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 15 - Sep 16
Tomorrow
Sep 16 - Sep 17
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Hillside family-friendly hotels

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 reception area with two reception desks, a central wall with a Holiday Inn Express sign, and a wooden panel design.
A modern bathroom with a toilet, sink, and mirror.

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$3,861
NT$4,323 total
includes taxes & fees
Sep 30 - Oct 1
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 gym with treadmills, elliptical machines, and weight equipment.
A hotel lobby with a buffet area, multiple seating arrangements, and a patterned carpet.
A bathroom with a shower, a sink with a mirror, and a towel rack.

2. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$3,176
NT$3,557 total
includes taxes & fees
Oct 4 - Oct 5
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 hotel room with two beds, a nightstand, a lamp, and a framed picture on the wall.
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$2,582
NT$2,891 total
includes taxes & fees
Oct 4 - Oct 5
MainStay Suites Chicago Hillside
A bar area with a high ceiling, bar stools, and a counter with bottles.
A modern interior with a bar area, wooden shelves with various items, and a 'FOUND' sign on the wall.
A modern interior with wooden shelves, tables, and chairs, and a large window with the word "FOUND" on the wall.
A multi-story building with a prominent 'FOUND' sign above the entrance.

4. FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
Downtown Chicago
NT$5,402
NT$6,341 total
includes taxes & fees
Sep 27 - Sep 28
FOUND Hotels, Chicago, Series by Marriott
A tall, modern hotel with a brick facade and numerous windows.
A modern hotel lobby with grey upholstered chairs, a wooden coffee table, and a large window offering a view of the city and an American flag.

5. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Downtown Chicago
NT$5,745
NT$6,831 total
includes taxes & fees
Sep 27 - Sep 28
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
A spacious lobby with a central coffee table, sofas, and a large mirror.
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.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

6. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NT$4,809
NT$5,717 total
includes taxes & fees
Sep 30 - Oct 1
The Chicago Hotel Collection Ambassador Gold Coast
An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.
A modern lobby with a wooden ceiling, leather sofas, and a coffee bar.
A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.
A rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.

7. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
  • Family-friendly Chicago escape with cribs, entertainment, and a prime location near Water Tower Place and the beach.
NT$4,675
NT$5,558 total
includes taxes & fees
Sep 20 - Sep 21
The Chicago Hotel Collection - Magnificent Mile
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.
A man in a suit sitting by a window with a vase of red flowers.
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$5,066
NT$6,023 total
includes taxes & fees
Sep 27 - Sep 28
River Hotel
A modern living room with a sofa set, ottoman, and armchairs.
A grand hallway with ornate ceiling, chandeliers, and a reception desk at the end.
A grand lobby with a central bar, high ceilings, and classical architecture.
A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.

9. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
  • Family delight in Chicago with a crib, TV channels, and city adventures near the heartbeat of Millennium Park.
NT$5,052
NT$6,007 total
includes taxes & fees
Sep 27 - Sep 28
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A hotel room with a large window, a bed, and a suitcase.
A modern living room with a fireplace, leather sofas, and a wooden floor.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

10. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
NT$5,604
NT$6,663 total
includes taxes & fees
Sep 20 - Sep 21
Club Quarters Hotel, Central Loop, Chicago
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 Chicago

Hyatt Regency Chicago

10/10 Excellent
"Clean room, nice view, very well situated to visit central Chicago."
Donald 1-night trip
Posted less than an hour ago
Hyatt Regency Chicago
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Helpful maintenence and cleaning staff. Well maintained property. Clean rooms. Good location!"
Taylor 3-night trip
Posted 5 hours ago
The Royal Sonesta Chicago Downtown
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Nice view. Really didn’t like the energy from the guy that checked my son and I in. Breakfast was included with our stay. But, he didn’t give us the voucher that was needed my son had to go get it. It was his 21st Birthday and I wanted him to stay somewhere nice"
Termeka 2-night trip
Posted 6 hours ago
The Chicago Hotel Collection - Magnificent Mile
Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"."
Carlos 2-night trip
Posted 7 hours ago
Eurostars Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Overall great location and staff was friendly."
Sergio 4-night trip
Posted 8 hours ago
Congress Plaza Hotel
River Hotel

River Hotel

10/10 Excellent
"Very nice hotel!!! Very close to everything"
Andrew 1-night trip
Posted 9 hours ago
River Hotel
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"Nice place. Perfect location."
Michael 1-night trip
Posted 9 hours ago
Hotel Saint Clair- Magnificent Mile
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"The hotel was clean and located a short walk away from millennium park. the staff was friendly and held our bags at the hotel while we strolled around the city on our last day after checkout."
Jeffrey 3-night trip
Posted 10 hours ago
L7 Chicago by LOTTE
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Clean and close to everything."
Steven 3-night trip
Posted 12 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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