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 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

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 gym with treadmills, elliptical machines, and weight equipment.
A bathroom with a shower, a sink with a mirror, and a towel rack.
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$2,934
NT$3,286 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Plus Chicago Hillside
A multi-story hotel with a central entrance, a flag, and a sign for Express Suites.
A reception area with two reception desks, a central wall with a Holiday Inn Express sign, and a wooden panel design.
A buffet with labeled containers of omelets and other dishes.
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.

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$3,641
NT$4,077 total
includes taxes & fees
Aug 30 - Aug 31
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 bathroom with a sink, toilet, and shower.
A reception area with a counter, two wall-mounted lamps, a framed artwork, and a sign for 'Mattress & Bedding.'

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,545
NT$2,850 total
includes taxes & fees
Sep 8 - Sep 9
MainStay Suites Chicago Hillside
A cityscape at dusk with high-rise buildings, including a Hilton hotel.
A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.
A modern hotel lobby with a central seating area, a reception desk, and a cityscape mural on the wall.
A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.

4. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
  • Chicago family suites near Michigan Avenue offer spacious, kid-friendly accommodations just minutes from beach fun.
NT$4,805
NT$5,713 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Chicago/Magnificent Mile Suites
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.
A bar area with a long counter, multiple stools, and a modern chandelier.
A spacious living room with a large window, a sofa, a black chair, and a coffee table.
A modern kitchen with a central island, bar stools, a chandelier, and a large flat-screen TV.

5. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
NT$3,640
NT$5,265 total
includes taxes & fees
Sep 7 - Sep 8
Claridge House Chicago, Tapestry Collection by Hilton
A spacious lobby with a central coffee table, sofas, and a large mirror.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.
A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.
A spacious lobby with high ceilings, large arched windows, and a grand staircase.

6. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NT$4,566
NT$5,429 total
includes taxes & fees
Aug 23 - Aug 24
The Chicago Hotel Collection Ambassador Gold Coast
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A modern living room with a fireplace, leather sofas, and a wooden floor.
A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.
A hotel room with a large bed, a TV, a desk, and a chair.

7. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
NT$3,896
NT$4,632 total
includes taxes & fees
Aug 23 - Aug 24
Central Loop Hotel
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.
A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.
A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.
A conference room with a long table, chairs, and a vase.

8. River Hotel

River Hotel
Downtown Chicago
NT$4,127
NT$4,907 total
includes taxes & fees
Aug 23 - Aug 24
River Hotel
A spacious lobby with a checkered floor, a large sofa, and multiple chairs.
A modern kitchen area with a long counter, various food items, and a coffee machine.
A modern kitchen with a built-in refrigerator, a coffee maker, and a flat-screen TV on the countertop.
A hotel room with two beds, a desk with a computer, a chair, a TV, and a large mirror.

9. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Downtown Chicago
NT$4,316
NT$5,132 total
includes taxes & fees
Aug 30 - Aug 31
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
A bar area with a high ceiling, bar stools, and a counter with bottles.
A multi-story building with a prominent 'FOUND' sign above the entrance.
A modern interior with a bar area, wooden shelves with various items, and a 'FOUND' sign on the wall.

10. FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
Downtown Chicago
NT$4,567
NT$5,361 total
includes taxes & fees
Aug 30 - Aug 31
FOUND Hotels, Chicago, Series by Marriott
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Choose what matters most at family-friendly hotels in Hillside

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Hillside Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Very nice hotel. We had a King size bed overlooking Buckingham fountain. Booking a park view room is highly recommended. The shower/bathroom is on the smaller end, however, knowing the history of the hotel, it comes at no surprise. The hotel itself has so much history and has quite a few famous guests throughout it's time. We are already planning our next trip back to Chicago and will likely stay here again! Highly recommend staying here!"
Alexandra 1-night trip
Posted 1 hour ago
Congress Plaza Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Staff were wonderful! Personable and helpful. Facilities were clean."
MAYPAHOU 2-night trip
Posted 2 hours ago
Holiday Inn Chicago Dwtn - The Mart by IHG
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"It was fantastic!"
Billy 1-night trip
Posted 3 hours ago
Hyatt Regency O'Hare Chicago
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Spacious, clean room with nice city view. Comfortable beds, loved to have a couch. Very friendly staff during check-in. Great location, block from RiverWalk and London House, where we had dinner. Great stay all together. Highly recommend."
Bella 1-night trip
Posted 6 hours ago
Fairmont Chicago at Millennium Park
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Nice"
Karisma 2-night trip
Posted 22 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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