Search Boutique Hotels in Chicago

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 Chicago Boutique Hotels

Our top choices for Chicago boutique hotels

Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3145)
"Great location "
United States
Christian
The price is 2.277.245 ₫
2.673.257 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
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, (3791)
"Comfortable Room, great location and Excellent Staff. "
United States
Charles
The price is 2.015.448 ₫
2.365.934 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Whitehall Hotel, BW Premier Collection
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, (1005)
"Great hotel location and friendly staff! "
United States
Kathleen
The price is 2.817.230 ₫
4.078.320 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Staypineapple, An Iconic Hotel, The Loop
Nightclub
Central Loop Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1928)
"Great and comfortable place "
United States
Olu
The price is 1.949.715 ₫
2.288.770 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Central Loop Hotel
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, (1115)
"Great hotel for price and location Everything clean and a huge room "
United States
James
The price is 2.506.521 ₫
2.942.403 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
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, (2309)
"Wonderful customer service, great location! "
United States
Michelle
The price is 2.922.519 ₫
4.273.272 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Royal Sonesta Chicago River North
55-inch LCD TV with cable channels, TV, pay films
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3356)
"I loved the location."
United States
Laura
The price is 3.710.809 ₫
4.356.117 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
L7 Chicago by LOTTE
Rooftop terrace
Virgin Hotels Chicago

Virgin Hotels Chicago

Virgin Hotels Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1419)
"Staff was wonderful."
United States
Jamie
The price is 5.766.051 ₫
7.665.688 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Virgin Hotels Chicago
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, (2432)
"Staff was amazing! "
United States
Erica
Hotel Felix River North/Magnificent Mile
Deluxe Single Room, 1 King Bed, Lake View | Minibar, in-room safe, desk, blackout curtains
The Buckingham Hotel

The Buckingham Hotel

The Buckingham Hotel
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1002)
"We loved staying here! The room was spacious, had a great view, secure check in, and great location!"
United States
Madison
The Buckingham 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 Chicago Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

Searching for a cosy accommodation option for your visit to Chicago?
A boutique hotel may be just what you're looking for if you enjoy smaller hotels with quality service and great atmosphere. Select from 26 boutique-style accommodation options in Chicago to find a property that captures the local spirit of this destination.
How many boutique hotels will I be able to find in Chicago?
Expedia has 26 boutique hotels in Chicago.
What's there to see and do in Chicago?
Visitors speak positively about this destination's major shopping centres, scenic landscape and art galleries. Major sights and activities around Chicago include Michigan Avenue, Wrigley Field and Soldier Field. You might also want to see spots like Navy Pier, Naval Base Great Lakes and United Center during your trip.
What kind of weather should I plan for when I travel to Chicago?
Getting an idea of what to expect from the weather in Chicago will help you enjoy your stay to the fullest. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Chicago is 1260 mm.
What's the best way to get to my boutique hotel in Chicago?
You have a few options for travelling to and around Chicago. The closest major airport is Chicago Midway Airport (MDW), which is located 8.6 mi (13.9 km) away, but Chicago O'Hare International Airport (ORD) may also be an option. You can access metro transport at Monroe Station (Red Line), Monroe Station (Blue Line) and Adams-Wabash Station.