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

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Check availability on Southwest Side Cheap Hotels

Tonight
30 Sep - 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 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.

1. Rainbow Motel

Rainbow Motel
Garfield Ridge
United States
Jerry
AED 283
AED 332 total
includes taxes & fees
5 Oct - 6 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 modern lobby with a vending machine, a statue, and an exit sign.

2. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Ashima
AED 481
AED 602 total
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 modern living room with a flat-screen TV mounted above a fireplace, flanked by two potted plants.
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 reception area with a wooden reception desk, a sofa, and a coffee table.

3. Carlton Inn Midway

Carlton Inn Midway
Archer Heights
United States
Icaro
AED 385
AED 452 total
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 bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.
A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.
A residential street with a sidewalk, houses, and greenery.

4. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Brad
AED 450
AED 499 total
includes taxes & fees
12 Oct - 13 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 hotel room with a large window, a bed, and a suitcase.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

5. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
United States
Julian
AED 543
AED 646 total
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 modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

6. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Alan
AED 609
AED 833 total
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 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 lobby with a reception desk, seating area, and a large window providing a view of the outdoors.
A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

7. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
United States
Aran
AED 684
AED 813 total
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
AED 573
AED 681 total
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 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.
A modern restaurant interior with a long counter, booths, and tables.

9. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
United States
Cecilia
AED 706
AED 839 total
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 lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.
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.

10. The Wade

The Wade
Downtown Chicago
United States
Erin
AED 547
AED 651 total
includes taxes & fees
25 Oct - 26 Oct
The Wade
View all properties

Top Southwest Side Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"Very comfortable beds.very nice bathroom. AC could be better"
Marek 5-night trip
Posted 1 hour ago
Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Easy check in/check out, easy and available parking, Friendly and helpful staff, clean and updated room"
Nicholas 1-night trip
Posted 1 hour ago
Hilton Chicago
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"EXCELLENT HOTEL. I will definitely stay there again when traveling to Chicago. Staff was amazing."
Lezlie 2-night trip
Posted 1 hour ago
Fairmont Chicago at Millennium Park
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"The room was really oddly laid out (It's an older building), but everything looked and felt nice. It has a nice modern look to everything, and the water was really hot which is rare for most hotels, especially in Chicago in my experience. The location is absolutely fantastic for downtown shopping, parks, pier, food. Two minute walk to the heart of the Magnificent Mile. There was a fridge, microwave, and coffee machine in the room. We stocked up on fresh pastries from a fantastic bakey a few stores down, and went to the 7-Eleven on the corner for drinks for late night snacks. I've stayed at maybe 10 different hotels in this class in Chicago and I think this is one of the better ones. For parking, just an app and save some(A LOT) money. Lots of garages nearby that discount heavily with apps."
Philip 1-night trip
Posted 1 hour ago
Hotel Saint Clair- Magnificent Mile
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Excelente"
David 1-night trip
Posted 3 hours ago
L7 Chicago by LOTTE
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"Clean room"
Connie 1-night trip
Posted 3 hours ago
The Chicago Hotel Collection - Magnificent Mile
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

8/10 Good
"Great location - very centrally located."
Synova 3-night trip
Posted 4 hours ago
Club Quarters Hotel, Central Loop, Chicago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"If I could give more than 5 stars I would. The staff was amazing and extremely accommodating and flexible. The rooms were gorgeous and the hotel was beautiful."
Afra 1-night trip
Posted 4 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"We enjoyed our stay and first visit to Chicago. All the staff were very helpful except one young lady at desk unable to help us with questions about the L train and told us to use our phones. We are an older couple 76& 80 and would have appreciated some assistance."
Loretta 4-night trip
Posted 4 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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