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
Aug 31 - Sep 1
Tomorrow
Sep 1 - Sep 2
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Hillside family-friendly hotels

1. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$2,912
NT$3,261 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Plus Chicago Hillside

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$3,636
NT$4,072 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,770
NT$3,101 total
includes taxes & fees
Sep 21 - Sep 22
MainStay Suites Chicago Hillside

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$3,870
NT$4,295 total
includes taxes & fees
Sep 10 - Sep 11
Carleton of Oak Park

5. Quality Inn O'Hare Airport

Quality Inn O'Hare Airport
Schiller Park
NT$2,763
NT$3,177 total
includes taxes & fees
Sep 28 - Sep 29
Quality Inn O'Hare Airport

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$3,162
NT$3,509 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Place Chicago/Lombard/Oak Brook

7. 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$2,930
NT$3,368 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Suites Chicago O'Hare Airport

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$2,553
NT$2,833 total
includes taxes & fees
Sep 1 - Sep 2
SureStay Plus Hotel by Best Western Chicago Lombard

9. 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$4,016
NT$4,738 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

10. Embassy Suites by Hilton Chicago O'Hare Rosemont

Embassy Suites by Hilton Chicago O'Hare Rosemont
Rosemont
  • Family escape with free breakfast, indoor pool, and entertainment district steps away from this chicago hotel.
NT$4,900
NT$5,585 total
includes taxes & fees
Sep 7 - Sep 8
Embassy Suites by Hilton Chicago O'Hare Rosemont
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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Thanks"
Noah 2-night trip
Posted 1 hour ago
Hyatt Regency O'Hare Chicago
The Wade

The Wade

10/10 Excellent
"Great place and location"
Judith 4-night trip
Posted 1 hour ago
The Wade
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"Staff is friendly and helpful. The only issue I had was no refrigerator in our rooms."
Rebecca 3-night trip
Posted 2 hours ago
Club Quarters Hotel, Central Loop, Chicago
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Check-in was super quick and staff was very efficient and helpful. Booked a standard room with a king size bed facing the lake and it was a very nice weekend stay. Room was very clean. The AC is off central heatingThe location is incredibly convenient if you’re going somewhere near the lake or downtown."
Andrew 2-night trip
Posted 2 hours ago
Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"We needed a larger room than the one we received upon arrival and they were wonderful. They moved our luggage to a beautiful corner room that was twice the size of the first. Our stay was great, just wished we could have stayed longer."
Steven 3-night trip
Posted 3 hours ago
InterContinental Chicago Magnificent Mile by IHG
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Location near the lake and very walkable to train, bus stations, restaurants and stores. Room was not very well cleaned"
Lilliam 3-night trip
Posted 3 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency Chicago

Hyatt Regency Chicago

8/10 Good
"The beds and pillows were so so.. clean rooms. The shower didn’t have great pressure and there was no bathroom fan. Great location Friendly staff Would stay there again"
SIMONA A 2-night trip
Posted 3 hours ago
Hyatt Regency Chicago
Hilton Chicago

Hilton Chicago

10/10 Excellent
"We stayed for one night at this beautiful and historic hotel. We enjoyed walking through the lobby looking at the history setup they had. The rooms were clean, the view from our room was amazing. We had a lake view + a view of the Buckingham Fountain. The staff was super helpful they were posted throughout the lobby floor ready to help and direct you to your destination. We had the breakfast buffet and the food was great, they had a good variety of breakfast food."
Antonio 1-night trip
Posted 3 hours ago
Hilton Chicago
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Very enjoyable stay. Clean and close to most tourists attractions. Great breakfast options, Liked the convenience of how close most things were."
Lluvia 4-night trip
Posted 4 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile

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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