A well-maintained garden with a lawn, a large tree, and a two-story house with a porch.

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Our top choices for Oak Park boutique hotels

Exterior detail

Carleton of Oak Park

Carleton of Oak Park
3.0 star property
Oak Park
9.2 out of 10, Wonderful, (1,074 reviews)
"We had a wonderful stay! The room was big, clean, and incredibly comfortable. We especially loved the wee kitchenette! We also came in completely exhausted so it was a real boon to have a restaurant on the ground floor."
United States
Laura
The price is ฿4,075
฿4,523 total
includes taxes & fees
16 Jul - 17 Jul
Carleton of Oak Park
Terrace/patio

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,935 reviews)
"Great stay and location."
United States
Tammy Lynn
The price is ฿16,855
฿20,038 total
includes taxes & fees
11 Aug - 12 Aug
Trump International Hotel & Tower Chicago
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, (4,341 reviews)
"Great location and hotel"
United States
Raul
The price is ฿9,951
฿11,831 total
includes taxes & fees
26 Jul - 27 Jul
L7 Chicago by LOTTE
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,723 reviews)
"Nice place great staff and a great location"
United States
Byron
The price is ฿6,659
฿7,916 total
includes taxes & fees
27 Jul - 28 Jul
Eurostars Magnificent Mile
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,277 reviews)
"Comfortable hotel in a good location. Lots of public transportation close."
United States
Dean
The price is ฿6,099
฿7,251 total
includes taxes & fees
9 Aug - 10 Aug
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
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, (1,440 reviews)
"The hotel staff was wonderful to deal with and met our travel needs with great rooms and vital city information!"
United States
Robert Mardis
The price is ฿7,461
฿9,820 total
includes taxes & fees
9 Aug - 10 Aug
Sports Illustrated Resorts Chicago
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, (1,732 reviews)
"Nice and comfortable place to stay"
Australia
Precious
The price is ฿5,568
฿6,620 total
includes taxes & fees
26 Jul - 27 Jul
The Chicago Hotel Collection - Magnificent Mile
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, (1,143 reviews)
"Beautiful historic building; dog friendly!"
United States
Zoe
The price is ฿6,926
฿9,222 total
includes taxes & fees
9 Aug - 10 Aug
Staypineapple, An Iconic Hotel, The Loop
Breakfast, lunch, dinner and brunch served

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,721 reviews)
"The best hotel I’ve ever stayed in! Spacious rooms, friendly and helpful staff and an incredible roof terrace with indoor pool. Amazing location too. Stay here if you visit Chicago!"
United Kingdom
Adel
The price is ฿6,492
฿8,785 total
includes taxes & fees
9 Aug - 10 Aug
The Royal Sonesta Chicago River North
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, (3,949 reviews)
"Great location, comfortable rooms, nice breakfast."
United States
Luis
The price is ฿5,177
฿6,155 total
includes taxes & fees
10 Aug - 11 Aug
The Whitehall Hotel, BW Premier 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 Oak Park Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"The location is great and within walking distance of the main parks, shoppiong and restaurants. The staff was extremely friendly and helpful. They went above and beyond. They approached to see if they could be of help before I even asked! Amazing! Definitely will stay here again!"
Carol 3-night trip
Posted less than an hour ago
The Royal Sonesta Chicago Downtown

Frequently asked questions

What's the best boutique-style accommodation in Oak Park?
Carleton of Oak Park is a favourite hotel with Expedia travellers looking for a stylish stay, and features 2 restaurants and 2 bars.
What's there to see and do in Oak Park?
The shopping, restaurants and cafes are just some of the things to enjoy while you're in the area. Favorite activities and sights around Oak Park include United Center, Wrigley Field and Michigan Avenue. You might also want to see places such as Soldier Field, Ernest Hemingway Museum and House and Pleasant Home during your trip.
What kind of weather should I plan for when I travel to Oak Park?
Understanding the weather in Oak Park 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. Average annual precipitation for Oak Park is 1207 mm.
What's the best way to get to my boutique hotel in Oak Park?
You have a few options for getting to and around Oak Park. The closest major airport is Chicago Midway Airport (MDW), which is located 7 mi (11.3 km) from the heart of the city, but Chicago O'Hare International Airport (ORD) may also be an option. You can walk to nearby metro stations including Ridgeland Station (Green Line), Oak Park Station (Green Line) and Oak Park Station (Blue Line). If you want to venture outside the area, hop aboard a train at Oak Park Station.