Book 5 Star Hotels in South Side

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Featured South Side 5 Stars Hotels

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

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

2.5 out of 5
6500 S Cicero Ave Chicago IL
Free Cancellation
7.22 mi from city center
$123 nightly
The price is $145 total per night
$145 total
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG features a 24-hour gym, free WiFi in public areas, and conference space. If you drive, self parking is USD 30 per night, or you can take advantage of the free airport shuttle (available 24 hours). The 24-hour front desk has multilingual staff ready to assist with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include a 24-hour business center, free newspapers, and laundry facilities.
Breakfast included
Free airport shuttle
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 out of 5
2357 S WENTWORTH AVE Chicago IL
Free Cancellation
Reserve now, pay when you stay
3.28 mi from city center
$112 nightly
The price is $131 total per night
$131 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
At SpringHill Suites by Marriott Chicago Chinatown, guests have access to a 24-hour gym, free WiFi in public areas, and a 24-hour business center. Self parking is offered for USD 30.00 per day. The 24-hour front desk has multilingual staff ready to assist with securing valuables and luggage storage. Additional amenities include coffee/tea in a common area, a meeting room, and a computer station.
Breakfast included
Free WiFi
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
6.72 mi from city center
$80 nightly
The price is $94 total per night
$94 total
Dec 7 - Dec 8
Total with taxes and fees
At Motel 6 - Chicago, IL, guests have access to coffee in a common area, laundry facilities, and a vending machine. A stay here includes free parking. The 24-hour front desk has staff always at the ready.
Pet friendly
Parking included
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
Free Cancellation
Reserve now, pay when you stay
3.53 mi from city center
$121 nightly
The price is $143 total per night
$143 total
Dec 14 - Dec 15
Total with taxes and fees
A 24-hour gym and free WiFi in public areas are features at Jaslin Hotel. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area.
Free WiFi
Air conditioning
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3 out of 5
5225 S Harper Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.07 mi from city center
$127 nightly
The price is $149 total per night
$149 total
Dec 7 - Dec 8
Total with taxes and fees
At Hyatt Place Chicago-South/University Medical Center, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. If you drive, self parking is USD 40.00 per night, and there's also a free area shuttle. The front desk is staffed 24/7 to help with tours or tickets, luggage storage, and dry cleaning/laundry. Additional amenities include a 24-hour business center, free newspapers, and a banquet hall.
Pet friendly
Free WiFi
Chinatown Hotel Chicago

Chinatown Hotel Chicago

1.5 out of 5
214 West 22nd Place Chicago IL
Free Cancellation
Reserve now, pay when you stay
3.46 mi from city center
$65 nightly
The price is $76 total per night
$76 total
Dec 7 - Dec 8
Total with taxes and fees
Chinatown Hotel Chicago features free WiFi in public areas, microwave in a common area, and refrigerator in a common area. The front desk is staffed 24/7 to help with tours or tickets, luggage storage, and securing valuables. Additional amenities include express check-out, free newspapers, and a vending machine.
Free WiFi
Air conditioning
Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

2.5 out of 5
7701, S Cicero Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.74 mi from city center
$94 nightly
The price is $109 total per night
$109 total
Dec 7 - Dec 8
Total with taxes and fees
Saratoga Motel By Capital O Near Midway Airport Chicago IL features free WiFi in public areas and an ATM. If you decide to drive, there's free parking. The 24-hour front desk has staff always at the ready. This hotel also has a vending machine.
Parking included
Free WiFi
Sophy Hyde Park

Sophy Hyde Park

4 out of 5
1411 East 53rd Street Chicago IL
1 mi from city center
$229 nightly
The price is $269 total per night
$269 total
Dec 12 - Dec 13
Total with taxes and fees
Sophy Hyde Park features a gym, free WiFi in public areas, and meeting rooms. Front-desk staff can answer questions 24/7, and assist with concierge services, luggage storage, and securing valuables. Other amenities at this luxury hotel include a 24-hour business center, a computer station, and a terrace.
Pet friendly
Free WiFi
Mccormick Place Guest House

Mccormick Place Guest House

3 out of 5
3643 South Indiana Avenue Chicago IL
1.71 mi from city center
$75 nightly
The price is $88 total per night
$88 total
Dec 5 - Dec 6
Total with taxes and fees
Mccormick Place Guest House features free WiFi in public areas and a garden. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a picnic area.
Parking included
Free WiFi
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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.

Best 5 star hotels in South Side

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in South Side. After all, treating yourself to the finer things is what vacations are about. 

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These South Side hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
South Side 5 star hotels and resorts typically offer luxury amenities such as:

  • Gourmet restaurant
  • Full-service fitness center with pool
  • Luxury spa 
  • Welcome gifts upon arrival
  • Top-of-the-line beds and linens 
  • Designer personal care products
  • Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in South Side with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place: 

  • Search hotels by price, ranging from $76 to $269
  • Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
  • Choose from 464 5 star hotels in South Side!

South Side hotels essential information

Accommodation
464 hotels
Lowest Price
$76
Highest Price
$269
Popular hotels
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG, SpringHill Suites by Marriott Chicago Chinatown, Motel 6 - Chicago, IL, Jaslin Hotel, Hyatt Place Chicago-South/University Medical Center, Chinatown Hotel Chicago, Saratoga Motel By Capital O Near Midway Airport Chicago IL, Sophy Hyde Park, Mccormick Place Guest House

Recent Reviews

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

5/5 Excellent
"Clean, good staff"
A verified traveler stayed at SpringHill Suites by Marriott Chicago Chinatown
Posted 1 day ago
SpringHill Suites by Marriott Chicago Chinatown

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