--- title: "Madison to Chicago cheap flights from $198 (MSN to MDW) - Expedia" description: "Cheap Flights from Madison (MSN) to Chicago (MDW) start at $198 for one-way and $467 for round trip. Earn your airline miles on top of our rewards!" canonical: "https://www.expedia.com/lp/flights/msn/mdw/madison-to-chicago" language: en-US market: US currency: USD prices_as_of: 2026-11-14T11:43:19Z --- # $198 Cheap Flights from Madison (MSN) to Chicago (MDW) ![An airplane exhibit labeled "Concourse A" in an airport terminal.](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium) [View $198 flight on Wed, Dec 30, 2026](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/30/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:197.20&airProductToken=AQpvCjUIxJgBEgQ0MTAyGMxsIMx8KLqYoQMwhZmhAzhFQABYAWoJTUFJTkJBU0lDcghWRldRQTBCUQo2CMSYARIENTE4OBjMfCDssAEoz5qhAzC8m6EDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNYM0JDEgwIARABGAEqAkRMMgAYASIECAEQASgCKAMoBDAB) Photo by by Midway Intl Airport ## Popular airlines from Dane County Regional Airport (MSN) to Chicago Midway Airport (MDW) [Delta](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:11/28/2026TANYT&leg2=from:MDW,to:MSN,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) ## Cheap Flights from Madison to Chicago (MSN-MDW) Prices were available within the past 7 days and start at $198 for one-way flights and $467 for roundtrip, for the period specified. Prices and availability are subject to change. All deals One way Roundtrip [Select Delta flight, departing Sat, Dec 26 from Madison to Chicago, returning Thu, Dec 31, priced at $467 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/26/2026TANYT&leg2=from:MDW,to:MSN,departure:12/31/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:466.40&airProductToken=AQpvCjUIxJgBEgQzNzkyGMxsIMx8KLjpoAMwieqgAzhFQABYAWoJTUFJTkJBU0lDcghWRldRQTBCUQo2CMSYARIENTMyMRjMfCDssAEoyeqgAzC%5F66ADOEVAAVgBaglNQUlOQkFTSUNyCFhBVlNBNUJRCm8KNgjEmAESBDUzMjEY7LABIMx8KIukoQMw9aShAzhFQABYAWoJTUFJTkJBU0lDcghYQVZTWDVCQwo1CMSYARIEMzc4NxjMfCDMbCj4p6EDMM2ooQM4RUABWAFqCU1BSU5CQVNJQ3IIVkZXUUEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) Sat, Dec 26 - Thu, Dec 31 · MSN · MDW · Roundtrip [Select Delta flight, departing Wed, Dec 16 from Madison to Chicago, returning Sat, Dec 19, priced at $516 Found 3 days ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/16/2026TANYT&leg2=from:MDW,to:MSN,departure:12/19/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:515.41&airProductToken=AQpvCjUIxJgBEgQzMTY2GMxsIMx8KPD4nwMwuPmfAzhFQABYAWoJTUFJTkJBU0lDcghURldHQTBCUQo2CMSYARIENDcxNBjMfCDssAEo7PyfAzDa%5FZ8DOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNYM0JDCm8KNgjEmAESBDUzMjEY7LABIMx8KIudoAMw9Z2gAzhFQABYAWoJTUFJTkJBU0lDcghUQVZTQTVCQwo1CMSYARIEMzc5NBjMfCDMbCj7n6ADMMugoAM4RUABWAFqCU1BSU5CQVNJQ3IIVkZXUUEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) Wed, Dec 16 - Sat, Dec 19 · MSN · MDW · Roundtrip [Select Delta flight, departing Thu, Dec 17 from Madison to Chicago, returning Mon, Jan 4, priced at $522 Found 2 days ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/17/2026TANYT&leg2=from:MDW,to:MSN,departure:1/4/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:521.41&airProductToken=AQpvCjUIxJgBEgQzMTY2GMxsIMx8KJCEoAMw2ISgAzhFQABYAWoJTUFJTkJBU0lDcghURldHQTBCUQo2CMSYARIENDcxNBjMfCDssAEojIigAzD6iKADOEVAAVgBaglNQUlOQkFTSUNyCFhBVlNYNUJDCm8KNgjEmAESBDQ4MjcY7LABIMx8KJzQoQMwhdGhAzhFQABYAWoJTUFJTkJBU0lDcghYQVZTWDVCQwo1CMSYARIENTM4NxjMfCDMbCj706EDMMrUoQM4RUABWAFqCU1BSU5CQVNJQ3IIVkZXUUEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) Thu, Dec 17 - Mon, Jan 4 · MSN · MDW · Roundtrip [Select Delta flight, departing Tue, Jan 12 from Madison to Chicago, returning Tue, Jan 19, priced at $536 Found 11 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:1/12/2027TANYT&leg2=from:MDW,to:MSN,departure:1/19/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:535.41&airProductToken=AQpxCjYIxJgBEgQ1MjA1GMxsIOO0ASivqqIDMIOrogM4RUAAWAFqCU1BSU5CQVNJQ3IIVkZXUUEwQlEKNwjEmAESBDQ2NzcY47QBIOywASiqraIDMICuogM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU1gyQkMKbwo2CMSYARIENDgyNxjssAEgzHwo%5FPiiAzDl-aIDOEVAAFgBaglNQUlOQkFTSUNyCFhBVlNYMkJDCjUIxJgBEgQ1Mzg3GMx8IMxsKNv8ogMwqv2iAzhFQAFYAWoJTUFJTkJBU0lDcghWRldRQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) Tue, Jan 12 - Tue, Jan 19 · MSN · MDW · Roundtrip [Select Delta flight, departing Sat, Dec 5 from Madison to Chicago, returning Mon, Dec 7, priced at $552 Found 6 days ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/5/2026TANYT&leg2=from:MDW,to:MSN,departure:12/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:551.40&airProductToken=AQpvCjUIxJgBEgQzMTY2GMxsIMx8KJD9ngMw2P2eAzhFQABYAWoJTUFJTkJBU0lDcghYRlZRQTBCUQo2CMSYARIENDcxNBjMfCDssAEojIGfAzD6gZ8DOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNYM0JDCnEKNwjEmAESBDQ3MTEY7LABIOO0ASiJlZ8DMNmVnwM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU1g1QkMKNgjEmAESBDUyNDUY47QBIMxsKKCYnwMw-5ifAzhFQAFYAWoJTUFJTkJBU0lDcghWRldRQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) Sat, Dec 5 - Mon, Dec 7 · MSN · MDW · Roundtrip [Select Delta flight, departing Fri, Dec 4 from Madison to Chicago, returning Mon, Dec 7, priced at $555 Found 12 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/4/2026TANYT&leg2=from:MDW,to:MSN,departure:12/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:554.40&airProductToken=AQpvCjUIxJgBEgQzMTY2GMxsIMx8KPDxngMwuPKeAzhFQABYAWoJTUFJTkJBU0lDcghYRlZRQTBCUQo2CMSYARIENDcxNBjMfCDssAEo7PWeAzDa9p4DOEVAAVgBaglNQUlOQkFTSUNyCFRBVlNYNkJDCm8KNgjEmAESBDU0NjkY7LABIMx8KLiVnwMwoZafAzhFQABYAWoJTUFJTkJBU0lDcghYQVZTWDVCQwo1CMSYARIENDA4OBjMfCDMbCj7mJ8DMMyZnwM4RUABWAFqCU1BSU5CQVNJQ3IIWEZWUUEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) Fri, Dec 4 - Mon, Dec 7 · MSN · MDW · Roundtrip [Select Delta flight, departing Wed, Dec 16 from Madison to Chicago, returning Sat, Dec 19, priced at $567 Found 3 days ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/16/2026TANYT&leg2=from:MDW,to:MSN,departure:12/19/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:566.41&airProductToken=AQpxCjYIxJgBEgQ1MjA1GMxsIOO0ASi7-p8DMI77nwM4RUAAWAFqCU1BSU5CQVNJQ3IIVkZXUUEwQlEKNwjEmAESBDQ2NzcY47QBIOywASjQ%5FZ8DMKH-nwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU1gzQkMKbwo2CMSYARIENTMyMRjssAEgzHwoi52gAzD1naADOEVAAFgBaglNQUlOQkFTSUNyCFRBVlNBNUJDCjUIxJgBEgQzNzg3GMx8IMxsKPigoAMwzaGgAzhFQAFYAWoJTUFJTkJBU0lDcghWRldRQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) Wed, Dec 16 - Sat, Dec 19 · MSN · MDW · Roundtrip [Select Delta flight, departing Thu, Dec 17 from Madison to Chicago, returning Mon, Jan 4, priced at $577 Found 2 days ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/17/2026TANYT&leg2=from:MDW,to:MSN,departure:1/4/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:576.41&airProductToken=AQpxCjYIxJgBEgQ1MjA1GMxsIOO0ASjbhaADMK6GoAM4RUAAWAFqCU1BSU5CQVNJQ3IIWEZWUUEwQlEKNwjEmAESBDQ2NzcY47QBIOywASjwiKADMMGJoAM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU1g1QkMKbwo2CMSYARIENDgyNxjssAEgzHwonNChAzCF0aEDOEVAAFgBaglNQUlOQkFTSUNyCFhBVlNYNUJDCjUIxJgBEgQ1Mzg3GMx8IMxsKPvToQMwytShAzhFQAFYAWoJTUFJTkJBU0lDcghWRldRQTBCURIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) Thu, Dec 17 - Mon, Jan 4 · MSN · MDW · Roundtrip [Select Delta flight, departing Sat, Dec 26 from Madison to Chicago, returning Thu, Dec 31, priced at $578 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/26/2026TANYT&leg2=from:MDW,to:MSN,departure:12/31/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:577.01&airProductToken=AQpvCjUIxJgBEgQzNzkyGMxsIMx8KLjpoAMwieqgAzhWQABYAWoJTUFJTkNMQVNDcghWRldRQTBNTAo2CMSYARIENTMyMRjMfCDssAEoyeqgAzC%5F66ADOFhAAVgBaglNQUlOQ0xBU0NyCFhBVlNBNU1MEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) Sat, Dec 26 - Thu, Dec 31 · MSN · MDW · Roundtrip · Found 1 da · y ago [Select Delta flight, departing Sat, Dec 26 from Madison to Chicago, returning Thu, Dec 31, priced at $587 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:MDW,departure:12/26/2026TANYT&leg2=from:MDW,to:MSN,departure:12/31/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:587.00&airProductToken=AQpxCjYIxJgBEgQ0MTAyGMxsIMx8KLrroAMwheygAzhTQABYAWoKQ09NRlRCQVNJQ3IIVkZXUUEwMUwKNwjEmAESBDUxODgYzHwg7LABKM%5FtoAMwvO6gAzhXQAFYAWoKQ09NRlRCQVNJQ3IIWEFWU0E1MkwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) Sat, Dec 26 - Thu, Dec 31 · MSN · MDW · Roundtrip ## Alternative airports near Chicago 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. Average driving time to city center is 23 minutes. Flights from $449](https://www.expedia.com/Flights-Search?leg1=from:MSN,to:ORD,departure:11/28/2026TANYT&leg2=from:ORD,to:MSN,departure:12/1/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 23 min ## 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 December. 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 $198 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\. The percentages you see are averages.* ## Frequently Asked Questions ### How much does a flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.) cost? You can find cheap one-way flights from $198 and cheap return flights $467 MSN to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when MSN to MDW ticket fares go up or down. ### What is the cheapest month to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.)? The cheapest month to fly from MSN to MDW is December when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route. ### Which airlines fly direct from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.)? Enter MSN to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights. ### What is the cheapest airline that flies from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.)? Delta and United are just some of the carriers that fly from Madison, WI (MSN) to Chicago, IL (MDW). Use Expedia's flight search tool to compare airlines on this route and find our cheapest option for your trip. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget. *\*Prices based on flights available on Expedia in the last year.* ### How do I find cheap flights from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.)? To find a cheap flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up [Price Tracking](https://www.expedia.com/why/price-tracking) and receive alerts when fares go up or down. ### What is the best time to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.)? The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience. ### What is the earliest flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.)? Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from MSN to MDW. To compare more early flights, use the "Early Morning" and "Morning" filters in your search. ### How long does it take to fly from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.)? Flights from MSN to MDW with one stop typically take around 5 hours 30 minutes, covering approximately 124 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic. ### Can you fly business or first class from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.)? Select the "Business class" and "First class" filters when looking for MSN to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip. ### How do I earn miles on a Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.) flight with Expedia? It's easy to earn miles on a Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of [One Key™](https://www.expedia.com/welcome-one-key), you can also earn OneKeyCash™\* on top of your airline miles when you book with Expedia. \*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands. ### What airports do you fly into for Chicago from Dane County Regional (MSN)? If you're planning to travel to Chicago from Dane County Regional (MSN), you can fly into O'Hare Intl. (ORD) Some flights may connect through major hubs like Dallas-Fort Worth Intl. (DFW), Charlotte-Douglas Intl. (CLT), Minneapolis - St. Paul Intl. (MSP) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans. ### Is it cheaper to buy a plane ticket from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.) at the last minute? Typically, booking a last minute flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare. ### Is it cheaper to book a Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.) flight and hotel package? Securing a Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.) [Chicago Vacation Packages](https://www.expedia.com/chicago.d178248.destination-travel-guides) is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars. ### Can I cancel or change the date of my flight from Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.)? If you booked your Madison, WI (MSN-Dane County Regional) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in [your itinerary](https://www.expedia.com/trips) or confirmation email. Or, head to our [Customer Service portal](https://www.expedia.com/helpcenter/) if you'd like more information. ## Travel information | Origin airport | Dane County Regional Airport | | ------------------- | ---------------------------- | | Destination airport | Chicago Midway Airport | | Distance | 123 miles away | | Airlines serving | Delta | | Popular airline | Delta | | Roundtrip price | $467 | ## Explore a world of travel with Expedia - [Flights](?equalTargetTab=tab-0) - [Flights from Savannah (SAV) to Chicago (ORD)](https://www.expedia.com/lp/flights/sav/ord/savannah-to-chicago) - [Flights from Des Moines (DSM) to Chicago (ORD)](https://www.expedia.com/lp/flights/dsm/ord/des-moines-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (ORD)](https://www.expedia.com/lp/flights/slc/ord/salt-lake-city-to-chicago) - [Flights from Fayetteville (XNA) to Chicago (ORD)](https://www.expedia.com/lp/flights/xna/ord/fayetteville-to-chicago) - [Flights from Houston (IAH) to Chicago (ORD)](https://www.expedia.com/lp/flights/iah/ord/houston-to-chicago) - [Flights from Richmond (RIC) to Chicago (ORD)](https://www.expedia.com/lp/flights/ric/ord/richmond-to-chicago) - [Flights from Houston (HOU) to Chicago (MDW)](https://www.expedia.com/lp/flights/hou/mdw/houston-to-chicago) - [Flights from Fresno (FAT) to Chicago (ORD)](https://www.expedia.com/lp/flights/fat/ord/fresno-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (ORD)](https://www.expedia.com/lp/flights/msp/ord/minneapolis-to-chicago) - [Flights from Norfolk (ORF) to Chicago (ORD)](https://www.expedia.com/lp/flights/orf/ord/norfolk-to-chicago) - [Flights from Seattle (SEA) to Chicago (ORD)](https://www.expedia.com/lp/flights/sea/ord/seattle-to-chicago) - [Flights from Houston (HOU) to Chicago (ORD)](https://www.expedia.com/lp/flights/hou/ord/houston-to-chicago) - [Flights from Atlanta (ATL) to Chicago (ORD)](https://www.expedia.com/lp/flights/atl/ord/atlanta-to-chicago) - [Flights from Amman (AMM) to Chicago (ORD)](https://www.expedia.com/lp/flights/amm/ord/amman-to-chicago) - [Flights from Tampa (TPA) to Chicago (ORD)](https://www.expedia.com/lp/flights/tpa/ord/tampa-to-chicago) - [Flights from Louisville (SDF) to Chicago (ORD)](https://www.expedia.com/lp/flights/sdf/ord/louisville-to-chicago) - [Flights from Delhi (DEL) to Chicago (ORD)](https://www.expedia.com/lp/flights/del/ord/delhi-to-chicago) - [Flights from Baltimore (BWI) to Chicago (ORD)](https://www.expedia.com/lp/flights/bwi/ord/baltimore-to-chicago) - [Flights from Memphis (MEM) to Chicago (ORD)](https://www.expedia.com/lp/flights/mem/ord/memphis-to-chicago) - [Flights from Düsseldorf (DUS) to Chicago (ORD)](https://www.expedia.com/lp/flights/dus/ord/dusseldorf-to-chicago) - [Flights from San Francisco (SFO) to Chicago (ORD)](https://www.expedia.com/lp/flights/sfo/ord/san-francisco-to-chicago) - [Flights from Syracuse (SYR) to Chicago (ORD)](https://www.expedia.com/lp/flights/syr/ord/syracuse-to-chicago) - [Flights from Buffalo (BUF) to Chicago (ORD)](https://www.expedia.com/lp/flights/buf/ord/buffalo-to-chicago) - [Flights from Dallas (DFW) to Chicago (ORD)](https://www.expedia.com/lp/flights/dfw/ord/dallas-to-chicago) - [Flights from Tulsa (TUL) to Chicago (ORD)](https://www.expedia.com/lp/flights/tul/ord/tulsa-to-chicago) - [Flights from Springfield (SGF) to Chicago (ORD)](https://www.expedia.com/lp/flights/sgf/ord/springfield-to-chicago) - [Flights from Mexico City (MEX) to Chicago (ORD)](https://www.expedia.com/lp/flights/mex/ord/mexico-city-to-chicago) - [Flights from Wichita (ICT) to Chicago (ORD)](https://www.expedia.com/lp/flights/ict/ord/wichita-to-chicago) - [Flights from Knoxville (TYS) to Chicago (ORD)](https://www.expedia.com/lp/flights/tys/ord/knoxville-to-chicago) - [Flights from Boise (BOI) to Chicago (ORD)](https://www.expedia.com/lp/flights/boi/ord/boise-to-chicago) - [Flights from Tucson (TUS) to Chicago (ORD)](https://www.expedia.com/lp/flights/tus/ord/tucson-to-chicago) - [Flights from New York (JFK) to Chicago (ORD)](https://www.expedia.com/lp/flights/jfk/ord/new-york-to-chicago) - [Flights from Orlando (MCO) to Chicago (ORD)](https://www.expedia.com/lp/flights/mco/ord/orlando-to-chicago) - [Flights from Indianapolis (IND) to Chicago (ORD)](https://www.expedia.com/lp/flights/ind/ord/indianapolis-to-chicago) - [Flights from Providence (PVD) to Chicago (ORD)](https://www.expedia.com/lp/flights/pvd/ord/providence-to-chicago) - [Flights from Manila (MNL) to Chicago (ORD)](https://www.expedia.com/lp/flights/mnl/ord/manila-to-chicago) - [Flights from Albany (ALB) to Chicago (ORD)](https://www.expedia.com/lp/flights/alb/ord/albany-to-chicago) - [Flights from Cancun (CUN) to Chicago (ORD)](https://www.expedia.com/lp/flights/cun/ord/cancun-to-chicago) - [Flights from San Jose (SJC) to Chicago (ORD)](https://www.expedia.com/lp/flights/sjc/ord/san-jose-to-chicago) - [Flights from Ontario Intl. Airport (ONT) to Chicago (ORD)](https://www.expedia.com/lp/flights/ont/ord/ontario-to-chicago) - [Flights from Oklahoma City (OKC) to Chicago (ORD)](https://www.expedia.com/lp/flights/okc/ord/oklahoma-city-to-chicago) - [Flights from Orange County (SNA) to Chicago (ORD)](https://www.expedia.com/lp/flights/sna/ord/orange-county-to-chicago) - [Flights from Austin (AUS) to Chicago (ORD)](https://www.expedia.com/lp/flights/aus/ord/austin-to-chicago) - [Flights from San Antonio (SAT) to Chicago (ORD)](https://www.expedia.com/lp/flights/sat/ord/san-antonio-to-chicago) - [Flights from Greenville (GSP) to Chicago (ORD)](https://www.expedia.com/lp/flights/gsp/ord/greenville-to-chicago) - [Flights from Grand Rapids (GRR) to Chicago (ORD)](https://www.expedia.com/lp/flights/grr/ord/grand-rapids-to-chicago) - [Flights from Birmingham (BHM) to Chicago (ORD)](https://www.expedia.com/lp/flights/bhm/ord/birmingham-to-chicago) - [Flights from Lexington (LEX) to Chicago (ORD)](https://www.expedia.com/lp/flights/lex/ord/lexington-to-chicago) - 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[Flights from Sacramento (SMF) to Chicago (ORD)](https://www.expedia.com/lp/flights/smf/ord/sacramento-to-chicago) - [Flights from Phoenix (PHX) to Chicago (ORD)](https://www.expedia.com/lp/flights/phx/ord/phoenix-to-chicago) - [Flights from Cincinnati (CVG) to Chicago (ORD)](https://www.expedia.com/lp/flights/cvg/ord/cincinnati-to-chicago) - [Flights from San Diego (SAN) to Chicago (ORD)](https://www.expedia.com/lp/flights/san/ord/san-diego-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (ORD)](https://www.expedia.com/lp/flights/phl/ord/philadelphia-to-chicago) - [Flights from Hyderabad (HYD) to Chicago (ORD)](https://www.expedia.com/lp/flights/hyd/ord/hyderabad-to-chicago) - [Flights from Milwaukee (MKE) to Chicago (ORD)](https://www.expedia.com/lp/flights/mke/ord/milwaukee-to-chicago) \*Available to One Key members. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/lp/flights/msn/mdw/madison-to-chicago en-US: https://www.expedia.com/lp/flights/msn/mdw/madison-to-chicago ar: https://www.expedia.sa/lp/flights/msn/mdw/madison-to-chicago pt-BR: https://www.expedia.com.br/lp/voos/msn/mdw/madison-para-chicago es: https://www.expedia.com/es/lp/vuelos/msn/mdw/madison-a-chicago ```