A cityscape with tall buildings, a river, and a bridge at dusk.

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Check availability on Oak Park Boutique Hotels

Tonight
4 Sep - 5 Sep
Tomorrow
5 Sep - 6 Sep
This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

Our top choices for Oak Park boutique hotels

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A residential street with a sidewalk, houses, and greenery.
A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

1. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Alan
฿3,358
฿3,726 total
includes taxes & fees
13 Sept - 14 Sept
Carleton of Oak Park
A hotel entrance with a marquee and string lights above the entrance.
A hotel entrance with a classic facade, an American flag, and a sign for Hotel Blake Chicago.
A hotel entrance with a marquee, American flag, and a person standing in front.

2. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
United States
Melanie
฿6,022
฿7,159 total
includes taxes & fees
7 Sept - 8 Sept
Hilton Vacation Club Hotel Blake Chicago
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A hotel room with a large bed, a TV, a desk, and a chair.
A person sitting on a couch with a laptop, reading a book, in a room with a large window and a framed picture on the wall.
A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.

3. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
United States
Yiyang
฿4,016
฿4,775 total
includes taxes & fees
7 Sept - 8 Sept
Central Loop Hotel
A room with two chairs and a small table, a large window with a city view at night.
A modern living room with a sectional sofa, a round ottoman, a dining area with chairs and a table, and a large mirror on the wall.
A bar area with a long counter, multiple stools, and a television screen.
A modern hotel lobby with a large window, seating area, and a reception desk.

4. Eurostars Magnificent Mile

Eurostars Magnificent Mile
Downtown Chicago
United States
Brennique
฿5,794
฿6,888 total
includes taxes & fees
7 Sept - 8 Sept
Eurostars Magnificent Mile
A bar area with a checkered floor, leather seating, and a bar counter with a visible liquor selection.
A modern lounge with a green sofa, armchairs, a coffee table, and a piano.
A building with a marquee sign reading 'ACME HOTEL COMPANY' and a 'VACANCY' sign.
A lounge area with a checkered floor, blue sofas, a bench, and a patterned coffee table.

5. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
Downtown Chicago
United States
Roslyn
฿5,539
฿6,585 total
includes taxes & fees
7 Sept - 8 Sept
ACME Hotel Chicago, Outset Collection by Hilton
An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.
A modern lobby with a wooden ceiling, leather sofas, and a coffee bar.
The Chicago Hotel Collection building with a glass facade, American flag, and signage for Barista Bar and Seighity events.
A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.

6. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
United States
Colten
฿3,530
฿4,196 total
includes taxes & fees
7 Sept - 8 Sept
The Chicago Hotel Collection - Magnificent Mile
A room with a brick wall, a large wooden door, a flat-screen TV, and a grey armchair.
A narrow alleyway with a brick building, a wooden door with glass panels, and a potted plant.
A bedroom with a large bed, a bench, a chair, and a mirror.
A modern kitchen with dark wood cabinets, a white countertop, and a built-in oven. There are two windows with patterned curtains, a stone accent wall, and a coffee maker on the counter.

7. The Golden Arm

The Golden Arm
West Town
United States
Myanauh
฿4,576
฿5,371 total
includes taxes & fees
7 Sept - 8 Sept
The Golden Arm
A historic building with a prominent casino sign, surrounded by modern skyscrapers.
A hotel room with two beds, a dining table with chairs, a city view, and a minibar.
A modern interior with a round table, four chairs, a vase with flowers, and a view of the street through large windows.
A person pouring a drink into a glass with ice and an orange slice garnish.

8. Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
Downtown Chicago
United States
DeWayne
฿3,710
฿5,507 total
includes taxes & fees
7 Sept - 8 Sept
Hotel Felix River North/Magnificent Mile
A corridor with ornate black metal railings and a patterned carpet.
A modern hotel room with a sofa, a small table, a bench, a TV, and a cabinet.
A dining area with tables and chairs, a hanging light fixture, and a view of the street through a window.
A bed with a pillow featuring a pineapple design and the text "Sleep with me." A window reveals a cityscape at night.

9. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
United States
marcus
฿4,800
฿6,683 total
includes taxes & fees
7 Sept - 8 Sept
Staypineapple, An Iconic Hotel, The Loop
A hotel bathroom with a large mirror, a sink, and a vanity.
A hotel with a classic facade, large windows, and a prominent entrance.
A gym with various exercise equipment, including treadmills and weight machines.
A hotel room with a view of a cityscape through a large window, a floor lamp, a sofa with cushions, and a small table with a plant.

10. Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
Downtown Chicago
United States
Jose Rafael
฿6,709
฿8,915 total
includes taxes & fees
10 Sept - 11 Sept
Sports Illustrated Resorts Chicago
View all properties

Top Oak Park Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"N/A"
Mary Babette 3-night trip
Posted 1 hour ago
Hyatt Regency Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great and Friendly staff from check-in to check-out."
Lisa 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile
River Hotel

River Hotel

10/10 Excellent
"My stay was truly a blessing; from the moment I arrived, Leo took great care of me and helped with the check-in... the housekeeping staff was friendly and did a great job. I had a beautiful view from my room on the 35th floor... I would definitely choose this hotel 🏨 again when I return to Chicago..."
Tayde 2-night trip
Posted 2 hours ago
River Hotel
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"The property was amazing! It was in a perfect location, walkable to everything. The view from our room was even better. We got upgraded to the river view."
Mia 2-night trip
Posted 5 hours ago
The Royal Sonesta Chicago Downtown
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Location and views from our room were excellent."
Clifford 2-night trip
Posted 5 hours ago
Fairmont Chicago at Millennium Park

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, Soldier Field and Navy Pier. You might also want to see places such as United Center, 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.

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