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

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

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

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

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

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

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

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

8. River Hotel

River Hotel
Downtown Chicago
NT$4,867
NT$5,787 total
includes taxes & fees
Sep 27 - Sep 28
River Hotel

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

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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