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 5 - Sep 6
Tomorrow
Sep 6 - Sep 7
Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20

Our top choices for Hillside family-friendly hotels

1. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$3,694
NT$4,137 total
includes taxes & fees
Sep 9 - Sep 10
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$3,639
NT$4,075 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,817
NT$3,155 total
includes taxes & fees
Oct 4 - Oct 5
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$3,227
NT$3,582 total
includes taxes & fees
Sep 9 - Sep 10
Carleton of Oak Park

5. 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$3,005
NT$3,335 total
includes taxes & fees
Sep 8 - Sep 9
SureStay Plus Hotel by Best Western Chicago Lombard

6. Quality Inn O'Hare Airport

Quality Inn O'Hare Airport
Schiller Park
NT$2,759
NT$3,173 total
includes taxes & fees
Sep 27 - Sep 28
Quality Inn O'Hare Airport

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$3,449
NT$3,827 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Place Chicago/Lombard/Oak Brook

8. 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$5,422
NT$6,181 total
includes taxes & fees
Sep 27 - Sep 28
Embassy Suites by Hilton Chicago O'Hare Rosemont

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$7,562
NT$8,619 total
includes taxes & fees
Sep 11 - Sep 12
Loews Chicago O'Hare Hotel

10. DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
Rosemont
  • Chicago O'Hare family escape with premium TV, comfy sofa beds, and a shuttle to nearby entertainment district.
NT$4,644
NT$5,293 total
includes taxes & fees
Sep 27 - Sep 28
DoubleTree by Hilton Chicago O'Hare Airport - 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

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Clean room and pool area."
Ivory 1-night trip
Posted 1 hour ago
InterContinental Chicago Magnificent Mile by IHG
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"We love the Fairmont!"
Jerry 1-night trip
Posted 1 hour ago
Fairmont Chicago at Millennium Park
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"Check in was super quick and easy!! The room has everything you need and would definitely stay here again!!"
Isabela 3-night trip
Posted 4 hours ago
Club Quarters Hotel, Central Loop, Chicago
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Good place to stay location is amazing can’t get any better"
Manuel 1-night trip
Posted 12 hours ago
Congress Plaza Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"A five-star hotel with a great staff. Everyone was very friendly. The view was great and all of the amenities were nice."
Eunice Eileen 3-night trip
Posted 13 hours ago
Hyatt Regency Chicago
River Hotel

River Hotel

8/10 Good
"Clean rooms, great location, only thing writes the room didn’t have a microwave or refrigerator."
CEDRIC 4-night trip
Posted 13 hours ago
River Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

8/10 Good
"Me and wife stay 3 nights is Hampton Inn from Aug 31 to Sept3 2026.It is 40 stories hotel. The hotel location is excellent, beautiful in Chicago, very close to Michgan Ave Magnificent Mile, the most beautiful area, high rise buildings and shopping stores. Close to Lake, close to chicago River side, close to Millennium park. Breakfast was ok, not high level, just so, so, Baggage in and out room service was not available when we reached we took our own bags to room. No swimming pool was available. Close to hospital block, .For food Asian food Indian restaurant available on walking distance. I recommend this hotel to tourists coming for Chicago buildings, and other attractions. Mahboob Mian Canada."
Mahboob 3-night trip
Posted 15 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"very nice location"
Lindsy 2-night trip
Posted 16 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Good, 10/10 the rooftop is also beautiful"
Jeffrey 4-night trip
Posted 19 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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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