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 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

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 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.
An indoor swimming pool with blue chairs and a tiled floor.
A reception area with two reception desks, a wall-mounted display, and a carpeted floor.

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$4,046
NT$4,531 total
includes taxes & fees
Oct 25 - Oct 26
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 room with a bed, a television, a desk, a chair, and a patterned carpet.
A bathroom with a shower, a sink with a mirror, and a towel rack.
A hotel lobby with a buffet area, multiple seating arrangements, and a patterned carpet.

2. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$3,469
NT$3,885 total
includes taxes & fees
Oct 18 - Oct 19
Best Western Plus Chicago Hillside
A MainStay Suites hotel with a large sign, a parking lot, and a building in the background.
A bathroom with a sink, toilet, and shower.
A living room with a sofa, a coffee table, a TV, and an air conditioner.
A hotel room with two beds, a nightstand, a lamp, and a framed picture on the wall.

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,653
NT$2,971 total
includes taxes & fees
Oct 25 - Oct 26
MainStay Suites Chicago Hillside
A modern dining area with round tables and white chairs, a kitchen area with a coffee machine, and a view of the outdoors through large windows.
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.
A modern bathroom with a dual sink vanity, a large mirror, and a toilet.
Front of property

4. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
NT$5,475
NT$6,510 total
includes taxes & fees
Nov 3 - Nov 4
Hilton Vacation Club Hotel Blake Chicago
A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.
A bar area with a long counter, multiple stools, and shelves stocked with bottles.
A spacious lobby with a wooden floor, a central dining table with chairs, a blue sofa, and a leather couch.
A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

5. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
  • Family-friendly Chicago adventure awaits just steps from Michigan Avenue with comfortable river views and boutique charm.
NT$5,962
NT$7,088 total
includes taxes & fees
Nov 1 - Nov 2
L7 Chicago by LOTTE
A dining table set for six with a cityscape view through large windows.
A modern hotel room with a large window offering a cityscape view, a green sofa, two armchairs, and a coffee table with flowers.
A modern hotel room with a large bed, a desk, a chair, and a view of the cityscape through large windows.
The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.

6. Swissotel - Chicago

Swissotel - Chicago
Downtown Chicago
  • Discover prime downtown Chicago adventure with family-friendly amenities near Millennium Park and the beach this summer.
NT$6,122
NT$8,407 total
includes taxes & fees
Oct 31 - Nov 1
Swissotel - Chicago
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 lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
A residential street with a sidewalk, houses, and greenery.

7. 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$3,900
NT$4,328 total
includes taxes & fees
Oct 4 - Oct 5
Carleton of Oak Park
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.
A modern room with a view of a river and high-rise buildings.
A modern hotel room with a large bed, a desk, a sofa, and a view of the city.

8. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
NT$7,528
NT$9,898 total
includes taxes & fees
Nov 1 - Nov 2
LondonHouse Chicago, Curio Collection by Hilton
A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.
A modern bathroom with a glass-enclosed shower, a white sink, and a large mirror.
A modern living room with a large window, a potted plant, and a variety of seating options including a sofa, armchairs, and ottoman.
A multi-story hotel with a modern glass facade, located in an urban setting with a parking lot and street views.

9. Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
Downtown Chicago
  • Centrally located Chicago hotel offers kids' comforts and breakfast within reach of family attractions.
NT$5,416
NT$6,440 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt Place Chicago/River North
A modern kitchen with a marble island, fruit bowls, and a city view.
A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.
A modern bar area with a central bar, seating, and a distinctive ceiling design.
A hotel room with a large bed, a desk, a sofa, and a view of the cityscape.

10. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
  • Lakefront luxury with kid-friendly activities offers the perfect balance between family fun and Chicago exploration.
NT$5,415
NT$7,580 total
includes taxes & fees
Oct 31 - Nov 1
Fairmont Chicago at Millennium Park
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

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

10/10 Excellent
"Great hotel - great rooms - nice restaurant and bar"
Carrie 1-night trip
Posted 3 hours ago
The Godfrey Hotel Chicago
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent
"We loved our stay it was so convenient ly located the rooms were comfortable and efficient staff was great and smiles"
Mounir 2-night trip
Posted 4 hours ago
Sports Illustrated Resorts Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"The hotel was a very convenient location from downtown and Lake Michigan. Definitely one of the better breakfasts I've had recently and the pricing sits just right for the amenities and convenience this hotel offers"
Sudeep 1-night trip
Posted 11 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Great location in the middle of et; amazing view of the river;"
Ramona 3-night trip
Posted 18 hours ago
The Royal Sonesta Chicago Downtown
Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Slight wear and tear on the furniture dates the place and I wish the rooms were brighter, but excellent location and great value. Loved the shower!"
Kholood 2-night trip
Posted 21 hours ago
Eurostars Magnificent Mile
Freehand Chicago

Freehand Chicago

10/10 Excellent
"We absolutely enjoyed our stay at the Kins Hotel. Our room was exceptionally clean, spacious and comfortable, and it was actually much larger than the images we had seen when booking, which was a lovely surprise. The staff were amazing and couldn’t have been more helpful or friendly. From the reception staff and valet team to the cleaners, everyone was welcoming, professional and always happy to assist whenever we had a question. Overall, we had a fantastic stay at the Kins Hotel and wouldn’t hesitate to recommend it to anyone looking for a great place to stay. We would happily return ourselves!"
Paul 1-night trip
Posted 2 days ago
Freehand 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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