Lodging Image

Find hotels in Southwest Side, IL from $64

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Filter by

Star rating

Guest rating

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 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.
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

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Fabian
$162 nightly
$188 total
Sep 27 - Sep 28
Total with taxes and fees
Holiday Inn Chicago – Midway Airport S by IHG
A hotel room with two beds, a desk, a chair, a dresser, and a bathroom visible through an open door.
A breakfast bar with coffee makers, a toaster, and a variety of pastries.
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.

2. Carlton Inn Midway

Carlton Inn Midway
Archer Heights
United States
Icaro
$119 nightly
$140 total
Sep 24 - Sep 25
Total with taxes and fees
Carlton Inn Midway
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 kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.
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.

3. Rainbow Motel

Rainbow Motel
Garfield Ridge
United States
Jerry
$86 nightly
$100 total
Sep 24 - Sep 25
Total with taxes and fees
Rainbow Motel
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
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.

4. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Suzanne
$133 nightly
$148 total
Sep 30 - Oct 1
Total with taxes and fees
Carleton of Oak Park
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.

5. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
United States
John
$316 nightly
$376 total
Oct 14 - Oct 15
Total with taxes and fees
Hilton Vacation Club Hotel Blake Chicago
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 modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

6. The Wade

The Wade
Downtown Chicago
United States
Fernanda
$149 nightly
$177 total
Sep 27 - Sep 28
Total with taxes and fees
The Wade
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
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.
A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

7. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
United States
John
$188 nightly
$223 total
Sep 27 - Sep 28
Total with taxes and fees
Congress Plaza Hotel
A large, historic building with a central courtyard surrounded by trees.
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.
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

8. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Alan
$208 nightly
$248 total
Oct 24 - Oct 25
Total with taxes and fees
Hilton Chicago
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 modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.

9. LIVN - West Loop Chicago

LIVN - West Loop Chicago
Downtown Chicago
Canada
chidubem
$182 nightly
$214 total
Sep 27 - Sep 28
Total with taxes and fees
LIVN - West Loop Chicago
A modern interior with a bar area, seating, and decorative wooden panels.
A reception area with a marble counter, decorative Buddha statues, and a wall with a quote.
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.

10. Best Western Grant Park Hotel

Best Western Grant Park Hotel
Downtown Chicago
United States
Paige
$188 nightly
$224 total
Sep 27 - Sep 28
Total with taxes and fees
Best Western Grant Park Hotel
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.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Shanequa
$320 nightly
$380 total
Sep 27 - Sep 28
Total with taxes and fees
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 hotel room with a large window, a bed, and a suitcase.
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.

12. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
United States
Michael
$142 nightly
$169 total
Sep 27 - Sep 28
Total with taxes and fees
Club Quarters Hotel, Central Loop, Chicago
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.
A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.
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.

13. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
Downtown Chicago
United States
Tremecka
$152 nightly
$179 total
Sep 27 - Sep 28
Total with taxes and fees
Travelodge by Wyndham Downtown Chicago
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.
A man in a suit sitting by a window with a vase of red flowers.
A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.
A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

14. River Hotel

River Hotel
Downtown Chicago
United States
Isabella
$179 nightly
$213 total
Sep 27 - Sep 28
Total with taxes and fees
River Hotel
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.

15. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
Downtown Chicago
United States
Tamika
$220 nightly
$262 total
Sep 27 - Sep 28
Total with taxes and fees
Hyatt Centric The Loop Chicago
A grand lobby with a central bar, high ceilings, and classical architecture.
A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.
A grand hallway with ornate ceiling, chandeliers, and a reception desk at the end.
A modern living room with a sofa set, ottoman, and armchairs.

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

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
United States
Amanda
$135 nightly
$161 total
Sep 27 - Sep 28
Total with taxes and fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
A bar area with a marble countertop, bar stools, and a variety of bottles.
A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.
A spacious lobby with a marble floor, a reception desk, and a glass partition.

17. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
Downtown Chicago
United States
Sean Robert
$289 nightly
$343 total
Oct 13 - Oct 14
Total with taxes and fees
Hotel Riu Plaza Chicago
A spacious lobby with a central coffee table, sofas, and a large mirror.
A spacious lobby with high ceilings, large arched windows, and a grand staircase.
A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

18. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
United States
Michael T.
$206 nightly
$245 total
Sep 27 - Sep 28
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
A cityscape at dusk with high-rise buildings, including a Hilton hotel.
A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.
A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.
A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

19. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
United States
Brian
$204 nightly
$239 total
Oct 1 - Oct 2
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites
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 modern restaurant with round tables and booths, a high ceiling with exposed beams, and a brick accent wall with the text "RVE DELTA".
A spacious lobby with a seating area, a reception desk, and a large screen.

20. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
Downtown Chicago
United States
Victoria
$189 nightly
$224 total
Sep 27 - Sep 28
Total with taxes and fees
Crowne Plaza Chicago West Loop by IHG
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 scene.
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

Balzekas Museum of Lithuanian Culture

10.0/10 (1 review)
You can spend time exploring the galleries in Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area, or check out 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

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.
Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"Really nice hotel. Clean and comfortable staff was very helpful. Rooftop bar was a plus. It was also quiet."
Shandaka 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Great Stay"
Johny 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Everything was excellent"
Shaira V 4-night trip
Posted 2 hours ago
L7 Chicago by LOTTE
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"Great hotel in a super location. We had a room with a living area which was lovely. Wish they had coffee all day and not just until 10/11’ish We will stay there again"
Miranda 4-night trip
Posted 4 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"I’ve stayed here for years. Every riot"
James 4-night trip
Posted 5 hours ago
Congress Plaza Hotel
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"The hotel was absolutely stunning! Loved the convenience of it being right down town!"
Amanda 1-night trip
Posted 8 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Great place"
James 3-night trip
Posted 10 hours ago
Hyatt Regency Chicago
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

10/10 Excellent
"amazing and friendly staff"
Amelia 2-night trip
Posted 23 hours ago
Holiday Inn Chicago – Midway Airport S by IHG

More cheap stays in Southwest Side

Motel 6 Naperville, IL

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL
$57 nightly
$64 total
Oct 7 - Oct 8
Total with taxes and fees
Motel 6 Naperville, IL
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL
$62 nightly
$70 total
Oct 4 - Oct 5
Total with taxes and fees
Motel 6 Elk Grove Village, IL - O'Hare
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL
$118 nightly
$139 total
Oct 13 - Oct 14
Total with taxes and fees
Sleep Inn Midway Airport Bedford Park
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL
$152 nightly
$179 total
Sep 27 - Sep 28
Total with taxes and fees
Travelodge by Wyndham Downtown Chicago
Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

640 N Wabash Ave Chicago IL
$190 nightly
$226 total
Sep 27 - Sep 28
Total with taxes and fees
8.4/10 Very Good! (1,347 reviews)
Holiday Inn Express Chicago - Magnificent Mile by IHG
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL
$195 nightly
$231 total
Sep 27 - Sep 28
Total with taxes and fees
Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Southwest Side with star-rating

Explore a world of travel with Expedia