Photo by Richard Remington

South Side Hotels from from S$89

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12 Dec - 13 Dec
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13 Dec - 14 Dec
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19 Dec - 21 Dec

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Our top choices for South Side hotels

View from property
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center
3.0 star property
Hyde Park
8.8 out of 10, Excellent, (1001)
Immerse yourself in a prime location at this business-friendly Chicago hotel, a short walk from the Hyde Park station. Enjoy convenient access to Lake Michigan, University of Chicago, and a 24-hour fitness centre. The property includes a restaurant and free area shuttle.
"Great stay"
United States
Nikhil
The price is S$193
includes taxes & fees
25 Dec - 26 Dec
Hyatt Place Chicago-South/University Medical Center
Lobby
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1000)
Experience convenience at this Chicago hotel near Wintrust Arena and State Street, with Cermak-Chinatown Station just 5 minutes away. Fuel your day with complimentary buffet breakfast and stay active in the 24-hour fitness centre. Soldier Field and Millennium Park are nearby attractions.
"Clean, good staff"
Canada
Veronique E
The price is S$170
includes taxes & fees
1 Jan - 2 Jan, 2026
SpringHill Suites by Marriott Chicago Chinatown
View from room
Sophy Hyde Park

Sophy Hyde Park

Sophy Hyde Park
4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (1001)
"Great staff, location and ambience."
United States
Jaison
The price is S$282
includes taxes & fees
21 Dec - 22 Dec
Sophy Hyde Park
Exterior
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

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

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
2.5 star property
Bedford Park
8.8 out of 10, Excellent, (1233)
Located just minutes from Midway Airport with 24-hour free shuttle service, this hotel puts you near restaurants and shops. Enjoy the daily buffet breakfast and comfortable beds. A quiet retreat with fitness centre access and helpful staff to enhance your Chicago stay.
"Will definitely stay there again ."
United States
Jose Remedios
The price is S$170
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Serves lunch, dinner and happy hour
Chicago Marriott Midway

Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very good, (910)
"The property was excellent the rooms fantastic and the staff were equally wonderful and helpful. "
United States
Leilani
The price is S$208
includes taxes & fees
19 Dec - 20 Dec
Chicago Marriott Midway
View from room
Jaslin Hotel

Jaslin Hotel

Jaslin Hotel
3.0 star property
Chinatown
9.0 out of 10, Wonderful, (1182)
This clean hotel near Cermak-Chinatown Station offers free WiFi and a 24-hour fitness centre. Within walking distance of McCormick Place and a short drive to Soldier Field and Lake Michigan, guests appreciate the helpful staff and convenient location.
"Excellent service, clean room, great location"
United States
Stefan
The price is S$184
includes taxes & fees
21 Dec - 22 Dec
Jaslin Hotel
Living area
Villa Dubois Guest House

Villa Dubois Guest House

Villa Dubois Guest House
2.0 star property
Bronzeville
8.6 out of 10, Excellent, (78)
Just 5 minutes from McCormick Place and Lake Michigan, this welcoming Chicago guesthouse offers complimentary WiFi and parking. Indiana Station is a 10-minute walk away, with Soldier Field and State Street nearby for exciting urban adventures.
"My stay was very pleasant. The accommodation was comfortable, easily accessible, and well connected to public transport. I highly recommend it to anyone visiting the area."
United States
Lizeth
The price is S$114
includes taxes & fees
14 Dec - 15 Dec
Villa Dubois Guest House
Living area
Mccormick Place Guest House

Mccormick Place Guest House

Mccormick Place Guest House
3.0 star property
Bronzeville
8.8 out of 10, Excellent, (47)
Charming guesthouse offering free WiFi and parking with a tranquil garden retreat. Just minutes from Rate Field and a quick drive to McCormick Place and Lake Michigan. Soldier Field and Millennium Park await nearby for urban exploration.
"Very good place,nice host "
Canada
Qiang
The price is S$114
includes taxes & fees
15 Dec - 16 Dec
Mccormick Place Guest House
Free WiFi, bed sheets
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

Motel 6 - Chicago, IL
2.0 star property
Washington Heights
7.0 out of 10, Good, (200)
Tranquil accommodation near Abbott Park and Martin Luther King Drive offer complimentary WiFi and parking. Just a 3-minute drive from 95th Street - Longwood Station and within 15 minutes of Lake Michigan, this motel provides 24-hour front desk service.
"Everything was very nice even staff"
United States
Maurice
The price is S$109
includes taxes & fees
26 Dec - 27 Dec
Motel 6 - Chicago, IL
Reception
Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport
2.5 star property
Burbank
6.6 out of 10, (1000)
Conveniently located within a 15-minute drive of Chicago Midway Airport, this hotel offers complimentary continental breakfast, WiFi, and self parking. The fitness centre keeps your workout routine intact while helpful staff ensure a pleasant stay near Chicago Ridge Shopping Mall.
"Room was very clean and staff did a great job at upkeeping. Not too far from Midway airport where you can use the CTA to get downtown if needed. "
United States
Markus
The price is S$138
includes taxes & fees
21 Dec - 22 Dec
Best Western Inn & Suites - Midway Airport
Restaurant
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.4 out of 10, Very good, (1000)
"Great stay"
United States
Maria
The price is S$174
includes taxes & fees
4 Jan - 5 Jan, 2026
Holiday Inn Chicago – Midway Airport S by IHG
Premium bedding, desk, laptop workspace, soundproofing
Carlton Inn Midway

Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.4 out of 10, (1001)
Located just minutes from Midway Airport, this hotel offers a complimentary shuttle service available 24 hours daily. Enjoy free Wi-Fi, parking, and continental breakfast each morning. The fitness centre provides workout options, while Pulaski Station is a 7-minute walk away.
"The room was clean and satisfied our needs. Was handy using their shuttle to Midway Airport."
United States
Charles
The price is S$150
includes taxes & fees
1 Jan - 2 Jan, 2026
Carlton Inn Midway
Front of property
Chinatown Hotel Chicago

Chinatown Hotel Chicago

Chinatown Hotel Chicago
1.5 star property
Chinatown
5.4 out of 10, (1000)
Situated just 3 minutes from Cermak-Chinatown Station, this Chicago hotel offers free WiFi and daily housekeeping. Explore nearby attractions like Lake Michigan, State Street shops, and local restaurants, all within a short drive or walk.
"Friendly staff and heater was working great "
United States
Anthony
The price is S$89
includes taxes & fees
21 Dec - 22 Dec
Chinatown Hotel Chicago
Exterior
Skylark Motel

Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.6 out of 10, (119)
Located in Chicago with easy access to McCormick Place and Wintrust Arena, this motel offers complimentary WiFi and parking. The 24-hour front desk ensures round-the-clock assistance, while Soldier Field and Lake Michigan are just a short drive away.
"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."
United States
Stephen
The price is S$127
includes taxes & fees
16 Dec - 17 Dec
Skylark Motel
Desk, iron/ironing board, free WiFi, bed sheets
Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL
2.5 star property
Ashburn
7.0 out of 10, Good, (29)
"Clean room friendly staff "
United States
Christian
The price is S$113
includes taxes & fees
14 Dec - 15 Dec
Saratoga Motel By Capital O Near Midway Airport Chicago IL
Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown
2.0 star property
Bridgeport
Stylish Apartment near Chicago Downtown
Exterior
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94
2.5 star property
Chatham
3.8 out of 10, (45)
Just 10 minutes from University of Chicago and Griffin Museum, this Chicago hotel provides free valet parking and convenient room service. Abbott Park attractions are nearby, with 91st Street Station just a 4-minute walk away for citywide exploration.
"Fine stay "
United States
Sharmaine
The price is S$123
includes taxes & fees
26 Dec - 27 Dec
Admiral Motel By Oyo Chicago I-94
Desk, bed sheets
Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.0 star property
Woodlawn
3.4 out of 10, (48)
Located just a short drive from University of Chicago and State Street, this motel offers free valet parking and convenient daily housekeeping. King Drive Station is a 7-minute walk away, making city exploration effortless while visiting nearby Griffin Museum of Science and Industry.
"Clean room "
United States
Pierre
The price is S$109
includes taxes & fees
11 Jan - 12 Jan, 2026
Best Motel By OYO Chicago I-90
Free WiFi, bed sheets
Rainbow Motel

Rainbow Motel

Rainbow Motel
2.0 star property
Garfield Ridge
5.8 out of 10, (18)
Located within a short drive of Chicago's top attractions, this hotel offers free WiFi and complimentary parking. Enjoy room service after exploring nearby Lake Michigan or catch a game at United Centre. SeatGeek Stadium is just minutes away.
"It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people "
United States
Conner
The price is S$160
includes taxes & fees
15 Dec - 16 Dec
Rainbow Motel
Exterior
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1478)
Enjoy facials and manicures at this tranquil urban retreat just minutes from Clark-Division Station. The coffee shop transforms into an evening cocktail bar, while Michigan Avenue and Chicago Riverwalk wait to be explored nearby.
"I really liked this location - we will stay here again. "
United States
Lynnsey
The price is S$142
includes taxes & fees
21 Dec - 22 Dec
Claridge House Chicago, Tapestry Collection by Hilton
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.
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Stay near popular Great Lakes attractions

Aerial View of a large University in the Chicago Neighborhood of Hyde Park

University of Chicago

4.3/5 (1,552 reviews)
Explore the campus of University of Chicago during your travels in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
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Beautiful Museum of Science and Industry captured through the blossomed trees in Chicago, USA

Griffin Museum of Science and Industry

4.6/5 (1,713 reviews)
A large museum close to downtown Chicago with plenty for all ages to see and do, with exhibits including a coal mine and World War II submarine.
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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
I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck.
Photo by Richard Remington
Open Photo by Richard Remington

Top South Side Hotel Reviews

Jaslin Hotel

Jaslin Hotel

10/10 Excellent
"Many dining options were within a few steps. The staff was very welcoming. The only disappointment was the lack of a continental breakfast. "
Thomas 6-night trip
Posted 2 days ago
Jaslin Hotel

More cheap stays in South Side

Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL
The price is S$109 per night from 26 Dec to 27 Dec
S$109
26 Dec - 27 Dec
includes taxes & fees
6.8/10 (199 reviews)

Hotels in South Side with star rating

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