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, (1,005 reviews)
The price is NT$3,715
NT$4,160 total
includes taxes & fees
Nov 23 - Nov 24
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, (1,011 reviews)
The price is NT$3,533
NT$3,956 total
includes taxes & fees
Nov 1 - Nov 2
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, (1,004 reviews)
The price is NT$2,639
NT$2,956 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, (1,207 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$3,989
NT$4,427 total
includes taxes & fees
Nov 3 - Nov 4
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$2,909
NT$3,229 total
includes taxes & fees
Oct 28 - Oct 29
SureStay Plus Hotel by Best Western Chicago Lombard
A modern lounge area with leather sofas, a coffee table, and a patterned rug.

6. 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, (3,211 reviews)
The price is NT$4,238
NT$4,888 total
includes taxes & fees
Nov 24 - Nov 25
Holiday Inn Chicago O'Hare – Rosemont by IHG
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

7. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,216 reviews)
The price is NT$5,224
NT$6,210 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.

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$3,627
NT$5,355 total
includes taxes & fees
Nov 23 - Nov 24
Hotel 505 River North
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.

9. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (5,118 reviews)
  • cleanliness
    Family-friendly Chicago adventure awaits just steps from Michigan Avenue with comfortable river views and boutique charm.
The price is NT$4,725
NT$5,617 total
includes taxes & fees
Nov 22 - Nov 23
L7 Chicago by LOTTE
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

10. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,882 reviews)
The price is NT$4,681
NT$6,535 total
includes taxes & fees
Nov 22 - Nov 23
LondonHouse Chicago, Curio Collection by Hilton
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Great location, spotless property, and great restaurants in the area."
Eugenio 3-night trip
Posted 2 hours ago
Eurostars Magnificent Mile

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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