Cheap Flights to South Side
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| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MCO | Chicago | August 10 to August 12 | $127 |
| MSP | Rockford | August 11 to August 12 | $138 |
| ATL | Chicago | July 25 to July 28 | $138 |
| ATL | Chicago | August 11 to August 13 | $168 |
| MCO | Rockford | August 5 to August 11 | $171 |
| LAX | Chicago | August 11 to August 15 | $176 |
| LAX | Chicago | July 22 to July 29 | $201 |
| ATL | Rockford | July 4 to July 8 | $211 |
| PHX | Chicago | August 18 to August 25 | $217 |
| DEN | Rockford | June 30 to July 1 | $221 |
| LAX | Rockford | September 2 to September 5 | $226 |
| PHX | Chicago | August 19 to August 24 | $234 |
| PHX | Rockford | August 12 to August 19 | $253 |
| FCO | Chicago | August 26 to September 30 | $597 |
| FCO | Chicago | August 1 to August 2 | $1,389 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | June 6 to June 9 | $234 |
| ATL | Chicago | June 6 to June 6 | $239 |
| MSP | Chicago | June 7 to June 11 | $315 |
| MCO | Chicago | June 6 to June 16 | $328 |
| PHX | Rockford | June 6 to June 10 | $346 |
| ATL | Rockford | June 6 to June 9 | $359 |
| PHX | Chicago | June 6 to June 10 | $369 |
| MSY | Chicago | June 5 to June 9 | $379 |
| PHX | Chicago | June 6 to June 8 | $385 |
| MSP | Chicago | June 5 to June 7 | $398 |
| LAX | Chicago | June 6 to June 11 | $427 |
| LAX | Chicago | June 5 to June 9 | $480 |
| MSP | Rockford | June 6 to June 7 | $552 |
| MSY | Chicago | June 5 to June 7 | $656 |
| FCO | Chicago | June 5 to June 21 | $684 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $127 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, American Airlines, Southwest Airlines, Delta, Icelandair, Condor |
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
$122 nightly
The price is $143 total per night from Jun 3 to Jun 4
$143 total
Jun 3 - Jun 4
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 (1,002 reviews)
"Bad experience. Staff terrible. No air conditioning. I do not recommend it at all."
Reviewed on May 28, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$227 nightly
The price is $270 total per night from Jun 1 to Jun 2
$270 total
Jun 1 - Jun 2
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! (1,217 reviews)
"There was a very clean room along with house cleaning. Fresh towels were given. Would be better if it included breakfast"
Reviewed on May 28, 2026
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$170 nightly
The price is $202 total per night from Jun 29 to Jun 30
$202 total
Jun 29 - Jun 30
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! (2,705 reviews)
"Doors were loud and we could hear people talking and laughing in the next room over. Walls are super thin. Hotel seems old and in need of renovation."
Reviewed on May 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
$254 nightly
The price is $302 total per night from Jun 30 to Jul 1
$302 total
Jun 30 - Jul 1
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! (1,085 reviews)
"I loved how nice the room was"
Reviewed on May 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.
Luxury Hotels in South Side
The Wheeler Mansion
2020 South Calumet Avenue Chicago IL
$620 nightly
The price is $724 total per night from Jun 20 to Jun 21
$724 total
Jun 20 - Jun 21
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
$170 nightly
The price is $202 total per night from Jun 29 to Jun 30
$202 total
Jun 29 - Jun 30
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! (2,705 reviews)
"Doors were loud and we could hear people talking and laughing in the next room over. Walls are super thin. Hotel seems old and in need of renovation."
Reviewed on May 30, 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
$254 nightly
The price is $302 total per night from Jun 30 to Jul 1
$302 total
Jun 30 - Jul 1
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! (1,085 reviews)
"I loved how nice the room was"
Reviewed on May 30, 2026
Save an average of 15% on thousands of hotels when you're signed in
Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
$122 nightly
The price is $143 total per night from Jun 3 to Jun 4
$143 total
Jun 3 - Jun 4
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 (1,002 reviews)
"Bad experience. Staff terrible. No air conditioning. I do not recommend it at all."
Reviewed on May 28, 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
$254 nightly
The price is $302 total per night from Jun 30 to Jul 1
$302 total
Jun 30 - Jul 1
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! (1,085 reviews)
"I loved how nice the room was"
Reviewed on May 30, 2026
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$170 nightly
The price is $202 total per night from Jun 29 to Jun 30
$202 total
Jun 29 - Jun 30
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! (2,705 reviews)
"Doors were loud and we could hear people talking and laughing in the next room over. Walls are super thin. Hotel seems old and in need of renovation."
Reviewed on May 30, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$227 nightly
The price is $270 total per night from Jun 1 to Jun 2
$270 total
Jun 1 - Jun 2
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! (1,217 reviews)
"There was a very clean room along with house cleaning. Fresh towels were given. Would be better if it included breakfast"
Reviewed on May 28, 2026
Save an average of 15% on thousands of hotels when you're signed in
Marriott Marquis Chicago
2121 South Prairie Avenue Chicago IL
$254 nightly
The price is $302 total per night from Jun 30 to Jul 1
$302 total
Jun 30 - Jul 1
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 ...
9/10 Wonderful! (1,004 reviews)
"Property was clean as were the rooms. We have been staying there since the hotel opened and we feel the rooms need a bit of a refresh to make it feel more crisp looking . After lots of use sometimes bathrooms and beds need to be refreshed. Service was good in the dining areas and rooms"
Reviewed on May 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.
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.
Don't see what you're looking for?
See all available trips from Philadelphia to South Side
View all tripsNeed a Car For After Your Flight?
Special
Schiller Park, Illinois, USA
$12
$56 total
found 2 days ago
Midsize
Schiller Park, Illinois, USA
$13
$58 total
found 2 days ago
Standard
Schiller Park, Illinois, USA
$13
$61 total
found 2 days ago
Compact SUV
Schiller Park, Illinois, USA
$16
$67 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
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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
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Things to do in South Side
Activities, attractions and tours