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
Oct 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Hillside family-friendly hotels

A multi-story hotel with a central entrance, a flag, and a sign for Express Suites.
A reception area with two reception desks, a wall-mounted display, and a carpeted floor.
A hotel room with a blue sofa, a wooden coffee table, a bed with white linens, a desk with a chair, and a window with curtains.
A modern bathroom with a toilet, sink, and mirror.

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
Hillside
NT$3,985
NT$4,463 total
includes taxes & fees
Nov 18 - Nov 19
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.
A hotel lobby with a buffet area, multiple seating arrangements, and a patterned carpet.
A gym with treadmills, elliptical machines, and weight equipment.
A hotel room with a bed, a television, a desk, a chair, and a patterned carpet.

2. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$3,511
NT$3,932 total
includes taxes & fees
Oct 25 - Oct 26
Best Western Plus Chicago Hillside
A MainStay Suites hotel with a large sign, a parking lot, and a building in the background.
A hotel room with two beds, a nightstand, a lamp, and a framed picture on the wall.
A reception area with a counter, two wall-mounted lamps, a framed artwork, and a sign for 'Mattress & Bedding.'
A bathroom with a sink, toilet, and shower.

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,837
NT$3,177 total
includes taxes & fees
Nov 9 - Nov 10
MainStay Suites Chicago Hillside
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.
A residential street with a sidewalk, houses, and greenery.
A hotel room with a bed, a desk, a chair, and a window with curtains.

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$3,966
NT$4,401 total
includes taxes & fees
Oct 27 - Oct 28
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.
A modern conference room with a marble table, patterned chairs, a flat-screen TV, and a large window with a view of trees and parked cars.
A spacious lobby with a modern design, featuring a seating area with sofas and chairs, a coffee table, and a large flat-screen TV mounted on the wall.
A hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

5. 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$3,136
NT$3,480 total
includes taxes & fees
Oct 26 - Oct 27
SureStay Plus Hotel by Best Western Chicago Lombard
A hotel room with a bed, a microwave, a refrigerator, and a coffee machine.
A hotel reception desk with two computer stations, a modern wall design, and a visible window.
A modern bathroom with a glass shower enclosure, a white sink with a mirror above it, and two white towels hanging on the wall.
A modern building with a large glass facade, a prominent circular structure on the right, and a landscaped entrance area.

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

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
Des Plaines
  • Family-friendly hotel offers indoor pool for kids and fitness facilities for parents near Allstate Arena.
NT$4,245
NT$5,008 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
Breakfast area
Room
Lobby
Bathroom

7. Best Western At O'Hare

Best Western At O'Hare
Rosemont
NT$3,277
NT$3,736 total
includes taxes & fees
Oct 25 - Oct 26
Best Western At O'Hare
A modern lounge area with leather sofas, a coffee table, and a patterned rug.
An outdoor patio with a wooden table and wicker chairs, surrounded by blue umbrellas, and a building with large windows in the background.
A modern living room with a brown leather sofa, a coffee table, and a side table with a lamp.
A modern living room with a sectional sofa, a fireplace, and a bar area.

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

Holiday Inn Chicago O'Hare – Rosemont by IHG
Rosemont
NT$4,245
NT$4,895 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Chicago O'Hare – Rosemont by IHG
A modern restaurant interior with a green wall, hanging lights, and a long dining area.
A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.
A rooftop terrace with green seating, a round table, and a view of city buildings.
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

9. Hotel 505 River North

Hotel 505 River North
Downtown Chicago
NT$5,800
NT$7,933 total
includes taxes & fees
Nov 15 - Nov 16
Hotel 505 River North
An indoor swimming pool with wooden beams, clear glass walls, and lounge chairs.
A hotel lobby with a dining area, a bar, and a seating area with curtains.
A modern room with a flat-screen TV, a yellow sofa, a round wooden table, a patterned armchair, and a painting on the wall.
A hotel room with two single beds, a desk with a chair, a flat-screen TV mounted on the wall, and a window with curtains.

10. Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream
Carol Stream
  • Splash into family fun at this poolside retreat with a fitness center and 24-hour amenities for adventures all day long.
NT$3,277
NT$3,637 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Chicago-Carol Stream
View all properties

Choose what matters most at family-friendly hotels in Hillside

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Hillside Hotel Reviews

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Staff was friendly and helpful! Gave my family and I great ideas for restaurants!"
Patrice 4-night trip
Posted less than an hour ago
L7 Chicago by LOTTE
River Hotel

River Hotel

10/10 Excellent
"The room size was big enough for me. I had a good view of the river and downtown. The staff was helpful. There was no restaurant in the building, but it was one on each side of the hotel."
Isaac Lee 3-night trip
Posted 2 hours ago
River Hotel
Freehand Chicago

Freehand Chicago

8/10 Good
"Has an older hotel personality. Definitely not five star, but ok. Staff was great. Apparently not all rooms have a TV which iriginally took me back. Ended up in bed early for the three nights I was there and all was well"
Joseph 3-night trip
Posted 2 hours ago
Freehand Chicago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good
"Clean room staff was great"
Dwayne 2-night trip
Posted 2 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Hilton Chicago

Hilton Chicago

8/10 Good
"My stay took place during an employee strike which made me upset. I hated having to cross the picket line to go to and from my lodging as I would've preferred to support the employees as they fought for their rights. Delores at the front desk was lovely and really made my check-in process so smooth."
Margaret 2-night trip
Posted 3 hours ago
Hilton Chicago
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"."
Eun Jung 1-night trip
Posted 5 hours ago
The Royal Sonesta Chicago Downtown
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"The hotel is very functional. They try to make it a nice experience by adding all the extras like music on weekends. I wish they they’d paid more attention to the basics like comfy pillows or bed sheets that were correctly sized to the bed. Ours were too small."
Matthias 2-night trip
Posted 8 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent
"The hotel room was clean and bigger than expected. The room was quiet and we had free drinks at their happy hour. The location was close to all the things we did. Will stay here again!"
Julio 5-night trip
Posted 11 hours ago
Sports Illustrated Resorts Chicago
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"To quality service from every staff member. Great views. Upgrade to the gold rooms for a wonderful view and access to the lounge. Lounge breakfast and dinner and dessert is WORTH THE $."
elvin 2-night trip
Posted 16 hours ago
Fairmont Chicago at Millennium Park

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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