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 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

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 buffet with multiple food stations, including omelets and other dishes.
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$3,488
NT$3,906 total
includes taxes & fees
Nov 23 - Nov 24
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 restaurant setting with round tables, chairs, and empty wine glasses.
A hotel room with a bed, a television, a desk, a chair, and a patterned carpet.
A conference room with a wooden door, two black office chairs, a black desk with a computer and printer, and two monitors on the wall.

2. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$3,533
NT$3,956 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Chicago Hillside
A MainStay Suites hotel with a large sign, a parking lot, and a building in the background.
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.'
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$2,639
NT$2,956 total
includes taxes & fees
Nov 22 - Nov 23
MainStay Suites Chicago Hillside
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 bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.
A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

4. 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$3,990
NT$4,429 total
includes taxes & fees
Oct 28 - Oct 29
Carleton of Oak Park
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.
A bar area with a long counter, multiple liquor bottles, and a variety of glasses.
A hotel entrance with a marquee sign, a glass awning, and a blue carpet leading to the door.

5. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
NT$5,226
NT$6,213 total
includes taxes & fees
Nov 5 - Nov 6
Hilton Vacation Club Hotel Blake Chicago
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.
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.

6. Hotel 505 River North

Hotel 505 River North
Downtown Chicago
NT$5,184
NT$7,206 total
includes taxes & fees
Nov 22 - Nov 23
Hotel 505 River North
A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.
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 snack and beverage kiosk with various snacks and drinks.
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.

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$2,909
NT$3,229 total
includes taxes & fees
Oct 28 - Oct 29
SureStay Plus Hotel by Best Western Chicago Lombard
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.
A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.

8. 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$4,727
NT$5,620 total
includes taxes & fees
Nov 22 - Nov 23
L7 Chicago by LOTTE
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
A modern interior with seating areas, a bar, and large windows offering city views.
A historic building with classical architecture, a prominent dome, and a modern glass facade.
A modern room with a view of a river and high-rise buildings.

9. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
NT$4,683
NT$6,536 total
includes taxes & fees
Nov 22 - Nov 23
LondonHouse Chicago, Curio Collection by Hilton
A modern lounge area with leather sofas, a coffee table, and a patterned rug.
An outdoor patio with a wooden table and wicker chairs, surrounded by blue umbrellas, and a building with large windows in the background.
A hotel room with two beds, a desk, a chair, a TV, and a large window with a city view.
A spacious hall with multiple round tables, each set with white tablecloths and gold chairs, and large windows allowing natural light.

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

Holiday Inn Chicago O'Hare – Rosemont by IHG
Rosemont
NT$4,238
NT$4,888 total
includes taxes & fees
Nov 23 - Nov 24
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Mattress was a bit too soft."
DOVER 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast
Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Overall. Our stay was comfortable. The rooms could use some updating; the carpet and furniture were old, they were stained or scratched. There was not enough storage for clothing or luggage, so it was a bit tight once you put your things down. The shower door did not close properly, so the bathroom would get soaking wet whenever you took a shower. Since our stay was only 3 nights and we didn’t have time to change rooms, we did not request a room change. On the other hand, the bed was comfortable. The water pressure in the shower was great, and the location was very convenient. The staff was very friendly and although we did not try the restaurant downstairs, it looked nice."
Athena 3-night trip
Posted less than an hour ago
Eurostars Magnificent Mile
The Wade

The Wade

10/10 Excellent
"Great stay"
Roena 3-night trip
Posted 1 hour ago
The Wade
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"First the good: the location is great, right on the river and easily walkable to the Loop of the Magnificent Mile, etc. I arrived early and asked to check my bag, but my room was ready, which was nice. Somehow I got a fabulous upgrade to a comfortable spacious corner room on the 38th floor with the most spectacular views (views plural). When I returned later to rest before dinner, I couldn’t stop looking out the windows—what a show at sunset! The bed was very comfortable, although really really high off the ground. Everything seemed clean. Now the not-so-good: lighting was very sparse in the room—half the room had no lighting at all. No place to charge devices—hello, this is 2026. I had a little trouble with the temperature and there was no way to call downstairs—everything has to be handled in the app. So do stay here, but bring a charging station to plug into the wall—which is far from the bed."
LINDA 1-night trip
Posted 5 hours ago
The Royal Sonesta Chicago Downtown
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Very Nice"
Donna 1-night trip
Posted 7 hours ago
Hilton Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Love it . Perfect location. Modern and clean ."
maggie 3-night trip
Posted 11 hours ago
L7 Chicago by LOTTE
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent
"Great spot!"
Sean 3-night trip
Posted 14 hours ago
Sports Illustrated Resorts Chicago
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"Very nice affordable place to stay !!!"
Jeff 2-night trip
Posted 16 hours ago
Hotel Saint Clair- Magnificent Mile
Freehand Chicago

Freehand Chicago

8/10 Good
"Good value"
Francis 3-night trip
Posted 17 hours 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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