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 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
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 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.
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$3,892
NT$4,359 total
includes taxes & fees
Oct 4 - Oct 5
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 bathroom with a shower, a sink with a mirror, and a towel rack.
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$3,189
NT$3,571 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 reception area with a counter, two wall-mounted lamps, a framed artwork, and a sign for 'Mattress & Bedding.'
A living room with a sofa, a coffee table, a TV, and an air conditioner.

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 room with a kitchenette, a bathroom, a seating area, and a desk.
A hotel room with a large bed, two bedside tables with lamps, a wooden headboard, and a carpeted floor.
A hotel room with a TV, a wooden desk, a chair, a sofa, and a small table.

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$2,859
NT$3,288 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Suites Chicago O'Hare Airport
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.
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

5. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
NT$6,086
NT$7,236 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Vacation Club Hotel Blake Chicago
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
A residential street with a sidewalk, houses, and greenery.
A hotel room with a bed, a desk, a chair, and a window with curtains.

6. 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$3,899
NT$4,327 total
includes taxes & fees
Oct 5 - Oct 6
Carleton of Oak Park
A multi-story hotel with a prominent entrance and a parking lot.
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.
A lobby with seating areas, a reception desk, and a decorative wall.

7. 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 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.
A modern living room with a brown leather sofa, a coffee table, and a side table with a lamp.

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

Holiday Inn Chicago O'Hare – Rosemont by IHG
Rosemont
NT$4,046
NT$4,667 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Chicago O'Hare – Rosemont by IHG
A restaurant interior with a stone accent wall, a bar area, and a seating section.
Exterior
A bar area with a bar counter, stools, and a variety of bottles and glasses.
Lobby lounge

9. 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 2 - Oct 3
Loews Chicago O'Hare Hotel
A La Quinta hotel with a modern exterior, a covered entrance, and a parking lot visible in the background.
A modern bathroom with a white sink, a large mirror with a circular light, and two wall-mounted paintings.
A hotel room with a gray sectional sofa, a bed with white bedding, a painting on the wall, and a patterned carpet.
A hotel room with a large bed, a desk, a chair, a TV, and a small table.

10. La Quinta by Wyndham Chicago O'Hare Airport

La Quinta by Wyndham Chicago O'Hare Airport
Rosemont
NT$3,813
NT$4,346 total
includes taxes & fees
Oct 4 - Oct 5
La Quinta by Wyndham Chicago O'Hare Airport
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Bar with jukebox and pool table is fun!"
Jayni 2-night trip
Posted less than an hour ago
Congress Plaza Hotel
River Hotel

River Hotel

10/10 Excellent
"Excellent location and great views! Will be back!"
Brandan 1-night trip
Posted 1 hour ago
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"My room was clean and spacious. The cleaning staff must use a fragrance that happened to"
Stephen 3-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago

Hilton Chicago

8/10 Good
"Having a Starbucks on property was very helpful! Good location and incredibly helpful staff."
Anna 3-night trip
Posted 1 hour ago
Hilton Chicago
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 2 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 4 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"An amazing location for Chicago and a beautiful hotel"
Lori 2-night trip
Posted 4 hours ago
Fairmont Chicago at Millennium Park
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 15 hours 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 17 hours 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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