Boutique Hotels & Resorts in Oak Park from NZ$154

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Check availability on Oak Park Boutique Hotels

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

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, (1003)
"Beautiful historical hotel!"
United States
Cheryl
Carleton of Oak Park
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
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, (3818)
" Breakfast is good, location is excellent, service staff is courteous."
United States
Luis
The price is NZ$154
includes taxes & fees
14 Jan - 15 Jan 2026
The Whitehall Hotel, BW Premier Collection
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3169)
"stunning hotel"
Canada
Yiwei
The price is NZ$188
includes taxes & fees
28 Jan - 29 Jan 2026
Eurostars Magnificent Mile
Lobby sitting area
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, (2487)
"The room was amazing and the customer service was great!"
United States
Chelsi
Hotel Felix River North/Magnificent Mile
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3458)
"Amazing place to stay and super accommodating "
United States
Carson
The price is NZ$283
includes taxes & fees
18 Jan - 19 Jan 2026
L7 Chicago by LOTTE
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1054)
"I love this hotel "
United States
Tiara
Ivy Boutique Hotel
Breakfast, lunch, dinner served; American cuisine
Central Loop Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1959)
"Good value and location worked well for our trip"
United States
Todd
The price is NZ$165
includes taxes & fees
12 Jan - 13 Jan 2026
Central Loop Hotel
Interior detail
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, (1014)
"Location was great, staff was very friendly, and the rooms were clean. "
United States
Lori
The price is NZ$241
includes taxes & fees
14 Jan - 15 Jan 2026
Staypineapple, An Iconic Hotel, The Loop
Terrace/patio
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, (2351)
"We had a great stay! The experience was great from beginning to end. "
United States
Melanie
The price is NZ$278
includes taxes & fees
27 Jan - 28 Jan 2026
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, (1135)
"Amazing hotel "
United States
Alondra
The price is NZ$192
includes taxes & fees
19 Jan - 20 Jan 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection 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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Clean room. Separate bedroom from living room. Booked stay as my son had early appt at children’s hospital. Very accessible location. "
Rebecca 1-night trip
Posted 7 hours ago
Hilton Chicago/Magnificent Mile Suites

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 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?
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.