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

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Check availability on Hillside Boutique Hotels

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

Our top choices for Hillside boutique hotels

Studio, 2 Double Beds | Bathroom | Shower, free toiletries, hair dryer, towels

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,418 reviews)
"The location is great and the rooms are comfortable and spacious. The free yoga classes were a nice bonus. It is clear that the hotel is going through a transition."
Canada
Caroline
The price is ₹17,486
₹23,481 total
includes taxes & fees
30 Jun - 1 Jul
Sports Illustrated Resorts Chicago
Nightclub

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,191 reviews)
"Great hotel with awesome location"
United States
Daniel
The price is ₹12,467
₹14,822 total
includes taxes & fees
1 Jul - 2 Jul
Central Loop Hotel
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,109 reviews)
"Good location, friendly staff"
United Kingdom
Philip
The price is ₹14,377
₹19,901 total
includes taxes & fees
6 Jul - 7 Jul
Staypineapple, An Iconic Hotel, The Loop
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,674 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is ₹14,391
₹17,110 total
includes taxes & fees
1 Jul - 2 Jul
Eurostars Magnificent Mile
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,615 reviews)
"Enjoyed our stay"
United States
keary
The price is ₹11,894
₹14,140 total
includes taxes & fees
29 Jun - 30 Jun
The Chicago Hotel Collection - Magnificent Mile
Lobby

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,789 reviews)
"Absolutely wonderful place to stay"
United States
catherine
The price is ₹11,622
₹16,957 total
includes taxes & fees
8 Jul - 9 Jul
Hotel Felix River North/Magnificent Mile
55-inch LCD TV with cable channels, TV, pay films

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (4,225 reviews)
"I would absolutely stay here again! Beautiful well thought out property, within walking distance of everything."
United States
Joel
The price is ₹25,478
₹30,291 total
includes taxes & fees
1 Jul - 2 Jul
L7 Chicago by LOTTE
Bar (on property)

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.4 out of 10, Very good, (3,940 reviews)
"Great location, comfortable rooms, nice breakfast."
United States
Luis
The price is ₹13,128
₹15,607 total
includes taxes & fees
30 Jun - 1 Jul
The Whitehall Hotel, BW Premier Collection
Champagne service

The Buckingham Hotel

The Buckingham Hotel
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,006 reviews)
"The view of the city was spectacular"
United States
Wilmer
The price is ₹14,398
₹18,230 total
includes taxes & fees
1 Jul - 2 Jul
The Buckingham Hotel
View from property

The Talbott, Autograph Collection

The Talbott, Autograph Collection
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (124 reviews)
"We will definitely stay here again!!"
United States
Hayley
The price is ₹17,102
₹23,698 total
includes taxes & fees
5 Jul - 6 Jul
The Talbott, Autograph Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillside Hotel Reviews

Freehand Chicago

Freehand Chicago

10/10 Excellent
"Was a great location right in the heart of Chicago, very close to many great restaurants and easy to access the trains and public transportation."
Elijah 3-night trip
Posted 1 hour ago
Freehand Chicago

Frequently asked questions

What's there to see and do in Hillside?
The shopping and restaurants are just some of the things to enjoy while you're in the area. While you're out and about in Hillside, popular attractions like Wrigley Field, Michigan Avenue and Soldier Field are worth a visit. You might also want to see spots like Navy Pier, United Center and Drury Lane Theater during your trip.
What kind of weather should I plan for when I travel to Hillside?
Getting an idea of what to expect from the weather in Hillside is important when planning your trip. 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 the best way to get to my boutique hotel in Hillside?
You have a few options for travelling to and around Hillside. The closest major airport is Chicago O'Hare International Airport (ORD), which is located 6.9 mi (11 km) from the heart of the city, but Chicago Midway Airport (MDW) may also be an option. If you'd like to explore around the area, consider renting a car to explore more sights.

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