Cheap Flights to South Side from $45

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How Much Does it Cost To Fly To South Side?

The cheapest prices found with in the last 7 days for return flights were $87 and $45 for one-way flights to South Side for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
ATLChicagoAugust 12 to August 16$87
DENChicagoAugust 18 to August 20$91
IAHChicagoAugust 15 to August 18$94
DENChicagoAugust 15 to August 18$94
PHXChicagoAugust 28 to August 31$104
PHXChicagoAugust 31 to September 4$104
MCOChicagoJune 25 to June 28$111
IAHChicagoJuly 26 to August 2$114
LAXChicagoJune 21 to June 25$118
FLLChicagoJuly 9 to July 16$128
MSPChicagoAugust 6 to August 10$129
MCOChicagoJune 14 to June 14$135
MSYChicagoJuly 1 to July 5$169
FCOChicagoSeptember 4 to September 11$399
FCOChicagoJune 17 to June 24$785
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ATLChicagoJune 8 to June 12$167
MSPChicagoJune 8 to June 14$195
MCOChicagoJune 7 to June 11$222
ATLChicagoJune 8 to June 11$225
LAXChicagoJune 8 to June 14$226
IAHChicagoJune 8 to June 14$244
MCOChicagoJune 8 to June 10$247
DENChicagoJune 7 to June 9$249
MSYChicagoJune 8 to June 15$249
LAXChicagoJune 8 to June 14$261
PHXChicagoJune 8 to August 14$267
MSPChicagoJune 8 to June 12$274
FLLChicagoJune 8 to June 20$315
PHXChicagoJune 7 to June 11$416
FCOChicagoJune 8 to June 22$841
*Prices include taxes and fees

South Side ORD Flight Information

Traveling to
South Side ORD
Lowest Price
$87
Number of Airlines Serving
16
Airlines Serving
Spirit Airlines
Number of Daily Flights
56
Airlines with Direct Flights
American Airlines, Qatar Airways, JAL, Aer Lingus, Emirates, Air New Zealand, United Airlines, Alaska Airlines, Cathay Pacific, Turkish Airlines, Royal Jordanian, Finnair, Iberia, ANA, Lufthansa, British Airways

Find The Perfect Hotel For After Your Flight

Amazing South Side Accommodation Deals

Chinatown Hotel Chicago

Chinatown Hotel Chicago

1.5 out of 5
214 West 22nd Place, Chicago, IL
$99 nightly
The price is $116 total per night from Jun 9 to Jun 10
$116 total
Jun 9 - Jun 10
Total includes taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the property condition in our reviews. Popular ...
5.4/10 (1,001 reviews)
"Quiet and close to good food and bar."

Reviewed on Jun 1, 2025

Chinatown Hotel Chicago
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
$137 nightly
The price is $161 total per night from Jul 6 to Jul 7
$161 total
Jul 6 - Jul 7
Total includes taxes and fees
Stay at this 3-star hotel in Chicago. Enjoy a 24-hour fitness center, a 24-hour front desk, and premium TV channels. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,050 reviews)
"The hotel was quiet and feel safe to stay."

Reviewed on Jun 4, 2025

Jaslin Hotel
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
$115 nightly
The price is $135 total per night from Jul 1 to Jul 2
$135 total
Jul 1 - Jul 2
Total includes taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,516 reviews)
"This was our second stay at this hotel and we loved it. We love how the pastry restaurant is also connected to the hotel and it’s in walking distance of all of the attractions."

Reviewed on Jun 1, 2025

Best Western Grant Park Hotel
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Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
$227 nightly
The price is $266 total per night from Jun 30 to Jul 1
$266 total
Jun 30 - Jul 1
Total includes taxes and fees
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,005 reviews)
"Check in and check out was super quick and room was nice and clean"

Reviewed on Jun 2, 2025

Hyatt Regency McCormick Place Chicago
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.

Luxury Hotels in South Side

The Wheeler Mansion

The Wheeler Mansion

4 out of 5
2020 South Calumet Avenue, Chicago, IL
$616 nightly
The price is $724 total per night from Jun 6 to Jun 7
$724 total
Jun 6 - Jun 7
Total includes taxes and fees
Stay at this 4-star luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Grant Park are located ...
The Wheeler Mansion
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
$115 nightly
The price is $135 total per night from Jul 1 to Jul 2
$135 total
Jul 1 - Jul 2
Total includes taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,516 reviews)
"This was our second stay at this hotel and we loved it. We love how the pastry restaurant is also connected to the hotel and it’s in walking distance of all of the attractions."

Reviewed on Jun 1, 2025

Best Western Grant Park Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
$227 nightly
The price is $266 total per night from Jun 30 to Jul 1
$266 total
Jun 30 - Jul 1
Total includes taxes and fees
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,005 reviews)
"Check in and check out was super quick and room was nice and clean"

Reviewed on Jun 2, 2025

Hyatt Regency McCormick Place Chicago
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Chinatown Hotel Chicago

Chinatown Hotel Chicago

1.5 out of 5
214 West 22nd Place, Chicago, IL
$99 nightly
The price is $116 total per night from Jun 9 to Jun 10
$116 total
Jun 9 - Jun 10
Total includes taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the property condition in our reviews. Popular ...
5.4/10 (1,001 reviews)
"Quiet and close to good food and bar."

Reviewed on Jun 1, 2025

Chinatown Hotel Chicago
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.

Family Friendly Hotels in South Side

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
$227 nightly
The price is $266 total per night from Jun 30 to Jul 1
$266 total
Jun 30 - Jul 1
Total includes taxes and fees
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,005 reviews)
"Check in and check out was super quick and room was nice and clean"

Reviewed on Jun 2, 2025

Hyatt Regency McCormick Place Chicago
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
$115 nightly
The price is $135 total per night from Jul 1 to Jul 2
$135 total
Jul 1 - Jul 2
Total includes taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,516 reviews)
"This was our second stay at this hotel and we loved it. We love how the pastry restaurant is also connected to the hotel and it’s in walking distance of all of the attractions."

Reviewed on Jun 1, 2025

Best Western Grant Park Hotel
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
$137 nightly
The price is $161 total per night from Jul 6 to Jul 7
$161 total
Jul 6 - Jul 7
Total includes taxes and fees
Stay at this 3-star hotel in Chicago. Enjoy a 24-hour fitness center, a 24-hour front desk, and premium TV channels. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,050 reviews)
"The hotel was quiet and feel safe to stay."

Reviewed on Jun 4, 2025

Jaslin Hotel
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Marriott Marquis Chicago

Marriott Marquis Chicago

4 out of 5
2121 South Prairie Avenue, Chicago, IL
$165 nightly
The price is $194 total per night from Jul 1 to Jul 2
$194 total
Jul 1 - Jul 2
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 9 restaurants, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
9.2/10 Wonderful! (1,004 reviews)
"This was a wonderful hotel. The room was very comfortable, clean, and nicely decorated. It was close enough to Soldier Field that we could easily walk there for a concert."

Reviewed on Jun 2, 2025

Marriott Marquis Chicago
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.

Need a Car For After Your Flight?

Lowest prices found within the past 2 hours. Prices and availability subject to change. Additional terms may apply.

Plane Tickets To South Side

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to South Side. Browse through our inventory to explore a wide range of cheap flights to South Side to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in South Side as you anxiously await to exit the plane and explore what South Side has to offer. Considering all the amazing local food and culture in South Side, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to South Side to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to South Side without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to South Side with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to South Side today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.