Title: St. John's to Chicago cheap flights from $242 (ANU to ORD) - 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) # $242 Cheap Flights from St. John's (ANU) to Chicago (ORD) [View $242 flight on Sun, Jun 14, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:ANU,to:ORD,departure:6/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:241.63&airProductToken=AQpoCjMIwYYBEgQxODMzGKCjASCYzgEo8tqPAzCy3Y8DOEdAAFgBagVCQVNJQ3IIR0xZRVQxQkEKMQjBhgESAzUxMRiYzgEgrhwoweePAzC56I8DOEdAAVgBagVCQVNJQ3IIR0xZRVQxQkESCggCEAEYAioCQUMYASIECAEQASgCKAMoBDAN) ## Popular airlines from V.C. Bird Intl. Airport (ANU) to Chicago O'Hare Intl. Airport (ORD) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada [](https://www.expedia.com/Flights-Search?leg1=from:ANU,to:ORD,departure:4/14/2026TANYT&leg2=from:ORD,to:ANU,departure:4/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.com/Flights-Search?leg1=from:ANU,to:ORD,departure:4/14/2026TANYT&leg2=from:ORD,to:ANU,departure:4/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](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 St. John's to Chicago (ANU-ORD) Prices were available within the past 7 days and start at $242 for one-way flights and $656 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, May 8 - Fri, May 15 ANU Antigua ORD Chicago $656 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:5/8/2026TANYT&leg2=from:ORD,to:ANU,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:655.63&airProductToken=AQpdCi0IwmwSAzc0MBigowEgqVEo8LmMAzCPvIwDOExAAFgBagJETnIIUEkyUUJWTDEKLAjCbBIDOTA1GKlRIK4cKLjBjAMw3MKMAzhMQAFYAWoCRE5yCFpJOVFCT0wxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, May 8 - Fri, May 15 ANU Antigua ORD Chicago $687 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:5/8/2026TANYT&leg2=from:ORD,to:ANU,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:686.98&airProductToken=AQpdCi0IwmwSAzc0MBigowEgqVEo8LmMAzCPvIwDOExAAFgBagJETnIIUEkyUUdWTDEKLAjCbBIDOTA1GKlRIK4cKLjBjAMw3MKMAzhMQAFYAWoCRE5yCFpJOVFCT0wxCl4KLQjCbBIEMTMwNhiuHCCpUSjPho0DMOCHjQM4TEAAWAFqAkROcghPSTJRQkhMMQotCMJsEgM3NDMYqVEgoKMBKKaRjQMwr5ONAzhMQAFYAWoCRE5yCFBJMlFHV0wxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, May 8 - Fri, May 15 ANU Antigua ORD Chicago $716 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:5/8/2026TANYT&leg2=from:ORD,to:ANU,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:715.63&airProductToken=AQpdCi0IwmwSAzc0MBigowEgqVEo8LmMAzCPvIwDOExAAFgBagJETnIIUEkyUUJWTDEKLAjCbBIDOTA1GKlRIK4cKLjBjAMw3MKMAzhMQAFYAWoCRE5yCFpJOVFCT0wxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, May 8 - Fri, May 15 ANU Antigua ORD Chicago $720 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:5/8/2026TANYT&leg2=from:ORD,to:ANU,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:719.43&airProductToken=AQpdCi0IwmwSAzc0MBigowEgqVEo8LmMAzCPvIwDOFBAAFgBagJBTnIIUEkyUUJWWTUKLAjCbBIDOTA1GKlRIK4cKLjBjAMw3MKMAzhaQAFYAWoCQU5yCFpJOVFCT1k1EgoIARABGAEqAkI2GAEiBAgBEAEoAigDKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, May 8 - Fri, May 15 ANU Antigua ORD Chicago $737 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:5/8/2026TANYT&leg2=from:ORD,to:ANU,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:736.69&airProductToken=AQpdCi0IwmwSAzc0MBigowEgqVEo8LmMAzCPvIwDOExAAFgBagJETnIIUEkyUUdWTDEKLAjCbBIDOTA1GKlRIK4cKLjBjAMw3MKMAzhMQAFYAWoCRE5yCFpJOVFCT0wxCo0BCi0IwmwSAzMxMhiuHCDBkwEomYeNAzCwiI0DOExAAFgBagJETnIIWkM3QVVFTDEKLQjCbBIDNTE3GMGTASCpUSiwiY0DMIqKjQM4TEABWAFqAkROcghaQzdBVUVMMQotCMJsEgM3NDMYqVEgoKMBKKaRjQMwr5ONAzhMQAFYAWoCRE5yCFBJMlFHV0wxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sun, May 10 - Sun, May 17 ANU Antigua ORD Chicago $768 Roundtrip found 4 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:5/10/2026TANYT&leg2=from:ORD,to:ANU,departure:5/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:767.03&airProductToken=AQpdCi0IwmwSAzc0MBigowEgqVEootCMAzDB0owDOExAAFgBagJETnIIUEkyUUdXTDEKLAjCbBIDOTA1GKlRIK4cKPjXjAMwnNmMAzhMQAFYAWoCRE5yCFBJMlFCU0wxCo0BCi0IwmwSAzMxMhiuHCDBkwEo2Z2NAzDwno0DOExAAFgBagJETnIITUMzQVVFTDEKLQjCbBIDNTE3GMGTASCpUSjcn40DMLegjQM4TEABWAFqAkROcghNQzNBVUVMMQotCMJsEgM3NDMYqVEgoKMBKOanjQMw76mNAzhMQAFYAWoCRE5yCFVJMlFSRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, May 8 - Fri, May 15 ANU Antigua ORD Chicago $773 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:5/8/2026TANYT&leg2=from:ORD,to:ANU,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:772.23&airProductToken=AQpdCi0IwmwSAzc0MBigowEgqVEo8LmMAzCPvIwDOFBAAFgBagJHTnIIUEkyUUJWWTgKLAjCbBIDOTA1GKlRIK4cKLjBjAMw3MKMAzhaQAFYAWoCR05yCFpJOVFCT1k4EgoIARABGAEqAkI2GAEiBAgBEAEoAigDKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, May 8 - Fri, May 15 ANU Antigua ORD Chicago $780 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:5/8/2026TANYT&leg2=from:ORD,to:ANU,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:779.43&airProductToken=AQpdCi0IwmwSAzc0MBigowEgqVEo8LmMAzCPvIwDOFBAAFgBagJBTnIIUEkyUUJWWTUKLAjCbBIDOTA1GKlRIK4cKLjBjAMw3MKMAzhaQAFYAWoCQU5yCFpJOVFCT1k1EgoIARABGAEqAkI2GAEiBAgBEAEoAigDKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Fri, May 8 - Fri, May 15 ANU Antigua ORD Chicago $781 Roundtrip found 6 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:5/8/2026TANYT&leg2=from:ORD,to:ANU,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:780.63&airProductToken=AQpdCi0IwmwSAzc0MBigowEgqVEo8LmMAzCPvIwDOExAAFgBagJETnIIUEkyUUJWTDEKLAjCbBIDOTA1GKlRIK4cKLjBjAMw3MKMAzhMQAFYAWoCRE5yCFpJOVFCT0wxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Apr 8 - Mon, Apr 13 ANU Antigua ORD Chicago $860 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ANU,to:ORD,departure:4/8/2026TANYT&leg2=from:ORD,to:ANU,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:859.03&airProductToken=AQpnCjIIwYIBEgQyNTgwGKCjASCMAijb6IkDMLnqiQM4QkAAWAFqBUJBU0lDcghHTlU3QUJCWgoxCMGCARIEMTE0MBiMAiCuHCiY7IkDMOXtiQM4QkABWAFqBUJBU0lDcghHTlU3QUJCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ## Find the cheapest month to fly from Osbourn (ANU) to Chicago (ORD) ### January is typically the cheapest month to fly From $432 - $1,420 per traveler. ## Frequently asked questions ### How much does a flight from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost? ### What is the cheapest month to fly from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.)? ### Which airlines fly direct from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.)? ### How do I find cheap flights from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.)? ### What is the best time to fly from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.)? ### What is the earliest flight from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.)? ### What are the most popular departure times for flights from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.)? ### How long does it take to fly from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.)? ### Can you fly business or first class from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.)? ### How do I earn miles on a St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia? ### What airports do you fly into for Chicago from V.C. Bird Intl. (ANU)? ### Is it cheaper to buy a plane ticket from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute? ### Is it cheaper to book a St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package? ### Can I cancel or change the date of my flight from St. John's (ANU-V.C. Bird Intl.) to Chicago, IL (ORD-O'Hare Intl.)? ## Travel information | Origin airport | V.C. Bird Intl. | | ------------------- | --------------- | | Destination airport | O'Hare Intl. | | Roundtrip price | $656 | | Distance | 2306 mi | ## Book with confidence # St. John's to Chicago Flights The cheapest times to fly from St. John's 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 St. John's to Chicago are during the month of May. You can find some of the cheapest flights from St. John's to Chicago with Expedia's search tool and vast selection of airlines. The best time to book a flight from St. John's to Chicago Sunday is one of the best days to book for cheap flights from St. John's 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 St. John's 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 St. John's to Chicago in 2026\. You can also book with separate airlines for your outbound and return journeys, from $242 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 St. John's 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 St. John's 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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