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

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$3,877
NT$4,341 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$3,176
NT$3,557 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Plus Chicago Hillside

3. MainStay Suites Chicago Hillside

MainStay Suites Chicago Hillside
Hillside
NT$2,539
NT$2,843 total
includes taxes & fees
Sep 29 - Sep 30
MainStay Suites Chicago Hillside

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

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

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

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

8. River Hotel

River Hotel
Downtown Chicago
NT$5,066
NT$6,023 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$5,052
NT$6,007 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$5,511
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

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 2 hours ago
InterContinental Chicago Magnificent Mile by IHG
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good
"The staff were extremely helpful, the check in/out process was seamless, the location is great for commuting to the loop offices, and we enjoyed the main lobby bar."
Bianca 1-night trip
Posted 3 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
River Hotel

River Hotel

10/10 Excellent
"Great value"
Brent 1-night trip
Posted 4 hours ago
River Hotel
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Perfect location and very clean."
Alexis 3-night trip
Posted 4 hours ago
L7 Chicago by LOTTE
Hilton Chicago

Hilton Chicago

8/10 Good
"Germain is the man, that get things done best worker there!"
Daniel 2-night trip
Posted 6 hours ago
Hilton Chicago
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 7 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

8/10 Good
"I checked in 9/11 around 8pm, when I was greeted and asked for my confirmation, employee informed me that my reservation had been canceled. I made my reservation through Expedia. My initial reservation was for three nights, shortly after making my reservation. I canceled the third night and received a new confirmation from Expedia. Apparently Expedia decided to cancel the entire reservation, although they sent me a new confirmation number. The funny thing is, a minute before I walked in the hotel Expedia sent me an email asking me how the check in process had gone. But the young lady (unfortunately I didn't get her name) working the front desk, made me a new reservation and got me checked in smoothly. Thank you to her."
Hector 2-night trip
Posted 8 hours ago
Travelodge by Wyndham Downtown Chicago
Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"It was a great location. Walked back from Soldier Field and close to restaurants and shopping. Spacious room."
Juhelia 1-night trip
Posted 11 hours ago
Congress Plaza Hotel
Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"."
Carlos 2-night trip
Posted 20 hours ago
Eurostars 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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