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
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top 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, (1024)
"Spacious room, quiet night's sleep in a very pleasant historic hotel."
United States
Edward
Carleton of Oak Park
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1029)
"Clean room Great location "
United States
ali
The price is AED 372
AED 436 total
includes taxes & fees
10 Dec - 11 Dec
Ivy Boutique Hotel
Exterior
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
Downtown Chicago
7.6 out of 10, Good, (1170)
"The room was spacious and clean and it was a good value."
United States
Dj
The Chicago Hotel Collection - Magnificent Mile
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3322)
"Great location, comfortable hotel "
Australia
Mark
The price is AED 518
AED 608 total
includes taxes & fees
1 Jan - 2 January 2026
L7 Chicago by LOTTE
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
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, (3767)
"Great location "
United States
Carlos
The price is AED 281
AED 330 total
includes taxes & fees
9 Dec - 10 Dec
The Whitehall Hotel, BW Premier Collection
Rooftop terrace
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1422)
"Excellent hotel the rooms are awesome "
United States
Devita
The price is AED 938
AED 1,226 total
includes taxes & fees
6 Dec - 7 Dec
Virgin Hotels Chicago
Bar (on property)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1783)
"Great stay "
United States
Mohammed
The price is AED 1,016
AED 1,192 total
includes taxes & fees
4 Jan - 5 January 2026
Trump International Hotel & Tower Chicago
Cocktail bar
ACME Hotel Company

ACME Hotel Company

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1916)
"Lived up to expectations. Bathroom was really nice. Would stay here again."
United States
Nolan
The price is AED 306
AED 359 total
includes taxes & fees
14 Dec - 15 Dec
ACME Hotel Company
Front of property
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (56)
"great location, loved the gym and large room"
United States
Paulina Renata Silva
The price is AED 465
AED 654 total
includes taxes & fees
21 Dec - 22 Dec
The Talbott, Autograph Collection
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, (1001)
"Perfect stay. Great location, lovely room with view of Marshall Fields State Street Christmas display. The people were just great."
United States
James
The price is AED 426
AED 607 total
includes taxes & fees
17 Dec - 18 Dec
Staypineapple, An Iconic Hotel, The Loop
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Very nice staff, beautiful hotel and a clean room"
Tara 3-night trip
Posted 7 hours ago
The Royal Sonesta Chicago Downtown

Explore a world of travel with Expedia

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.