Cheap Flights to South Side from $28
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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 $66 and $28 for one-way flights to South Side for the period specified. Prices and availability are subject to change. Additional terms apply
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$66 Roundtrip, just found
$66
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MCO | Chicago | April 30 to May 4 | $69 |
| ATL | Chicago | April 24 to April 27 | $73 |
| MCO | Chicago | April 30 to May 4 | $79 |
| PHX | Chicago | April 30 to May 4 | $80 |
| MSP | Chicago | June 9 to June 16 | $117 |
| MSP | Chicago | June 9 to June 16 | $117 |
| PHX | Chicago | May 2 to May 4 | $129 |
| MSP | Rockford | June 16 to June 17 | $138 |
| MCO | Rockford | June 3 to June 10 | $169 |
| LAX | Chicago | April 18 to April 22 | $180 |
| ATL | Rockford | May 27 to June 2 | $196 |
| LAX | Rockford | April 23 to April 28 | $220 |
| PHX | Rockford | May 13 to May 19 | $259 |
| FCO | Chicago | April 17 to April 21 | $580 |
| FCO | Chicago | April 19 to June 23 | $1,109 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| IAH | Chicago | April 10 to April 13 | $126 |
| ATL | Chicago | April 11 to April 18 | $164 |
| ATL | Chicago | April 12 to April 16 | $175 |
| MSY | Chicago | April 11 to April 19 | $215 |
| DEN | Chicago | April 11 to April 14 | $239 |
| MSP | Chicago | April 12 to April 16 | $240 |
| PHX | Chicago | April 10 to April 17 | $259 |
| LAX | Chicago | April 12 to April 24 | $310 |
| LAX | Chicago | April 10 to April 13 | $357 |
| DEN | Rockford | April 10 to April 11 | $377 |
| PHX | Rockford | April 10 to April 11 | $384 |
| ATL | Rockford | April 12 to April 14 | $423 |
| MSP | Rockford | April 12 to April 14 | $629 |
| MSP | Chicago | April 12 to April 14 | $646 |
| LAX | Rockford | April 10 to April 13 | $790 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $66 |
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
214 West 22nd Place Chicago IL
$67 nightly
The price is $79 total per night from Apr 9 to Apr 10
$79 total
Apr 9 - Apr 10
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Grant Park are located ...
5.6/10 (1,001 reviews)
Amazing location. Not a bad place. If you need a clean safe place with nothing fancy it works. Solid stay for the price.
Reviewed on Mar 30, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$107 nightly
The price is $126 total per night from Apr 28 to Apr 29
$126 total
Apr 28 - Apr 29
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,197 reviews)
The hotel was in a prime location to allowing easy access to explore the China Town. It was also in close enough distance to the event we were there for at the McCormick place which allowed us to take a quick bus ride there. The hotel was extremely clean and well kept. The staff were friendly and ...
Reviewed on Apr 7, 2026
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$113 nightly
The price is $132 total per night from Apr 16 to Apr 17
$132 total
Apr 16 - Apr 17
Total with 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 ...
8.2/10 Very Good! (2,671 reviews)
The entire property felt like it wasn’t level, the room slanted in the middle, the carpeting was ripped and disgusting. Furniture and fixtures were outdated and very worn. Overall, just a terrible hotel. Would not stay again…ever.
Reviewed on Apr 7, 2026
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
$210 nightly
The price is $247 total per night from May 7 to May 8
$247 total
May 7 - May 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,075 reviews)
Room newly renovated and beautiful.
Reviewed on Apr 6, 2026
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
2020 South Calumet Avenue Chicago IL
$620 nightly
The price is $724 total per night from Apr 12 to Apr 13
$724 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Grant Park are located ...
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$113 nightly
The price is $132 total per night from Apr 16 to Apr 17
$132 total
Apr 16 - Apr 17
Total with 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 ...
8.2/10 Very Good! (2,671 reviews)
The entire property felt like it wasn’t level, the room slanted in the middle, the carpeting was ripped and disgusting. Furniture and fixtures were outdated and very worn. Overall, just a terrible hotel. Would not stay again…ever.
Reviewed on Apr 7, 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
$210 nightly
The price is $247 total per night from May 7 to May 8
$247 total
May 7 - May 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,075 reviews)
Room newly renovated and beautiful.
Reviewed on Apr 6, 2026
Save an average of 15% on thousands of hotels when you're signed in
Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
$67 nightly
The price is $79 total per night from Apr 9 to Apr 10
$79 total
Apr 9 - Apr 10
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Grant Park are located ...
5.6/10 (1,001 reviews)
Amazing location. Not a bad place. If you need a clean safe place with nothing fancy it works. Solid stay for the price.
Reviewed on Mar 30, 2026
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
2233 S Martin Luther King Dr Chicago IL
$210 nightly
The price is $247 total per night from May 7 to May 8
$247 total
May 7 - May 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,075 reviews)
Room newly renovated and beautiful.
Reviewed on Apr 6, 2026
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$113 nightly
The price is $132 total per night from Apr 16 to Apr 17
$132 total
Apr 16 - Apr 17
Total with 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 ...
8.2/10 Very Good! (2,671 reviews)
The entire property felt like it wasn’t level, the room slanted in the middle, the carpeting was ripped and disgusting. Furniture and fixtures were outdated and very worn. Overall, just a terrible hotel. Would not stay again…ever.
Reviewed on Apr 7, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$107 nightly
The price is $126 total per night from Apr 28 to Apr 29
$126 total
Apr 28 - Apr 29
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,197 reviews)
The hotel was in a prime location to allowing easy access to explore the China Town. It was also in close enough distance to the event we were there for at the McCormick place which allowed us to take a quick bus ride there. The hotel was extremely clean and well kept. The staff were friendly and ...
Reviewed on Apr 7, 2026
Save an average of 15% on thousands of hotels when you're signed in
Marriott Marquis Chicago
2121 South Prairie Avenue Chicago IL
$269 nightly
The price is $316 total per night from Apr 10 to Apr 11
$316 total
Apr 10 - Apr 11
Total with taxes and fees
Book a stay at this 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! (1,002 reviews)
Very clean room
Reviewed on Apr 7, 2026
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.
Best South Side Flight and Hotel Packages
South Side flight + hotel packages - economy flights
Price found within the past 48 hours. Click for updated prices.
South Side flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
South Side flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Special
Schiller Park, Illinois, USA
$13
$59 total
found 2 days ago
Midsize SUV
Schiller Park, Illinois, USA
$15
$65 total
found 2 days ago
Compact SUV
Schiller Park, Illinois, USA
$17
$69 total
found 2 days ago
Standard
Schiller Park, Illinois, USA
$18
$72 total
found 2 days ago
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.
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!
More Ways To Wander
South Side Hotels
Find the perfect hotel after your flight
South Side Vacation Rentals
Great Deals on alternative accommodations
South Side Car Rentals
Affordable cars to get you around town
South Side Vacations
Save more by combining flights, hotels and cars
Things to do in South Side
Activities, attractions and tours