Cheap Flights to South Side from $30
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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 $58 and $30 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* |
|---|---|---|---|
| PHX | Chicago | January 31 to February 7 | $59 |
| PHX | Chicago | February 19 to February 26 | $59 |
| ATL | Chicago | January 24 to February 3 | $98 |
| ATL | Chicago | January 14 to January 25 | $98 |
| MSP | Chicago | April 5 to April 9 | $101 |
| LAX | Chicago | March 10 to March 17 | $130 |
| MSP | Chicago | January 17 to January 18 | $135 |
| ATL | Rockford | February 11 to February 14 | $140 |
| MSP | Rockford | January 17 to January 20 | $144 |
| MCO | Rockford | February 13 to February 18 | $179 |
| LAX | Chicago | January 12 to January 26 | $182 |
| PHX | Rockford | February 4 to February 25 | $201 |
| LAX | Rockford | March 31 to April 7 | $239 |
| FCO | Chicago | February 17 to March 1 | $470 |
| FCO | Chicago | February 16 to February 28 | $800 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | January 2 to January 19 | $224 |
| ATL | Chicago | January 2 to January 6 | $246 |
| MCO | Chicago | January 2 to January 30 | $291 |
| PHX | Chicago | January 4 to January 11 | $310 |
| MSP | Chicago | January 4 to January 5 | $314 |
| PHX | Chicago | January 3 to February 18 | $329 |
| MCO | Chicago | January 3 to January 7 | $362 |
| LAX | Chicago | January 4 to January 31 | $399 |
| ATL | Rockford | January 3 to January 10 | $449 |
| MSP | Rockford | January 3 to January 5 | $460 |
| MCO | Rockford | January 3 to January 10 | $563 |
| LAX | Rockford | January 3 to January 5 | $666 |
| MSP | Chicago | January 2 to January 3 | $723 |
| LAX | Chicago | January 3 to January 5 | $780 |
| FCO | Chicago | January 4 to September 25 | $1,547 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $58 |
Number of Airlines Serving | |
Airlines Serving | Frontier 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
Excellent
Reviewed on Dec 19, 2025
Jaslin Hotel
Staff was friendly and very helpful. Hotel was really clean
Reviewed on Dec 21, 2025
Best Western Grant Park Hotel
Affordable
Reviewed on Dec 29, 2025
Hyatt Regency McCormick Place Chicago
Great place to stay to walk to Soldier Stadium!
Reviewed on Dec 23, 2025
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
Affordable
Reviewed on Dec 29, 2025
Hyatt Regency McCormick Place Chicago
Great place to stay to walk to Soldier Stadium!
Reviewed on Dec 23, 2025
Chinatown Hotel Chicago
Excellent
Reviewed on Dec 19, 2025
Family Friendly Hotels in South Side
Hyatt Regency McCormick Place Chicago
Great place to stay to walk to Soldier Stadium!
Reviewed on Dec 23, 2025
Best Western Grant Park Hotel
Affordable
Reviewed on Dec 29, 2025
Jaslin Hotel
Staff was friendly and very helpful. Hotel was really clean
Reviewed on Dec 21, 2025
Marriott Marquis Chicago
Clean, modern hotel. If you’re in town for an event at the convention center or arena, you can’t beat it for convenience. Gym was nice, also has a few food options as well.
Reviewed on Dec 18, 2025
Best South Side Flight and Hotel Packages
South Side flight + hotel packages - economy flights
South Side flight + hotel packages - premium economy flights
Need a Car For After Your Flight?
Special
$4
Midsize SUV
$7
Compact SUV
$8
Standard
$9
Frequently asked questions
Plane Tickets To South Side
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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!