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.
A reception area with two reception desks, a central wall with a Holiday Inn Express sign, and a wooden panel design.
An indoor swimming pool with blue chairs and a tiled floor.
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$3,888
NT$4,354 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 hotel room with a bed, a television, a desk, a chair, and a patterned carpet.
A gym with treadmills, elliptical machines, and weight equipment.
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 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.'
A living room with a sofa, a coffee table, a TV, and an air conditioner.

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,546
NT$2,852 total
includes taxes & fees
Sep 29 - Sep 30
MainStay Suites Chicago Hillside
A bar area with a high ceiling, bar stools, and a counter with bottles.
A modern interior with wooden shelves, tables, and chairs, and a large window with the word "FOUND" on the wall.
A modern interior with a bar area, wooden shelves with various items, and a 'FOUND' sign on the wall.

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 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.
A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

6. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
NT$4,829
NT$5,741 total
includes taxes & fees
Sep 20 - Sep 21
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 lounge area with leather sofas, wooden coffee tables, and ambient lighting.
The Chicago Hotel Collection building with a glass facade, American flag, and signage for Barista Bar and Seighity events.
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$4,694
NT$5,581 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 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$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 lobby with a central bar area, high ceilings, and ornate columns.
A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.
A grand hallway with ornate ceiling, chandeliers, and a reception desk at the end.

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 restaurant interior with brick walls, wooden tables and chairs, and a bar area.
A bar with a brick archway, wooden bar counter, and stools.
A hotel room with a large window, a bed, and a suitcase.

10. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
NT$5,511
NT$6,552 total
includes taxes & fees
Sep 27 - Sep 28
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

River Hotel

River Hotel

10/10 Excellent
"Location was perfect. Staff were nice."
Trish 3-night trip
Posted less than an hour ago
River Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

8/10 Good
"Make sure to keep the card they give you that shows the discounts and food/drink credit that comes with your room"
Destiny 3-night trip
Posted 1 hour ago
Hyatt Regency Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"The rooms were clean a bit dated but comfortable for my family. Leo (valet) was absolutely the best help while traveling with a toddler. Sadly, we experienced cold water but overall pleasant hotel with great view."
Ivory 5-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

8/10 Good
"Room was very, very outdated and the lack of a mini fridge was disappointing. But the room was clean, location was convenient and the staff were nice."
Tanna 1-night trip
Posted 2 hours ago
Travelodge by Wyndham Downtown Chicago
The Wade

The Wade

10/10 Excellent
"Great stay"
Fernanda 1-night trip
Posted 3 hours ago
The Wade
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"Awesome"
Marcos 2-night trip
Posted 4 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Hilton Chicago

Hilton Chicago

10/10 Excellent
"From the very start at check in Stephen was so kind and helpful. Throughout my stay the staff was very friendly. The restaurant was excellent & I was grateful to have a chance to take a swim!"
Darlene 2-night trip
Posted 5 hours ago
Hilton Chicago
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Great location. Nice indoor pull."
Eduardo 1-night trip
Posted 7 hours ago
InterContinental Chicago Magnificent Mile by IHG
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

8/10 Good
"The location and room itself worked well for us after a wedding on the Southside and using a Spot Hero parking place. The breakfast was very good, made fresh with good options but the tables needed to be bused and wiped down. The lobby needed tending to as well"
Annette 1-night trip
Posted 12 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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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