Cheap Flights to South Side from $32
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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 $60 and $32 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.
$60 Roundtrip, found 2 hours ago
$60
Roundtrip
found 2 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MSP | Chicago | August 13 to August 16 | $77 |
| MCO | Chicago | October 9 to October 11 | $90 |
| IAH | Chicago | October 20 to October 27 | $90 |
| FLL | Chicago | August 20 to August 27 | $99 |
| MSY | Chicago | September 8 to September 11 | $108 |
| PHX | Chicago | August 28 to August 31 | $126 |
| MSY | Chicago | September 4 to September 8 | $149 |
| FLL | Chicago | September 6 to September 8 | $157 |
| DEN | Rockford | October 23 to October 27 | $205 |
| MSP | Rockford | October 23 to October 26 | $268 |
| PHX | Rockford | October 31 to November 10 | $316 |
| LAX | Rockford | October 24 to October 26 | $385 |
| IAH | Rockford | October 23 to October 26 | $396 |
| FCO | Chicago | October 17 to November 7 | $534 |
| FCO | Chicago | September 18 to October 21 | $732 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | August 2 to August 12 | $82 |
| ATL | Chicago | August 3 to September 8 | $135 |
| DEN | Chicago | August 2 to August 18 | $186 |
| MSP | Chicago | August 2 to August 9 | $192 |
| DEN | Chicago | August 2 to August 5 | $203 |
| MSP | Chicago | August 3 to August 10 | $212 |
| FLL | Chicago | August 1 to August 5 | $223 |
| MSY | Chicago | August 3 to August 16 | $223 |
| IAH | Chicago | August 2 to August 5 | $231 |
| FLL | Chicago | August 3 to August 10 | $242 |
| LAX | Chicago | August 2 to August 5 | $254 |
| IAH | Chicago | August 1 to August 11 | $275 |
| PHX | Chicago | August 1 to August 7 | $309 |
| LAX | Chicago | August 2 to August 5 | $310 |
| FCO | Chicago | August 3 to August 18 | $807 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $60 |
Number of Airlines Serving | |
Airlines Serving | Spirit Airlines, 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
$89 nightly
The price is $104 total per night from Jul 27 to Jul 28
$104 total
Jul 27 - Jul 28
Total includes taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the property condition in our reviews. Popular ...
5.4/10 (1,003 reviews)
"It’s OK"
Reviewed on Jul 24, 2025
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
$129 nightly
The price is $152 total per night from Aug 4 to Aug 5
$152 total
Aug 4 - Aug 5
Total includes taxes and fees
Stay at this 3-star hotel in Chicago. Enjoy a 24-hour fitness center, a 24-hour front desk, and premium TV channels. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,097 reviews)
"I enjoyed my stay at this affordable hotel in Chinatown. The staff were great, my room was clean, and good food, public transit, and parking were all in easy walking distance."
Reviewed on Jul 24, 2025
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
$123 nightly
The price is $145 total per night from Aug 24 to Aug 25
$145 total
Aug 24 - Aug 25
Total includes 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 ...
8/10 Very Good! (2,587 reviews)
Good location!
"Overall stay was good. Bathroom was cramped for my family of five. Staff was great. Love the location!"
Reviewed on Jul 26, 2025
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
$209 nightly
The price is $245 total per night from Aug 20 to Aug 21
$245 total
Aug 20 - Aug 21
Total includes taxes and fees
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,008 reviews)
"Amazing"
Reviewed on Jul 22, 2025
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
$616 nightly
The price is $724 total per night from Aug 12 to Aug 13
$724 total
Aug 12 - Aug 13
Total includes taxes and fees
Stay at this 4-star luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Grant Park are located ...
10/10 Exceptional! (1 review)
"A unique place to stay near the convention centre."
Reviewed on Jun 23, 2025
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
$123 nightly
The price is $145 total per night from Aug 24 to Aug 25
$145 total
Aug 24 - Aug 25
Total includes 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 ...
8/10 Very Good! (2,587 reviews)
Good location!
"Overall stay was good. Bathroom was cramped for my family of five. Staff was great. Love the location!"
Reviewed on Jul 26, 2025
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
$209 nightly
The price is $245 total per night from Aug 20 to Aug 21
$245 total
Aug 20 - Aug 21
Total includes taxes and fees
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,008 reviews)
"Amazing"
Reviewed on Jul 22, 2025
Save an average of 15% on thousands of hotels when you're signed in
Chinatown Hotel Chicago
214 West 22nd Place, Chicago, IL
$89 nightly
The price is $104 total per night from Jul 27 to Jul 28
$104 total
Jul 27 - Jul 28
Total includes taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the property condition in our reviews. Popular ...
5.4/10 (1,003 reviews)
"It’s OK"
Reviewed on Jul 24, 2025
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
$209 nightly
The price is $245 total per night from Aug 20 to Aug 21
$245 total
Aug 20 - Aug 21
Total includes taxes and fees
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,008 reviews)
"Amazing"
Reviewed on Jul 22, 2025
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
$123 nightly
The price is $145 total per night from Aug 24 to Aug 25
$145 total
Aug 24 - Aug 25
Total includes 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 ...
8/10 Very Good! (2,587 reviews)
Good location!
"Overall stay was good. Bathroom was cramped for my family of five. Staff was great. Love the location!"
Reviewed on Jul 26, 2025
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
$129 nightly
The price is $152 total per night from Aug 4 to Aug 5
$152 total
Aug 4 - Aug 5
Total includes taxes and fees
Stay at this 3-star hotel in Chicago. Enjoy a 24-hour fitness center, a 24-hour front desk, and premium TV channels. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,097 reviews)
"I enjoyed my stay at this affordable hotel in Chinatown. The staff were great, my room was clean, and good food, public transit, and parking were all in easy walking distance."
Reviewed on Jul 24, 2025
Save an average of 15% on thousands of hotels when you're signed in
Marriott Marquis Chicago
2121 South Prairie Avenue, Chicago, IL
$242 nightly
The price is $284 total per night from Aug 21 to Aug 22
$284 total
Aug 21 - Aug 22
Total includes taxes and fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 9 restaurants, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
9/10 Wonderful! (1,016 reviews)
"The housekeepers were amazing! So friendly and did an excellent job!"
Reviewed on Jul 23, 2025
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
$20
$77 total
found 18 hours ago
Midsize
Schiller Park, Illinois, USA
$21
$79 total
found 18 hours ago
Standard
Schiller Park, Illinois, USA
$22
$81 total
found 18 hours ago
Compact SUV
Schiller Park, Illinois, USA
$24
$87 total
found 18 hours ago
Lowest prices found within the past 18 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
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