Southwest Side Hotel & Accommodation Deals 2026 from AU$100 - Compare prices by date

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

Spa

Pool

Spa pool

Apart hotel

Family friendly

Condo

Apartment

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Southwest Side hotels

A modern bar area with a bar counter, seating, and large windows offering a view of the street.

A modern bar area with a curved counter, multiple stools, and pendant lighting. A menu board is visible on the wall, and a coffee machine is on the counter.

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

1. Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Fabian

AU$254

includes taxes & fees

25 Oct - 26 Oct

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 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.

A breakfast bar with coffee makers, a toaster, and a variety of pastries.

2. Carlton Inn Midway

Archer Heights

Icaro

AU$175

includes taxes & fees

28 Sept - 29 Sept

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

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

A reception desk with a glass partition, a no pets allowed sign, a no smoking sign, a QR code for check-in, and a sign indicating a 1-minute wait for guests.

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

3. Rainbow Motel

Garfield Ridge

Jerry

AU$128

includes taxes & fees

28 Sept - 29 Sept

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 lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

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

4. Carleton of Oak Park

Oak Park

Suzanne

AU$193

includes taxes & fees

28 Sept - 29 Sept

A spacious lobby with a central coffee table, sofas, and a large mirror.

A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

A spacious lobby with high ceilings, large arched windows, and a grand staircase.

5. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Michael T.

AU$273

includes taxes & fees

25 Oct - 26 Oct

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.

6. The Wade

Downtown Chicago

Fernanda

AU$253

includes taxes & fees

27 Sept - 28 Sept

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

7. Congress Plaza Hotel

Downtown Chicago

John

AU$272

includes taxes & fees

26 Oct - 27 Oct

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 hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.

8. LIVN - West Loop Chicago

Downtown Chicago

chidubem

AU$270

includes taxes & fees

27 Sept - 28 Sept

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

A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

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.

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

Downtown Chicago

Shanequa

AU$559

includes taxes & fees

27 Sept - 28 Sept

A large, historic building with a central courtyard surrounded by trees.

A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

10. Hilton Chicago

Downtown Chicago

Alan

AU$313

includes taxes & fees

24 Oct - 25 Oct

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

A conference room with a long table, chairs, and a vase.

A man in a suit sitting by a window with a vase of red flowers.

11. River Hotel

Downtown Chicago

Isabella

AU$290

includes taxes & fees

27 Sept - 28 Sept

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".

12. Crowne Plaza Chicago West Loop by IHG

Downtown Chicago

Victoria

AU$287

includes taxes & fees

27 Sept - 28 Sept

A modern hotel with a glass facade, multiple floors, and a prominent sign.

A modern conference room with a large oval table, multiple chairs, and a city view through large windows.

A hotel reception desk with a marble counter, a digital kiosk, and a sign indicating Hilton Honors.

A modern dining area with a central island, chairs, pendant lights, and a decorative wall with a motivational quote.

13. Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

Rebecca

AU$349

includes taxes & fees

27 Sept - 28 Sept

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 restaurant interior with brick walls, wooden tables and chairs, and a bar area.

A hotel room with a large window, a bed, and a suitcase.

14. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

Michael

AU$247

includes taxes & fees

25 Oct - 26 Oct

A hotel entrance with a marquee sign, a glass awning, and a blue carpet leading to the door.

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

A modern bathroom with a dual sink vanity, a large mirror, and a toilet.

15. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

John

AU$533

includes taxes & fees

14 Oct - 15 Oct

A grand lobby with a central bar, high ceilings, and classical architecture.

A modern living room with a sofa set, ottoman, and armchairs.

A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.

A modern living room with a round dining table, bar stools, a purple armchair, and a sofa with cushions.

16. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Amanda

AU$270

includes taxes & fees

27 Sept - 28 Sept

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

A conference room with a long table, chairs, and a projector screen.

A grilled pineapple on top of a stack of meat, served on a pan.

The exterior of the Hyatt Centric The Loop hotel with a prominent American flag, a classic facade, and a glass entrance.

17. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

AU$374

includes taxes & fees

27 Sept - 28 Sept

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 reception area with a marble counter, decorative Buddha statues, and a wall with a quote.

18. Best Western Grant Park Hotel

Downtown Chicago

Damilola

AU$289

includes taxes & fees

25 Oct - 26 Oct

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

A gym with treadmills, ellipticals, and weight machines.

A modern high-rise hotel with multiple floors, large windows, and a well-lit entrance area.

A modern indoor swimming pool with blue seating and a view of the city through large windows.

19. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Carmina

AU$323

includes taxes & fees

27 Sept - 28 Sept

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 restaurant with booths, tables, and a green wall in the background.

A compact kitchen with a microwave, coffee maker, and sink.

20. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Tremecka

AU$270

includes taxes & fees

25 Oct - 26 Oct

View all properties

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

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

Union Stock Yard Gate

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

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

Recent Reviews in Southwest Side

Congress Plaza Hotel

10/10 Excellent

"Tina in cafe at breakfast was awesome! Made my day! See you-all next time!"

Hyatt Regency Chicago

8/10 Good

"Staff was great. View room was nice and quiet. Just know this is a very busy hotel. Elevators were an adventure."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"We loved the vintage feel and location."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"staff was super friendly and helpful!"

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Great location, close to the pink line, river is walkable distance, lots of restaurants etc. close parking if you don’t want to pay valet. Downside: no coffee in the room, they have it in the lobby but I like a good garbage coffee before I get dressed (Starbucks is attached as well if you want to pay for coffee). Second was many of the restaurants close on the weekend since it’s the business district."

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"The room was very clean and spacious. Our check in was easy and the staff was very helpful with recommendations. Didn't make it for the breakfast but it sounded like it was good after meeting some other guest."

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"The room was nice, small, but clean and nice! Staff were friendly and very helpful! It was in a great area with plenty of places in walking distance!"

More cheap accommodation in Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook

7535 Kingery Highway Willowbrook IL

AU$100

30 Sept - 1 Oct

includes taxes & fees

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

AU$101

28 Sept - 29 Sept

includes taxes & fees

6.8/10 (2,341 reviews)

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

AU$153

4 Oct - 5 Oct

includes taxes & fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

AU$236

27 Sept - 28 Sept

includes taxes & fees

9.4/10 Exceptional! (2,385 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

AU$270

25 Oct - 26 Oct

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

AU$330

27 Sept - 28 Sept

includes taxes & fees

Explore a world of travel with Expedia

Activities in Chicago

Book Hotels in Southwest Side on Expedia.com

Search Southwest Side hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Southwest Side

Check prices for these dates

Filter by

Property class

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. Carleton of Oak Park

5. The Chicago Hotel Collection Ambassador Gold Coast

6. The Wade

7. Congress Plaza Hotel

8. LIVN - West Loop Chicago

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

10. Hilton Chicago

11. River Hotel

12. Crowne Plaza Chicago West Loop by IHG

13. Hampton Inn Chicago West Loop Fulton Market Area

14. Club Quarters Hotel, Central Loop, Chicago

15. Hilton Vacation Club Hotel Blake Chicago

16. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

17. Hyatt Centric The Loop Chicago

18. Best Western Grant Park Hotel

19. Aloft by Marriott Chicago Mag Mile

20. Travelodge by Wyndham Downtown Chicago

Stay near popular Southwest Side attractions

Marquette Park

Balzekas Museum of Lithuanian Culture

Union Stock Yard Gate

S.S. Peter and Paul Church

Ephraim Bajar Cultural Center

Learn more about Southwest Side

Top Southwest Side Hotel Reviews

Recent Reviews in Southwest Side

Congress Plaza Hotel

Hyatt Regency Chicago

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection - Magnificent Mile

The Allegro Royal Sonesta Hotel Chicago Loop

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Hotel Saint Clair- Magnificent Mile

More cheap accommodation in Southwest Side

Red Roof Inn PLUS+ Chicago - Willowbrook

Motel 6 Schiller Park, IL - Chicago O'Hare

SureStay Plus Hotel by Best Western Chicago Lombard

Hampton Inn Chicago-O'Hare International Airport

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

Explore a world of travel with Expedia

Go further with the Expedia app