--- title: "Casper to Chicago cheap flights from $328 (CPR to CHI) - Expedia" description: "Cheap Flights from Casper (CPR) to Chicago (CHI) start at $328 for one-way and $368 for round trip. Earn your airline miles on top of our rewards!" canonical: "https://www.expedia.com/lp/flights/cpr/chi/casper-to-chicago" language: en-US market: US currency: USD prices_as_of: 2026-11-14T03:35:43Z --- # $328 Cheap Flights from Casper (CPR) 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 $328 flight on Sun, Dec 6, 2026](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:12/6/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:327.90&airProductToken=AQpxCjcI1YIBEgQ1NTEzGOKLASCDaSiQiJ8DMOuInwM4TkAAWAFqCjFfYmFzaWNlY29yCFdBQTJBREJOCjYI1YIBEgQxOTI4GINpIK4cKLWJnwMwz4qfAzhOQABYAWoKMV9iYXNpY2Vjb3IIV0FBMkFEQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ## Popular airlines from Casper, WY (CPR-Natrona County Intl.) to Chicago [United](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:CHI,departure:11/28/2026TANYT&leg2=from:CHI,to:CPR,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) ### 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 Casper to Chicago (CPR-CHI) Prices were available within the past 7 days and start at $328 for one-way flights and $368 for roundtrip, for the period specified. Prices and availability are subject to change. All deals One way Roundtrip [Select United flight, departing Thu, Dec 24 from Casper to Chicago, returning Fri, Jan 1, priced at $368 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:12/24/2026TANYT&leg2=from:ORD,to:CPR,departure:1/1/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:367.80&airProductToken=AQpwCjcI1YIBEgQ0NjU4GOKLASCDaSjD1qADMJ7XoAM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjUI1YIBEgM0ODUYg2kgrhwo-NegAzCY2aADOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCTgpxCjYI1YIBEgQyNDY1GK4cIINpKM-voQMw%5FrChAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KNwjVggESBDUyOTQYg2kg4osBKOmxoQMwtbKhAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) Thu, Dec 24 - Fri, Jan 1 · CPR · ORD · Roundtrip [Select United flight, departing Sat, Jun 12 from Casper to Chicago, returning Sat, Jun 19, priced at $381 Found 2 days ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:6/12/2027TANYT&leg2=from:ORD,to:CPR,departure:6/19/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:380.70&airProductToken=AQpwCjcI1YIBEgQ1ODc5GOKLASCDaSi7z68DMJDQrwM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjUI1YIBEgM0NzgYg2kgrhwoztCvAzDl0a8DOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCTgpxCjYI1YIBEgQyODA2GK4cIINpKLSZsAMw1pqwAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KNwjVggESBDU3NDMYg2kg4osBKNGbsAMwlZywAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) Sat, Jun 12 - · CPR · ORD · Roundtrip [Select United flight, departing Wed, Apr 14 from Casper to Chicago, returning Sun, Apr 18, priced at $383 Found 4 days ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:4/14/2027TANYT&leg2=from:ORD,to:CPR,departure:4/18/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:382.85&airProductToken=AQpwCjcI1YIBEgQ1ODc5GOKLASCDaSjbt6oDMLC4qgM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjUI1YIBEgM0NzgYg2kgrhwo7riqAzCFuqoDOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCTgpxCjYI1YIBEgQyODA2GK4cIINpKPTfqgMwluGqAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KNwjVggESBDU3NDMYg2kg4osBKJHiqgMw1eKqAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) Wed, Apr 14 - Sun, Apr 18 · CPR · ORD · Roundtrip [Select United flight, departing Thu, Dec 24 from Casper to Chicago, returning Fri, Jan 1, priced at $387 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:12/24/2026TANYT&leg2=from:ORD,to:CPR,departure:1/1/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:386.08&airProductToken=AQpxCjcI1YIBEgQ0NjMxGOKLASCDaSii1KADMIHVoAM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjYI1YIBEgQyODY1GINpIK4cKMfVoAMw59agAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KcQo2CNWCARIEMjQ2NRiuHCCDaSjPr6EDMP6woQM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjcI1YIBEgQ1Mjk0GINpIOKLASjpsaEDMLWyoQM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) Thu, Dec 24 - Fri, Jan 1 · CPR · ORD · Roundtrip [Select United flight, departing Thu, Dec 24 from Casper to Chicago, returning Fri, Jan 1, priced at $388 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:12/24/2026TANYT&leg2=from:ORD,to:CPR,departure:1/1/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:387.15&airProductToken=AQpxCjcI1YIBEgQ1NTEzGOKLASCDaSjf0qADMLvToAM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjYI1YIBEgQxOTI4GINpIK4cKPDToAMwj9WgAzhOQABYAWoKMV9iYXNpY2Vjb3IITEZBMkFEQk4KcQo2CNWCARIEMjQ2NRiuHCCDaSjPr6EDMP6woQM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjcI1YIBEgQ1Mjk0GINpIOKLASjpsaEDMLWyoQM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) Thu, Dec 24 - Fri, Jan 1 · CPR · ORD · Roundtrip [Select United flight, departing Thu, Dec 24 from Casper to Chicago, returning Fri, Dec 25, priced at $393 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:12/24/2026TANYT&leg2=from:ORD,to:CPR,departure:12/25/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:392.53&airProductToken=AQpwCjcI1YIBEgQ1MjEyGOKLASCDaSiC1aADMNvVoAM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjUI1YIBEgM2MTcYg2kgrhwoydagAzDp16ADOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCTgpwCjUI1YIBEgM2MTYYrhwgg2koot6gAzDP36ADOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCTgo3CNWCARIENTc0MxiDaSDiiwEohOCgAzDW4KADOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) Thu, Dec 24 - Fri, Dec 25 · CPR · ORD · Roundtrip [Select United flight, departing Thu, Dec 24 from Casper to Chicago, returning Fri, Jan 1, priced at $406 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:12/24/2026TANYT&leg2=from:ORD,to:CPR,departure:1/1/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:405.70&airProductToken=AQpwCjcI1YIBEgQ0NjY2GOKLASCDaSjc2KADMLXZoAM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjUI1YIBEgMzNjEYg2kgrhwojdqgAzCm26ADOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCTgpxCjYI1YIBEgQyODAzGK4cIINpKN-woQMwjrKhAzhOQABYAWoKMV9iYXNpY2Vjb3IIVEZBNEFEQk4KNwjVggESBDU1ODUYg2kg4osBKM2yoQMwnrOhAzhOQABYAWoKMV9iYXNpY2Vjb3IIVEZBNEFEQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) Thu, Dec 24 - Fri, Jan 1 · CPR · ORD · Roundtrip [Select United flight, departing Fri, Feb 19 from Casper to Chicago, returning Sun, Feb 21, priced at $407 Found 3 days ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:2/19/2027TANYT&leg2=from:ORD,to:CPR,departure:2/21/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:406.77&airProductToken=AQpwCjcI1YIBEgQ1ODc5GOKLASCDaSjX2KUDMLHZpQM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjUI1YIBEgM1NzIYg2kgrhwo9tmlAzCS26UDOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCTgpxCjYI1YIBEgQxMjE3GK4cIINpKOzqpQMwm-ylAzhOQABYAWoKMV9iYXNpY2Vjb3IIVEZBNEFEQk4KNwjVggESBDQ2ODcYg2kg4osBKLbtpQMwg-6lAzhOQABYAWoKMV9iYXNpY2Vjb3IIVEZBNEFEQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) Fri, Feb 19 - Sun, Feb 21 · CPR · ORD · Roundtrip [Select United flight, departing Thu, Dec 24 from Casper to Chicago, returning Fri, Dec 25, priced at $408 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:12/24/2026TANYT&leg2=from:ORD,to:CPR,departure:12/25/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:407.85&airProductToken=AQpwCjcI1YIBEgQ0NjY2GOKLASCDaSjc2KADMLXZoAM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjUI1YIBEgMzNjEYg2kgrhwojdqgAzCm26ADOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCTgpwCjUI1YIBEgM3NjcYrhwgg2koseOgAzDg5KADOE5AAFgBagoxX2Jhc2ljZWNvcghURkE0QURCTgo3CNWCARIENTIyNhiDaSDiiwEomuWgAzDr5aADOE5AAFgBagoxX2Jhc2ljZWNvcghURkE0QURCThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) Thu, Dec 24 - Fri, Dec 25 · CPR · ORD · Roundtrip [Select United flight, departing Thu, Dec 24 from Casper to Chicago, returning Fri, Jan 1, priced at $409 Found 1 day ago](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:12/24/2026TANYT&leg2=from:ORD,to:CPR,departure:1/1/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:408.92&airProductToken=AQpwCjcI1YIBEgQ1MjQ1GOKLASCDaSjZ1aADMLDWoAM4TkAAWAFqCjFfYmFzaWNlY29yCExGQTJBREJOCjUI1YIBEgMzMzAYg2kgrhwowdegAzDh2KADOE5AAFgBagoxX2Jhc2ljZWNvcghMRkEyQURCTgpwCjUI1YIBEgM3NjcYrhwgg2kokbKhAzDAs6EDOE5AAFgBagoxX2Jhc2ljZWNvcghURkE0QURCTgo3CNWCARIENTIyNhiDaSDiiwEo-rOhAzDLtKEDOE5AAFgBagoxX2Jhc2ljZWNvcghURkE0QURCThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAs) Thu, Dec 24 - Fri, Jan 1 · CPR · 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 $949](https://www.expedia.com/Flights-Search?leg1=from:CPR,to:ORD,departure:11/28/2026TANYT&leg2=from:ORD,to:CPR,departure:11/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 23 min ## Book with confidence ### Casper to Chicago Flights #### The cheapest times to fly from Casper 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 Casper to Chicago are during the month of December. You can find some of the cheapest flights from Casper to Chicago with Expedia's search tool and vast selection of airlines. #### The best time to book a flight from Casper to Chicago Sunday is one of the best days to book for cheap flights from Casper 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 Casper 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 Casper to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $328 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 Casper 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 Casper 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 | Casper, WY | | ------------------- | -------------- | | Destination airport | Chicago, IL | | Distance | 945 miles away | | Roundtrip price | $368 | ## Explore a world of travel with Expedia - [Flights](?equalTargetTab=tab-0) - [Flights from Houston (HOU) to Chicago (ORD)](https://www.expedia.com/lp/flights/hou/ord/houston-to-chicago) - [Flights from Orange County (SNA) to Chicago (CHI)](https://www.expedia.com/lp/flights/sna/chi/orange-county-to-chicago) - [Flights from Kansas City (MCI) to Chicago (CHI)](https://www.expedia.com/lp/flights/mci/chi/kansas-city-to-chicago) - [Flights from Cleveland (CLE) to Chicago (CHI)](https://www.expedia.com/lp/flights/cle/chi/cleveland-to-chicago) - [Flights from Washington (WAS) to Chicago (CHI)](https://www.expedia.com/lp/flights/was/chi/washington-to-chicago) - [Flights from Columbus (CMH) to Chicago (CHI)](https://www.expedia.com/lp/flights/cmh/chi/columbus-to-chicago) - [Flights from Atlanta (ATL) to Chicago (CHI)](https://www.expedia.com/lp/flights/atl/chi/atlanta-to-chicago) - [Flights from Nashville (BNA) to Chicago (CHI)](https://www.expedia.com/lp/flights/bna/chi/nashville-to-chicago) - [Flights from Miami (MIA) to Chicago (ORD)](https://www.expedia.com/lp/flights/mia/ord/miami-to-chicago) - [Flights from Miami (MIA) to Chicago (CHI)](https://www.expedia.com/lp/flights/mia/chi/miami-to-chicago) - [Flights from Indianapolis (IND) to Chicago (ORD)](https://www.expedia.com/lp/flights/ind/ord/indianapolis-to-chicago) - [Flights from Dallas (DFW) to Chicago (ORD)](https://www.expedia.com/lp/flights/dfw/ord/dallas-to-chicago) - [Flights from Louisville (SDF) to Chicago (CHI)](https://www.expedia.com/lp/flights/sdf/chi/louisville-to-chicago) - [Flights from Düsseldorf (DUS) to Chicago (CHI)](https://www.expedia.com/lp/flights/dus/chi/dusseldorf-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI)](https://www.expedia.com/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Mackinac Island (MCD) to Chicago (CHI)](https://www.expedia.com/lp/flights/mcd/chi/mackinac-island-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (ORD)](https://www.expedia.com/lp/flights/lax/ord/los-angeles-to-chicago) - [Flights from Newark Liberty Intl. 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