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 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
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 hotel lobby with a buffet area, multiple seating arrangements, and a patterned carpet.
A hotel room with a bed, a television, a desk, a chair, and a patterned carpet.
A bathroom with a shower, a sink with a mirror, and a towel rack.

1. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$2,715
NT$3,040 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Plus Chicago Hillside
A multi-story hotel with a central entrance, a flag, and a sign for Express Suites.
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.
A reception area with two reception desks, a central wall with a Holiday Inn Express sign, and a wooden panel design.

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$3,643
NT$4,079 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$2,546
NT$2,852 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 bed, a desk, a television, a sofa, and a large window with a city view.
A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.
A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape 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$4,590
NT$5,457 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 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.
A bar area with a long counter, multiple stools, and a modern chandelier.

5. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
Downtown Chicago
NT$3,642
NT$5,268 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 spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.
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$4,568
NT$5,431 total
includes taxes & fees
Aug 30 - Aug 31
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 hotel room with a large bed, a TV, a desk, and a chair.
A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.
A person sitting on a couch with a laptop, reading a book, in a room with a large window and a framed picture on the wall.

7. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
NT$3,898
NT$4,635 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 conference room with a long table, chairs, and a vase.
A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.
A man in a suit sitting by a window with a vase of red flowers.

8. River Hotel

River Hotel
Downtown Chicago
NT$4,174
NT$4,963 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 hotel room with two beds, a desk with a computer, a chair, a TV, and a large mirror.
A modern room with a checkered floor, two round tables, two armchairs, and a large window with a view of the outside.

9. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Downtown Chicago
NT$4,319
NT$5,134 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 wooden shelves, tables, and chairs, and a large window with the word "FOUND" on the wall.

10. FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
Downtown Chicago
NT$4,569
NT$5,364 total
includes taxes & fees
Aug 30 - Aug 31
FOUND Hotels, Chicago, Series by Marriott
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
"Open layout and adjacent parking were a plus."
Scott 2-night trip
Posted 1 hour ago
Hyatt Regency O'Hare Chicago
Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"I had an outstanding stay at Eurostars Magnificent Mile. I was lucky enough to get an early check-in along with an upgrade, which was an amazing way to start my trip. The staff was excellent from beginning to end. I was always greeted by the front desk, and the head of security was especially great and made me feel welcomed throughout my stay. The attached restaurant also had great food, and the location made it easy for me to get out and explore Chicago. Overall, the hospitality really stood out. Chicago showed out, and Eurostars was a big part of that experience. I’ll absolutely be staying here again when I return."
Ricky 3-night trip
Posted 3 hours ago
Eurostars Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"."
Roberto 2-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Prime location on the Mile. All Staff were top notch!"
Leititia 4-night trip
Posted 11 hours ago
InterContinental Chicago Magnificent Mile by IHG
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"This is our 2nd time staying here, our 1st was for a wedding held there last year. It was great & we stayed in a renovated room. Amazing & we will be back. Rooms were spacious, very clean, & amazing room. We decided to splurge & upgrade to a lakeside view. Check in was easy, great area, & love that they can hold baggage as well after you check out. Lastly great sleep! Bed was very comfy & pillows were amazing. Until next time"
Priscilla 1-night trip
Posted 15 hours ago
Congress Plaza Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"We traveled with 2 kids and the staff were very accommodating with our needs. The room was spacious enough for the 4 of us! Great stay!"
Bridgit 2-night trip
Posted 15 hours ago
Hyatt Regency Chicago
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"This is a beautiful hotel and wonderful staff. We loved the design and the decor. The coffee area was so well set up and very thoughtful with honey, almond milk, lemons for water and tea. Very clean and delicious. The gym was a bit small but had all of the equipment and weights needed. They had chilled eucalyptus face towels that I loved so much at the end of my workout. The location was great. We loved the Nederlander theater and seeing The Notebook! My husband and I had an amazing time. Chicago was great! This hotel will not disappoint."
Amy 3-night trip
Posted 20 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"L7 is centrally located and is the perfect hotel for exploring the city. Easy access to everything. Clean property and more boutique and small compared to the larger hotels, which I prefer. The staff was amazing. So very friendly - especially Alex at the front desk. It was so nice that he was the first person we met because he set the tone for a wonderful trip. He answered every question and was so pleasant and helpful. He truly took great care of us! I look forward to coming back!"
David 3-night trip
Posted 20 hours ago
L7 Chicago by LOTTE
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Free coffee Free printing Early check in fee available"
Sean 1-night trip
Posted 1 day ago
Crowne Plaza Chicago West Loop by IHG

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 United Center and Wrigley Field. Make sure you have plenty of time to take in activities in the area like Soldier Field, Navy Pier, and Michigan Avenue.

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