Cheap Flights to South Side from $56
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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 $76 and $56 for one-way flights to South Side for the period specified. Prices and availability are subject to change. Additional terms apply
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$127 Roundtrip, found 3 days ago
$127
Roundtrip
found 3 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Rockford | October 1 to October 4 | $76 |
| MSP | Chicago | November 3 to November 7 | $117 |
| MSP | Chicago | September 28 to September 29 | $117 |
| MSP | Rockford | September 19 to September 21 | $140 |
| ATL | Chicago | September 9 to September 12 | $140 |
| LAX | Chicago | October 10 to October 13 | $140 |
| AZA | Rockford | October 28 to November 2 | $142 |
| ATL | Chicago | September 10 to September 12 | $175 |
| LAX | Rockford | September 25 to September 30 | $197 |
| DEN | Rockford | September 19 to September 26 | $212 |
| LAX | Chicago | November 4 to November 9 | $217 |
| PHX | Chicago | December 5 to December 7 | $229 |
| MCO | Rockford | September 16 to September 30 | $236 |
| MCO | Chicago | November 7 to November 9 | $237 |
| ATL | Rockford | September 10 to September 12 | $250 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | September 5 to September 6 | $102 |
| ATL | Chicago | September 4 to September 6 | $248 |
| FLL | Chicago | September 6 to September 9 | $266 |
| PHX | Rockford | September 5 to September 19 | $272 |
| DEN | Chicago | September 5 to September 9 | $298 |
| MSP | Chicago | September 6 to September 7 | $324 |
| LAX | Chicago | September 5 to September 8 | $348 |
| DEN | Rockford | September 6 to September 9 | $377 |
| MSP | Rockford | September 5 to September 6 | $388 |
| MSY | Rockford | September 6 to September 8 | $425 |
| IAH | Rockford | September 6 to September 12 | $438 |
| LAX | Rockford | September 6 to September 6 | $450 |
| ATL | Rockford | September 4 to September 14 | $482 |
| FCO | Chicago | September 6 to September 20 | $670 |
| FLL | Rockford | September 4 to September 7 | $881 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $76 |
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
$109 nightly
The price is $128 total per night from Sep 1 to Sep 2
$128 total
Sep 1 - Sep 2
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 (1,006 reviews)
"Honestly, our room was more expensive than what it's worth because there was a big concert in downtown Chicago and everything closer was easily more expensive or in really sketchy areas. It is pretty rundown and need of a deep clean (it smelled like dust and mildew pretty much everywhere but in our ..."
Reviewed on Aug 30, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$145 nightly
The price is $173 total per night from Sep 29 to Sep 30
$173 total
Sep 29 - Sep 30
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! (1,336 reviews)
"This is my second stay at the Jaslin and I cannot recommend this hotel enough. The staff is kind and professional, the rooms have everything we need and are well kept, the view is incredible, and the location is awesome! You can easily walk to anywhere in Chinatown. My friend and I even walked to ..."
Reviewed on Aug 30, 2026
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$143 nightly
The price is $170 total per night from Sep 7 to Sep 8
$170 total
Sep 7 - Sep 8
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! (2,750 reviews)
"Staffs were nice and hotel is walking distance to all the popular sites."
Reviewed on Aug 30, 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
$244 nightly
The price is $290 total per night from Sep 1 to Sep 2
$290 total
Sep 1 - Sep 2
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 ...
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 Sep 1 to Sep 2
$724 total
Sep 1 - Sep 2
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
$143 nightly
The price is $170 total per night from Sep 7 to Sep 8
$170 total
Sep 7 - Sep 8
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! (2,750 reviews)
"Staffs were nice and hotel is walking distance to all the popular sites."
Reviewed on Aug 30, 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
$244 nightly
The price is $290 total per night from Sep 1 to Sep 2
$290 total
Sep 1 - Sep 2
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
$109 nightly
The price is $128 total per night from Sep 1 to Sep 2
$128 total
Sep 1 - Sep 2
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 (1,006 reviews)
"Honestly, our room was more expensive than what it's worth because there was a big concert in downtown Chicago and everything closer was easily more expensive or in really sketchy areas. It is pretty rundown and need of a deep clean (it smelled like dust and mildew pretty much everywhere but in our ..."
Reviewed on Aug 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
$244 nightly
The price is $290 total per night from Sep 1 to Sep 2
$290 total
Sep 1 - Sep 2
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 ...
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$143 nightly
The price is $170 total per night from Sep 7 to Sep 8
$170 total
Sep 7 - Sep 8
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! (2,750 reviews)
"Staffs were nice and hotel is walking distance to all the popular sites."
Reviewed on Aug 30, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$145 nightly
The price is $173 total per night from Sep 29 to Sep 30
$173 total
Sep 29 - Sep 30
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! (1,336 reviews)
"This is my second stay at the Jaslin and I cannot recommend this hotel enough. The staff is kind and professional, the rooms have everything we need and are well kept, the view is incredible, and the location is awesome! You can easily walk to anywhere in Chinatown. My friend and I even walked to ..."
Reviewed on Aug 30, 2026
Save an average of 15% on thousands of hotels when you're signed in
Marriott Marquis Chicago
2121 South Prairie Avenue Chicago IL
$288 nightly
The price is $342 total per night from Sep 6 to Sep 7
$342 total
Sep 6 - Sep 7
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! (1,022 reviews)
"Clean rooms with plenty of amenities and comfortable beds."
Reviewed on Aug 31, 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.
Don't see what you're looking for?
See all available trips from Charlotte to South Side
View all tripsSouth Side flight + hotel packages - business class 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?
Standard
Schiller Park, Illinois, USA
$14
$63 total
found 14 hours ago
Compact SUV
Schiller Park, Illinois, USA
$19
$76 total
found 14 hours ago
Economy Crossover
SCHILLER PARK, USA
$40
$133 total
found 8 hours ago
Fullsize Recreational Vehicle
Chicago, Illinois, USA
$51
$165 total
found 14 hours ago
Lowest prices found within the past 14 hours. 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