A lush green valley with a winding road, steep mountains, and a misty atmosphere.

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Check availability on Hillside Family-Friendly Hotels

Tonight
25 Sept - 26 Sept
Tomorrow
26 Sept - 27 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Choose what matters most at family-friendly hotels in Hillside

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Hillside Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent
"Great price, very convenient, walkable to downtown/river area. Staff was very helpful with directions and pleasant at all times. Bathroom was very small, but fine for a solo traveler."
Richard 2-night trip
Posted less than an hour ago
Hotel Saint Clair- Magnificent Mile
L7 Chicago by LOTTE

L7 Chicago by LOTTE

8/10 Good
"Great hotel in perfect loction. The front desk staff was very unhelpful. The guy who checked me in should not work in hospitality. He ignores you when talking to him. No eye contact at all. I booked room with river view. I asked for a quite room. He assigned room facing a wall !! And close to the main HVAC equipments for the whole hotel. Very noisey. I went downstairs and told him that's not what I booked. He tried to tell me River view is sold out and tried to give a $25 food credit. When I refused and got frustrated , a river view room suddenly became available. I would stay in this hotel again in a heart beat , once they improve thier front desk."
Radwan 2-night trip
Posted 1 hour ago
L7 Chicago by LOTTE
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"The hotel was in a great location and the Stetson restaurant that was attached was excellent!! The room was perfect! Would stay there again in a heartbeat!"
Tony 2-night trip
Posted 1 hour ago
Hyatt Regency Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"Very Nice place to stay"
Anand 4-night trip
Posted 1 hour ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Good location and mostly everything was kind of just average — took about 15 min to check in BUT check out was <1 min. Need to make it up a couple of stairs with your luggage to get in the lobby. Elevator wait could take a few minutes but nothing too bad. Room was large and nice view but there was no closet or anything to hang clothes with/on. The shower has a shower curtain which wasn’t very hygienic. They clean every 3 days and they call it a “unique hotel experience”. It was nice that every night if we needed water the main desk has bottles. Overall, it’s just very average. It was nice enough, clean enough, good enough."
alexandra 4-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast
Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Clean room. But very loud AC and area."
Sonia 4-night trip
Posted 1 hour ago
Eurostars Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Cool"
Carlos Joel 2-night trip
Posted 4 hours ago
Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Z"
Teanna 1-night trip
Posted 5 hours ago
The Chicago Hotel Collection - Magnificent Mile

Frequently asked questions

What's Hillside like for family-friendly holidays?
The relaxing destination of Hillside is a great choice if you've been considering a holiday with the children. The entertainment, forests and restaurants are just a few things that make this an attractive spot for a family holiday. Fly into Chicago O'Hare International Airport (ORD), which is the closest airport, or Chicago Midway Airport (MDW), which is located 10.4 mi (16.7 km) from the city centre.
When's the best time to book a family-friendly holiday in Hillside?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillside are January, November, February and December, with each month seeing an average of 13 cm of snowfall.
What's there to see and do with your family in Hillside?
While you are holidaying in Hillside, you and the family may want to see some interesting spots such as Wrigley Field and Soldier Field. Make sure that you have plenty of time to take in activities in the area such as Navy Pier, United Center and Michigan Avenue.

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