Title: Jackson to Chicago cheap flights from $99 (MKL to ORD) - Expedia.com ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $99 Cheap Flights from Jackson (MKL) to Chicago (ORD) [View $99 flight on Fri, Jul 10, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MKL,to:ORD,departure:7/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:99.00&airProductToken=AQooCiYIy44BEgQ1ODgwGMxaIK4cKP79kQMw4v6RAzhUQABYAXIEVDIxThIKCAEQARgBKgJLRxgBIgQIARABKAIoAygEMAE) ## Popular airlines from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago O'Hare Intl. Airport (ORD) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_KG.svg) Denver Air Connection [](https://www.expedia.com/Flights-Search?leg1=from:MKL,to:ORD,departure:3/25/2026TANYT&leg2=from:ORD,to:MKL,departure:4/1/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"KG"}}]) ## Cheap Flights from Jackson to Chicago (MKL-ORD) Prices were available within the past 7 days and start at $99 for one-way flights and $198 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Mon, Apr 13 - Fri, Apr 17 MKL Jackson ORD Chicago $198 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:4/13/2026TANYT&leg2=from:ORD,to:MKL,departure:4/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:197.99&airProductToken=AQooCiYIy44BEgQ1ODgwGMxaIK4cKP6figMw4qCKAzhUQABYAXIEVDIxTgooCiYIy44BEgQ1ODgyGK4cIMxaKO7OigMw3M-KAzhUQABYAXIEVDIxThIKCAEQARgBKgJLRxgBIgQIARABKAIoAygEMAE) ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Sat, Apr 25 - Sun, Apr 26 MKL Jackson ORD Chicago $204 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:4/25/2026TANYT&leg2=from:ORD,to:MKL,departure:4/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:203.99&airProductToken=AQooCiYIy44BEgQ1ODgwGMxaIK4cKP6miwMw4qeLAzhUQABYAXIEVDIxTgooCiYIy44BEgQ1ODgyGK4cIMxaKI60iwMw_LSLAzhWQABYAXIEVjIxThIKCAEQARgBKgJLRxgBIgQIARABKAIoAygEMAE) ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Fri, Apr 17 - Sun, Apr 19 MKL Jackson ORD Chicago $210 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:4/17/2026TANYT&leg2=from:ORD,to:MKL,departure:4/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:209.99&airProductToken=AQooCiYIy44BEgQ1ODgwGMxaIK4cKP7MigMw4s2KAzhWQABYAXIEVjIxTgooCiYIy44BEgQ1ODgyGK4cIMxaKK7ligMwnOaKAzhWQABYAXIEVjIxThIMCAEQARgBKgJLRzIAGAEiBAgBEAEoAigDKAQwAQ) ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Thu, Mar 26 - Thu, Apr 2 MKL Jackson ORD Chicago $224 Roundtrip found 19 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:3/26/2026TANYT&leg2=from:ORD,to:MKL,departure:4/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:224.00&airProductToken=AQooCiYIy44BEgQ1ODgwGMxaIK4cKL7ViAMwotaIAzhRQABYAXIEUTE0TgooCiYIy44BEgQ1ODgyGK4cIMxaKI6miQMw_KaJAzhUQABYAXIEVDIxThIMCAEQARgBKgJLRzIAGAEiBAgBEAEoAigDKAQwAQ) ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Tue, Mar 24 - Sun, Apr 12 MKL Jackson ORD Chicago $230 Roundtrip found 5 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:3/24/2026TANYT&leg2=from:ORD,to:MKL,departure:4/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:230.00&airProductToken=AQoiCiAIy44BEgQ1ODgwGMxaIK4cKP6-iAMw4r-IAzhRQABYAQoiCiAIy44BEgQ1ODgyGK4cIMxaKM6WigMwvJeKAzhWQABYARIKCAEQARgBKgJLRxgBIgQIARABKAQwAQ) ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Thu, Mar 12 - Fri, Mar 27 MKL Jackson ORD Chicago $244 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:3/12/2026TANYT&leg2=from:ORD,to:MKL,departure:3/27/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:243.99&airProductToken=AQoiCiAIy44BEgQ1ODgwGMxaIK4cKP63hwMw4riHAzhIQABYAQoiCiAIy44BEgQ1ODgyGK4cIMxaKM7iiAMwvOOIAzhUQABYARIKCAEQARgBKgJLRxgBIgQIARABKAQwAQ) ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Thu, Mar 26 - Fri, Mar 27 MKL Jackson ORD Chicago $250 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:3/26/2026TANYT&leg2=from:ORD,to:MKL,departure:3/27/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:250.00&airProductToken=AQooCiYIy44BEgQ1ODgwGMxaIK4cKL7ViAMwotaIAzhRQABYAXIEUTE0TgooCiYIy44BEgQ1ODgyGK4cIMxaKM7iiAMwvOOIAzhRQABYAXIEUTE0ThIKCAEQARgBKgJLRxgBIgQIARABKAIoAygEMAE) ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Tue, Mar 17 - Wed, Mar 25 MKL Jackson ORD Chicago $270 Roundtrip found 11 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:3/17/2026TANYT&leg2=from:ORD,to:MKL,departure:3/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:270.00&airProductToken=AQoiCiAIy44BEgQ1ODgwGMxaIK4cKJ7whwMwgvGHAzhIQABYAQoiCiAIy44BEgQ1ODgyGK4cIMxaKI7MiAMw_MyIAzhRQABYARIKCAEQARgBKgJLRxgBIgQIARABKAQwAQ) ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Sat, Apr 11 - Sun, Apr 12 MKL Jackson ORD Chicago $275 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:4/11/2026TANYT&leg2=from:ORD,to:MKL,departure:4/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:274.80&airProductToken=AQpcCigIy44BEgQ1ODcwGMxaIOBcKOyHigMwqIiKAzhUQABYAXIGVDE0TkNYCjAIwYIBEgQyNzM3GOBcIK4cKPKLigMwh42KAzhPQAFYAWoETUFJTnIIT1dBSUpTTTMKKQonCMuOARIENTg4MhiuHCDMWijOlooDMLyXigM4UUAAWAFyBVEwTkNYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwAQ) ![KEY LIME AIR DBA DENVER AIR CONNECTION](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/KG.gif) Sat, Apr 11 - Tue, Apr 14 MKL Jackson ORD Chicago $278 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MKL,to:ORD,departure:4/11/2026TANYT&leg2=from:ORD,to:MKL,departure:4/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:277.80&airProductToken=AQoqCigIy44BEgQ1ODgwGMxaIK4cKL6JigMwooqKAzhUQABYAXIGVDE0TkNYClwKMAjBggESBDQwODUYrhwg4Fwo_KiKAzD7qYoDOE9AAFgBagRNQUlOcghPV0FVVU5NMwooCMuOARIENTg3MhjgXCDMWijEqooDMICrigM4VEABWAFyBlQxNE5DWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAE) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## Frequently asked questions ### How much does a flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.) cost? ### What is the cheapest month to fly from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### Which airlines fly direct from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### What is the cheapest airline that flies from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### How do I find cheap flights from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### What is the best airline to fly with from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### What is the best time to fly from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### How many flights per day from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### What is the earliest flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### What are the most popular departure times for flights from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### How long does it take to fly from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### Can you fly business or first class from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ### How do I earn miles on a Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia? ### What airports do you fly into for Chicago from McKellar-Sipes Regional (MKL)? ### Is it cheaper to buy a plane ticket from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.) at the last minute? ### Is it cheaper to book a Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package? ### Can I cancel or change the date of my flight from Jackson, TN (MKL-McKellar-Sipes Regional) to Chicago, IL (ORD-O'Hare Intl.)? ## Travel information | Origin airport | McKellar-Sipes Regional | | ------------------- | -------------------------------------- | | Destination airport | O'Hare Intl. | | Airlines serving | KEY LIME AIR DBA DENVER AIR CONNECTION | | Roundtrip price | $192 | | Distance | 443 mi | | Average flight time | 1 hour 40 mins | ## Book with confidence # Jackson to Chicago Flights The cheapest times to fly from Jackson to Chicago On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Jackson to Chicago are during the month of April. You can find some of the cheapest flights from Jackson to Chicago with Expedia's search tool and vast selection of airlines. The best time to book a flight from Jackson to Chicago Sunday is one of the best days to book for cheap flights from Jackson to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance. How to find cheap round-trip tickets from Jackson to Chicago Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Jackson to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $99 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members. Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Jackson to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps. You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Jackson to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures. \*Terms apply. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [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) - [Hotels near O'Hare Station ](https://www.expedia.com/OHare-Station-Hotels.d6210225.Travel-Guide-Hotels) - [Rosemont Hotels ](https://www.expedia.com/Rosemont-Hotels.d7581.Travel-Guide-Hotels) - [Hotels near Donald E. 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