Cheap Flights to South Side from $43
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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 $82 and $43 for one-way flights to South Side for the period specified. Prices and availability are subject to change. Additional terms apply
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 11 hours ago
$94
Roundtrip
found 11 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | September 8 to September 8 | $82 |
| ATL | Chicago | August 12 to August 16 | $87 |
| DEN | Chicago | August 19 to August 30 | $87 |
| IAH | Chicago | August 21 to August 25 | $94 |
| IAH | Chicago | August 15 to August 18 | $94 |
| PHX | Chicago | August 15 to August 21 | $104 |
| MSP | Chicago | September 6 to September 9 | $109 |
| LAX | Chicago | August 15 to August 17 | $110 |
| MSP | Chicago | August 6 to August 10 | $129 |
| MCO | Chicago | July 19 to July 26 | $138 |
| FLL | Chicago | August 14 to August 25 | $143 |
| MSY | Chicago | July 1 to July 5 | $169 |
| LAX | Chicago | August 21 to August 24 | $176 |
| FCO | Chicago | August 29 to September 13 | $498 |
| FCO | Chicago | June 17 to June 24 | $785 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MSP | Chicago | June 8 to June 14 | $195 |
| ATL | Chicago | June 8 to June 11 | $197 |
| ATL | Chicago | June 7 to June 11 | $213 |
| FLL | Chicago | June 8 to June 12 | $231 |
| FLL | Chicago | June 6 to June 9 | $239 |
| IAH | Chicago | June 8 to June 14 | $244 |
| LAX | Chicago | June 8 to June 12 | $247 |
| MCO | Chicago | June 7 to June 10 | $253 |
| PHX | Chicago | June 8 to August 14 | $267 |
| DEN | Chicago | June 6 to June 16 | $273 |
| MSP | Chicago | June 8 to June 12 | $274 |
| MCO | Chicago | June 7 to June 16 | $284 |
| DEN | Chicago | June 7 to June 9 | $294 |
| PHX | Chicago | June 7 to June 11 | $389 |
| FCO | Chicago | June 8 to June 22 | $780 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $82 |
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 $105 total per night from Jun 12 to Jun 13
$105 total
Jun 12 - Jun 13
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)
"Quiet and close to good food and bar."
Reviewed on Jun 1, 2025
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
$143 nightly
The price is $168 total per night from Jun 23 to Jun 24
$168 total
Jun 23 - Jun 24
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! (1,050 reviews)
"The hotel was quiet and feel safe to stay."
Reviewed on Jun 4, 2025
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
$115 nightly
The price is $135 total per night from Jul 1 to Jul 2
$135 total
Jul 1 - Jul 2
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! (2,516 reviews)
"This was our second stay at this hotel and we loved it. We love how the pastry restaurant is also connected to the hotel and it’s in walking distance of all of the attractions."
Reviewed on Jun 1, 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
$227 nightly
The price is $266 total per night from Jun 30 to Jul 1
$266 total
Jun 30 - Jul 1
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! (1,005 reviews)
"Check in and check out was super quick and room was nice and clean"
Reviewed on Jun 2, 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 Jun 5 to Jun 6
$724 total
Jun 5 - Jun 6
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 ...
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
$115 nightly
The price is $135 total per night from Jul 1 to Jul 2
$135 total
Jul 1 - Jul 2
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! (2,516 reviews)
"This was our second stay at this hotel and we loved it. We love how the pastry restaurant is also connected to the hotel and it’s in walking distance of all of the attractions."
Reviewed on Jun 1, 2025
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
$227 nightly
The price is $266 total per night from Jun 30 to Jul 1
$266 total
Jun 30 - Jul 1
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! (1,005 reviews)
"Check in and check out was super quick and room was nice and clean"
Reviewed on Jun 2, 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 $105 total per night from Jun 12 to Jun 13
$105 total
Jun 12 - Jun 13
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)
"Quiet and close to good food and bar."
Reviewed on Jun 1, 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
$227 nightly
The price is $266 total per night from Jun 30 to Jul 1
$266 total
Jun 30 - Jul 1
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! (1,005 reviews)
"Check in and check out was super quick and room was nice and clean"
Reviewed on Jun 2, 2025
Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
$115 nightly
The price is $135 total per night from Jul 1 to Jul 2
$135 total
Jul 1 - Jul 2
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! (2,516 reviews)
"This was our second stay at this hotel and we loved it. We love how the pastry restaurant is also connected to the hotel and it’s in walking distance of all of the attractions."
Reviewed on Jun 1, 2025
Jaslin Hotel
261 West Cermak Rd, Chicago, IL
$143 nightly
The price is $168 total per night from Jun 23 to Jun 24
$168 total
Jun 23 - Jun 24
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! (1,050 reviews)
"The hotel was quiet and feel safe to stay."
Reviewed on Jun 4, 2025
Save an average of 15% on thousands of hotels when you're signed in
Marriott Marquis Chicago
2121 South Prairie Avenue, Chicago, IL
$165 nightly
The price is $194 total per night from Jul 1 to Jul 2
$194 total
Jul 1 - Jul 2
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 ...
9.2/10 Wonderful! (1,004 reviews)
"This was a wonderful hotel. The room was very comfortable, clean, and nicely decorated. It was close enough to Soldier Field that we could easily walk there for a concert."
Reviewed on Jun 2, 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.
Don't see what you're looking for?
See all available trips from Philadelphia to South Side
View all tripsSouth 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
$13
$60 total
found 10 hours ago
Special
Schiller Park, Illinois, USA
$14
$63 total
found 10 hours ago
Midsize
Schiller Park, Illinois, USA
$15
$65 total
found 10 hours ago
Compact SUV
Schiller Park, Illinois, USA
$18
$71 total
found 10 hours ago
Lowest prices found within the past 10 hours. Prices and availability subject to change. Additional terms may apply.
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
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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
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