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 2 - Oct 3
Tomorrow
Oct 3 - Oct 4
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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.
An indoor swimming pool with blue chairs and a tiled 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$4,530 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 gym with treadmills, elliptical machines, and weight equipment.
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$3,184
NT$3,566 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 hotel room with two beds, a nightstand, a lamp, and a framed picture on the wall.
A living room with a sofa, a coffee table, a TV, and an air conditioner.
A reception area with a counter, two wall-mounted lamps, a framed artwork, and a sign for 'Mattress & Bedding.'

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,646
NT$2,963 total
includes taxes & fees
Oct 25 - Oct 26
MainStay Suites Chicago Hillside
A restaurant interior with a retro 1943 theme, featuring hanging pendant lights, a checkered floor, and a large illuminated 'CHICAGO' sign.
A hotel lobby with a patterned carpet, a blue sofa, a reception desk, and a sign for the restaurant.
A hotel room with a TV, a wooden desk, a chair, a sofa, and a small table.
A hotel room with a kitchenette, a bathroom, a seating area, and a desk.

4. 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$2,880
NT$3,312 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Suites Chicago O'Hare Airport
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A hotel room with a bed, a desk, a chair, and a window with curtains.
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.

5. 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$3,918
NT$4,349 total
includes taxes & fees
Oct 4 - Oct 5
Carleton of Oak Park
A multi-story hotel with a prominent entrance and a parking lot.
A hotel lobby with seating areas, a fireplace, a bar, and a dining area.
A hotel room with a large bed, a sofa, a desk, and a TV.
An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables, under a high ceiling with visible structural beams.

6. Hyatt Place Chicago/Lombard/Oak Brook

Hyatt Place Chicago/Lombard/Oak Brook
Lombard
  • Fun family stays with an indoor pool create lasting memories at this centrally located Lombard hotel.
NT$3,186
NT$3,535 total
includes taxes & fees
Oct 25 - Oct 26
Hyatt Place Chicago/Lombard/Oak Brook
A restaurant interior with a stone accent wall, a bar area, and a seating section.
A modern living room with a flat-screen TV, bookshelves, a fireplace, and comfortable seating.
Exterior
Lobby lounge

7. Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel
Rosemont
  • Vibrant family stays with cribs, babysitting, and 24-hour airport shuttles just steps from Parkway Bank Park entertainment district.
NT$6,976
NT$7,952 total
includes taxes & fees
Oct 24 - Oct 25
Loews Chicago O'Hare Hotel
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 modern bathroom with a sink, toilet, and bathtub.
A hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

8. 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$3,329
NT$3,694 total
includes taxes & fees
Oct 4 - Oct 5
SureStay Plus Hotel by Best Western Chicago Lombard
A modern building with a glass facade and a curved structure.
A conference room with a long table, purple chairs, and framed pictures on the walls.
A woman running on a treadmill in a gym with another person in the background.
A reception area with a marble wall, multiple reception counters, and a modern design.

9. Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago
Rosemont
NT$5,143
NT$5,862 total
includes taxes & fees
Oct 23 - Oct 24
Hyatt Regency O'Hare Chicago
A modern lounge area with leather sofas, a coffee table, and a patterned rug.
A hotel room with two beds, a desk, a chair, a TV, and a large window with a city view.
A modern living room with a sectional sofa, a fireplace, and a bar area.
An outdoor patio with a wooden table and wicker chairs, surrounded by blue umbrellas, and a building with large windows in the background.

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

Holiday Inn Chicago O'Hare – Rosemont by IHG
Rosemont
NT$4,173
NT$4,812 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Chicago O'Hare – Rosemont by IHG
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

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"Older hotel. Everything seemed tight (room, hallways, elevator. Sometimes it takes a while for valet since the drivers had to manage two hotels, averaging around 10-15min. The staff were very friendly though. Would I stay here again? Probably not."
Choua 2-night trip
Posted 1 hour ago
Hotel Saint Clair- Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Great experience on my first trip to Chicago"
Gary 5-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

10/10 Excellent
"The room and the facility were just right, and the location was lovely. But the best thing about the stay was the helpfulness and interest from the staff. From upgrading our room (to include the great view!), to helping us find one of the five Starbucks Roasterys in the world, and storing our luggage after we checked out, the service was personal and effective. Jock was especially helpful, and really seemed to enjoy helping us with every part of our stay. I would definitely return to this hotel for my next Chicago visit."
Marilyn 1-night trip
Posted 4 hours ago
River Hotel
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"Everything was awesome love this place"
Jared 2-night trip
Posted 5 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"Excellent location!"
Jean 6-night trip
Posted 14 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Nice place! Perfect location!"
Franchisca 4-night trip
Posted 16 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Hotel was very clean, grateful housekeeping came in everyday and provided clean towels. Room view was very nice and as advertised."
Erica 4-night trip
Posted 1 day ago
The Royal Sonesta Chicago Downtown
Central Loop Hotel

Central Loop Hotel

10/10 Excellent
"I liked the location and staff"
Murray 1-night trip
Posted 1 day ago
Central Loop Hotel

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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