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 14 - Sep 15
Tomorrow
Sep 15 - Sep 16
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 29 - Sep 30
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 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.
A hotel lobby with a buffet area, multiple seating arrangements, and a patterned carpet.

2. Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside
NT$3,163
NT$3,542 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 hotel room with two beds, a nightstand, a lamp, and a framed picture on the wall.
A living room with a sofa, a coffee table, a TV, and an air conditioner.
A bathroom with a sink, toilet, and shower.

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,571
NT$2,879 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 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.
A modern interior with wooden shelves, tables, and chairs, and a large window with the word "FOUND" on the wall.

4. FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
Downtown Chicago
NT$4,810
NT$5,646 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 hotel room with a large window, a bed, a desk, a chair, and a lamp.

5. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Downtown Chicago
NT$5,721
NT$6,802 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 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$4,809
NT$5,717 total
includes taxes & fees
Sep 29 - Sep 30
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 rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.
The Chicago Hotel Collection building with a glass facade, American flag, and signage for Barista Bar and Seighity events.

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 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.
A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.

8. River Hotel

River Hotel
Downtown Chicago
NT$4,867
NT$5,787 total
includes taxes & fees
Sep 27 - Sep 28
River Hotel
A modern living room with a sofa set, ottoman, and armchairs.
A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.
A grand lobby with a central bar area, high ceilings, and ornate columns.
A grand lobby with a central bar, high ceilings, and classical architecture.

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$5,031
NT$5,982 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 restaurant interior with brick walls, wooden tables and chairs, and a bar area.
A modern living room with a fireplace, leather sofas, and a wooden floor.

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
"My room was clean; the staff was nice and very helpful. I appreciated the credit for the amenities and the breakfast buffet was amazing. I would definitely stay here again."
Danyelle 2-night trip
Posted 1 hour ago
Hyatt Regency Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Right in the heart of Chicago. Fascinating windows with built- in seating. Get a corner suite - well worth the money."
Daniel 3-night trip
Posted 1 hour 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 1 hour ago
Hampton Inn Chicago Downtown/Magnificent Mile
The Wade

The Wade

10/10 Excellent
"Bathroom was dirty."
Maria Lourdes 1-night trip
Posted 2 hours ago
The Wade
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Everything was fine except that the mini-refrigerator in our room did not work."
NANCY 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago

Hilton Chicago

10/10 Excellent
"We liked the lake view Room service staff were very helpful Very comfortable beds Great decor inside the room"
SANJAY 3-night trip
Posted 2 hours ago
Hilton Chicago
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Excellent stay as always."
Amit 2-night trip
Posted 3 hours ago
Fairmont Chicago at Millennium Park
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Great weekend stay. Everything was amazing, down to location of getting around in the city. The ONLY downside was the cost of parking. It’s valet only and the price was not listed anywhere. It’s $88 a night if you’re doing overnight."
Brea 2-night trip
Posted 3 hours ago
InterContinental Chicago Magnificent Mile by IHG
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"The staff were friendly for the most part (some were friendlier and helpful than others). The in-hotel restaurant, while a tad expensive, had very good quality breakfast and lunch/dinner. I was also mostly happy with the restaurant staff. The fitness facilities on the 7th floor were quite good and there were many machines, i.e. not just your typical tiny hotel gym but an actually sizeable gym. I did not park on the property so I can't comment on that. The only downside is the street noise, with cars always f*ing revving their engines for no reason at like midnight and after and the ceaseless blaring of sirens from emergency vehicles evey like 10 minutes. If you're a light sleeper it's actually hard to get a restful sleep. This is not the hotel's fault but the police and authorities need to enforce some quiet at late hours (especially on a weekday) and they're nowhere to be seen at midnight, when some selfish punk is revving his/her vehicle seeking attention due to their insecurities."
Behzad 5-night trip
Posted 3 hours ago
The Royal Sonesta Chicago Downtown

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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