Cheap Flights to South Side from $41

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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 $80 and $41 for one-way flights to South Side for the period specified. Prices and availability are subject to change. Additional terms apply

Wed, Nov 5 - Tue, Nov 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$80 Roundtrip, found 6 hours ago
$80
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Nov 5 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Nov 11, priced at $80 found 6 hours ago
OriginDestinationTravel DatesFlights From*
MCOChicagoOctober 24 to October 27$80
MCOChicagoOctober 30 to October 30$87
MSPChicagoDecember 5 to December 12$88
ATLChicagoOctober 15 to October 22$96
MSPChicagoOctober 21 to October 21$97
ATLChicagoOctober 30 to November 1$99
LAXChicagoNovember 1 to November 8$140
ATLRockfordOctober 29 to November 1$141
MSPRockfordOctober 23 to October 24$144
MCORockfordDecember 4 to December 7$159
LAXChicagoOctober 23 to October 27$179
PHXRockfordOctober 28 to October 29$202
LAXRockfordNovember 13 to November 15$219
FCOChicagoNovember 13 to November 26$457
FCOChicagoNovember 2 to November 5$1,843
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOChicagoOctober 5 to October 9$122
ATLChicagoOctober 5 to October 15$150
MSYChicagoOctober 3 to October 6$156
MSPChicagoOctober 3 to October 10$156
FLLChicagoOctober 3 to October 8$156
IAHChicagoOctober 3 to October 6$164
DENChicagoOctober 4 to October 6$178
LAXChicagoOctober 4 to November 1$179
ATLChicagoOctober 4 to October 6$180
LAXChicagoOctober 3 to October 5$221
MSPChicagoOctober 5 to October 9$222
IAHChicagoOctober 4 to October 6$227
PHXChicagoOctober 4 to October 8$238
PHXChicagoOctober 5 to October 12$247
FCOChicagoOctober 5 to November 28$649
*Prices include taxes and fees

South Side Flight Information

Traveling to
South Side
Lowest Price
$80
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

Chinatown Hotel Chicago

1.5 out of 5
214 West 22nd Place, Chicago, IL
$95 nightly
The price is $112 total per night from Sep 30 to Oct 1
$112 total
Sep 30 - Oct 1
Total with 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 (1,008 reviews)
"Great location. Cheap room. We knew the room would be small. We wanted a clean place to sleep near Chinatown. This place is a block from the subway (L) station. It’s right off one of the main shopping streets in old Chinatown. It’s in an old building which was less clean than I would have liked but ..."

Reviewed on Sep 13, 2025

Opens in a new windowChinatown Hotel Chicago
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
$169 nightly
The price is $198 total per night from Oct 29 to Oct 30
$198 total
Oct 29 - Oct 30
Total with taxes and fees
Stay at this 3-star 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 ...
8.8/10 Excellent! (1,170 reviews)
"This was a great place. Staff is awesome and the whole hotel was super clean!"

Reviewed on Sep 22, 2025

Opens in a new windowJaslin Hotel
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
$140 nightly
The price is $165 total per night from Oct 2 to Oct 3
$165 total
Oct 2 - Oct 3
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 ...
8/10 Very Good! (2,655 reviews)
"clean room"

Reviewed on Sep 24, 2025

Opens in a new windowBest Western Grant Park Hotel
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Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
$289 nightly
The price is $339 total per night from Oct 1 to Oct 2
$339 total
Oct 1 - Oct 2
Total with 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! (1,031 reviews)
Loved it!
"Enjoyed my stay!!"

Reviewed on Sep 21, 2025

Opens in a new windowHyatt Regency McCormick Place Chicago
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

The Wheeler Mansion

4 out of 5
2020 South Calumet Avenue, Chicago, IL
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! (2 reviews)
"A unique place to stay near the convention centre."

Reviewed on Jun 23, 2025

Get rates
Opens in a new windowThe Wheeler Mansion
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
$140 nightly
The price is $165 total per night from Oct 2 to Oct 3
$165 total
Oct 2 - Oct 3
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 ...
8/10 Very Good! (2,655 reviews)
"clean room"

Reviewed on Sep 24, 2025

Opens in a new windowBest Western Grant Park Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
$289 nightly
The price is $339 total per night from Oct 1 to Oct 2
$339 total
Oct 1 - Oct 2
Total with 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! (1,031 reviews)
Loved it!
"Enjoyed my stay!!"

Reviewed on Sep 21, 2025

Opens in a new windowHyatt Regency McCormick Place Chicago
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Chinatown Hotel Chicago

Chinatown Hotel Chicago

1.5 out of 5
214 West 22nd Place, Chicago, IL
$95 nightly
The price is $112 total per night from Sep 30 to Oct 1
$112 total
Sep 30 - Oct 1
Total with 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 (1,008 reviews)
"Great location. Cheap room. We knew the room would be small. We wanted a clean place to sleep near Chinatown. This place is a block from the subway (L) station. It’s right off one of the main shopping streets in old Chinatown. It’s in an old building which was less clean than I would have liked but ..."

Reviewed on Sep 13, 2025

Opens in a new windowChinatown Hotel Chicago
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

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr, Chicago, IL
$289 nightly
The price is $339 total per night from Oct 1 to Oct 2
$339 total
Oct 1 - Oct 2
Total with 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! (1,031 reviews)
Loved it!
"Enjoyed my stay!!"

Reviewed on Sep 21, 2025

Opens in a new windowHyatt Regency McCormick Place Chicago
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
$140 nightly
The price is $165 total per night from Oct 2 to Oct 3
$165 total
Oct 2 - Oct 3
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 ...
8/10 Very Good! (2,655 reviews)
"clean room"

Reviewed on Sep 24, 2025

Opens in a new windowBest Western Grant Park Hotel
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd, Chicago, IL
$169 nightly
The price is $198 total per night from Oct 29 to Oct 30
$198 total
Oct 29 - Oct 30
Total with taxes and fees
Stay at this 3-star 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 ...
8.8/10 Excellent! (1,170 reviews)
"This was a great place. Staff is awesome and the whole hotel was super clean!"

Reviewed on Sep 22, 2025

Opens in a new windowJaslin Hotel
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Marriott Marquis Chicago

Marriott Marquis Chicago

4 out of 5
2121 South Prairie Avenue, Chicago, IL
$359 nightly
The price is $421 total per night from Oct 1 to Oct 2
$421 total
Oct 1 - Oct 2
Total with 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! (1,024 reviews)
"Buffet should have different variety for breakfast"

Reviewed on Sep 21, 2025

Opens in a new windowMarriott Marquis Chicago
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.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $344, price is now $229 per person
$229
per person
Nov 16 - Nov 19
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,310, price is now $738 per person
$738
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
Price was $1,511, price is now $1,032 per person
$1,032
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Atlanta to South Side
View all trips

South Side flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was $1,540, price is now $1,310 per person
$1,310
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was $2,268, price is now $1,722 per person
$1,722
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was $2,404, price is now $1,898 per person
$1,898
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from San Francisco to South Side
View all trips

Need a Car For After Your Flight?

Special

  • 5 people
  • Unlimited mileage
Schiller Park, Illinois, USA

$20

$76 total
found 4 hours ago
Special undefined

Midsize

  • 5 people
  • Unlimited mileage
Schiller Park, Illinois, USA

$20

$78 total
found 4 hours ago
Midsize undefined

Standard

  • 5 people
  • Unlimited mileage
Schiller Park, Illinois, USA

$21

$80 total
found 4 hours ago
Standard undefined

Economy

  • 4 people
  • Unlimited mileage
Chicago, Illinois, USA

$31

$62 total
found 12 hours ago
Economy undefined
Lowest prices found within the past 4 hours. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to South Side?
In the last seven days, the cheapest roundtrip flight to South Side cost $80 on our site. Browse through our superb deals, secure your booking and start planning your next fun vacation. This price was available on Travelocity for flights to South Side departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to South Side?
Make sure you leave November free in your calendar, because it's the most affordable month to jet to South Side. That's according to Travelocity's direct flight demand from January to December last year. With more money in your wallet, you can splurge on a hotel upgrade, go for a fancy dinner or whatever else you like!
How can I check my flight status to South Side?
Get alerts about your flight status and gate numbers with Trips. This handy Travelocity portal is located at the top of our homepage and is where you can view and manage your bookings. Create your account in just a few seconds and away you go. Or, download the Travelocity app and look up the details of your flight to South Side while you're out and about — and even when offline. Travelocity's app can sort out all your booking needs. Whether you'd like to add transportation to or from the airport or share travel details with any members of your family flying with you, our intuitive app can help.
How do I find the best deals on flights to South Side?
Be flexible with your travel dates and you might just find an awesome deal. When searching for flights on Travelocity, tap on the "Flexible dates" box above your results to reveal prices for surrounding days. Also try to book ahead of time and avoid vacation periods. In the last seven days, the lowest price for a roundtrip flight to South Side was $80. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to South Side with Travelocity?
An amazing vacation is just a click or two away when you arrange your trip with Travelocity. With competitive deals on cheap family flights, places to stay, activities and more, we make it easy to locate the best prices to suit your needs. You can also take advantage of our round-the-clock customer support and free cancellations on most hotels during every stage of the process. Wander wisely with us and lock in your cheap flights to South Side today.
What are the most popular flight routes to South Side?
As a much-loved destination for tourists, there are plenty of connections to South Side. Here are some of the major routes:

  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 4,203 flights a month.
  • Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.) to O'Hare Intl. Airport (ORD) - 4,155 flights a month.
  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 4,138 flights a month.

How much is a flight to South Side on average?
Get your next dream vacation off to a great start by picking up an incredible deal with Travelocity. In the last seven days, roundtrip flights to South Side cost between $80 and $1,843. Take a look at our site and lock in an airfare that works with your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to South Side?
Below you'll find a number of leading direct flights to South Side as well as their average flight duration:

  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 29 minutes
  • Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 20 minutes
  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 41 minutes

What can I expect on a flight to South Side?
The duration of your flight and whether you're traveling with a budget or full-service airline will largely determine this. If you're seeking long-haul flights to South Side, entertainment, drinks and food should be included. Wondering about cheap flights for family vacations? Check out the fares with low-cost carriers. These airlines generally don't offer as many inclusions, or you'll have to pay a fee for them.

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!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.