A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

South Side Two Star Hotels from S$123

  • 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 South Side 2 Star Hotels

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for South Side 2-star hotels

A modern bar area with a curved counter, multiple stools, and pendant lighting.
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 modern bar area with a bar counter, seating, and large windows offering a view of the street.

1. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Laura
S$179
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Chicago – Midway Airport S by IHG
A modern hotel room with a large bed, a bedside table, a nightstand, and a wall-mounted light fixture.
A bathroom with a marble wall, a bathtub, a toilet, and a shower curtain.
A multi-story motel with a parking lot.
A modern hotel room with a large bed, a nightstand, a wall-mounted lamp, and a door.

2. Motel 6 - Chicago, IL

Motel 6 - Chicago, IL
Washington Heights
United States
DENNIS
S$135
includes taxes & fees
8 Nov - 9 Nov
Motel 6 - Chicago, IL
A modern interior with a staircase, green upholstered seating, and artwork on the walls.
A hotel reception desk with a modern design, including a digital display and a sign indicating it is a non-smoking property.
A buffet area with various food options, including omelets and other dishes, displayed in stainless steel containers.
A hotel with a covered entrance, multiple windows, and a clear sky.

3. Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Bedford Park
United States
Ambreauna
S$191
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
A hotel room with two beds, a desk, a chair, a dresser, and a bathroom visible through an open door.
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.
A breakfast bar with coffee makers, a toaster, and a variety of pastries.

4. Carlton Inn Midway

Carlton Inn Midway
Archer Heights
United States
stephen T
S$161
includes taxes & fees
26 Oct - 27 Oct
Carlton Inn Midway
A room with large windows, a wooden floor, and a built-in air conditioning unit.
Parking
Reception
A hotel room with a large bed, a wooden headboard, a patterned bedspread, and a view through an open door to another room.

5. Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
Woodlawn
United States
Saul
S$123
includes taxes & fees
8 Nov - 9 Nov
Best Motel By OYO Chicago I-90
A hallway with wooden flooring, a dining area with a table and chairs, and a blue sofa.
A room with a wooden herringbone ceiling, a wall clock, and shelves with various decorative items and books.
A modern kitchen with white cabinets, stainless steel appliances, and patterned wallpaper.
A dining area with a wooden table and chairs, a rock sculpture centerpiece, and a large green wall art piece.

6. Villa Dubois Guest House

Villa Dubois Guest House
Bronzeville
United States
Yohannes
S$211
includes taxes & fees
2 Nov - 3 Nov
Villa Dubois Guest House
A hotel room with a bed, a desk, a chair, a lamp, and a window with curtains.
A motel with a row of parking spaces and a building with a red roof and beige walls.
Fitness facility
A room with a microwave on a counter, a door with a 'No Smoking' sign, and a window with a view of cars and trees.

7. Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL
Ashburn
United States
Pedro
S$140
includes taxes & fees
26 Oct - 27 Oct
Saratoga Motel By Capital O Near Midway Airport Chicago IL
A modern bathroom with a white vanity, a mirror, and a built-in sink.
A small bathroom with a white sink, a mirror, and a window with an air conditioning unit.
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 compact kitchen with a dining table and chairs, a built-in oven, and a refrigerator.

8. Rainbow Motel

Rainbow Motel
Garfield Ridge
United States
Jerry
S$126
includes taxes & fees
26 Oct - 27 Oct
Rainbow Motel
A multi-story building with a brick facade, multiple windows, and a covered walkway.
A brick building with a sign for the Admiral Motel.
A hallway with a glass door, a window with a view of the outside, and a ceiling-mounted air conditioning unit.
A bathroom with a toilet, sink, and bathtub.

9. Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94
Chatham
United States
Arlex
S$123
includes taxes & fees
8 Nov - 9 Nov
Admiral Motel By Oyo Chicago I-94
A hotel with a swimming pool, multiple balconies, and a row of lounge chairs.
A multi-story building with a yellow facade, parked cars, and a tree in the foreground.
A buffet area with a counter, chairs, and tables.
A hotel bathroom with a sink, mirror, and shower.

10. Chicago Lake Shore Hotel

Chicago Lake Shore Hotel
Kenwood
United States
Irma
Chicago Lake Shore Hotel
Exterior
Front of property
Room
Reception

11. Capital O Empire Motel Chicago I-94

Capital O Empire Motel Chicago I-94
Greater Grand Crossing
United States
Kylen
Capital O Empire Motel Chicago I-94
Exterior
Room
Dining
Bathroom

12. Amber Inn

Amber Inn
Bronzeville
United States
Anonymous traveller
Amber Inn
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in South Side.
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

4900 S Lake Shore Dr Chicago IL
S$212
1 Nov - 2 Nov
includes taxes & fees
Chicago Lake Shore Hotel
Jaslin Hotel

Jaslin Hotel

261 West Cermak Rd Chicago IL
S$213
4 Nov - 5 Nov
includes taxes & fees
9/10 Wonderful! (1,423 reviews)
Jaslin Hotel
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

2357 S WENTWORTH AVE Chicago IL
S$190
22 Nov - 23 Nov
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
SpringHill Suites by Marriott Chicago Chinatown
Still don't see what you're looking for?
See all properties in South Side.
You can also use these popular filters to refine your search.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about South Side

Discover the metropolitan area of South Side—museums, skyscrapers and top sights like Lake Michigan.

See all hotels in South Side
A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Top South Side Hotel Reviews

Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"Close to Midway with a free 25 hour shuttle. Newly renovated with super helpful staff. Great for the price."
Leslie 1-night trip
Posted 7 hours ago
Carlton Inn Midway
Villa Dubois Guest House

Villa Dubois Guest House

10/10 Excellent
"The room and interior are nice. There weren’t other people when I was staying. Getting in was easy. The place was clean."
Jason 3-night trip
Posted 11 days ago
Villa Dubois Guest House
Rainbow Motel

Rainbow Motel

8/10 Good
"Be careful not to get one of the themed rooms. We got the space ship room and it looked nothing like the picture on the website. If you get a regular room it's amazing."
Jacob 3-night trip
Posted 11 days ago
Rainbow Motel

Find out more about South Side

Find Your Ideal 2 Star Hotels in South Side

When you've got to get away to a new or favourite destination without breaking the bank, South Side awaits with top 2 star hotels and a change of scenery. Stay on your feet visiting top attractions that draw several of visitors, or settle in for a hot cuppa nearby and enjoy some R & R. You're about to find out why locals and travellers alike love this place. Pack your bags and get ready for new experiences and a relaxing stay in a city with strong overall 2 star hotels ratings. Guest reviews recommend their 2 star hotels in South Side, and it's time to find out why.

The Ideal Hotel at the Perfect Price

Motels are in high demand in South Side. You'll find the best deals right here, so book early and save on a great getaway. Thanks to budget-friendly prices and traveller-friendly amenities, past travellers have found an accommodation that's just right. Browse guest reviews to find out what they loved, liked, and can't wait to try again. The best travel is all about hospitality, and these motels have a strong service, these rooms are tidy and cosy. When you book with Expedia, you can stay all over the world, and the journey starts in South Side.

Reserve a Stay in a Two-Star Hotel Today!

Book your stay in this popular place today -- South Side is a destination on the rise. It's no secret that South Side is a great place to stay, so get the best deals while you can, and get to know exactly what everyone loves about South Side. Your home away from home is waiting. Book the best deals on 2-star hotels and motels in South Side now.

Explore a world of travel with Expedia