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

Cheap Hotels & Resorts in Southwest Side from NZ$159

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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 bar area with a bar counter, seating, and large windows offering a view of the street.
A modern lobby with a vending machine, a statue, and an exit sign.
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 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
Ashima
NZ$289
includes taxes & fees
28 Oct - 29 Oct
Holiday Inn Chicago – Midway Airport S by IHG
A modern hotel room with a large bed, a flat-screen TV mounted on the ceiling, and a nightstand with a lamp.
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.
A compact kitchen with a dining table and chairs, a built-in oven, and a refrigerator.

2. Rainbow Motel

Rainbow Motel
Garfield Ridge
United States
Jerry
NZ$159
includes taxes & fees
13 Oct - 14 Oct
Rainbow Motel
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 breakfast bar with coffee makers, a toaster, and a variety of pastries.
A modern living room with a flat-screen TV mounted above a fireplace, flanked by two potted plants.

3. Carlton Inn Midway

Carlton Inn Midway
Archer Heights
United States
Icaro
NZ$217
includes taxes & fees
1 Oct - 2 Oct
Carlton Inn Midway
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A residential street with a sidewalk, houses, and greenery.
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
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
Brad
NZ$240
includes taxes & fees
12 Oct - 13 Oct
Carleton of Oak Park
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 hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

5. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Alan
NZ$402
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
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.

6. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
United States
Guadalupe
NZ$310
includes taxes & fees
26 Oct - 27 Oct
Congress Plaza Hotel
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
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.
A modern living room with a fireplace, leather sofas, and a wooden floor.

7. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
United States
Julian
NZ$310
includes taxes & fees
25 Oct - 26 Oct
Club Quarters Hotel, Central Loop, 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.

8. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
United States
Aran
NZ$393
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 restaurant with booths, tables, and a green wall in the background.
A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.
A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.

9. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
Downtown Chicago
United States
Sandra
NZ$327
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.
A modern restaurant interior with a long counter, booths, and tables.
A modern living room with a sectional sofa, a fireplace, and a large window offering a city view.
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

10. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
United States
Cecilia
NZ$403
includes taxes & fees
25 Oct - 26 Oct
Homewood Suites by Hilton Chicago Downtown South Loop
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 7 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 10 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 10 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 10 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 11 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 15 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile

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