Hillside family-friendly hotels

1. 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$3,861
NT$4,323 total
includes taxes & fees
Sep 29 - Sep 30
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

2. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$3,163
NT$3,542 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Plus Chicago Hillside

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,571
NT$2,879 total
includes taxes & fees
Oct 4 - Oct 5
MainStay Suites Chicago Hillside

4. FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
Downtown Chicago
NT$4,810
NT$5,646 total
includes taxes & fees
Sep 27 - Sep 28
FOUND Hotels, Chicago, Series by Marriott

5. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Downtown Chicago
NT$4,076
NT$4,846 total
includes taxes & fees
Oct 14 - Oct 15
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

6. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NT$5,663
NT$6,733 total
includes taxes & fees
Oct 13 - Oct 14
The Chicago Hotel Collection Ambassador Gold Coast

7. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
  • Family-friendly Chicago escape with cribs, entertainment, and a prime location near Water Tower Place and the beach.
NT$4,461
NT$5,304 total
includes taxes & fees
Oct 14 - Oct 15
The Chicago Hotel Collection - Magnificent Mile

8. River Hotel

River Hotel
Downtown Chicago
NT$4,867
NT$5,787 total
includes taxes & fees
Sep 27 - Sep 28
River Hotel

9. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
  • Family delight in Chicago with a crib, TV channels, and city adventures near the heartbeat of Millennium Park.
NT$5,031
NT$5,982 total
includes taxes & fees
Sep 27 - Sep 28
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
NT$5,879
NT$6,989 total
includes taxes & fees
Sep 27 - Sep 28
Club Quarters Hotel, Central Loop, Chicago
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

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"The staff was amazing"
Jorge 1-night trip
Posted less than an hour ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"Everything about this hotel was lovely. The views were fantastic from our room. Staff were a delight. My only complaint is our room got pretty hot even with the curtains closed. The AC works very hard to cool room but isn’t able to so I was a bit warm in the evening while I slept. I understand this is something that is mostly outside of the hotel’s control. Overall, I would highly recommend staying with the Royal Sonesta"
Sarah 3-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Easy check in, rooms were clean, convenient location."
John 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
"Great place to stay and close to a lot of the downtown things to see."
Tim 1-night trip
Posted 2 hours ago
InterContinental Chicago Magnificent Mile by IHG
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"The service was great and hotel was cleaned. We will definitely stay here again"
Sameth 2-night trip
Posted 2 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

8/10 Good
"Really nice place."
Francisco 1-night trip
Posted 8 hours ago
Fairmont Chicago at Millennium Park
The Wade

The Wade

10/10 Excellent
"Great location, within walking distance of many different places, great food at the hotel, rooms are nice"
Jessica 2-night trip
Posted 14 hours ago
The Wade
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

10/10 Excellent
"Buena ubicación, personal muy atento y cortés. Muy cerca de Millenium Park. Las habitaciones necesitan unidad de aire acondicionado con más potencia."
Hilda M 3-night trip
Posted 16 hours ago
Travelodge by Wyndham Downtown 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 Wrigley Field and Soldier Field. Make sure you have plenty of time to take in activities in the area like Navy Pier, United Center, and Michigan Avenue.

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