Cheap Flights to South Side from $27
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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 $46 and $27 for one-way flights to South Side for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MCO | Chicago | April 25 to May 2 | $46 |
| PHX | Chicago | April 24 to May 3 | $56 |
| ATL | Chicago | March 9 to March 11 | $59 |
| ATL | Chicago | April 28 to May 2 | $74 |
| PHX | Chicago | April 23 to April 26 | $78 |
| LAX | Chicago | April 25 to May 2 | $89 |
| MSP | Chicago | March 10 to March 11 | $97 |
| ATL | Rockford | April 14 to April 15 | $141 |
| MSP | Rockford | April 18 to April 21 | $155 |
| PHX | Rockford | April 18 to April 25 | $178 |
| LAX | Chicago | April 22 to April 25 | $190 |
| LAX | Rockford | April 22 to April 25 | $197 |
| MCO | Rockford | March 10 to March 11 | $201 |
| FCO | Chicago | May 1 to May 3 | $579 |
| FCO | Chicago | March 9 to March 10 | $1,842 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | February 21 to February 23 | $113 |
| MCO | Chicago | February 21 to March 1 | $131 |
| MCO | Chicago | February 21 to February 23 | $170 |
| PHX | Chicago | February 21 to February 28 | $191 |
| DEN | Chicago | February 22 to February 23 | $204 |
| MSP | Chicago | February 20 to February 22 | $274 |
| MSP | Chicago | February 20 to February 22 | $274 |
| LAX | Chicago | February 22 to February 28 | $281 |
| PHX | Chicago | February 20 to February 27 | $286 |
| ATL | Rockford | February 21 to February 24 | $305 |
| PHX | Rockford | February 21 to March 1 | $361 |
| MSP | Rockford | February 20 to February 22 | $479 |
| MCO | Rockford | February 20 to February 23 | $582 |
| LAX | Rockford | February 21 to February 23 | $675 |
| FCO | Chicago | February 21 to February 22 | $1,842 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $46 |
Number of Airlines Serving | |
Airlines Serving | Spirit Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing South Side Accommodation Deals
Chinatown Hotel Chicago
Great rooms With upgraded, Recently Renovated!
Reviewed on Feb 2, 2026
Jaslin Hotel
Great service and clean roomd
Reviewed on Jan 23, 2026
Best Western Grant Park Hotel
Location
Reviewed on Feb 9, 2026
Hyatt Regency McCormick Place Chicago
Great place to stay
Reviewed on Feb 10, 2026
Luxury Hotels in South Side
The Wheeler Mansion
A unique place to stay near the convention centre.
Reviewed on Jun 23, 2025
Best Western Grant Park Hotel
Location
Reviewed on Feb 9, 2026
Hyatt Regency McCormick Place Chicago
Great place to stay
Reviewed on Feb 10, 2026
Chinatown Hotel Chicago
Great rooms With upgraded, Recently Renovated!
Reviewed on Feb 2, 2026
Family Friendly Hotels in South Side
Hyatt Regency McCormick Place Chicago
Great place to stay
Reviewed on Feb 10, 2026
Best Western Grant Park Hotel
Location
Reviewed on Feb 9, 2026
Jaslin Hotel
Great service and clean roomd
Reviewed on Jan 23, 2026
Marriott Marquis Chicago
Connected to Wintrust Arena 👏
Reviewed on Feb 9, 2026
Best South Side Flight and Hotel Packages
South Side flight + hotel packages - economy flights
South Side flight + hotel packages - premium economy flights
South Side flight + hotel packages - first class flights
Need a Car For After Your Flight?
Special
$22
Midsize
$23
Standard
$24
Compact
$27
Frequently asked questions
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!