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, (1,002 reviews)
The price is NT$3,612
NT$4,045 total
includes taxes & fees
Nov 30 - Dec 1
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, (1,005 reviews)
The price is NT$3,785
NT$4,239 total
includes taxes & fees
Nov 5 - Nov 6
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, (1,000 reviews)
The price is NT$2,621
NT$2,935 total
includes taxes & fees
Nov 22 - Nov 23
MainStay Suites Chicago Hillside
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

4. Carleton of Oak Park

Carleton of Oak Park
3.0 star property
Oak Park
9.2 out of 10, Wonderful, (1,213 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 22 - Nov 23
Carleton of Oak Park
A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

5. 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, (3,111 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 16 - Nov 17
SureStay Plus Hotel by Best Western Chicago Lombard
A hotel lobby with a sofa, chairs, a TV, and artwork on the walls.

6. 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, (2,069 reviews)
  • cleanliness
    Family-friendly hotel offers indoor pool for kids and fitness facilities for parents near Allstate Arena.
The price is NT$3,873
NT$4,569 total
includes taxes & fees
Nov 27 - Nov 28
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
A modern lounge area with leather sofas, a coffee table, and a patterned rug.

7. Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG
3.0 star property
Rosemont
9.0 out of 10, Wonderful, (3,218 reviews)
The price is NT$4,377
NT$5,045 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Chicago O'Hare – Rosemont by IHG
A modern restaurant interior with a green wall, hanging lights, and a long dining area.

8. Hotel 505 River North

Hotel 505 River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,989 reviews)
The price is NT$3,608
NT$5,328 total
includes taxes & fees
Nov 22 - Nov 23
Hotel 505 River North
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

9. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,215 reviews)
The price is NT$5,197
NT$6,178 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Vacation Club Hotel Blake Chicago
An indoor swimming pool with wooden beams, clear glass walls, and lounge chairs.

10. Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream
2.5 star property
Carol Stream
8.6 out of 10, Excellent, (1,016 reviews)
  • cleanliness
    Splash into family fun at this poolside retreat with a fitness center and 24-hour amenities for adventures all day long.
The price is NT$3,555
NT$3,945 total
includes taxes & fees
Oct 31 - Nov 1
Hampton Inn Chicago-Carol Stream
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

River Hotel

River Hotel

10/10 Excellent
"Front desk and housekeeping were amazing. Made my stay a wonderful experience."
Jesse 4-night trip
Posted 7 hours ago
River Hotel

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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