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
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
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.
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$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 room with a bed, a television, a desk, a chair, and a patterned carpet.
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.

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 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.
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$2,650
NT$2,967 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 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 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.

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$3,899
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 hotel lobby with seating areas, a fireplace, a bar, and a dining area.

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$3,191
NT$3,541 total
includes taxes & fees
Oct 25 - Oct 26
Hyatt Place Chicago/Lombard/Oak Brook
A modern office space with a desk, chairs, a glass table, a sofa, and a TV on the wall.
A spacious lobby with a central seating area, large wooden columns, and potted plants.
A terrace with round tables and chairs, a view of a lake, and a building with a white facade.
A multi-story hotel with a prominent "WESTIN" sign on the top.

7. The Westin Chicago Lombard

The Westin Chicago Lombard
Lombard
  • Chicago suburban oasis for family fun provides splash zone, premium channels, and movies for children of all ages.
NT$4,173
NT$4,631 total
includes taxes & fees
Oct 11 - Oct 12
The Westin Chicago Lombard
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

8. 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 23 - Oct 24
Loews Chicago O'Hare Hotel
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 modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
A modern bathroom with a dual sink vanity, a large mirror, and a toilet.
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

9. 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 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 modern interior with wooden flooring, black furniture, and large windows offering city views.
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

10. Hotel 505 River North

Hotel 505 River North
Downtown Chicago
NT$8,298
NT$10,888 total
includes taxes & fees
Oct 4 - Oct 5
Hotel 505 River North
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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Second time at this property. Short stay but easy to get to and fit our needs perfectly."
Elizabeth 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast
Central Loop Hotel

Central Loop Hotel

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

River Hotel

10/10 Excellent
"Great location. Clean room. Helpful staff."
Melissa 2-night trip
Posted 2 hours ago
River Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Raymond was great upon check in! Other staff great as well. One issue Chicago is a sports town many guests visit coming to sporting events. We could not get ESPN with the Roku service. HORRIBLE!!! that would a deal breaker on me choosing where to stay next time. It’s a very basic service. Other than that great play convenient location"
John 2-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Convenient location walk to anything you might need, restaurants, shopping, Room was so nice and comfortable"
Jenessa 1-night trip
Posted 3 hours ago
Hilton Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Great location, hotel was very modern and loved the window nook in the room"
Chantel 3-night trip
Posted 4 hours ago
L7 Chicago by LOTTE
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"We only stayed for a night but it was in a Great location and the staff and room was excellent. Would definitely stay again."
lakesha 1-night trip
Posted 5 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"The room was really oddly laid out (It's an older building), but everything looked and felt nice. It has a nice modern look to everything, and the water was really hot which is rare for most hotels, especially in Chicago in my experience. The location is absolutely fantastic for downtown shopping, parks, pier, food. Two minute walk to the heart of the Magnificent Mile. There was a fridge, microwave, and coffee machine in the room. We stocked up on fresh pastries from a fantastic bakey a few stores down, and went to the 7-Eleven on the corner for drinks for late night snacks. I've stayed at maybe 10 different hotels in this class in Chicago and I think this is one of the better ones. For parking, just an app and save some(A LOT) money. Lots of garages nearby that discount heavily with apps."
Philip 1-night trip
Posted 8 hours ago
Hotel Saint Clair- Magnificent Mile
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"If I could give more than 5 stars I would. The staff was amazing and extremely accommodating and flexible. The rooms were gorgeous and the hotel was beautiful."
Afra 1-night trip
Posted 11 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio 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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