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Hotels in Prairie District

October 2026
14
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 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.
A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

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
Jodi
$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 large bed, a flat-screen TV, a desk with a lamp, and a chair.
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.

2. Best Western Grant Park Hotel

Best Western Grant Park Hotel
The Loop, 1.3 km from Prairie District
United States
Matthew
$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.
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.
A modern restaurant interior with a long counter, booths, and tables.

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 marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
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
Charlie
$166
$226 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 modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.
A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.

5. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
The Loop, 2 km from Prairie District
United States
Dean
$172
$204 total
includes taxes & fees
Nov 3 - Nov 4
Hilton Vacation Club Hotel Blake Chicago
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.
A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.
A compact kitchen with a microwave, coffee maker, and sink.
A restaurant with booths, tables, and a green wall in the background.

6. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
The Loop, 1.9 km from Prairie District
United States
Mara
$115
$137 total
includes taxes & fees
Nov 12 - Nov 13
Travelodge by Wyndham Downtown 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 cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

7. Congress Plaza Hotel

Congress Plaza Hotel
The Loop, 2 km from Prairie District
United States
Angela
$129
$153 total
includes taxes & fees
Nov 10 - Nov 11
Congress Plaza Hotel
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 view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

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
$201
$273 total
includes taxes & fees
Nov 12 - Nov 13
Sable at Navy Pier Chicago, Curio Collection by Hilton
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A bar with a brick archway, wooden bar counter, and stools.
A hotel room with a large window, a bed, and a suitcase.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

9. 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 spacious lobby with a glass entrance, escalators, and a tiled floor.
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.

10. 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 living room with a dark sofa set, a glass coffee table, and a decorative chandelier.
A cityscape with modern skyscrapers, a waterfront, and a winter setting.
A modern bar area with a bar counter, multiple stools, and a chandelier.

11. 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 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 spacious lobby with a seating area, a reception desk, and a large screen.
A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

12. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.3 km from Prairie District
United States
Bethany
$169
$201 total
includes taxes & fees
Nov 1 - Nov 2
Crowne Plaza Chicago West Loop by IHG
A cozy room with a sofa, a dining table, and a window with a view of buildings.
A hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.
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.

13. LIVN - West Loop Chicago

LIVN - West Loop Chicago
2.8 km from Prairie District
United States
Jasmin
$222
$261 total
includes taxes & fees
Oct 15 - Oct 16
LIVN - West Loop Chicago
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 grand ballroom with ornate chandeliers, round tables with floral centerpieces, and elegant chairs.
A person overlooking a cityscape from a high vantage point.

14. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Theatre District, 2.6 km from Prairie District
United States
Melinda
$190
$256 total
includes taxes & fees
Oct 31 - Nov 1
Palmer House a Hilton Hotel
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.
A modern lounge area with seating, a bar, and large windows offering views.
A modern interior with a long counter, glass partitions, and a brick wall backdrop.
A view from a window with a cityscape in the background, including modern buildings and a clear sky.

15. 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
Lobby
A modern living room with a fireplace, leather armchairs, a sofa, and a coffee table.
A hotel with a classic facade, multiple flags, and a prominent entrance.
A spacious hotel lobby with a bar area, dining tables, and a central seating area.

16. The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop
Theatre District, 3.1 km from Prairie District
United States
Cynthia
$149
$209 total
includes taxes & fees
Nov 12 - Nov 13
The Allegro Royal Sonesta Hotel Chicago Loop
A snack bar with various packaged snacks and beverages.
A modern hotel lobby with a bar area, seating arrangements, and a television screen.
A modern hotel room with a cityscape mural, a desk with a chair, a sofa, a small table, and a lamp.
A modern hotel lobby with a seating area, a refrigerator stocked with beverages, and a table with snacks.

17. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
Theatre District, 3 km from Prairie District
United States
sylvie
$158
$187 total
includes taxes & fees
Nov 1 - Nov 2
Cambria Hotel Chicago Loop - Theatre District
A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.
A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.
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.

18. 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
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 modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.
A modern living room with a fireplace, leather sofas, and a wooden floor.

19. 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
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.
A rooftop pool area with lounge chairs and a view of the city skyline.
A bar with multiple shelves of bottles, a long counter, and several stools.
A cozy reading area with a dark blue sofa, multiple bookshelves, and a small table with a drink and a glass.

20. The Hoxton, Chicago

The Hoxton, Chicago
3.8 km from Prairie District
United States
Rebecca
$219
$290 total
includes taxes & fees
Nov 1 - Nov 2
The Hoxton, Chicago
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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 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.
A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

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 modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.
A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.

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.
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.
A modern restaurant interior with a long counter, booths, and tables.

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 large bed, a flat-screen TV, a desk with a lamp, and a chair.
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.

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 marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
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 view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

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 living room with a dark sofa set, a glass coffee table, and a decorative chandelier.
A cityscape with modern skyscrapers, a waterfront, and a winter setting.
A modern bar area with a bar counter, multiple stools, and a chandelier.

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
Downtown Chicago

10/10 Exceptional

United States
Dorothy
Silversmith Hotel Chicago Downtown
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 cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago

10/10 Exceptional

United States
Julie
Congress Plaza 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 spacious lobby with a seating area, a reception desk, and a large screen.
A modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".

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 hotel room with a large bed, two armchairs, a desk, and a view of a cityscape through large windows.
A spacious lobby with a glass entrance, escalators, and a tiled floor.
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.

The Buckingham Hotel

The Buckingham Hotel
Downtown Chicago

10/10 Exceptional

United States
Roger
The Buckingham Hotel
A cozy room with a sofa, a dining table, and a window with a view of buildings.
A hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.
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 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 multi-story building with a grid of windows, surrounded by other high-rise buildings.
A dining area with tables and chairs, a hanging light fixture, and a view of the street through a window.

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 modern hotel lobby with large windows, leather sofas, and a view of the cityscape.
A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.
A compact kitchen with a microwave, coffee maker, and sink.
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 building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A bar with a brick archway, wooden bar counter, and stools.
A hotel room with a large window, a bed, and a suitcase.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

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 rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.
A modern lounge area with seating, a bar, and large windows offering views.
A modern interior with a long counter, glass partitions, and a brick wall backdrop.
A view from a window with a cityscape in the background, including modern buildings and a clear sky.

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
Lobby
A modern living room with a fireplace, leather armchairs, a sofa, and a coffee table.
A hotel with a classic facade, multiple flags, and a prominent entrance.
A spacious hotel lobby with a bar area, dining tables, and a central seating area.

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago

10/10 Exceptional

United States
Philippe
The Allegro Royal Sonesta Hotel Chicago Loop
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.
A rooftop pool area with lounge chairs and a view of the city skyline.
A bar with multiple shelves of bottles, a long counter, and several stools.
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
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago

10/10 Exceptional

United States
Erin
L7 Chicago by LOTTE
The Intercontinental hotel facade with a large American flag and a floral display.
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago

10/10 Exceptional

United States
Rosemary
InterContinental Chicago Magnificent Mile by IHG