Find Boutique Hotels in Oak Park, IL

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Check availability on Oak Park Boutique Hotels

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Oak Park boutique hotels

Exterior detail
Carleton of Oak Park

Carleton of Oak Park

Carleton of Oak Park
3.0 star property
Oak Park
9.2 out of 10, Wonderful, (1005)
"Beautiful historical hotel!"
United States
Cheryl
Carleton of Oak Park
Bar (on property)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (3789)
"Clean room, good location, friendly staff"
United States
Zacharias
The price is NT$2,412
NT$2,831 total
includes taxes & fees
Jan 7 - 2026/1/8
The Whitehall Hotel, BW Premier Collection
55-inch LCD TV with cable channels, TV, pay movies
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3429)
"Very good stay "
United States
david
The price is NT$4,367
NT$5,126 total
includes taxes & fees
Dec 28 - Dec 29
L7 Chicago by LOTTE
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3158)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is NT$2,952
NT$3,466 total
includes taxes & fees
Jan 22 - 2026/1/23
Eurostars Magnificent Mile
Lobby
Hotel Felix River North/Magnificent Mile

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, (2467)
"Decent hotel in a great location with extremely helpful staff. "
United States
Aaron
Hotel Felix River North/Magnificent Mile
Bar (on property)
Ivy Boutique Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1051)
"I love this hotel "
United States
Tiara
Ivy Boutique Hotel
Dinner served, American cuisine
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1003)
"Great hotel location and friendly staff! "
United States
Kathleen
The price is NT$3,371
NT$4,880 total
includes taxes & fees
Jan 11 - 2026/1/12
Staypineapple, An Iconic Hotel, The Loop
Exterior
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

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, (1125)
"Amazing hotel "
United States
Alondra
The price is NT$2,999
NT$3,521 total
includes taxes & fees
Jan 13 - 2026/1/14
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Breakfast, lunch, dinner served; American cuisine
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2328)
"The room was beautiful ❤️❤️ I enjoyed the hot tub and the views !! "
United States
Mary
The price is NT$3,493
NT$5,109 total
includes taxes & fees
Jan 4 - 2026/1/5
The Royal Sonesta Chicago River North
Nightclub
Central Loop Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1949)
"Good value and location worked well for our trip"
United States
Todd
The price is NT$2,355
NT$2,765 total
includes taxes & fees
Dec 25 - Dec 26
Central Loop Hotel
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 Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Great location to access downtown, easy parking, nice quality room with comfy bed, good happy hour deals, enjoyed ambiance and food in the restaurant. Will def stay here again "
Jennifer 2-night trip
Posted 12 hours ago
The Whitehall Hotel, BW Premier Collection

Frequently asked questions

What's the best boutique accommodation in Oak Park?
Carleton of Oak Park is a favorite hotel with Expedia travelers 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 Wrigley Field, Michigan Avenue, and United Center. You might also want to see places such as Soldier Field, Ernest Hemingway Museum and House, and Madison Street Theatre during your trip.
What kind of weather should I plan for when I travel to Oak Park?
Getting an idea of what to expect from the weather in Oak Park is important when you plan your trip. 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 31°F. Average annual precipitation for Oak Park is 48 inches.
What's the best way to get to my boutique hotel in Oak Park?
You have a few options for getting to 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 Intl. Airport (ORD) may also be an option. Walk to nearby metro stations like Ridgeland Station (Green Line), Oak Park Station (Green Line), and Oak Park Station (Blue Line). If you want to venture outside of the area, ride aboard one of the trains from Oak Park Station.

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