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Oct 30 - Nov 1
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Top South Side 2 Star hotels

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundable
$121 nightly
The price is $140 total per night from Nov 22 to Nov 23
$140 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
8.2/10 Very Good! (1,008 reviews)
"Good"

Reviewed on Oct 23, 2026

Opens in a new windowHoliday Inn Chicago – Midway Airport S by IHG
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $117 total per night from Oct 25 to Oct 26
$117 total
Oct 25 - Oct 26
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. Laundry facilities are provided for your convenience.
Opens in a new windowMotel 6 - Chicago, IL
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
Fully refundable
$127 nightly
The price is $149 total per night from Nov 22 to Nov 23
$149 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling for business? Take advantage of ...
9/10 Wonderful! (1,371 reviews)
"Room was clean. Building well maintained. Breakfast was usual hotel fare. Parking was a bit congested. Had to park a good way from building. Only complaint, we were on 4th floor. There was a loud roar all night long. Must have been something on the roof. It was not the planes from the airport. Those ..."

Reviewed on Oct 24, 2026

Opens in a new windowHoliday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Carlton Inn Midway

Carlton Inn Midway

2 out of 5
4944 S Archer Ave Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $126 total per night from Oct 25 to Oct 26
$126 total
Oct 25 - Oct 26
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take ...
Opens in a new windowCarlton Inn Midway
Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90

2.5 out of 5
6535 S King Dr Chicago IL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $110 total per night from Oct 25 to Oct 26
$110 total
Oct 25 - Oct 26
Total with taxes and fees
Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free parking.
3.4/10 (157 reviews)
"This property should not be available for rent. Based on the reviews and our own experience, Expedia should seriously consider removing this place from its listings. I wouldn’t recommend it to anyone—not even my worst enemy. Neither the motel nor the surrounding neighborhood is suitable for tourists. ..."

Reviewed on Oct 19, 2026

Opens in a new windowBest Motel By OYO Chicago I-90
Villa Dubois Guest House

Villa Dubois Guest House

2 out of 5
3722 S Calumet Ave Chicago IL
$129 nightly
The price is $152 total per night from Nov 23 to Nov 24
$152 total
Nov 23 - Nov 24
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a communal living room, and express check-in are also on ...
Opens in a new windowVilla Dubois Guest House
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
$95 nightly
The price is $110 total per night from Oct 26 to Oct 27
$110 total
Oct 26 - Oct 27
Total with taxes and fees
A gym is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock ...
Opens in a new windowSaratoga Motel By Capital O Near Midway Airport Chicago IL
Rainbow Motel

Rainbow Motel

2 out of 5
7050 W Archer Ave Chicago IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Oct 26 to Oct 27
$109 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock ...
Opens in a new windowRainbow Motel
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

2.5 out of 5
9118 S Cottage Grove Ave Chicago IL
$94 nightly
The price is $110 total per night from Oct 25 to Oct 26
$110 total
Oct 25 - Oct 26
Total with taxes and fees
Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free parking.
4/10 (81 reviews)
"DO NOT book this Motel. We stayed 15 minutes and we had to leave. The clerk even said the pictures used for the rooms weren't those. We got put in a room that had partical board holding the mattress up. The bathroom door was complete busted out were the knob should be and 1 of the door panels was ..."

Reviewed on Oct 10, 2026

Opens in a new windowAdmiral Motel By Oyo Chicago I-94
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

2 out of 5
4900B S Lake Shore Dr, Chicago, IL, Chicago IL
This hotel features an outdoor pool and an indoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas.
10/10 Exceptional! (1 review)
"Clean room but in need of renovation"

Reviewed on May 22, 2023

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Opens in a new windowChicago Lake Shore Hotel
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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.

2 Star Hotels South Side

Looking to break out of your routine for some much needed rest and relaxation? Or maybe you’ve already decided it’s time for a trip and are trying to find affordable hotels in South Side that won’t bust your travel budget?

South Side 2 star hotels will give you everything you need to enjoy the city like a local, saving a ton of money so you can hit all the hot spots in town.

Have a delicious breakfast at your hotel to fuel up for your day of sightseeing, then enjoy amenities like fresh towels and linens, as well as a nice hot shower to unwind after a busy day of experiencing everything the city has to offer.

As you explore a new locale, or one you love to visit over and over, you can rest easy knowing you’re staying in a great hotel that lets you discover South Side and welcomes you back to a clean, comfortable room at night.

Browse Travelocity’s wide selection of 2 star hotels in South Side and find one that’s perfectly priced and places you next to all the best activities and sights. The town is your oyster, and we can help you seek out its secrets while sticking to your budget.

Recent South Side hotel reviews by fellow wanderers

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

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

4 out of 5
Posted 11 hours ago
Travelocity Verified Review
"Room was clean. Building well maintained. Breakfast was usual hotel fare. Parking was a bit congested. Had to park a good way from building. Only complaint, we were on 4th floor. There was a loud roar all night long. Must have been something on the roof. It was not the planes from the airport. Those were not bothersome. Over all it was a good hotel and area. We would stay there again."
A verified traveler stayed at Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

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