Title: $28 Cheap Flights to South Side, IL - Expedia.com ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $28 Cheap Flights to South Side, IL [View $28 flight on Thu, Apr 30, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:EWR,to:MDW,departure:4/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:27.98&airProductToken=AQoyCjAIxnISBDE0MTMYxI0BIOywASji3osDMPjfiwM4RUAAWAFqBFBDXzFyB0syMVJYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) [South Side Travel Guide](https://expedia.com/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.com/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Things to do in South Side](https://expedia.com/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[Car Rentals in South Side](https://expedia.com/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.com/South-Side.d553248635074842823.Destination-Travel-Guides) ## Popular airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## How much is the cheapest flight to South Side? Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Tue, Apr 21 - Wed, Apr 29 ATL Atlanta MDW Chicago $69 Roundtrip found 19 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ATL,to:MDW,departure:4/21/2026TANYT&leg2=from:MDW,to:ATL,departure:4/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:68.97&airProductToken=AQowCi4IxnISBDI3NzkY4Fwg7LABKIb-igMwgv-KAzhLQABYAWoDRUNPcgdLMjFFWFMyEgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwAQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Thu, Apr 23 - Wed, Apr 29 ATL Atlanta ORD Chicago $73 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ATL,to:ORD,departure:4/23/2026TANYT&leg2=from:ORD,to:ATL,departure:4/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:72.18&airProductToken=AQotCisIzpYBEgMzOTcY4Fwgrhwo-I6LAzD7j4sDOFdAAFgBagJSUHIGV0ExNE5SCi0KKwjOlgESAzM5NhiuHCDgXCj804sDMPPUiwM4V0AAWAFqAlJQcgZXQTE0TlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, May 13 - Tue, May 19 BOS Boston MDW Chicago $135 Roundtrip found 20 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:5/13/2026TANYT&leg2=from:MDW,to:BOS,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:134.80&airProductToken=AQoxCi8I15wBEgM4OTgYwZMBIOywASix8owDMNHzjAM4VkAAWAFqA1dHQXIHVkJOVkgyTAoyCjAI15wBEgQxMjgwGOywASDBkwEo37aNAzDrt40DOFZAAFgBagNXR0FyB1ZCTlZIMkwSCggCEAEYAioCV04YASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Apr 14 - Tue, Apr 21 BOS Boston RFD Rockford $139 Roundtrip found 16 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:BOS,to:RFD,departure:4/14/2026TANYT&leg2=from:RFD,to:BOS,departure:4/21/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:138.20&airProductToken=AQpnCjIIwYIBEgQxMDA5GMGTASCuHCiYrooDMNivigM4QkAAWAFqBUJBU0lDcghPVUFJS1NCVgoxCMGCARIENjU3OBiuHCCxGSiosIoDMIexigM4QkABWAFqBUJBU0lDcghPVUFJS1NCVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Apr 29 - Tue, May 5 LAX Los Angeles ORD Chicago $277 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LAX,to:ORD,departure:4/29/2026TANYT&leg2=from:ORD,to:LAX,departure:5/5/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:276.41&airProductToken=AQplCjEIwaYBEgM2OTgYi7gBIJIBKPXWiwMwpNiLAzhYQABYAWoFU0FWRVJyCEdINU9YSkJOCjAIwaYBEgMzMjgYkgEgrhwogduLAzD83IsDOFhAAVgBagVTQVZFUnIIR0g1T1hKQk4KZQowCMGmARIDNzE1GK4cIJIBKPSUjAMwhJeMAzhYQABYAWoFU0FWRVJyCEdINU9YSkJOCjEIwaYBEgM1MzMYkgEgi7gBKI2YjAMwu5mMAzhYQAFYAWoFU0FWRVJyCEdINU9YSkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwDQ) ## Alternative airports Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:4/10/2026TANYT&leg2=from:ORD,to:CMH,departure:4/16/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. [Flights from $315 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:4/10/2026TANYT&leg2=from:ORD,to:CMH,departure:4/16/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:4/10/2026TANYT&leg2=from:MDW,to:CMH,departure:4/17/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. Cheapest [Flights from $225 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:4/10/2026TANYT&leg2=from:MDW,to:CMH,departure:4/17/2026TANYT&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? ### Which US cities have the cheapest flights to South Side? ### Which US cities fly direct to South Side? > - New York > - Washington > - Dallas > - Boston > - Phoenix ### How to find a cheap flight to South Side? ### How to get a cheap last-minute flight to South Side? ### How far in advance should I book a flight to South Side? ### Which day of the week is the cheapest day to buy a plane ticket to South Side? ### Which airlines fly to South Side? > - 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? ### Can I save money by booking a South Side trip package? ### Can I change or cancel my flight to South Side? \*Flight schedules are subject to change. \*Available to One Key members. ## Book with confidence # Tips to find the cheapest flights to South Side **The cheapest day to fly** Get started finding a cheap flight to South Side on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you. **The cheapest month to fly** April is the cheapest month to fly to South Side. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to South Side. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute. **The most affordable time to book a flight** Typically, a Sunday can be the cheapest time to book a flight to South Side, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation. **The cheapest round-trip tickets to South Side** The lowest price for round-trip flights to South Side in 2026 starts from from $56, while one-way tickets start from from $28\. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to South Side. If you have a preferred departure time or airline, you can use the handy filters to customize your search. **The cheapest airlines flying to South Side** Spirit Airlines, Frontier Airlines, American Airlines, Southwest Airlines, JetBlue Airways, Alaska Airlines are just some of the airlines that can typically offer cheap tickets to South Side. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to South Side and countless more destinations worldwide. **The most affordable airports to fly into** To view the cheapest airports to fly into for South Side, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to South Side. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia. **Save with a package** With Expedia's amazing [package deals](https://www.expedia.com/package-deals), you could save hundreds of dollars by booking your South Side plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving. **Date flexibility for the cheapest flights to South Side** If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to South Side. **Stopover savings** The cheapest tickets to South Side are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to South Side. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved. **Get Expedia's Price Drop Protection** Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference\*. This gives you peace of mind that you're getting one of the cheapest flights to South Side for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members. \*Terms apply. **Use our Price Tracking feature** Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to South Side. Simply download the free Expedia app to your smart device and activate South Side flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices. **Book with Expedia** As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to South Side. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. ## Travel information | Destination airport | Midway Intl. | | ----------------------------- | ------------ | | Destination airport IATA code | MDW | | Destination city name | Chicago | | Roundtrip price | $56 | ## Trending flights to South Side Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sat, Apr 25 - Wed, Apr 29 EWR New York MDW Chicago $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:EWR,to:MDW,departure:4/25/2026TANYT&leg2=from:MDW,to:EWR,departure:4/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQoyCjAIxnISBDE0MTMYxI0BIOywASjCposDMNiniwM4RUAAWAFqBFBDXzFyB0syMVNYUzIKMgowCMZyEgQxNDE0GOywASDEjQEojtKLAzCO04sDOEVAAFgBagRQQ18xcgdLMjFYWFMyEgoIARABGAEqAkY5GAEiBAgBEAEoAigDMA0) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - 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