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 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Hillside family-friendly hotels

A lobby with a reception desk, patterned sofas, a glass-top table with a potted plant, and a decorative mirror.
A bathroom with a shower, a sink with a mirror, and a towel rack.
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.

1. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$3,174
NT$3,554 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Plus Chicago Hillside
A multi-story hotel with a central entrance, a flag, and a sign for Express Suites.
An indoor swimming pool with blue chairs and a tiled 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.

2. 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$3,874
NT$4,338 total
includes taxes & fees
Sep 29 - Sep 30
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
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 bathroom with a sink, toilet, and shower.
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$2,605
NT$2,917 total
includes taxes & fees
Oct 18 - Oct 19
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 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.

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$3,053
NT$3,510 total
includes taxes & fees
Oct 4 - Oct 5
Comfort Suites Chicago O'Hare Airport
A modern building entrance with a car parked in front.
A modern living room with a flat-screen TV, bookshelves, a fireplace, and comfortable seating.
A modern interior with a wall-mounted fireplace, a rock installation, and a green wall.
A restaurant interior with a stone accent wall, a bar area, and a seating section.

5. 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$6,954
NT$7,926 total
includes taxes & fees
Oct 23 - Oct 24
Loews Chicago O'Hare Hotel
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.
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.

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

Holiday Inn Chicago O'Hare – Rosemont by IHG
Rosemont
NT$4,890
NT$5,629 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Chicago O'Hare – Rosemont by IHG
A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.
A hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.
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 modern bathroom with a sink, toilet, and bathtub.

7. 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$3,073
NT$3,411 total
includes taxes & fees
Sep 29 - Sep 30
SureStay Plus Hotel by Best Western Chicago Lombard
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 hotel room with a bed, a desk, a chair, and a window with curtains.

8. 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$3,886
NT$4,313 total
includes taxes & fees
Oct 4 - Oct 5
Carleton of Oak Park
A multi-story hotel with a prominent "Hyatt Place" sign, a well-lit entrance, and a landscaped front yard.
A hotel room with a bed, a sofa, a desk, and a television.
A banquet hall with round tables set for a formal event, featuring floral centerpieces and elegant table settings.
An indoor swimming pool with clear lanes, lounge chairs, and a tiled floor.

9. Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport
Rosemont
  • Family-friendly fun awaits near Chicago with pools, complimentary breakfast, and airport shuttles.
NT$4,774
NT$5,441 total
includes taxes & fees
Sep 28 - Sep 29
Hyatt Place Chicago/O'Hare Airport
A hotel room with a bed, a microwave, a refrigerator, and a coffee machine.
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 hotel reception desk with two computer stations, a modern wall design, and a visible window.
A modern building with a large glass facade, a prominent circular structure on the right, and a landscaped entrance area.

10. 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$4,160
NT$4,907 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Express & Suites Chicago O'Hare Airport 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

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"Great location & decor. Staff very welcoming on arrival."
Jo 3-night trip
Posted 3 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop
The Wade

The Wade

10/10 Excellent
"The room was very clean. Great staff. Very accommodating and quick. Great hotel in a great area. Good views of the Lake"
Richard 5-night trip
Posted 4 hours ago
The Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"Stayed in a junior suite !! Very nice until the A/C broke (97* outside) had to drag all of our stuff back to the lobby just to get another room !! When, they should have come up and given us the key to the new room !! Next (2) days in the the room we had no hot water in the morning to take a shower so the next three days were cold showers in the morning (very annoying). I would love to stay there again but I’m not so sure."
Dawn 1-night trip
Posted 5 hours ago
The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Great location! Everything you need was at the hotel."
Angela 3-night trip
Posted 7 hours ago
Hyatt Regency Chicago
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"The hotel needs remodeling, but it was truly a wonderful stay. We had a comfortable bed, an air conditioned room, and the most helpful staff. It would have been nice to have more updated elevators, and for the breakfast to be with real plates, cups, and utensils. But otherwise, we really enjoyed the centralized location and comfortable suite."
Priscilla 3-night trip
Posted 8 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

8/10 Good
"Easy check-in and out. Staff was nice and helpful. The building was built before a/c was common, but the little window unit worked just fine. I loved the easy walking distance to Grant Park and Michigan Ave. Rooms are clean and neat."
Jon 1-night trip
Posted 10 hours ago
Travelodge by Wyndham Downtown Chicago
River Hotel

River Hotel

10/10 Excellent
"Property is centrally located and staff is over the top accommodating! We’ve stayed two times already. This is our go to hotel in the loop"
Susan 3-night trip
Posted 10 hours ago
River Hotel
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Very nice property in a great location. Clean room, nice amenities, friendly staff."
Stephen 1-night trip
Posted 15 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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