--- title: "Des Moines to Chicago cheap flights from $135 (DSM to CHI) - Expedia" description: "Cheap Flights from Des Moines (DSM) to Chicago (CHI) start at $135 for one-way and $260 for round trip. Earn your airline miles on top of our rewards!" canonical: "https://www.expedia.com/lp/flights/dsm/chi/des-moines-to-chicago" language: en-US market: US currency: USD prices_as_of: 2026-11-15T14:48:00Z --- # $135 Cheap Flights from Des Moines (DSM) to Chicago (CHI) ![A river with a yellow boat, surrounded by tall buildings and a bridge.](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) [View $135 flight on Tue, Dec 8, 2026](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:ORD,departure:12/8/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:134.40&airProductToken=AQo4CjYI1YIBEgQ1NjMzGMNkIK4cKJehnwMw-6GfAzhOQABYAWoKMV9iYXNpY2Vjb3IITEFVMkFLQlMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ## Popular airlines from Des Moines International Airport (DSM) to Chicago [Delta](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:CHI,departure:11/29/2026TANYT&leg2=from:CHI,to:DSM,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) [American Airlines](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:CHI,departure:11/29/2026TANYT&leg2=from:CHI,to:DSM,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) [United](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:CHI,departure:11/29/2026TANYT&leg2=from:CHI,to:DSM,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) [Southwest Airlines](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:CHI,departure:11/29/2026TANYT&leg2=from:CHI,to:DSM,departure:12/6/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) ### Be in the know Get alerts if flight prices drop or rise\* ### Book smarter Save up to 30% on select hotels after you book a flight\* ### 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 Des Moines to Chicago (DSM-CHI) Prices were available within the past 7 days and start at $135 for one-way flights and $260 for roundtrip, for the period specified. Prices and availability are subject to change. All deals One way Roundtrip [Select Southwest Airlines flight, departing Wed, Mar 3 from Des Moines to Chicago, returning Sat, Mar 6, priced at $260 Found 3 days ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:MDW,departure:3/3/2027TANYT&leg2=from:MDW,to:DSM,departure:3/6/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:259.99&airProductToken=AQowCi4I15wBEgM4MjQYw2Qg7LABKIzfpgMw3N-mAzhWQABYAWoDV0dBcgdWRE5WTjJFEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ) Wed, Mar 3 - Sat, Mar 6 · DSM · MDW · Roundtrip [Select Southwest Airlines flight, departing Wed, Mar 3 from Des Moines to Chicago, returning Sat, Mar 6, priced at $270 Found 3 days ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:MDW,departure:3/3/2027TANYT&leg2=from:MDW,to:DSM,departure:3/6/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:269.79&airProductToken=AQphCi4I15wBEgQxNjI3GMNkIINpKKfbpgMwpNymAzhWQABYAWoDV0dBcgdWREFWTjJFCi8I15wBEgQxNDk4GINpIOywASjb3KYDMOzdpgM4VkABWAFqA1dHQXIHVkRBVk4yRRIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE) Wed, Mar 3 - Sat, Mar 6 · DSM · MDW · Roundtrip [Select Delta flight, departing Tue, Dec 8 from Des Moines to Chicago, returning Wed, Dec 9, priced at $279 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:ORD,departure:12/8/2026TANYT&leg2=from:ORD,to:DSM,departure:12/9/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:278.60&airProductToken=AQpuCjUIxJgBEgQ0OTk4GMNkIMx8KP2gnwMwwaGfAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQzJCQwo1CMSYARIEMTQ3MRjMfCCuHCjsop8DMNOjnwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0MyQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) Tue, Dec 8 - Wed, Dec 9 · DSM · ORD · Roundtrip [Select United flight, departing Fri, Dec 11 from Des Moines to Chicago, returning Wed, Dec 16, priced at $289 Found 5 days ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:ORD,departure:12/11/2026TANYT&leg2=from:ORD,to:DSM,departure:12/16/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:288.10&airProductToken=AQo4CjYI1YIBEgQ1Mjc5GMNkIK4cKILCnwMw6MKfAzhOQABYAWoKMV9iYXNpY2Vjb3IIVEFQMkFLQlMKOAo2CNWCARIENTgwNhiuHCDDZCiU%5FZ8DMPL9nwM4TkAAWAFqCjFfYmFzaWNlY29yCExBSzJBS0JTEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) Fri, Dec 11 - Wed, Dec 16 · DSM · ORD · Roundtrip [Select Delta flight, departing Tue, Dec 8 from Des Moines to Chicago, returning Wed, Dec 9, priced at $289 Found 2 days ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:MDW,departure:12/8/2026TANYT&leg2=from:MDW,to:DSM,departure:12/9/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:288.40&airProductToken=AQpvCjUIxJgBEgQ0OTk4GMNkIMx8KP2gnwMwwaGfAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQzJCQwo2CMSYARIENDcxNBjMfCDssAEo7KKfAzDao58DOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNDMkJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) Tue, Dec 8 - Wed, Dec 9 · DSM · MDW · Roundtrip [Select Southwest Airlines flight, departing Sat, Feb 27 from Des Moines to Chicago, returning Tue, Mar 2, priced at $289 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:MDW,departure:2/27/2027TANYT&leg2=from:MDW,to:DSM,departure:3/2/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:288.80&airProductToken=AQowCi4I15wBEgM4MjQYw2Qg7LABKKWypgMw8LKmAzhEQABYAWoDV0dBcgdEWk5WUzJFCjEKLwjXnAESBDQxMDYY7LABIMNkKKLWpgMw99amAzhWQABYAWoDV0dBcgdWQk5WTjJFEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ) Sat, Feb 27 - Tue, Mar 2 · DSM · MDW · Roundtrip [Select United flight, departing Mon, Dec 21 from Des Moines to Chicago, returning Tue, Dec 22, priced at $294 Found 4 days ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:ORD,departure:12/21/2026TANYT&leg2=from:ORD,to:DSM,departure:12/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:293.10&airProductToken=AQo4CjYI1YIBEgQ1NDUxGMNkIK4cKJa1oAMw-LWgAzhOQABYAWoKMV9iYXNpY2Vjb3IIVEFHMkFLQlMKOAo2CNWCARIENTM5NhiuHCDDZCizw6ADMJ3EoAM4TkAAWAFqCjFfYmFzaWNlY29yCExBSzJBS0JTEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) Mon, Dec 21 - Tue, Dec 22 · DSM · ORD · Roundtrip [Select Southwest Airlines flight, departing Tue, Feb 2 from Des Moines to Chicago, returning Wed, Feb 3, priced at $294 Found 2 days ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:MDW,departure:2/2/2027TANYT&leg2=from:MDW,to:DSM,departure:2/3/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:293.71&airProductToken=AQpgCi4I15wBEgQxNjI3GMNkIINpKIeVpAMwhJakAzhWQABYAWoDV0dBcgdWQkFWTjJFCi4I15wBEgM0NDMYg2kg7LABKNGXpAMwvJmkAzhWQAFYAWoDV0dBcgdWQkFWTjJFCmAKLwjXnAESBDI2NTcY7LABIINpKOChpAMwgKOkAzhWQABYAWoDV0dBcgdWQkFWTjJFCi0I15wBEgM4NjIYg2kgw2Qo96WkAzDgpqQDOFZAAVgBagNXR0FyB1ZCQVZOMkUSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB) Tue, Feb 2 - Wed, Feb 3 · DSM · MDW · Roundtrip [Select Southwest Airlines flight, departing Wed, Mar 3 from Des Moines to Chicago, returning Sat, Mar 6, priced at $295 Found 3 days ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:MDW,departure:3/3/2027TANYT&leg2=from:MDW,to:DSM,departure:3/6/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:294.99&airProductToken=AQowCi4I15wBEgM4MjQYw2Qg7LABKIzfpgMw3N-mAzhWQABYAWoDUExVcgdWRE5WTjRFEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ) Wed, Mar 3 - Sat, Mar 6 · DSM · MDW · Roundtrip [Select American Airlines flight, departing Wed, Dec 16 from Des Moines to Chicago, returning Tue, Dec 22, priced at $359 Found 6 hours ago](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:ORD,departure:12/16/2026TANYT&leg2=from:ORD,to:DSM,departure:12/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:358.80&airProductToken=AQoyCjAIwYIBEgQ0Mzg4GMNkIK4cKJr5nwMwjvqfAzhPQABYAWoETUFJTnIIT1ZBSUtTTTEKMgowCMGCARIEMzkyMxiuHCDDZCjpvKADMMq9oAM4T0AAWAFqBE1BSU5yCE9WQUlLU00xEgwIARABGAEqAkFBMgAYASIECAEQASgCKAMoBDAB) Wed, Dec 16 - Tue, Dec 22 · DSM · ORD · 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 $502](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:ORD,departure:11/29/2026TANYT&leg2=from:ORD,to:DSM,departure:11/30/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 23 min [Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $567](https://www.expedia.com/Flights-Search?leg1=from:DSM,to:MDW,departure:11/29/2026TANYT&leg2=from:MDW,to:DSM,departure:11/30/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 16 min ## Book with confidence ### Des Moines to Chicago Flights #### The cheapest times to fly from Des Moines 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 Des Moines to Chicago are during the month of March. You can find some of the cheapest flights from Des Moines to Chicago with Expedia's search tool and vast selection of airlines. #### The best time to book a flight from Des Moines to Chicago Sunday is one of the best days to book for cheap flights from Des Moines 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 Des Moines 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 Des Moines to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $135 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 Des Moines 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 Des Moines 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.* ## Travel information | Origin airport | Des Moines International Airport | | ------------------- | -------------------------------- | | Destination airport | Chicago Midway Airport | | Distance | 305 miles away | | Airlines serving | Southwest Airlines, Delta | | Popular airline | Southwest Airlines | | Roundtrip price | $260 | | Average flight time | 1 hour 26 mins | ## Explore a world of travel with Expedia - [Flights](?equalTargetTab=tab-0) - [Flights from San Diego (SAN) to Chicago (CHI)](https://www.expedia.com/lp/flights/san/chi/san-diego-to-chicago) - [Flights from Washington (WAS) to Chicago (CHI)](https://www.expedia.com/lp/flights/was/chi/washington-to-chicago) - [Flights from Los Angeles (QLA) to Chicago (CHI)](https://www.expedia.com/lp/flights/qla/chi/los-angeles-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI)](https://www.expedia.com/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Memphis (MEM) to Chicago (CHI)](https://www.expedia.com/lp/flights/mem/chi/memphis-to-chicago) - [Flights from Memphis (MEM) to Chicago (ORD)](https://www.expedia.com/lp/flights/mem/ord/memphis-to-chicago) - [Flights from Mackinac Island (MCD) to Chicago (CHI)](https://www.expedia.com/lp/flights/mcd/chi/mackinac-island-to-chicago) - [Flights from Denver (DEN) to Chicago (CHI)](https://www.expedia.com/lp/flights/den/chi/denver-to-chicago) - [Flights from Oklahoma City (OKC) to Chicago (CHI)](https://www.expedia.com/lp/flights/okc/chi/oklahoma-city-to-chicago) - [Flights from Phoenix (PHX) to Chicago (CHI)](https://www.expedia.com/lp/flights/phx/chi/phoenix-to-chicago) - [Flights from Rome (FCO) to Chicago (CHI)](https://www.expedia.com/lp/flights/fco/chi/rome-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (ORD)](https://www.expedia.com/lp/flights/phl/ord/philadelphia-to-chicago) - [Flights from Orlando (MCO) to Chicago (CHI)](https://www.expedia.com/lp/flights/mco/chi/orlando-to-chicago) - [Flights from Indianapolis (IND) to Chicago (CHI)](https://www.expedia.com/lp/flights/ind/chi/indianapolis-to-chicago) - [Flights from New Orleans (MSY) to Chicago (ORD)](https://www.expedia.com/lp/flights/msy/ord/new-orleans-to-chicago) - [Flights from San Diego (SAN) to Chicago (ORD)](https://www.expedia.com/lp/flights/san/ord/san-diego-to-chicago) - [Flights from New York (NYC) to Chicago (CHI)](https://www.expedia.com/lp/flights/nyc/chi/new-york-to-chicago) - [Flights from San Juan (SJU) to Chicago (CHI)](https://www.expedia.com/lp/flights/sju/chi/san-juan-to-chicago) - [Flights from Honolulu (HNL) to Chicago (CHI)](https://www.expedia.com/lp/flights/hnl/chi/honolulu-to-chicago) - [Flights from Orange County (SNA) to Chicago (CHI)](https://www.expedia.com/lp/flights/sna/chi/orange-county-to-chicago) - [Flights from Joliet (JOT) to Chicago (CHI)](https://www.expedia.com/lp/flights/jot/chi/joliet-to-chicago) - [Flights from Atlanta (ATL) to Chicago (CHI)](https://www.expedia.com/lp/flights/atl/chi/atlanta-to-chicago) - [Flights from Omaha (OMA) to Chicago (CHI)](https://www.expedia.com/lp/flights/oma/chi/omaha-to-chicago) - [Flights from Houston (HOU) to Chicago (ORD)](https://www.expedia.com/lp/flights/hou/ord/houston-to-chicago) - [Flights from Newark Liberty Intl. 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