Cheap Flights to South Side from $25
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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 $50 and $25 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 | March 4 to March 7 | $57 |
| PHX | Chicago | February 19 to February 26 | $68 |
| MCO | Chicago | March 5 to March 10 | $91 |
| MSP | Chicago | March 31 to April 7 | $97 |
| MSP | Chicago | February 24 to February 25 | $100 |
| LAX | Chicago | March 17 to March 18 | $110 |
| DEN | Chicago | February 21 to February 28 | $131 |
| MSP | Rockford | February 24 to February 25 | $142 |
| ATL | Rockford | March 5 to March 7 | $162 |
| LAX | Chicago | February 12 to February 21 | $180 |
| DEN | Rockford | February 28 to March 3 | $183 |
| IAH | Rockford | April 15 to April 18 | $192 |
| PHX | Rockford | April 18 to April 25 | $218 |
| LAX | Rockford | March 10 to March 11 | $247 |
| FCO | Chicago | February 20 to February 27 | $467 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | February 7 to February 9 | $59 |
| ATL | Chicago | February 7 to February 9 | $80 |
| PHX | Chicago | February 6 to February 15 | $197 |
| ATL | Rockford | February 6 to February 28 | $207 |
| DEN | Chicago | February 8 to February 18 | $208 |
| LAX | Chicago | February 7 to February 10 | $234 |
| FLL | Chicago | February 6 to February 9 | $251 |
| MSP | Chicago | February 8 to February 9 | $252 |
| MSP | Chicago | February 8 to February 15 | $267 |
| FLL | Rockford | February 7 to February 10 | $303 |
| LAX | Chicago | February 6 to February 9 | $321 |
| DEN | Rockford | February 6 to February 10 | $329 |
| MCO | Rockford | February 7 to February 9 | $386 |
| PHX | Rockford | February 7 to February 9 | $397 |
| FCO | Chicago | February 6 to February 10 | $654 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $50 |
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
t
Reviewed on Jan 15, 2026
Jaslin Hotel
Great service and clean roomd
Reviewed on Jan 23, 2026
Best Western Grant Park Hotel
Clean rooms and friendly, helpful staff. Thin walls and you will hear the Columbia College students playing their music from across the street if facing that way. But we didn’t mind!
Reviewed on Jan 29, 2026
Hyatt Regency McCormick Place Chicago
The room and staff were great
Reviewed on Jan 6, 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
Clean rooms and friendly, helpful staff. Thin walls and you will hear the Columbia College students playing their music from across the street if facing that way. But we didn’t mind!
Reviewed on Jan 29, 2026
Hyatt Regency McCormick Place Chicago
The room and staff were great
Reviewed on Jan 6, 2026
Chinatown Hotel Chicago
t
Reviewed on Jan 15, 2026
Family Friendly Hotels in South Side
Hyatt Regency McCormick Place Chicago
The room and staff were great
Reviewed on Jan 6, 2026
Best Western Grant Park Hotel
Clean rooms and friendly, helpful staff. Thin walls and you will hear the Columbia College students playing their music from across the street if facing that way. But we didn’t mind!
Reviewed on Jan 29, 2026
Jaslin Hotel
Great service and clean roomd
Reviewed on Jan 23, 2026
Marriott Marquis Chicago
Great view
Reviewed on Jan 25, 2026
Best South Side Flight and Hotel Packages
South Side flight + hotel packages - economy flights
South Side flight + hotel packages - first class flights
Need a Car For After Your Flight?
Special
$3
Midsize
$4
Standard
$4
Compact SUV
$5
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!