A lush green valley with a winding road, steep mountains, and a misty atmosphere.

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Check availability on Hillside Family Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Hillside family-friendly hotels

A multi-story hotel with a central entrance, a flag, and a sign for Express Suites.

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
2.5 star property
Hillside
7.4 out of 10, Good, (1,001 reviews)
The price is NT$3,833
NT$4,292 total
includes taxes & fees
Nov 26 - Nov 27
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
A restaurant setting with round tables, chairs, and empty wine glasses.

2. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
3.0 star property
Hillside
7.6 out of 10, Good, (1,003 reviews)
The price is NT$3,785
NT$4,239 total
includes taxes & fees
Nov 3 - Nov 4
Best Western Plus Chicago Hillside
A MainStay Suites hotel with a large sign, a parking lot, and a building in the background.

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
2.5 star property
Hillside
6.2 out of 10, (1,007 reviews)
The price is NT$2,626
NT$2,941 total
includes taxes & fees
Nov 22 - Nov 23
MainStay Suites Chicago Hillside
A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

4. Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
2.5 star property
Schiller Park
9.4 out of 10, Exceptional, (2,408 reviews)
The price is NT$4,020
NT$4,622 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Chicago-O'Hare International Airport
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

5. Carleton of Oak Park

Carleton of Oak Park
3.0 star property
Oak Park
9.2 out of 10, Wonderful, (1,212 reviews)
  • cleanliness
    Family fun awaits at this boutique Oak Park hotel with kitchenettes, premium TV, and easy access to the conservatory.
The price is NT$3,968
NT$4,404 total
includes taxes & fees
Nov 5 - Nov 6
Carleton of Oak Park
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

6. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,213 reviews)
The price is NT$5,197
NT$6,178 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Vacation Club Hotel Blake Chicago
A modern restaurant interior with a green wall, hanging lights, and a long dining area.

7. Hotel 505 River North

Hotel 505 River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,986 reviews)
The price is NT$3,608
NT$5,328 total
includes taxes & fees
Nov 23 - Nov 24
Hotel 505 River North
A hotel lobby with a sofa, chairs, a TV, and artwork on the walls.

8. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
3.0 star property
Des Plaines
8.8 out of 10, Excellent, (2,067 reviews)
  • cleanliness
    Family-friendly hotel offers indoor pool for kids and fitness facilities for parents near Allstate Arena.
The price is NT$3,858
NT$4,552 total
includes taxes & fees
Nov 26 - Nov 27
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

9. SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard
2.5 star property
Highland Hills
9.0 out of 10, Wonderful, (3,103 reviews)
  • cleanliness
    Chicago's family escape with free breakfast and premium entertainment includes free parking and Netflix streaming.
The price is NT$3,138
NT$3,483 total
includes taxes & fees
Nov 5 - Nov 6
SureStay Plus Hotel by Best Western Chicago Lombard
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

10. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (5,129 reviews)
  • cleanliness
    Family-friendly Chicago adventure awaits just steps from Michigan Avenue with comfortable river views and boutique charm.
The price is NT$4,701
NT$5,589 total
includes taxes & fees
Nov 23 - Nov 24
L7 Chicago by LOTTE
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at family-friendly hotels in Hillside

Breakfast included
Pool

Top Hillside Hotel Reviews

The Wade

The Wade

10/10 Excellent
"Great stay"
Sara 6-night trip
Posted 1 hour ago
The Wade

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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