--- title: "$27 Cheap Flights to South Side, IL - Expedia" description: "Looking for cheap flights to South Side? Many airlines offer no change fee on selected flights and book now to earn your airline miles on top of our rewards! Find great 2026 South Side flight deals now!" canonical: "https://www.expedia.com/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights" language: en-US market: US currency: USD prices_as_of: 2026-11-14T04:30:01Z --- # $29 Cheap Flights to South Side, IL ![A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) [View $29 flight on Fri, Dec 18, 2026](https://www.expedia.com/Flights-Search?leg1=from:FLL,to:ORD,departure:12/18/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:28.98&airProductToken=AQowCi4IxnISBDIyMDYY5VogrhwozJKgAzCjlKADOEVAAFgBagRQQ18xcgdLMjFJWFMzEgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwDQ) ## Popular airlines Delta Frontier Airlines American Airlines United Alaska Airlines JetBlue Airways Southwest Airlines ## How much is the cheapest flight to South Side? Prices were available within the past 7 days and start at $29 for one-way flights and $64 for roundtrip, for the period specified. Prices and availability are subject to change. All deals One way Roundtrip [Select Frontier Airlines flight, departing Thu, Jan 7 from Columbus to Chicago, returning Sun, Jan 10, priced at $170 Found 2 hours ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:1/7/2027TANYT&leg2=from:ORD,to:CMH,departure:1/10/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:169.72&airProductToken=AQpgCi4IxnISBDI1MzkYgjsg4FwowvWhAzCx9qEDOEVAAFgBagRQQ18xcgdLMjFSWFMzCi4IxnISBDE1OTUY4Fwgrhwoz%5FehAzDZ-KEDOEVAAVgBagRQQ18xcgdLMjFSWFMzCmAKLgjGchIEMTU5NhiuHCDgXCiEkqIDMJKTogM4RUAAWAFqBFBDXzFyB1ozMFBYUzYKLgjGchIEMjU0MBjgXCCCOyiHlqIDMOqWogM4RUABWAFqBFBDXzFyB1ozMFBYUzYSCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAN) Thu, Jan 7 - Sun, Jan 10 · CMH · ORD · Roundtrip [Select Frontier Airlines flight, departing Wed, Jan 6 from Columbus to Chicago, returning Thu, Jan 7, priced at $188 Found 15 hours ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:1/6/2027TANYT&leg2=from:ORD,to:CMH,departure:1/7/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:187.34&airProductToken=AQpgCi4IxnISBDE2MTIYgjsgzHAov-qhAzDS66EDOEVAAFgBagRQQ18xcgdSMjFPWFA0Ci4IxnISBDEzNDkYzHAgrhwop-yhAzDm7aEDOEVAAVgBagRQQ18xcgdSMjFPWFA0CmAKLgjGchIEMTU5NhiuHCDgXCik8KEDMLLxoQM4RUAAWAFqBFBDXzFyB1ozMFBYUzYKLgjGchIEMjU0MBjgXCCCOyin9KEDMIr1oQM4RUABWAFqBFBDXzFyB1ozMFBYUzYSCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAN) Wed, Jan 6 - Thu, Jan 7 · CMH · ORD · Roundtrip [Select Frontier Airlines flight, departing Sun, Jan 10 from Columbus to Chicago, returning Sat, Jan 16, priced at $193 Found 6 hours ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:1/10/2027TANYT&leg2=from:ORD,to:CMH,departure:1/16/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:192.34&airProductToken=AQpgCi4IxnISBDI1MzkYgjsg4FwoopeiAzCRmKIDOEVAAFgBagRQQ18xcgdLMjFZWFMzCi4IxnISBDE1OTUY4Fwgrhwor5miAzC5mqIDOEVAAVgBagRQQ18xcgdLMjFZWFMzCmAKLgjGchIEMTM1MBiuHCDMcCjU2qIDMIrcogM4RUAAWAFqBFBDXzFyB1IyMU9YUDQKLgjGchIEMjc1NxjMcCCCOyjj5aIDMPzmogM4RUABWAFqBFBDXzFyB1IyMU9YUDQSCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAN) Sun, Jan 10 - Sat, Jan 16 · CMH · ORD · Roundtrip [Select Frontier Airlines flight, departing Thu, Jan 7 from Columbus to Chicago, returning Sat, Jan 9, priced at $200 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:1/7/2027TANYT&leg2=from:ORD,to:CMH,departure:1/9/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:199.16&airProductToken=AQpgCi4IxnISBDI1MzkYgjsg4FwowvWhAzCx9qEDOEVAAFgBagRQQ18xcgdLMjFSWFMzCi4IxnISBDE1OTUY4Fwgrhwoz%5FehAzDZ-KEDOEVAAVgBagRQQ18xcgdLMjFSWFMzEgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwDQ) Thu, Jan 7 - Sat, Jan 9 · CMH · ORD · Roundtrip [Select Frontier Airlines flight, departing Sun, Jan 10 from Columbus to Chicago, returning Wed, Jan 20, priced at $205 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:1/10/2027TANYT&leg2=from:ORD,to:CMH,departure:1/20/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:204.16&airProductToken=AQpgCi4IxnISBDI1MzkYgjsg4FwoopeiAzCRmKIDOEVAAFgBagRQQ18xcgdLMjFZWFMzCi4IxnISBDE1OTUY4Fwgrhwor5miAzC5mqIDOEVAAVgBagRQQ18xcgdLMjFZWFMzEgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwDQ) Sun, Jan 10 - Wed, Jan 20 · CMH · ORD · Roundtrip [Select Frontier Airlines flight, departing Thu, Jan 7 from Columbus to Chicago, returning Sat, Jan 16, priced at $208 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:1/7/2027TANYT&leg2=from:ORD,to:CMH,departure:1/16/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:207.34&airProductToken=AQpgCi4IxnISBDI1MzkYgjsg4FwowvWhAzCx9qEDOEVAAFgBagRQQ18xcgdLMjFSWFMzCi4IxnISBDE1OTUY4Fwgrhwoz%5FehAzDZ-KEDOEVAAVgBagRQQ18xcgdLMjFSWFMzCmAKLgjGchIEMTM1MBiuHCDMcCjU2qIDMIrcogM4RUAAWAFqBFBDXzFyB0cxNE9YUDQKLgjGchIEMTYxMRjMcCCCOyjo4KIDMILiogM4RUABWAFqBFBDXzFyB0cxNE9YUDQSCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAN) Thu, Jan 7 - Sat, Jan 16 · CMH · ORD · Roundtrip [Select JetBlue Airways flight, departing Fri, Jan 8 from Columbus to Chicago, returning Sun, Jan 10, priced at $240 Found 1 hour ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:1/8/2027TANYT&leg2=from:ORD,to:CMH,departure:1/10/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:239.76&airProductToken=AQpdCi0IwmwSBDE1MDcYgjsg5Voo9PqhAzCe%5FKEDOExAAFgBagJETnIIUEk0UVVFWTEKLAjCbBIDNjYzGOVaIK4cKNb%5FoQMwt4GiAzhMQAFYAWoCRE5yCFBJNFFVRVkxEgoIARABGAEqAkI2GAEiBAgBEAEoAigDKAQwAQ) Fri, Jan 8 - Sun, Jan 10 · CMH · ORD · Roundtrip [Select Southwest Airlines flight, departing Wed, Dec 16 from Columbus to Chicago, returning Tue, Jan 12, priced at $299 Found 3 days ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:12/16/2026TANYT&leg2=from:MDW,to:CMH,departure:1/12/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:298.80&airProductToken=AQoxCi8I15wBEgQxNzE4GII7IOywASi-%5Fp8DMIT%5FnwM4VkAAWAFqA1dHQXIHVkROVk4yRQoxCi8I15wBEgQ0MDA3GOywASCCOyjnraIDMLeuogM4VkAAWAFqA1dHQXIHVkROVk4yRRIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE) Wed, Dec 16 - Tue, Jan 12 · CMH · MDW · Roundtrip [Select United flight, departing Tue, Feb 9 from Columbus to Chicago, returning Wed, Feb 17, priced at $309 Found 2 hours ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:2/9/2027TANYT&leg2=from:ORD,to:CMH,departure:2/17/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:308.80&airProductToken=AQo3CjUI1YIBEgM0NjYYgjsgrhwovOOkAzCl5KQDOE5AAFgBagoxX2Jhc2ljZWNvcghUQVUyQUtCUwo4CjYI1YIBEgQ1NjU2GK4cIII7KK7BpQMwkMKlAzhOQABYAWoKMV9iYXNpY2Vjb3IIVEFVMkFLQlMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) Tue, Feb 9 - Wed, Feb 17 · CMH · ORD · Roundtrip [Select American Airlines flight, departing Tue, Feb 2 from Columbus to Chicago, returning Wed, Feb 3, priced at $309 Found 8 hours ago](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:2/2/2027TANYT&leg2=from:ORD,to:CMH,departure:2/3/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:308.80&airProductToken=AQozCjEIwYIBEgQzMzUzGII7IK4cKPCWpAMwz5ekAzhCQABYAWoFQkFTSUNyCFFWQUlLU0JaCjMKMQjBggESBDM3NDMYrhwggjso%5FqGkAzDgoqQDOEJAAFgBagVCQVNJQ3IIUVZBSUtTQloSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) Tue, Feb 2 - Wed, Feb 3 · CMH · ORD · Roundtrip ## Alternative airports Prices were available within the past 7 days. Prices and availability are subject to change. [Select flight to O'Hare Intl. ORD. Cheapest option available. Flights from $501](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:11/28/2026TANYT&leg2=from:ORD,to:CMH,departure:11/30/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flights from $ [Select flight to Midway Intl. MDW. Cheapest option available. Flights from $501](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:11/28/2026TANYT&leg2=from:MDW,to:CMH,departure:11/30/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently Asked Questions ### What month is the cheapest to fly to South Side? The cheapest month to fly to South Side is December when demand is low. Off-peak months are typically when you'll find cheap fares. To keep costs down, steer clear of flying during major holidays and school breaks. ### Which US cities have the cheapest flights to South Side? Typically, you'll find that New York, Washington and Dallas have cheap flights to South Side. However, flexibility is always key to bagging the lowest fares. Fly during low season or midweek to keep costs as low as possible. ### Which US cities fly direct to South Side? You can fly to South Side without any stops from 150 US cities. To find a nonstop journey, use the "Direct flights only" filter when searching for flights to South Side on Expedia. Then, explore your choices and pick the best departure from any of these cities: - New York - Washington - Dallas - Boston - Phoenix ### How to find a cheap flight to South Side? Book well in advance or search for cheap flights to South Side during the low season, such as December and January. Jetting off on a Thursday could also save you an average of 16% compared to a Sunday departure.\* The [Expedia app](https://www.expedia.com/app) makes it even easier to know exactly when to book. Just turn on the toggle for "Watch prices" and you'll receive a notification as soon as there's a better deal. *\*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.* ### How to get a cheap last-minute flight to South Side? While booking in advance is typically the easiest way to save cash, don't worry if your South Side getaway is last minute. You can still get cheap flights to South Side, especially if your plans have a little wiggle room. Try switching up your travel dates, looking at different ticket options or departing from an alternative airport. ### How far in advance should I book a flight to South Side? To pick up some of the best deals on domestic journeys, book your flight to South Side 28 days ahead of your travel dates. For international flights, book between two and four months in advance. This improves your chances of locking in the departure dates and seats you want.\* *\*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.* ### Which day of the week is the cheapest day to buy a plane ticket to South Side? You can generally find cheap flights to South Side on a Sunday. You'll save about 8% on average compared to those who book on a Friday, which is often the most expensive day for tickets.\* *\*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.* ### Which airlines fly to South Side? Grab a seat with one of these airlines and South Side will be all yours to discover: - United Airlines - 13,391 flights to South Side each month, including 13,391 flights to O'Hare Intl. Airport (ORD) per month. - American Airlines - 10,417 flights to South Side each month, including 10,417 flights to O'Hare Intl. Airport (ORD) per month. - Delta Air Lines - 1,213 flights to South Side each month, including 1,213 flights to O'Hare Intl. Airport (ORD) per month. ### Where do you fly into South Side? If you're flying to South Side, the main airport for arrivals is Midway Intl. Airport (MDW). You can also head for nearby hubs like O'Hare Intl. Airport (ORD), Lewis University Airport (LOT) or Gary, IN (GYY-Gary - Chicago Intl.). Another possibility worth considering when you fly to South Side is Chicago Executive Airport (PWK). ### Can I save money by booking a South Side trip package? Book a [South Side, Chicago (and vicinity) flight and hotel package deal](https://www.expedia.com/South-Side.d553248635074842823.Destination-Travel-Guides) on Expedia, and you could benefit from significant savings. It's easy to bundle your flights and accommodations, and you can even add car rentals and activities to create your own customized South Side trip. Plus, there's nothing like the convenience of booking everything in one place. ### Can I change or cancel my flight to South Side? If you reserved your flight to South Side in the last 24 hours, you can typically change or cancel it without fees. After that, additional costs may apply depending on the airline's terms of service. To learn more, head to our [Customer Service Portal](https://www.expedia.com/service/?langid=1033). Remember that some flights are non-refundable, so you may receive a credit for a future trip rather than a direct refund. When browsing on Expedia, select the "No cancel fee" or "Changes included" filters to see fares with flexible change policies. ## Travel information | Airlines serving | Southwest Airlines, Delta, Frontier Airlines, Volaris, WestJet, KLM, Air France, Virgin Atlantic, Aeromexico, LATAM Airlines Group, Allegiant Air, Korean Air | | ---------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Popular airline | Southwest Airlines | | Roundtrip price | $170 | ## Explore a world of travel with Expedia - [Lodging](?equalTargetTab=tab-0) - [Flights](?equalTargetTab=tab-1) - [Packages](?equalTargetTab=tab-2) - [Cars](?equalTargetTab=tab-3) - [Vacation Rentals](?equalTargetTab=tab-4) - [Things to Do](?equalTargetTab=tab-5) - [Hotels with Suites in Chicago](https://www.expedia.com/Chicago-Hotels-Hotel-Suites.0-0-d178248-tHotelSuites.Travel-Guide-Filter-Hotels) - [All-Inclusive Resorts in Chicago](https://www.expedia.com/Chicago-Hotels-All-Inclusive-Hotel.0-0-d178248-tAllinclusiveHotel.Travel-Guide-Filter-Hotels) - 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Prices and availability are subject to change. All deals One way Roundtrip [Select Frontier Airlines flight, departing Sat, Dec 19 from Fort Lauderdale to Chicago, returning Tue, Jan 12, priced at $64 Just found](https://www.expedia.com/Flights-Search?leg1=from:FLL,to:ORD,departure:12/19/2026TANYT&leg2=from:ORD,to:FLL,departure:1/12/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:63.96&airProductToken=AQowCi4IxnISBDIyMDYY5Vogrhwo5Z2gAzC8n6ADOEVAAFgBagRQQ18xcgdLMjFTWFMzCjAKLgjGchIEMjIwNRiuHCDlWii3raIDMIivogM4RUAAWAFqBFBDXzFyB0syMUVYUzMSCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAN) Sat, Dec 19 - Tue, Jan 12 · FLL · ORD · Roundtrip \*Available to One Key members. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights es: https://www.expedia.com/es/Vuelos-Baratos-South-Side.d553248635074842823.Guia-de-vuelos en-IE: https://www.expedia.ie/Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights zh-hans-HK: https://www.expedia.com.hk/cn/Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights en-CA: https://www.expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights de-DE: https://www.expedia.de/Billigflug-South-Side.d553248635074842823.Reise-Angebote-Flug zh-TW: https://www.expedia.com.tw/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights fr-BE: https://www.expedia.be/fr/Vols-South-Side.d553248635074842823.Guide-De-Vol da-DK: https://www.expedia.dk/Fly-Til-South-Side.d553248635074842823.Rejse-Guide-Fly en-SG: https://www.expedia.com.sg/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights zh-hant-HK: https://www.expedia.com.hk/Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights nl-NL: https://www.expedia.nl/Goedkope-Vliegtickets-South-Side.d553248635074842823.Reisgids-Vliegtickets en-AU: https://www.expedia.com.au/Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights en-NZ: https://www.expedia.co.nz/Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights nl-BE: https://www.expedia.be/Destinations-In-South-Side.d553248635074842823.Vliegtickets sv-SE: https://www.expedia.se/Flyg-Till-South-Side.d553248635074842823.Reseguide-Flyg fr-CA: https://www.expedia.ca/fr/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights nb-NO: https://www.expedia.no/Fly-Til-South-Side.d553248635074842823.Reise-Guide-Fly es-MX: https://www.expedia.mx/Vuelos-Baratos-South-Side.d553248635074842823.Guia-de-vuelos en-MY: https://www.expedia.com.my/Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights ja-JP: https://www.expedia.co.jp/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights en-TW: https://www.expedia.com.tw/en/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights en-GB: https://www.expedia.co.uk/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights en-HK: https://www.expedia.com.hk/en/Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights zh-CN: https://www.expedia.com/cn/Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights fi-FI: https://www.expedia.fi/Halvat-Lennot-South-Side.d553248635074842823.Matkaopas-Lennot en-US: https://www.expedia.com/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights en-IN: https://www.expedia.co.in/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights it-IT: https://www.expedia.it/Voli-Per-South-Side.d553248635074842823.Guida-Voli-aerei en-JP: https://www.expedia.co.jp/en/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights de-CH: https://www.expedia.ch/Billigflug-South-Side.d553248635074842823.Reise-Angebote-Flug fr-CH: https://www.expedia.ch/fr/Vols-Pas-Cher-South-Side.d553248635074842823.Voyage-Guide-Vols ko-KR: https://www.expedia.co.kr/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights en-KR: https://www.expedia.co.kr/en/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights pt-BR: https://www.expedia.com.br/Voos-Para-South-Side.d553248635074842823.guia-de-voos de-AT: https://www.expedia.at/Billigflug-South-Side.d553248635074842823.Reise-Angebote-Flug ```