Cheap flights To South Side (CHI) from $68

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Cheap Flights to South Side from $68 One Way, $69 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Oct 24 - Tue, Oct 27
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$69 Roundtrip, found 2 days ago
$69
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Oct 27, priced at $69 found 2 days ago
Tue, Oct 6 - Tue, Oct 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 1 hour ago
$83
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Oct 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Oct 13, priced at $83 found 1 hour ago
Tue, Nov 17 - Thu, Dec 3
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 3 days ago
$83
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Dec 3, priced at $83 found 3 days ago
Tue, Nov 17 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Nov 19, priced at $84 found 2 days ago
Sat, Oct 17 - Fri, Oct 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 15 hours ago
$138
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Los Angeles Intl. to O'Hare Intl., returning Fri, Oct 23, priced at $138 found 15 hours ago
Tue, Oct 27 - Sun, Nov 1
LAX
Los Angeles Intl.
MDW
Midway Intl.
$217 Roundtrip, found 4 hours ago
$217
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Oct 27 from Los Angeles Intl. to Midway Intl., returning Sun, Nov 1, priced at $217 found 4 hours ago
Tue, Nov 10 - Sun, Nov 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Nov 10 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 15, priced at $217 found 1 hour ago
Thu, Oct 29 - Mon, Nov 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select American Airlines flight, departing Thu, Oct 29 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 2, priced at $217 just found
Tue, Sep 29 - Wed, Sep 30
LGA
LaGuardia
ORD
O'Hare Intl.
$222 Roundtrip, found 4 days ago
$222
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Sep 29 from LaGuardia to O'Hare Intl., returning Wed, Sep 30, priced at $222 found 4 days ago
Wed, Sep 30 - Wed, Oct 7
LGA
LaGuardia
MDW
Midway Intl.
$232 Roundtrip, found 4 days ago
$232
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Sep 30 from LaGuardia to Midway Intl., returning Wed, Oct 7, priced at $232 found 4 days ago

South Side Flight Information

Traveling To
South Side
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Southwest Airlines, American Airlines, Delta
Flight Price
$69
Earliest Departing Flight
Latest Departing Flight

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South Side economy flight packages

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
4.0-star property

La Banque Hotel

Oct 18 - Oct 21

3 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $602, price is now $434 per person
$434
per person
found 9 hours ago
Hilton Grand Vacations Club Chicago Magnificent Mile
3.5-star property

Hilton Grand Vacations Club Chicago Magnificent Mile

Oct 28 - Nov 2

5 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Los Angeles (LAX)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,347, price is now $940 per person
$940
per person
found 11 hours ago
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

Oct 14 - Oct 17

3 night stay

Dallas (DAL) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $1,271, price is now $893 per person
$893
per person
found 1 day ago
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South Side premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,174 reviews)

Oct 30 - Nov 1

2 night stay

Houston (IAH) to Chicago (ORD)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $975, price is now $741 per person
$741
per person
found 10 hours ago
Clean room, but not room services available

Reviewed on Sep 14, 2026

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,512 reviews)

Oct 14 - Oct 17

3 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,534, price is now $1,014 per person
$1,014
per person
found 5 hours ago

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,681 reviews)

Oct 14 - Oct 17

3 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,127, price is now $820 per person
$820
per person
found 5 hours ago
The staff was very great. From valet. Front desk check in. Very clean and nice . Room was great clean and I loved the ac work very well that is on top of my list of things how great properties are were we stay . We had breakfast at the hotel and staff and food was amazing.😀.

Reviewed on Sep 13, 2026

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South Side business class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,174 reviews)

Nov 6 - Nov 9

3 night stay

Los Angeles (LAX) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,511, price is now $1,179 per person
$1,179
per person
found 2 hours ago
Clean room, but not room services available

Reviewed on Sep 14, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (1,995 reviews)

Nov 6 - Nov 9

3 night stay

Los Angeles (LAX) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,941, price is now $1,439 per person
$1,439
per person
found 2 hours ago

The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

9.4/10 Exceptional! (165 reviews)

Nov 6 - Nov 9

3 night stay

Los Angeles (LAX) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,607, price is now $1,231 per person
$1,231
per person
found 2 hours ago

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South Side first class flight packages

Price found within the past 48 hours. Click for updated prices.
LakeWood Inn & Suites
2.0-star property

LakeWood Inn & Suites

7.6/10 Good! (146 reviews)

Nov 5 - Nov 10

5 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,090, price is now $1,046 per person
$1,046
per person
found 1 day ago

Goldberry Woods
3.5-star property

Goldberry Woods

9.8/10 Exceptional! (43 reviews)

Nov 5 - Nov 10

5 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,223, price is now $3,168 per person
$3,168
per person
found 1 day ago
Stayed for 4 nights. Pleasant trip and hosts. Will return.

Reviewed on Jun 3, 2026

Holiday Inn Express Hotel & Suites Niles by IHG
2.5-star property

Holiday Inn Express Hotel & Suites Niles by IHG

9/10 Wonderful! (797 reviews)

Nov 5 - Nov 10

5 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,923, price is now $1,895 per person
$1,895
per person
found 1 day ago
The hotel was clean and the staff was super helpful

Reviewed on Sep 7, 2026

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South Side

Orbitz is your one stop for guaranteed low prices on South Side flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to South Side and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to South Side Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to South Side from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

Frequently asked questions

Which airlines fly to South Side?
Have a look at the deals from the 20 airlines that offer flights to South Side. Whether you'd love to live large in first class or save cash in economy, they'll have a seat for you. Make your way to O'Hare Intl. Airport (ORD) with one of these trusted carriers:

  • United Airlines - 612 flights to South Side per month
  • American Airlines - 339 flights to South Side per month
  • Air Canada - 190 flights to South Side per month

What is the best airport to fly to in South Side?
O'Hare Intl. Airport (ORD) is the main entry point for this popular destination. Once you've walked out of the arrivals area, the options are endless when it comes to exploring South Side.
How much is a flight to South Side?
Round-trip prices started as low as $69 this past week to South Side, and rose as high as $232. Several lucky passengers departing Atlanta (ATL) managed to get their hands on one-way fares starting at just $68.
How to book the cheapest flight to South Side?
With Orbitz, you'll uncover some of the most competitive flight deals around from a wide selection of airlines. But if you want to improve your chances of picking up cheap flights to South Side, here are some pointers to keep in mind:

  • Taking off from or arriving at other airports may be more affordable. Enter your preferred departure and arrival airports. Next, click on the 'Nearby airports' function below to see what your options are.
  • Also, click on the 'Show flexible dates' option to view the fares on days around your chosen departure. You may be able to find cheaper flight deals if your itinerary is flexible.
  • To fine tune your results, click on 'Show options.' You can search based on seating class, airlines, nonstop flights and refundable flights. You can also choose the time of day you'd like to fly under 'Sort & Filter' to the left.
  • Book your airfare as soon as you've figured out your travel dates. While you can get lucky once in a while, tickets rarely get more affordable as your departure date gets closer.
  • Make greater savings on your vacation by bundling your hotel, flights and car rental into an Orbitz package deal. Your travel budget will thank you.
  • Flying during the busy season can mean expensive airfares. If possible, plan your trip outside of popular periods, such as Christmas, New Year's Eve and Easter.

How long is a flight to South Side?
Your point of origin, which airport you depart from and whether you travel nonstop — the flight time depends on lots of factors. But we've put together the average times for some of the most common routes to South Side:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 40 minutes
  • Boston, MA (BOS-Logan Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 51 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to O'Hare Intl. Airport (ORD) - 2 hours and 13 minutes

What is the best time to book a flight to South Side?
On average, the cheapest month to book your journey is January. This is closely followed by February then August. When seeking a cheap flight to South Side, be ready to book. Cheap deals emerge quickly and don't wait around!
What day of the week is the cheapest to book a flight to South Side?
To land an unbeatable flight deal, make a booking on a Tuesday, Wednesday or Saturday. These are typically the cheapest days of the week to purchase seats to South Side.
What is the cheapest day of the week to fly to South Side?
Look into going early in the week to score cheap flights to South Side. Orbitz data from 2020 indicates Monday is normally the cheapest day to take off, followed by Tuesday. Saturday was found to have the highest airfares. This is probably because many passengers prefer to start their break when the weekend rolls around.
What is the cheapest month to fly to South Side?
To pick up cheap flights to South Side, you should pack your bags and depart in August. Orbitz data shows that this is generally a great month to save loads on your fare. If you're hoping to fly to South Side during June, bear in mind that this is the most expensive time to travel.
Which airlines allow free cancellation?
When you search for flights on Orbitz, select "Filter by flexible change policies." This filter will quickly find all the airlines offering free cancellation within 24 hours of booking and no change fees. That means you can breathe easy knowing that if things change, your reservation can too.
What do I need for the flight to South Side?
Nothing beats flying to a new place, but it pays to be prepared. This list of handy tips will help get your journey off to a smooth start:

  • Your travel documents are the most important things you'll need to carry on your flight to South Side. To avoid any confusion at check-in time, make sure that the personal information on your ticket is correct and matches your government-issued photo ID.
  • Take some activities to keep you occupied on your trip to South Side. Magazines, books and devices like e-readers and laptops are perfect. Don't forget to take a bottle of water too. Even on short flights, it's important to keep hydrated.
  • No matter the weather outside, plane cabins can get a bit chilly. Take a light jacket on board to keep yourself cozy.

How many direct flights are there to South Side?
There are 2,332 direct flights to South Side every month, which means you won't have to bother about long stopovers. Lock in a fare with United Airlines or American Airlines and then kick back, relax and enjoy the flight. Delta Air Lines, Southwest Airlines, Spirit Airlines and Air Canada also operate nonstop services to South Side.
How do I get cheap first-class/business deals to South Side?
If you think a first or business-class fare is out of your reach, think again. Here are some practical tips to help you score a premium flight to South Side for a whole lot less:

  • Be flexible with your travel dates and wait for deals on first or business-class airfares.
  • Look for a budget carrier that offers business-class seats. They often come with extra legroom and a glass of Champagne — but without the high price.
  • Bid for an upgrade in online auctions (if available) or upgrade your fare through your frequent flyer program.

What is the best time to go to South Side?
If you want to soak up the culture of South Side in peak season, May, June and July are the top months to visit. June 20 marks the first day of summer in the Northern Hemisphere and is a fantastic time to travel if you love the open air. During this time of the year, average daily temperatures normally range from 65 ºF to 75 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.