Title: Cheap flights from Washington to Chicago ( DCA - MDW) - 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) # $105 Cheap Flights from Washington (DCA) to Chicago (MDW) [View $105 flight on Wed, Apr 29, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:DCA,to:MDW,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:104.40&airProductToken=AQowCi4I15wBEgQyOTk3GEMg7LABKNHTiwMwydSLAzhEQABYAWoDV0dBcgdEQk5WTjJFEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ) ## Popular airlines from Ronald Reagan Washington National Airport (DCA) to Chicago Midway Airport (MDW) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:DCA,to:MDW,departure:3/20/2026TANYT&leg2=from:MDW,to:DCA,departure:3/27/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](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:DCA,to:MDW,departure:3/20/2026TANYT&leg2=from:MDW,to:DCA,departure:3/27/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](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 Washington to Chicago (DCA-MDW) Prices were available within the past 7 days and start at $105 for one-way flights and $217 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Sat, May 9 - Tue, May 12 DCA Washington MDW Chicago $217 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:5/9/2026TANYT&leg2=from:MDW,to:DCA,departure:5/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:216.10&airProductToken=AQowCi4I15wBEgQyOTk3GEMg7LABKNDDjAMwzcSMAzhEQABYAWoDV0dBcgdERE5WSDJFCjAKLgjXnAESBDEzNzAY7LABIEMor-eMAzCQ6YwDOERAAFgBagNXR0FyB0REQVZIMkUSCggCEAEYAioCV04YASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, May 6 - Sat, May 9 DCA Washington MDW Chicago $220 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:5/6/2026TANYT&leg2=from:MDW,to:DCA,departure:5/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:219.80&airProductToken=AQowCi4I15wBEgQxNzQ4GEMg7LABKOSljAMw4aaMAzhEQABYAWoDV0dBcgdEQk5WTjJFCjAKLgjXnAESBDMyNTgY7LABIEMoisOMAzD4w4wDOERAAFgBagNXR0FyB0RETlZIMkUSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, Apr 22 - Sat, Apr 25 DCA Washington MDW Chicago $221 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:4/22/2026TANYT&leg2=from:MDW,to:DCA,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:220.60&airProductToken=AQowCi4I15wBEgQxNzg0GEMg7LABKL-JiwMwt4qLAzhEQABYAWoDV0dBcgdERE5WSDJFCmAKLwjXnAESBDM4MTAY7LABIMwiKMKmiwMw76aLAzhEQABYAWoDV0dBcgdEREFWSDJFCi0I15wBEgQxNDA0GMwiIEMouqeLAzCoqIsDOERAAVgBagNXR0FyB0REQVZIMkUSCggCEAEYAioCV04YASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, Apr 1 - Wed, Apr 8 DCA Washington MDW Chicago $225 Roundtrip found 2 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:4/1/2026TANYT&leg2=from:MDW,to:DCA,departure:4/8/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:224.70&airProductToken=AQowCi4I15wBEgQzMjI1GEMg7LABKMyYiQMw5puJAzhEQABYAWoDV0dBcgdEQkFWTjJFCjAKLgjXnAESBDEzNzAY7LABIEMo7-iJAzDQ6okDOERAAFgBagNXR0FyB0RCQVZOMkUSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Sat, May 9 - Tue, May 12 DCA Washington MDW Chicago $226 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:5/9/2026TANYT&leg2=from:MDW,to:DCA,departure:5/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:225.90&airProductToken=AQpfCi0I15wBEgQzMzY1GEMgoQMopseMAzCeyIwDOERAAFgBagNXR0FyB0REQVZIMkUKLgjXnAESAzY5OBihAyDssAEo88iMAzDXyYwDOERAAVgBagNXR0FyB0REQVZIMkUKMAouCNecARIEMTM3MBjssAEgQyiv54wDMJDpjAM4REAAWAFqA1dHQXIHRERBVkgyRRIKCAIQARgCKgJXThgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, Apr 21 - Sat, Apr 25 DCA Washington MDW Chicago $227 Roundtrip found 12 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:4/21/2026TANYT&leg2=from:MDW,to:DCA,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:226.79&airProductToken=AQowCi4I15wBEgQxNzQ3GEMg7LABKLz7igMwvvyKAzhEQABYAWoDV0dBcgdEQk5WTjJFCjAKLgjXnAESBDQxMjgY7LABIEMop6qLAzCaq4sDOEpAAFgBagNXR0FyB0paTlZOMkUSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, May 6 - Sat, May 9 DCA Washington MDW Chicago $230 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:5/6/2026TANYT&leg2=from:MDW,to:DCA,departure:5/9/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:229.60&airProductToken=AQowCi4I15wBEgQxNzQ4GEMg7LABKOSljAMw4aaMAzhEQABYAWoDV0dBcgdEQk5WTjJFCmAKLwjXnAESBDM1NDgY7LABIMxAKILEjAMw3MSMAzhEQABYAWoDV0dBcgdEREFWSDJFCi0I15wBEgQxNzYxGMxAIEMojsWMAzCfxowDOERAAVgBagNXR0FyB0REQVZIMkUSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Sat, Apr 18 - Sat, May 2 DCA Washington MDW Chicago $231 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:4/18/2026TANYT&leg2=from:MDW,to:DCA,departure:5/2/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:230.79&airProductToken=AQowCi4I15wBEgQxNDA5GEMg7LABKLzYigMwtNmKAzhEQABYAWoDV0dBcgdERE5WSDJFCjAKLgjXnAESBDQxMjgY7LABIEMoh_mLAzD6-YsDOERAAFgBagNXR0FyB0RETlZIMkUSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Sat, May 2 - Wed, May 6 DCA Washington MDW Chicago $233 Roundtrip found 15 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:5/2/2026TANYT&leg2=from:MDW,to:DCA,departure:5/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:232.09&airProductToken=AQowCi4I15wBEgQxNDA5GEMg7LABKPz1iwMw9PaLAzhKQABYAWoDV0dBcgdKWk5WTjJFCjAKLgjXnAESBDEzNzAY7LABIEMo76OMAzDQpYwDOERAAFgBagNXR0FyB0RCQVZOMkUSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, May 13 - Sat, May 16 DCA Washington MDW Chicago $244 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:MDW,departure:5/13/2026TANYT&leg2=from:MDW,to:DCA,departure:5/16/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:243.60&airProductToken=AQptCjMIxJgBEgM0MTAYQyDgXCi47owDMKbvjAM4RUAAWAFqCU1BSU5CQVNJQ3IIWEFXTkE1QkMKNgjEmAESBDEwNjMY4Fwg7LABKPHvjAMw5PCMAzhFQAFYAWoJTUFJTkJBU0lDcghYQVdOQTVCQxIMCAEQARgBKgJETDIAGAEiBAgBEAEoAigDKAQwAQ) ![](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_) ## 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:DCA,to:ORD,departure:3/20/2026TANYT&leg2=from:ORD,to:DCA,departure:3/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. 23 min [Flights from $460 ](https://www.expedia.com/Flights-Search?leg1=from:DCA,to:ORD,departure:3/20/2026TANYT&leg2=from:ORD,to:DCA,departure:3/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Washington (DCA) to Chicago (MDW) ### August is typically the cheapest month to fly From $116 - $395 per traveler. ## Frequently asked questions ### How much does a flight from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW) cost? ### What is the cheapest month to fly from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)? ### Which airlines fly direct from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)? ### What is the cheapest airline that flies from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)? ### How many flights per day from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)? ### What are the most popular departure times for flights from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)? ### What day of the week has the most flights from DCA to MDW? ### What is the earliest flight from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)? ### How long does it take to fly from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)? ### What is the best time to fly from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)? ### What airports do you fly into for Chicago from Ronald Reagan Washington National Airport (DCA)? ### Is it cheaper to buy a plane ticket from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW) last-minute? ### Is it cheaper to book a DCA to MDW flight and hotel package? ### Can I cancel or change the date of my flight from Ronald Reagan Washington National Airport (DCA) to Midway Intl. Airport (MDW)? ## Travel information | Origin airport | Ronald Reagan Washington National | | ------------------- | --------------------------------- | | Destination airport | Midway Intl. | | Airlines serving | Delta, Southwest Airlines | | Roundtrip price | $191 | | Distance | 598 mi | | Average flight time | 1 hour 36 mins | ## Book with confidence # Washington to Chicago Flights The cheapest times to fly from Washington 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 Washington to Chicago are during the month of May. You can find some of the cheapest flights from Washington to Chicago with Expedia's search tool and vast selection of airlines. The best time to book a flight from Washington to Chicago Sunday is one of the best days to book for cheap flights from Washington 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 Washington 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 Washington to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $105 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 Washington 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 Washington 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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