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$3,696
NT$4,139 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
A lobby with a reception desk, patterned sofas, a glass-top table with a potted plant, and a decorative mirror.

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$3,782
NT$4,236 total
includes taxes & fees
Nov 12 - Nov 13
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 modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

4. Hotel 505 River North

Hotel 505 River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,988 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.

5. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,214 reviews)
The price is NT$5,197
NT$6,178 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Vacation Club Hotel Blake Chicago
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

6. 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 hotel lobby with a sofa, chairs, a TV, and artwork on the walls.

7. 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, (2,068 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.

8. 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, (3,104 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 rooftop terrace with outdoor seating, a view of the city skyline, and a river.

9. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,873 reviews)
The price is NT$4,657
NT$6,501 total
includes taxes & fees
Nov 22 - Nov 23
LondonHouse Chicago, Curio Collection by Hilton
A modern lounge area with leather sofas, a coffee table, and a patterned rug.

10. 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, (3,216 reviews)
The price is NT$4,255
NT$4,907 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Chicago O'Hare – Rosemont by IHG
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Great location. Walking distance to everything tourist. Would stay here again!"
Valeria 1-night trip
Posted 1 hour ago
Hilton 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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