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 $63 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.
ORD
O'Hare Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
LGA
LaGuardia
ORD
O'Hare Intl.
$81 Roundtrip, just found
$81
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | May 22 to May 29 | $63 |
| IAH | Chicago | May 14 to June 9 | $78 |
| FLL | Chicago | May 29 to June 1 | $79 |
| MCO | Chicago | May 28 to June 3 | $83 |
| MCO | Chicago | July 10 to July 14 | $98 |
| DEN | Chicago | May 27 to May 28 | $100 |
| LAX | Chicago | July 2 to July 2 | $100 |
| MSY | Chicago | June 9 to June 12 | $111 |
| DEN | Chicago | June 16 to June 20 | $116 |
| PHX | Chicago | June 9 to June 13 | $156 |
| MSY | Chicago | July 12 to July 15 | $159 |
| PHX | Chicago | July 31 to August 7 | $166 |
| MSP | Chicago | May 25 to May 27 | $173 |
| LAX | Chicago | May 31 to June 2 | $191 |
| FCO | Chicago | June 13 to June 29 | $615 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | May 11 to May 12 | $95 |
| ATL | Chicago | May 11 to May 25 | $126 |
| PHX | Chicago | May 11 to May 25 | $188 |
| MCO | Chicago | May 11 to May 14 | $199 |
| LAX | Chicago | May 11 to May 14 | $228 |
| LAX | Chicago | May 9 to May 14 | $231 |
| IAH | Chicago | May 11 to May 24 | $233 |
| MSY | Chicago | May 11 to May 18 | $260 |
| MSP | Chicago | May 11 to May 15 | $264 |
| FLL | Chicago | May 11 to May 14 | $267 |
| DEN | Chicago | May 11 to May 19 | $270 |
| PHX | Chicago | May 11 to May 15 | $285 |
| FLL | Chicago | May 10 to May 10 | $317 |
| MSP | Chicago | May 11 to May 12 | $415 |
| FCO | Chicago | May 10 to May 17 | $691 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $63 |
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
214 West 22nd Place, Chicago, IL
The price is $112 per night from May 12 to May 13
$112
includes taxes & fees
$95 per night
May 12 - May 13
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 (1,000 reviews)
"This as a cute little place glad we stayed"
Reviewed on Apr 28, 2025
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
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! (1,051 reviews)
"Every thing was great The only unusual thing was that on the last night of my stay the room was 77 degrees even though I set the thermostat to 67."
Reviewed on May 2, 2025
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
The price is $109 per night from May 27 to May 28
$109
includes taxes & fees
$93 per night
May 27 - May 28
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,517 reviews)
"Property is very dated and needs updating. It’s clean and staff are helpful. Great bakery next to it which you can enter without leaving the building. This can get very busy at breakfast time and isn’t cheap but is very good. Right opposite Grant Park which is huge and busy so feels safe even after ..."
Reviewed on May 4, 2025
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Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
The price is $268 per night from May 27 to May 28
$268
includes taxes & fees
$228 per night
May 27 - May 28
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! (1,004 reviews)
"Great location for conference. Generally amazing housekeeping. A few minor things would have helped me eg cotton pads in bath and a small notepad at the desk"
Reviewed on Apr 30, 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
The price is $724 per night from May 8 to May 9
$724
includes taxes & fees
$616 per night
May 8 - May 9
Stay at this 4-star luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Chicago Riverwalk are located ...
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
The price is $109 per night from May 27 to May 28
$109
includes taxes & fees
$93 per night
May 27 - May 28
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,517 reviews)
"Property is very dated and needs updating. It’s clean and staff are helpful. Great bakery next to it which you can enter without leaving the building. This can get very busy at breakfast time and isn’t cheap but is very good. Right opposite Grant Park which is huge and busy so feels safe even after ..."
Reviewed on May 4, 2025
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
The price is $268 per night from May 27 to May 28
$268
includes taxes & fees
$228 per night
May 27 - May 28
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! (1,004 reviews)
"Great location for conference. Generally amazing housekeeping. A few minor things would have helped me eg cotton pads in bath and a small notepad at the desk"
Reviewed on Apr 30, 2025
Save an average of 15% on thousands of hotels when you're signed in
Chinatown Hotel Chicago
214 West 22nd Place, Chicago, IL
The price is $112 per night from May 12 to May 13
$112
includes taxes & fees
$95 per night
May 12 - May 13
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 (1,000 reviews)
"This as a cute little place glad we stayed"
Reviewed on Apr 28, 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
The price is $268 per night from May 27 to May 28
$268
includes taxes & fees
$228 per night
May 27 - May 28
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! (1,004 reviews)
"Great location for conference. Generally amazing housekeeping. A few minor things would have helped me eg cotton pads in bath and a small notepad at the desk"
Reviewed on Apr 30, 2025
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
The price is $109 per night from May 27 to May 28
$109
includes taxes & fees
$93 per night
May 27 - May 28
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,517 reviews)
"Property is very dated and needs updating. It’s clean and staff are helpful. Great bakery next to it which you can enter without leaving the building. This can get very busy at breakfast time and isn’t cheap but is very good. Right opposite Grant Park which is huge and busy so feels safe even after ..."
Reviewed on May 4, 2025
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
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! (1,051 reviews)
"Every thing was great The only unusual thing was that on the last night of my stay the room was 77 degrees even though I set the thermostat to 67."
Reviewed on May 2, 2025
Save an average of 15% on thousands of hotels when you're signed in
Marriott Marquis Chicago
2121 South Prairie Avenue, Chicago, IL
The price is $252 per night from May 25 to May 26
$252
includes taxes & fees
$215 per night
May 25 - May 26
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! (1,003 reviews)
Great place to stay in Chicago for conferences
"Great service, perfect location, safe choice for people visiting the McCormick Place for conferences and businesses."
Reviewed on May 4, 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 SUV
Schiller Park, Illinois, USA
$13
$59 total
found 13 hours ago
Compact SUV
Schiller Park, Illinois, USA
$14
$63 total
found 13 hours ago
Midsize SUV
Schiller Park, Illinois, USA
$14
$62 total
found 13 hours ago
Standard
Schiller Park, Illinois, USA
$16
$67 total
found 13 hours ago
Lowest prices found within the past 13 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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