Find Boutique Hotels in Oak Park, IL

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Oak Park Boutique Hotels

Tonight
Dec 20 - Dec 21
Tomorrow
Dec 21 - Dec 22
Next weekend
Dec 26 - Dec 28
In two weeks
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, (1002)
"Spacious room, quiet night's sleep in a very pleasant historic hotel."
United States
Edward
Carleton of Oak Park
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3163)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is NT$3,030
NT$3,557 total
includes taxes & fees
Jan 4 - 2026/1/5
Eurostars Magnificent Mile
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, (3803)
"Clean room, good location, friendly staff"
United States
Zacharias
The price is NT$2,416
NT$2,836 total
includes taxes & fees
Dec 23 - Dec 24
The Whitehall Hotel, BW Premier Collection
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, (2458)
"Decent hotel in a great location with extremely helpful staff. "
United States
Aaron
Hotel Felix River North/Magnificent Mile
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, (1007)
"Great hotel location and friendly staff! "
United States
Kathleen
The price is NT$3,377
NT$4,889 total
includes taxes & fees
Jan 4 - 2026/1/5
Staypineapple, An Iconic Hotel, The Loop
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, (2324)
"The room was beautiful ❤️❤️ I enjoyed the hot tub and the views !! "
United States
Mary
The price is NT$3,503
NT$5,123 total
includes taxes & fees
Jan 4 - 2026/1/5
The Royal Sonesta Chicago River North
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$3,005
NT$3,527 total
includes taxes & fees
Jan 11 - 2026/1/12
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
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, (3402)
"Enjoyed my stay"
United States
Karen
The price is NT$3,664
NT$4,302 total
includes taxes & fees
Dec 23 - Dec 24
L7 Chicago by LOTTE
Nightclub
Central Loop Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1946)
"Good value and location worked well for our trip"
United States
Todd
The price is NT$2,574
NT$3,021 total
includes taxes & fees
Jan 3 - 2026/1/4
Central Loop Hotel
Bar (on property)
Ivy Boutique Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1045)
"Staff was amazing! "
United States
Ahren
Ivy Boutique 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.
View all properties

Top Oak Park Hotel Reviews

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"Great"
Alison 2-night trip
Posted 10 hours ago
LondonHouse Chicago, Curio Collection by Hilton

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.

Explore a world of travel with Expedia