Cheap Flights to South Side
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| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MCO | Chicago | August 10 to August 17 | $124 |
| MSP | Chicago | September 3 to September 8 | $130 |
| MSP | Chicago | August 11 to August 12 | $137 |
| MSP | Rockford | August 11 to August 12 | $138 |
| ATL | Chicago | July 25 to July 28 | $138 |
| ATL | Chicago | June 23 to June 30 | $162 |
| MCO | Rockford | August 5 to August 11 | $171 |
| LAX | Chicago | July 22 to July 29 | $201 |
| ATL | Rockford | July 4 to July 8 | $211 |
| PHX | Chicago | August 18 to August 25 | $217 |
| LAX | Rockford | September 2 to September 5 | $226 |
| PHX | Chicago | August 4 to August 8 | $252 |
| PHX | Rockford | August 12 to August 19 | $253 |
| FCO | Chicago | August 26 to September 30 | $597 |
| FCO | Chicago | August 1 to August 2 | $1,389 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | June 6 to June 9 | $234 |
| MCO | Chicago | June 6 to June 17 | $253 |
| ATL | Chicago | June 6 to June 8 | $253 |
| PHX | Chicago | June 6 to June 13 | $262 |
| MSP | Chicago | June 6 to June 12 | $321 |
| MCO | Chicago | June 6 to June 16 | $328 |
| PHX | Rockford | June 6 to June 10 | $346 |
| ATL | Rockford | June 6 to June 9 | $359 |
| PHX | Chicago | June 6 to June 13 | $367 |
| MSP | Chicago | June 6 to June 7 | $378 |
| LAX | Chicago | June 6 to June 11 | $427 |
| LAX | Chicago | June 7 to June 9 | $461 |
| MSP | Rockford | June 6 to June 7 | $550 |
| LAX | Rockford | June 7 to June 9 | $609 |
| FCO | Chicago | June 5 to June 21 | $684 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $124 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, American Airlines, Southwest Airlines, Delta, Icelandair, Condor |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing South Side Accommodation Deals
Chinatown Hotel Chicago
"Bad experience. Staff terrible. No air conditioning. I do not recommend it at all."
Reviewed on May 28, 2026
Jaslin Hotel
"👌"
Reviewed on May 30, 2026
Best Western Grant Park Hotel
"Doors were loud and we could hear people talking and laughing in the next room over. Walls are super thin. Hotel seems old and in need of renovation."
Reviewed on May 30, 2026
Hyatt Regency McCormick Place Chicago
"I loved how nice the room was"
Reviewed on May 30, 2026
Luxury Hotels in South Side
The Wheeler Mansion
Best Western Grant Park Hotel
"Doors were loud and we could hear people talking and laughing in the next room over. Walls are super thin. Hotel seems old and in need of renovation."
Reviewed on May 30, 2026
Hyatt Regency McCormick Place Chicago
"I loved how nice the room was"
Reviewed on May 30, 2026
Chinatown Hotel Chicago
"Bad experience. Staff terrible. No air conditioning. I do not recommend it at all."
Reviewed on May 28, 2026
Family Friendly Hotels in South Side
Hyatt Regency McCormick Place Chicago
"I loved how nice the room was"
Reviewed on May 30, 2026
Best Western Grant Park Hotel
"Doors were loud and we could hear people talking and laughing in the next room over. Walls are super thin. Hotel seems old and in need of renovation."
Reviewed on May 30, 2026
Jaslin Hotel
"👌"
Reviewed on May 30, 2026
Marriott Marquis Chicago
"It was clean room and had an amazing view on the 36th floor."
Reviewed on May 30, 2026
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
$12
Midsize
$13
Standard
$13
Compact SUV
$16
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!