𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Southwest Side from RM369 (2026) - Fully Refundable Options

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

Go beyond your typical stay in Southwest Side

Pet friendly

Apartment

Apart hotel

Condo

Spa

Pool

Family friendly

Hot tub

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Southwest Side hotels

A modern bar area with a curved counter, multiple stools, and pendant lighting.

A reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.

A hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.

A modern lobby with a vending machine, a statue, and an exit sign.

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Laura

RM453

RM573 total

includes taxes & fees

22 Nov - 23 Nov

A hotel room with two beds, a desk, a chair, a dresser, and a bathroom visible through an open door.

A modern living room with a grey sofa, a round coffee table, and a chair. There are framed pictures on the wall and a window providing natural light.

A modern living room with a flat-screen TV mounted above a fireplace, flanked by two potted plants.

A reception area with a wooden reception desk, a sofa, and a coffee table.

2. Carlton Inn Midway

Archer Heights

stephen T

RM437

RM513 total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel room with a large bed, a flat-screen TV mounted on the ceiling, and a nightstand with a lamp.

A small bathroom with a white sink, a mirror, and a window with an air conditioning unit.

A compact kitchen with a dining table and chairs, a built-in oven, and a refrigerator.

A compact kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.

3. Rainbow Motel

Garfield Ridge

Jerry

RM342

RM402 total

includes taxes & fees

6 Nov - 7 Nov

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

A modern conference room with a wooden table, white chairs, a potted plant, and a large window with decorative plants.

A hotel room with two beds, a television, a desk with a lamp, and a patterned carpet.

A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.

4. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

Sotina

RM655

RM778 total

includes taxes & fees

15 Nov - 16 Nov

A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

A hotel lobby with a large Christmas tree, a sofa with red and white pillows, a glass coffee table, and a large window with a view of the street.

A modern interior with wooden flooring, black furniture, and large windows offering city views.

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

5. Hotel 505 River North

Downtown Chicago

Jordan

RM649

RM903 total

includes taxes & fees

23 Nov - 24 Nov

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

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.

A modern gym with various exercise equipment, large windows, and a city view.

6. Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

Georgianna

RM552

RM656 total

includes taxes & fees

23 Nov - 24 Nov

A modern hotel with a glass facade, multiple floors, and a visible entrance.

A gym with cardio machines, weight benches, and a large window offering a city view.

A reception area with a modern design, including a reception desk, a decorative wall, and a display case with snacks.

A modern hotel room with a large window, a desk with a lamp, a sofa, and a chair.

7. Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Cordula

RM482

RM573 total

includes taxes & fees

23 Nov - 24 Nov

A modern kitchen with a large window, a dining area, and a view of the sea.

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

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.

8. Homewood Suites by Hilton Chicago Downtown South Loop

Downtown Chicago

Cynthia

RM448

RM533 total

includes taxes & fees

23 Nov - 24 Nov

A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

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.

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

Downtown Chicago

Angela

RM535

RM777 total

includes taxes & fees

23 Nov - 24 Nov

A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise 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 entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

10. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Aran

RM396

RM471 total

includes taxes & fees

23 Nov - 24 Nov

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

A hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

A modern conference room with a marble table, patterned chairs, a flat-screen TV, and a large window with a view of trees and parked cars.

A spacious lobby with a modern design, featuring a seating area with sofas and chairs, a coffee table, and a large flat-screen TV mounted on the wall.

11. SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

Sergio

RM395

RM439 total

includes taxes & fees

3 Nov - 4 Nov

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

A residential street with a sidewalk, houses, and greenery.

12. Carleton of Oak Park

Oak Park

Brad

RM500

RM555 total

includes taxes & fees

27 Oct - 28 Oct

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

A modern lobby with a reception desk, seating area, staircase, and decorative lighting.

A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.

A modern hotel with a corner location, large windows, and a green awning.

13. Hampton Inn & Suites Chicago Downtown

Downtown Chicago

Tracy

RM432

RM514 total

includes taxes & fees

24 Nov - 25 Nov

A spacious hotel lobby with a large seating area, a flat-screen TV, and a view of the ocean.

A hotel lobby with seating areas, a fireplace, and a staircase.

A spacious lobby with a grand piano, comfortable seating areas, and a fireplace.

A grand ballroom with ornate chandeliers, a multi-tiered wedding cake centerpiece, and elegant floral arrangements on tables.

14. Hilton Chicago

Downtown Chicago

Anna

RM552

RM776 total

includes taxes & fees

22 Nov - 23 Nov

A multi-story hotel with a prominent sign reading "Crowne Plaza."

A hotel room with a large bed, a desk with a computer, a TV, and a seating area with a chair and ottoman.

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".

15. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Chriselda

RM511

RM607 total

includes taxes & fees

23 Nov - 24 Nov

A cityscape at dusk with illuminated skyscrapers and a river.

A modern bar area with a long counter, multiple bar stools, and a large flat-screen TV.

An outdoor dining area with tables and umbrellas, overlooking a river with a bridge and high-rise buildings in the background.

A spacious lobby with a central bar area, seating, and a large window offering a city view.

16. Holiday Inn Chicago Dwtn - The Mart by IHG

Downtown Chicago

Pamela

RM535

RM758 total

includes taxes & fees

23 Nov - 24 Nov

A modern hotel lobby with seating areas, a reception desk, and an elevator.

A modern interior with a bar area, seating, and decorative wooden panels.

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

A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.

17. Best Western Grant Park Hotel

Downtown Chicago

Colin

RM401

RM477 total

includes taxes & fees

23 Nov - 24 Nov

A rooftop terrace with outdoor seating, a pergola, and a view of surrounding high-rise buildings.

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 hotel room with a sofa, a small table, a kitchen area with wine bottles, and large windows offering a view of the building's exterior.

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

Downtown Chicago

Brock

RM552

RM656 total

includes taxes & fees

22 Nov - 23 Nov

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

A spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.

A multi-level indoor area with a central water feature, surrounded by seating areas and greenery.

A multi-story hotel with a prominent 'Embassy Suites' sign, a Starbucks Coffee shop, and a well-lit street at night.

19. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

RM517

RM615 total

includes taxes & fees

22 Nov - 23 Nov

A hotel with a classic facade, large windows, and flags.

A hotel lobby with leather seating, a flat-screen TV, and large windows with a view of the cityscape.

A hotel lobby with a bar area, a chandelier, and a reception desk.

A view through a circular window of a cityscape with modern buildings and a body of water in the distance.

20. Residence Inn Chicago Downtown/Loop

Downtown Chicago

Karla

RM584

RM695 total

includes taxes & fees

22 Nov - 23 Nov

View all properties

Compare top hotels in Southwest Side

Holiday Inn Chicago – Midway Airport S by IHG West Lawn View	Carlton Inn Midway Archer Heights View	Rainbow Motel Garfield Ridge View	Hilton Vacation Club Hotel Blake Chicago Downtown Chicago View	Hotel 505 River North Downtown Chicago View
8.2 Very good 1,009 reviews	5.8 1,008 reviews	5.4 71 reviews	9.6 Exceptional 1,214 reviews	9.2 Wonderful 2,973 reviews
RM453 RM573 total includes taxes & fees 22 Nov - 23 Nov	RM437 RM513 total includes taxes & fees 25 Oct - 26 Oct	RM342 RM402 total includes taxes & fees 6 Nov - 7 Nov	RM655 RM778 total includes taxes & fees 15 Nov - 16 Nov	RM649 RM903 total includes taxes & fees 23 Nov - 24 Nov

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)

After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

See properties

Union Stock Yard Gate

You can find out about the history of Chicago with a trip to Union Stock Yard Gate.

See properties

Balzekas Museum of Lithuanian Culture

10.0/10 (1 review)

You can spend time studying the exhibits at Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area or visit its top-notch restaurants.

See properties

S.S. Peter and Paul Church

After visiting S.S. Peter and Paul Church, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

See properties

Ephraim Bajar Cultural Center

Enjoy an outing to Ephraim Bajar Cultural Center during your stay in Chicago. Amble around the area's parks or visit its churches.

See properties

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

See all hotels in Southwest Side

An airport with multiple runways, parked airplanes, and a large terminal building.

Top Southwest Side Hotel Reviews

L7 Chicago by LOTTE

10/10 Excellent

"Great location and very nice room"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Great place to stay! Cool rooftop."

The Wade

8/10 Good

"I don’t know if this is normal but u can always hear the elevator all night long going up and down, Beds are hard, not my ting"

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Buena ubicación y precio"

Arlo Chicago

10/10 Excellent

"Very nice hotel."

More cheap stays in Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

RM330

RM369 total

3 Nov - 4 Nov

includes taxes & fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

RM372

RM437 total

15 Nov - 16 Nov

includes taxes & fees

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

RM395

RM439 total

3 Nov - 4 Nov

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

RM483

RM574 total

22 Nov - 23 Nov

includes taxes & fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

RM511

RM587 total

1 Nov - 2 Nov

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

RM527

RM627 total

9 Nov - 10 Nov

includes taxes & fees

7.8/10 Good! (2,938 reviews)

Southwest Side hotels from RM369

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Southwest Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Southwest Side hotels

1. Holiday Inn Chicago – Midway Airport S by IHG

2. Carlton Inn Midway

3. Rainbow Motel

4. Hilton Vacation Club Hotel Blake Chicago

5. Hotel 505 River North

6. Hyatt House Chicago/West Loop-Fulton Market

7. Hyatt Place Chicago/Downtown - The Loop

8. Homewood Suites by Hilton Chicago Downtown South Loop

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

10. Hilton Garden Inn Chicago Downtown South Loop

11. SureStay Plus Hotel by Best Western Chicago Lombard

12. Carleton of Oak Park

13. Hampton Inn & Suites Chicago Downtown

14. Hilton Chicago

15. Crowne Plaza Chicago West Loop by IHG

16. Holiday Inn Chicago Dwtn - The Mart by IHG

17. Best Western Grant Park Hotel

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

19. Embassy Suites by Hilton Chicago Downtown River North

20. Residence Inn Chicago Downtown/Loop

Compare top hotels in Southwest Side

Holiday Inn Chicago – Midway Airport S by IHG

Carlton Inn Midway

Rainbow Motel

Hilton Vacation Club Hotel Blake Chicago

Hotel 505 River North

Stay near popular Southwest Side attractions

Marquette Park

Union Stock Yard Gate

Balzekas Museum of Lithuanian Culture

S.S. Peter and Paul Church

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

L7 Chicago by LOTTE

The Chicago Hotel Collection - Magnificent Mile

The Wade

Hotel Saint Clair- Magnificent Mile

Arlo Chicago

More cheap stays in Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook

Sleep Inn Midway Airport Bedford Park

SureStay Plus Hotel by Best Western Chicago Lombard

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago-O'Hare International Airport

Travelodge by Wyndham Downtown Chicago

Explore a world of travel with Expedia

Go further with the Expedia app