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Hotels in Prairie District

October 2026
15
November 2026

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This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Where to stay in Prairie District?

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.
A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.
A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

1. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
The Loop, 1.3 km from Prairie District
United States
Alexander
$127
$151 total
includes taxes & fees
Nov 9 - Nov 10
Hilton Garden Inn Chicago Downtown South Loop
A modern interior with a bar area, seating, and decorative wooden panels.
A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.
A hotel room with a flat-screen TV, a wooden cabinet, a round table, a blue sofa, a desk with a computer, and a large window with curtains.
A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.

2. Best Western Grant Park Hotel

Best Western Grant Park Hotel
The Loop, 1.3 km from Prairie District
United States
Anthony
$125
$149 total
includes taxes & fees
Nov 9 - Nov 10
Best Western Grant Park Hotel
A modern kitchen with a large window, a dining area, and a view of the sea.
A modern bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern living room with a sectional sofa, a fireplace, and a large window offering a city view.

3. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
The Loop, 1.3 km from Prairie District
United States
Josue
$144
$171 total
includes taxes & fees
Nov 10 - Nov 11
Homewood Suites by Hilton Chicago Downtown South Loop
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A conference room with a long table, chairs, and a large screen.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

4. Hilton Chicago

Hilton Chicago
The Loop, 1.7 km from Prairie District
United States
James
$166
$227 total
includes taxes & fees
Oct 30 - Oct 31
Hilton Chicago
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.
A bar area with a long counter, multiple liquor bottles, and a variety of glasses.
A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.
A restaurant with booths and tables, a television on the wall, and a view of the street outside.

5. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
The Loop, 2 km from Prairie District
United States
Rachel L
$172
$204 total
includes taxes & fees
Nov 4 - Nov 5
Hilton Vacation Club Hotel Blake Chicago
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.
A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

6. Congress Plaza Hotel

Congress Plaza Hotel
The Loop, 2 km from Prairie District
United States
Nancy
$129
$153 total
includes taxes & fees
Nov 10 - Nov 11
Congress Plaza Hotel
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.
A compact kitchen with a microwave, coffee maker, and sink.
A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.
A restaurant with booths, tables, and a green wall in the background.

7. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
The Loop, 1.9 km from Prairie District
United States
Gabrielle
$118
$140 total
includes taxes & fees
Nov 11 - Nov 12
Travelodge by Wyndham Downtown Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

8. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Streeterville, 4.1 km from Prairie District
United States
Kendra
$198
$270 total
includes taxes & fees
Nov 15 - Nov 16
Sable at Navy Pier Chicago, Curio Collection by Hilton
A modern hotel with a glass facade, multiple floors, and a prominent sign.
A modern living room with a large bookshelf, a sofa, a coffee table, and a view of the cityscape.
A modern retail space with a central wooden counter, a cityscape mural, and shelves stocked with snacks and beverages.
A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.

9. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
3.4 km from Prairie District
United States
Cleveland
$212
$252 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn Chicago West Loop Fulton Market Area
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.
A bar with a brick archway, wooden bar counter, and stools.
A modern living room with a fireplace, leather sofas, and a wooden floor.

10. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Theatre District, 2.5 km from Prairie District
United States
Brandi
$148
$176 total
includes taxes & fees
Oct 25 - Oct 26
Club Quarters Hotel, Central Loop, Chicago
A hotel room with a large bed, two armchairs, a desk, and a view of a cityscape through large windows.
A hotel room with a large window, a dining area with a table and chairs, a sofa, a TV, and a decorative light fixture.
A hotel room with a city view, a dining area, a sofa, and a TV.
A spacious lobby with a glass entrance, escalators, and a tiled floor.

11. The Buckingham Hotel

The Buckingham Hotel
The Loop, 2.2 km from Prairie District
United States
Michael
$206
$256 total
includes taxes & fees
Nov 9 - Nov 10
The Buckingham Hotel
A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.
A modern bar area with a bar counter, multiple stools, and a chandelier.
A cityscape with modern skyscrapers, a waterfront, and a winter setting.
A man and a woman walking down a marble staircase in a hotel lobby with a chandelier and a sign indicating an exit.

12. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
Theatre District, 2.7 km from Prairie District
United States
Nicholas
$161
$222 total
includes taxes & fees
Nov 1 - Nov 2
Silversmith Hotel Chicago Downtown
A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.
A conference room with a long table, chairs, a projector screen, and a television on the wall.
A hotel room with two beds, a desk with a television, a chair, a ceiling fan, and a window with a view of a building.
A modern office setup with two monitors, a keyboard, and leather chairs.

13. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.4 km from Prairie District
United States
Carolyn
$228
$271 total
includes taxes & fees
Oct 30 - Oct 31
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.
A modern building with large glass windows and a covered walkway.
A formal dining room with a round table set for eight, surrounded by leather chairs, a chandelier, and potted plants.
A grand ballroom with ornate chandeliers, round tables with floral centerpieces, and elegant chairs.

14. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Theatre District, 2.6 km from Prairie District
United States
Deirdre
$190
$256 total
includes taxes & fees
Oct 31 - Nov 1
Palmer House a Hilton Hotel
A multi-story hotel with a prominent sign reading "Crowne Plaza."
A spacious lobby with high wooden pillars, a seating area with sofas and a bench, a fire feature, and a modern design.
A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".
A hotel room with a large bed, a desk with a computer, a TV, and a seating area with a chair and ottoman.

15. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.3 km from Prairie District
United States
Bethany
$161
$191 total
includes taxes & fees
Nov 15 - Nov 16
Crowne Plaza Chicago West Loop by IHG
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.
A modern gym with various exercise equipment, large windows, and a city view.
A view from a window with a cityscape in the background, including modern buildings and a clear sky.
A modern lounge area with seating, a bar, and large windows offering views.

16. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.9 km from Prairie District
United States
Sara
$195
$232 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt House Chicago/West Loop-Fulton Market
A spacious lobby with a long bar area, red curtains, and a patterned carpet.
A corridor with a checkered floor, rows of blue and white chairs, and string lights.
A large, historic building with a classic architectural style, featuring multiple floors and large windows.
A modern living room with a yellow sectional sofa, a red armchair, a blue patterned rug, and a marble coffee table.

17. Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
The Loop, 2.5 km from Prairie District
United States
Jamie
$228
$271 total
includes taxes & fees
Oct 25 - Oct 26
Canopy by Hilton Chicago Central Loop
A cozy room with a sofa, a dining table, and a window with a view of buildings.
A modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.
A lobby with two brown leather chairs, a marble table, and a large potted plant.
A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

18. LIVN - West Loop Chicago

LIVN - West Loop Chicago
2.8 km from Prairie District
United States
Jasmin
$238
$279 total
includes taxes & fees
Oct 16 - Oct 17
LIVN - West Loop Chicago
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.
A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.
A modern lobby with a seating area, a bar, and a green wall.

19. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Streeterville, 3.9 km from Prairie District
United States
Nicole
$131
$156 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Chicago - Magnificent Mile
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A modern living room with a fireplace, leather sofas, and a wooden floor.
A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.
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.

20. Central Loop Hotel

Central Loop Hotel
Theatre District, 2.5 km from Prairie District
Canada
Ziad
$148
$176 total
includes taxes & fees
Oct 25 - Oct 26
Central Loop Hotel
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Our prices for hotels in Chicago are cheapest in January

Price trends for hotels in Chicago

Pricing is based on two traveler single night rates
View properties in October

October

High 16°C / low 10°C. Sunny most days.
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Top landmarks in Prairie District

Glessner House Museum

Glessner House Museum is just one of the attractions in Near South Side, Chicago so you might want to stop by during your trip. If you want to experience more of the culture Chicago has to offer, head to Soldier Field, McCormick Place, and Millennium Park.
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Clarke House Museum

If museums are on your list of things to see, you might want to browse the collections at Clarke House Museum in Near South Side. Our travelers also like the art galleries and monuments in the area. If you want to see more of the museums in Chicago, you can easily walk to National Vietnam Veterans Art Museum or Glessner House Museum.
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Elbridge G Keith House

If you're planning a bit of sightseeing head to Elbridge G Keith House— just one of the monuments in Near South Side. Our travelers also love the museums and art galleries in the area— your sightseeing tour starts here.
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Chicago Women's Park

Chicago Women's Park is worth a pic or two when discovering Near South Side. Hotels.com travelers also like the art galleries, museums, and monuments in the area.
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William K Kimball House

10.0/10 (1 review)
If you're planning a bit of sightseeing head to William K Kimball House— just one of the monuments in Near South Side. Our travelers also love the art galleries and museums in the area— your sightseeing tour starts here.
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National Vietnam Veterans Art Museum

National Vietnam Veterans Art Museum is just one of the attractions in Near South Side, Chicago so you might want to stop by during your trip. If you want to experience more of the culture Chicago has to offer, head to Soldier Field, McCormick Place, and Millennium Park.
See properties

Joseph G Coleman House

If you're planning a bit of sightseeing head to Joseph G Coleman House— just one of the monuments in Near South Side. Our travelers also love the museums and art galleries in the area— your sightseeing tour starts here.
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Check out reviews of Prairie District hotels guests love

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.
A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.
A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago

10/10 Exceptional

United States
Jason
Hilton Garden Inn Chicago Downtown South Loop
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.
A bar area with a long counter, multiple liquor bottles, and a variety of glasses.
A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.
A restaurant with booths and tables, a television on the wall, and a view of the street outside.

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Exceptional

United States
Jennifer
Hilton Vacation Club Hotel Blake Chicago
A modern kitchen with a large window, a dining area, and a view of the sea.
A modern bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern living room with a sectional sofa, a fireplace, and a large window offering a city view.

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago

10/10 Exceptional

United States
Abra
Homewood Suites by Hilton Chicago Downtown South Loop
A modern interior with a bar area, seating, and decorative wooden panels.
A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.
A hotel room with a flat-screen TV, a wooden cabinet, a round table, a blue sofa, a desk with a computer, and a large window with curtains.
A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.

Best Western Grant Park Hotel

Best Western Grant Park Hotel
Downtown Chicago

10/10 Exceptional

United States
brian
Best Western Grant Park Hotel
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A conference room with a long table, chairs, and a large screen.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

Hilton Chicago

Hilton Chicago
Downtown Chicago

10/10 Exceptional

United States
Melissa
Hilton Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago

10/10 Exceptional

United States
Griffin
Sable at Navy Pier Chicago, Curio Collection by Hilton
A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.
A modern bar area with a bar counter, multiple stools, and a chandelier.
A cityscape with modern skyscrapers, a waterfront, and a winter setting.
A man and a woman walking down a marble staircase in a hotel lobby with a chandelier and a sign indicating an exit.

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
Downtown Chicago

10/10 Exceptional

United States
Dorothy
Silversmith Hotel Chicago Downtown
A modern hotel with a glass facade, multiple floors, and a prominent sign.
A modern living room with a large bookshelf, a sofa, a coffee table, and a view of the cityscape.
A modern retail space with a central wooden counter, a cityscape mural, and shelves stocked with snacks and beverages.
A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
Downtown Chicago

10/10 Exceptional

United States
Alexander
Hampton Inn Chicago West Loop Fulton Market Area
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.
A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago

10/10 Exceptional

United States
Julie
Congress Plaza Hotel
A hotel room with a large bed, two armchairs, a desk, and a view of a cityscape through large windows.
A hotel room with a large window, a dining area with a table and chairs, a sofa, a TV, and a decorative light fixture.
A hotel room with a city view, a dining area, a sofa, and a TV.
A spacious lobby with a glass entrance, escalators, and a tiled floor.

The Buckingham Hotel

The Buckingham Hotel
Downtown Chicago

10/10 Exceptional

United States
Roger
The Buckingham Hotel
A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.
A conference room with a long table, chairs, a projector screen, and a television on the wall.
A hotel room with two beds, a desk with a television, a chair, a ceiling fan, and a window with a view of a building.
A modern office setup with two monitors, a keyboard, and leather chairs.

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Downtown Chicago

10/10 Exceptional

United States
Lyn
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
A spacious lobby with a long bar area, red curtains, and a patterned carpet.
A corridor with a checkered floor, rows of blue and white chairs, and string lights.
A large, historic building with a classic architectural style, featuring multiple floors and large windows.
A modern living room with a yellow sectional sofa, a red armchair, a blue patterned rug, and a marble coffee table.

Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
Downtown Chicago

10/10 Exceptional

United States
Chelsea
Canopy by Hilton Chicago Central Loop
A corridor with ornate black metal railings and a patterned carpet.
A bed with a pillow featuring a pineapple design and the text "Sleep with me." A window reveals a cityscape at night.
A modern hotel room with a sofa, a small table, a bench, a TV, and a cabinet.
A multi-story building with a grid of windows, surrounded by other high-rise buildings.

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago

10/10 Exceptional

United States
Natalya
Staypineapple, An Iconic Hotel, The Loop
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.
A bar with a brick archway, wooden bar counter, and stools.
A modern living room with a fireplace, leather sofas, and a wooden floor.

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago

10/10 Exceptional

United States
Yuanhui
Club Quarters Hotel, Central Loop, Chicago
A multi-story hotel with a prominent sign reading "Crowne Plaza."
A spacious lobby with high wooden pillars, a seating area with sofas and a bench, a fire feature, and a modern design.
A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".
A hotel room with a large bed, a desk with a computer, a TV, and a seating area with a chair and ottoman.

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
Downtown Chicago

10/10 Exceptional

United States
Priya
Crowne Plaza Chicago West Loop by IHG
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.
A compact kitchen with a microwave, coffee maker, and sink.
A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.
A restaurant with booths, tables, and a green wall in the background.

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
Downtown Chicago

10/10 Exceptional

United States
Jose
Travelodge by Wyndham Downtown Chicago
A cozy room with a sofa, a dining table, and a window with a view of buildings.
A modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.
A lobby with two brown leather chairs, a marble table, and a large potted plant.
A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

LIVN - West Loop Chicago

LIVN - West Loop Chicago
Downtown Chicago

10/10 Exceptional

United States
Megan
LIVN - West Loop Chicago
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.
A modern gym with various exercise equipment, large windows, and a city view.
A view from a window with a cityscape in the background, including modern buildings and a clear sky.
A modern lounge area with seating, a bar, and large windows offering views.

Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
Downtown Chicago

10/10 Exceptional

United States
Valia
Hyatt House Chicago/West Loop-Fulton Market
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.
A bar with multiple shelves of bottles, a long counter, and several stools.
A spacious lobby with a fireplace, comfortable seating, and a modern chandelier.
A cozy reading area with a dark blue sofa, multiple bookshelves, and a small table with a drink and a glass.

The Hoxton, Chicago

The Hoxton, Chicago
Downtown Chicago

10/10 Exceptional

United States
Theoni
The Hoxton, Chicago