Title: Madison to Chicago cheap flights from $164 (MSN to CHI) - 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) # $164 Cheap Flights from Madison (MSN) to Chicago (CHI) [View $164 flight on Sat, Jul 4, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MSN,to:ORD,departure:7/4/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:163.95&airProductToken=AQozCjEIwYIBEgQ2NDk0GMxsIK4cKLi3kQMw_7eRAzhCQABYAWoFQkFTSUNyCE5WQVhaTkJaEgwIARABGAEqAkFBMgAYASIECAEQASgCKAMoBDAL) ## Popular airlines from Dane County Regional Airport (MSN) to Chicago - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:CHI,departure:4/13/2026TANYT&leg2=from:CHI,to:MSN,departure:4/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:CHI,departure:4/13/2026TANYT&leg2=from:CHI,to:MSN,departure:4/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:CHI,departure:4/13/2026TANYT&leg2=from:CHI,to:MSN,departure:4/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](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) ## Cheap Flights from Madison to Chicago (MSN-CHI) Prices were available within the past 7 days and start at $164 for one-way flights and $239 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, Jul 3 - Tue, Jul 14 MSN Madison ORD Chicago $239 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:7/3/2026TANYT&leg2=from:ORD,to:MSN,departure:7/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:238.80&airProductToken=AQo4CjYI1YIBEgQ1OTAyGMxsIK4cKJiskQMw5ayRAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KOAo2CNWCARIENTg0MxiuHCDMbCjHqpIDMJCrkgM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sun, May 31 - Sat, Jun 6 MSN Madison ORD Chicago $246 Roundtrip found 3 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:5/31/2026TANYT&leg2=from:ORD,to:MSN,departure:6/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:245.25&airProductToken=AQo4CjYI1YIBEgQ1NTY4GMxsIK4cKLe9jgMw_r2OAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KOAo2CNWCARIEMjc4MxiuHCDMbCiog48DMO2DjwM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sun, May 31 - Sat, Jun 6 MSN Madison ORD Chicago $249 Roundtrip found 3 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:5/31/2026TANYT&leg2=from:ORD,to:MSN,departure:6/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.48&airProductToken=AQo4CjYI1YIBEgQ1MzU4GMxsIK4cKMy7jgMwmbyOAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KOAo2CNWCARIENDc3OBiuHCDMbCi6go8DMIKDjwM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Jul 3 - Tue, Jul 14 MSN Madison ORD Chicago $249 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:7/3/2026TANYT&leg2=from:ORD,to:MSN,departure:7/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.60&airProductToken=AQozCjEIwYIBEgQzNzE3GMxsIK4cKNGykQMwq7ORAzhCQABYAWoFQkFTSUNyCFFWRkhaTkJYCmcKMgjBggESBDI3NTQYrhwgo7EBKIGtkgMwqK6SAzhCQABYAWoFQkFTSUNyCFFWRkhaTkJYCjEIwYIBEgM4NzYYo7EBIMxsKKCvkgMwqbCSAzhCQAFYAWoFQkFTSUNyCFFWRkhaTkJYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, May 27 - Sat, Jun 20 MSN Madison ORD Chicago $252 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:5/27/2026TANYT&leg2=from:ORD,to:MSN,departure:6/20/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:251.70&airProductToken=AQo4CjYI1YIBEgQ0NjAzGMxsIK4cKPWRjgMwwJKOAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KOAo2CNWCARIENTM4NRiuHCDMbCjRnZADMJSekAM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Apr 21 - Sat, Apr 25 MSN Madison ORD Chicago $253 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:4/21/2026TANYT&leg2=from:ORD,to:MSN,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:252.78&airProductToken=AQo4CjYI1YIBEgQ0NTc3GMxsIK4cKNb5igMwnPqKAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KOAo2CNWCARIEMzQ3NhiuHCDMbCjLp4sDMIuoiwM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, Apr 17 - Sun, Apr 19 MSN Madison ORD Chicago $254 Roundtrip found 6 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:4/17/2026TANYT&leg2=from:ORD,to:MSN,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:253.80&airProductToken=AQo4CjYI1YIBEgQxOTA3GMxsIK4cKJ_RigMw3dGKAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBNEFEQk4KOAo2CNWCARIEMzY2OBiuHCDMbCil6IoDMOroigM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, Apr 15 - Tue, Apr 21 MSN Madison ORD Chicago $255 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:4/15/2026TANYT&leg2=from:ORD,to:MSN,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:254.84&airProductToken=AQo4CjYI1YIBEgQxNTgwGMxsIK4cKIq1igMwzbWKAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBNEFEQk4KOAo2CNWCARIEMzY4NRiuHCDMbCid-IoDMOX4igM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, Apr 17 - Fri, Apr 24 MSN Madison ORD Chicago $259 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:4/17/2026TANYT&leg2=from:ORD,to:MSN,departure:4/24/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:258.10&airProductToken=AQo4CjYI1YIBEgQ0NTc3GMxsIK4cKNbMigMwnM2KAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBNEFEQk4KOAo2CNWCARIENDQyMxiuHCDMbCjImosDMI-biwM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Apr 28 - Tue, May 5 MSN Madison ORD Chicago $460 Roundtrip found 14 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MSN,to:ORD,departure:4/28/2026TANYT&leg2=from:ORD,to:MSN,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:459.30&airProductToken=AQpuCjUIxJgBEgQ0MTAzGMxsIMx8KLbIiwMwhsmLAzhFQABYAWoJTUFJTkJBU0lDcghWRldRQTBCUQo1CMSYARIENTExMBjMfCCuHCjzy4sDMNTMiwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0E1QkMKbQo0CMSYARIDNDI2GK4cIMsBKMuWjAMwz5eMAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwo1CMSYARIENTYzMxjLASDMbCihmowDMMebjAM4RUABWAFqCU1BSU5CQVNJQ3IIVkZWU0gzQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:ORD,departure:4/13/2026TANYT&leg2=from:ORD,to:MSN,departure:4/14/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 23 min [Flights from $627 ](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:ORD,departure:4/13/2026TANYT&leg2=from:ORD,to:MSN,departure:4/14/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Travel information | Origin airport | Dane County Regional | | ------------------- | -------------------- | | Destination airport | O'Hare Intl. | | Roundtrip price | $233 | | Distance | 108 mi | ## Book with confidence # Madison to Chicago Flights The cheapest times to fly from Madison 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 Madison to Chicago are during the month of July. You can find some of the cheapest flights from Madison to Chicago with Expedia's search tool and vast selection of airlines. The best time to book a flight from Madison to Chicago Sunday is one of the best days to book for cheap flights from Madison 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 Madison 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 Madison to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $164 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 Madison 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 Madison 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\. 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