An airplane exhibit labeled "Concourse A" in an airport terminal.

Southwest Side Hotel Guide - Cheap Hotels in Southwest Side, Chicago

  • 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

Check availability on Southwest Side Cheap Hotels

Tonight
30 Sept - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Southwest Side cheap hotels

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 compact kitchenette with a built-in refrigerator, a coffee maker, and a small countertop.
A small bathroom with a white sink, a mirror, and a window with an air conditioning unit.

1. Rainbow Motel

Rainbow Motel
Garfield Ridge
United States
Jerry
€79
includes taxes & fees
6 Oct - 7 Oct
Rainbow Motel
A modern bar area with a bar counter, seating, and large windows offering a view of the street.
A reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.
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.

2. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Ashima
€144
includes taxes & fees
28 Oct - 29 Oct
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 reception area with a wooden reception desk, a sofa, and a coffee table.
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.

3. Carlton Inn Midway

Carlton Inn Midway
Archer Heights
United States
Icaro
€108
includes taxes & fees
5 Oct - 6 Oct
Carlton Inn Midway
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

Carleton of Oak Park
Oak Park
United States
Brad
€120
includes taxes & fees
5 Oct - 6 Oct
Carleton of Oak Park
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 bar with a brick archway, wooden bar counter, and stools.

5. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
United States
Julian
€155
includes taxes & fees
25 Oct - 26 Oct
Club Quarters Hotel, Central Loop, Chicago
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 hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

6. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Alan
€200
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.
A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.
A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

7. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
United States
Aran
€195
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Chicago Downtown South Loop
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.

8. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
Downtown Chicago
United States
Sandra
€164
includes taxes & fees
25 Oct - 26 Oct
Travelodge by Wyndham Downtown 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 bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.

9. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
United States
Cecilia
€201
includes taxes & fees
25 Oct - 26 Oct
Homewood Suites by Hilton Chicago Downtown South Loop
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 hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

10. The Wade

The Wade
Downtown Chicago
United States
Erin
€156
includes taxes & fees
25 Oct - 26 Oct
The Wade
View all properties

Top Southwest Side Hotel Reviews

Hilton Chicago

Hilton Chicago

8/10 Good
"It was my first time in Chicago. Stay was ok. But breakfast was not included."
Monica 3-night trip
Posted 8 hours ago
Hilton Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

8/10 Good
"The breakfast at Sonesta was very good! Could add more seating when when girl is full."
Carole 3-night trip
Posted 10 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Muy bueno todo . Excelente ubicación"
Julio 4-night trip
Posted 11 hours ago
The Chicago Hotel Collection - Magnificent Mile
River Hotel

River Hotel

8/10 Good
"The rooms were clean and beds were comfortable. The staff were very helpful and friendly"
Richard 2-night trip
Posted 11 hours ago
River Hotel
L7 Chicago by LOTTE

L7 Chicago by LOTTE

8/10 Good
"Nice bed in our king room. Location was perfect for us for all we had planned and coming in the CTA from midway . Disappointed no bar just the one next door at the restaurant that wasn’t open late at all . We flew in very early in morning hoped to get into a room early even if we had to pay extra but the check in person was no help at all in regards to check in early or any of our questions . Our family came in the next morning same time and this time a different check in person actually offered them to check in early ! We had nowhere to go so we walked a lot of the city waiting to check in . I think we walked 13 miles . Our room ,once we got it ,was nice tho we didn’t get the city view just the view across to a building and parking . Location was definitely the highlight of this hotel ."
sandra 2-night trip
Posted 11 hours ago
L7 Chicago by LOTTE
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Great"
justin 3-night trip
Posted 11 hours ago
The Royal Sonesta Chicago Downtown
Central Loop Hotel

Central Loop Hotel

10/10 Excellent
"Clean room"
Gordon 1-night trip
Posted 12 hours ago
Central Loop Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"The only improvement would be lighting above the desk."
Kevin 1-night trip
Posted 13 hours ago
Club Quarters Hotel, Central Loop, Chicago
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Traveling cross country and stayed at several hotel. This one was on point, from entering the hotel, smelling clean, the staff checking in was great, and the room was clean. I had an awesome stay."
Jose 2-night trip
Posted 16 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile

Explore a world of travel with Expedia