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
Aug 13 - Aug 14
Tomorrow
Aug 14 - Aug 15
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

Our top choices for Hillside family-friendly hotels

1. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$2,740
NT$3,069 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Plus Chicago Hillside

2. 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$3,795
NT$4,250 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,600
NT$2,911 total
includes taxes & fees
Sep 9 - Sep 10
MainStay Suites Chicago Hillside

4. Carleton of Oak Park

Carleton of Oak Park
Oak Park
  • Family fun awaits at this boutique Oak Park hotel with kitchenettes, premium TV, and easy access to the conservatory.
NT$3,936
NT$4,369 total
includes taxes & fees
Aug 31 - Sep 1
Carleton of Oak Park

5. Quality Inn O'Hare Airport

Quality Inn O'Hare Airport
Schiller Park
NT$2,874
NT$3,304 total
includes taxes & fees
Sep 7 - Sep 8
Quality Inn O'Hare Airport

6. Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport
Schiller Park
  • Family escapes with arcade games and free airport shuttle at O'Hare's welcoming destination for all generations.
NT$3,253
NT$3,740 total
includes taxes & fees
Sep 3 - Sep 4
Comfort Suites Chicago O'Hare Airport

7. SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard
Highland Hills
  • Chicago's family escape with free breakfast and premium entertainment includes free parking and Netflix streaming.
NT$3,113
NT$3,455 total
includes taxes & fees
Aug 24 - Aug 25
SureStay Plus Hotel by Best Western Chicago Lombard

8. Best Western Chicago - Downers Grove

Best Western Chicago - Downers Grove
Downers Grove
  • Create family fun by the poolside at this child-friendly Chicago hotel with outdoor amenities.
NT$2,870
NT$3,200 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Chicago - Downers Grove

9. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
Downtown Chicago
  • Kids enjoy premium TV while steps from Millennium Park, creating unforgettable family adventures with breakfast included.
NT$4,615
NT$6,062 total
includes taxes & fees
Sep 8 - Sep 9
La Quinta Inn & Suites by Wyndham Chicago Downtown

10. Freehand Chicago

Freehand Chicago
Downtown Chicago
NT$2,091
NT$4,016 total
includes taxes & fees
Aug 31 - Sep 1
Freehand Chicago
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Choose what matters most at family-friendly hotels in Hillside

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Hillside Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Amazing location, incredible restaurant, and friendly staff!"
matthew 1-night trip
Posted less than an hour ago
InterContinental Chicago Magnificent Mile by IHG
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Lolla 2026. Close and nice room."
David 2-night trip
Posted 1 hour ago
Fairmont Chicago at Millennium Park
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"The complimentary breakfast was hot with multiple items to choose from and the night bar was very accommodating. The staff was pleasant and helpful. "
Delano 4-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile
Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"They make sure the rooms is always clean when you leave and come back"
Deelasauntay 4-night trip
Posted 3 hours ago
Eurostars Magnificent Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Modern building, comfortable room, great amenities and helpful staff. Location is excellent."
Afshin 3-night trip
Posted 3 hours ago
Hyatt Regency Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Endroit calme, propre et très bien entretenu. Merci à toute l'équipe pour l'accueil !"
Amar 1-night trip
Posted 4 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

8/10 Good
"Needed better cleaning of rooms"
Candice 5-night trip
Posted 6 hours ago
Holiday Inn & Suites Chicago - Downtown by IHG
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

8/10 Good
"My first time staying here, I was booked for a yoga conference and found this hotel on a Chicago hotel site and decided to bill a stay. I loved the retro decor and the staff was very helpful. Planning to visit again soon."
geralyn 1-night trip
Posted 6 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Great stay. Will come back"
Richard 4-night trip
Posted 11 hours ago
Hyatt Regency O'Hare 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 United Center and Wrigley Field. Make sure you have plenty of time to take in activities in the area like Soldier Field, Navy Pier, and Michigan Avenue.

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