Title: CA $77 Cheap Flights from Fort Myers (RSW) to Chicago (ORD) - Expedia.ca ![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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $77 Cheap Flights from Fort Myers (RSW) to Chicago (ORD) [View CA $77 flight on Thu, Dec 4, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:RSW,to:ORD,departure:04/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:76.73&airProductToken=AQoxCi8IzpYBEgQxMDg4GNG0ASCuHCjY6f4CMJbr_gI4R0AAWAFqAlJQcghHMTRTWUJZNBIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Southwest Florida Intl. Airport (RSW) to Chicago O'Hare International Airport (ORD) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:rsw,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:rsw,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:rsw,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:rsw,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:rsw,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:rsw,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:rsw,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:rsw,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:rsw,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:rsw,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:rsw,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:rsw,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:rsw,to:ord,departure:23/10/2025TANYT&leg2=from:ord,to:rsw,departure:30/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) ![notification illustration](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\* ![deals illustration](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\* ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Fort Myers (RSW) to Chicago (ORD) Prices were available within the past 7 days and start at CA $77 for one-way flights and CA $239 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Oct 29 - Fri, Oct 31 RSW Fort Myers ORD Chicago CA $239 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:RSW,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:238.21&airProductToken=AQo0CjIIwYIBEgQyNTYxGNG0ASCuHCiG1vsCMMXX-wI4QkAAWAFqBUJBU0lDcghOVUFMSU5CWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Oct 29 - Fri, Oct 31 RSW Fort Myers ORD Chicago CA $252 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:RSW,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:251.81&airProductToken=AQpvCjYIxJgBEgQxMzk1GNG0ASDgXCi-0vsCMKjT-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFVTks4QkcKNQjEmAESBDE0NzcY4FwgrhwokdX7AjCL1vsCOEVAAVgBaglNQUlOQkFTSUNyCFZBVU5LOEJHEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Oct 29 - Fri, Oct 31 RSW Fort Myers ORD Chicago CA $264 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:RSW,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:263.07&airProductToken=AQpgCi8IwmwSBDIwNjYY0bQBIMGTASib1PsCMN3V-wI4TEAAWAFqAkROcghQSTRRVUVMMQotCMJsEgM4MTEYwZMBIK4cKIvW-wIwv9f7AjhMQAFYAWoCRE5yCFBJN1FCRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Oct 29 - Fri, Oct 31 RSW Fort Myers ORD Chicago CA $272 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:RSW,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:271.75&airProductToken=AQpfCi4IwmwSBDEwMzAY0bQBIKlRKI7V-wIwudb7AjhMQABYAWoCRE5yCFBJNFFVRUwxCi0IwmwSBDIxMDUYqVEgrhwoxNf7AjDw2PsCOExAAVgBagJETnIIUEk3UUJFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Oct 29 - Fri, Oct 31 RSW Fort Myers ORD Chicago CA $295 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:RSW,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:294.11&airProductToken=AQozCjEIwYIBEgQyNTYxGNG0ASCuHCiG1vsCMMXX-wI4TkAAWAFqBE1BSU5yCE5VQUxJTk0zEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Oct 29 - Fri, Oct 31 RSW Fort Myers ORD Chicago CA $300 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:RSW,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:299.11&airProductToken=AQppCjMIwYIBEgQxOTMwGNG0ASDimgEor9f7AjCn2PsCOEJAAFgBagVCQVNJQ3IITjdBVVVOQlgKMgjBggESBDMxODgY4poBIK4cKObY-wIw6tn7AjhCQAFYAWoFQkFTSUNyCE43QVVVTkJYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Oct 29 - Fri, Oct 31 RSW Fort Myers ORD Chicago CA $305 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:RSW,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:304.71&airProductToken=AQpuCjUIxJgBEgM4MTQY0bQBIMsBKLbT-wIw29T7AjhFQABYAWoJTUFJTkJBU0lDcghYQVVTQTBCQwo1CMSYARIEMjc2MBjLASCuHCj01vsCMJnY-wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFVU0wwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Oct 29 - Fri, Oct 31 RSW Fort Myers ORD Chicago CA $308 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:RSW,departure:31/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:307.71&airProductToken=AQpvCjYIxJgBEgQxMzk1GNG0ASDgXCi-0vsCMKjT-wI4VkAAWAFqCU1BSU5DTEFTQ3IIVkFVTks4TUYKNQjEmAESBDE0NzcY4FwgrhwokdX7AjCL1vsCOFZAAVgBaglNQUlOQ0xBU0NyCFZBVU5LOE1GEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Nov 21 - Sun, Nov 23 RSW Fort Myers ORD Chicago CA $405 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:21/11/2025TANYT&leg2=from:ORD,to:RSW,departure:23/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:404.12&airProductToken=AQouCiwIzpYBEgQxNTQ4GNG0ASCuHCin1v0CMN7X_QI4VkAAWAFqAlNEcgVWQTNOUgouCiwIzpYBEgQxNTQ5GK4cING0ASix7_0CMOLw_QI4VEAAWAFqAlNEcgVUQTdOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Fri, Nov 21 - Sun, Nov 23 RSW Fort Myers ORD Chicago CA $676 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:RSW,to:ORD,departure:21/11/2025TANYT&leg2=from:ORD,to:RSW,departure:23/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:675.30&airProductToken=AQpsCjQI1YIBEgM2NTcY0bQBIMSNASjd2_0CMIvd_QI4R0AAWAFqB0VDT05PTVlyCEdEQTRQRkROCjQI1YIBEgQyNDQwGMSNASCuHCjC4P0CMOnh_QI4R0ABWAFqB0VDT05PTVlyCEdBQTdKSEROCjYKNAjVggESBDE5NDYYrhwg0bQBKLfw_QIw7PH9AjhTQABYAWoHRUNPTk9NWXIIU0FBNUFLRE4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Fort Myers (RSW) to Chicago (ORD) ### February is typically the cheapest month to fly From CA $95 - CA $334 per traveller. Flight from Fort Myers to Chicago (RSW - ORD) route information | Origin airport | Southwest Florida Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | American Airlines, Delta, JetBlue Airways, Spirit Airlines | | Roundtrip price | CA $238 | | Distance | 1796 km | | Average flight time | 2 hours 13 mins | ## Fort Myers to Chicago Flights **The easy way to book your flights from Fort Myers to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Fort Myers whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.   Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Fort Myers to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Southwest Florida Intl., RSW to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Fort Myers to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Fort Myers currently is just CA $239 rising to CA $676.   Here are more money-saving tips:  - Fly in October when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Chicago   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to Chicago from Fort Myers**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Frequently asked questions ### How much is a flight from RSW to O'Hare Airport? > Within the past 7 days on Expedia, for flights departing within the next year, the lowest price listed for a round-trip journey between RSW and O'Hare Airport was CA $239. Fares this good don't last long, so book yours today. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Southwest Florida Intl. Airport to O'Hare Airport? > Every airline has a different set of terms and conditions. If you decide to cancel your vacation, head to our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD) that have flexible change policies? > Flights from Southwest Florida Intl. Airport to ORD offering flexible change policies are available with many airlines. Simply use our "No change fees" filter while searching. You'll only need to cover the difference in ticket price, with no additional fees to worry about. ### How many hours is the flight from Southwest Florida Intl. Airport to ORD? > The flight time between Southwest Florida Intl. Airport and O'Hare Airport is 3 hours and 13 minutes. If you get peckish on longer flights, pack some snacks in your hand luggage. ### How far is the flight from Southwest Florida Intl. Airport (RSW) to ORD? > Around 1,800 kilometres separates Fort Myers and Chicago, so pack something to keep you busy for a couple of hours. That action-packed novel you haven't finished will be just the ticket. ### Which airlines fly direct from RSW to ORD? > You have a lot of choice when flying from Southwest Florida Intl. Airport (RSW) to O'Hare Airport. Lock in your ticket with one of these popular airlines: > > > > - United Airlines - (UA) with 139 monthly flights > - American Airlines - (AA) with 60 monthly flights > - Spirit Airlines - (NK) with 47 monthly flights > - Frontier Airlines - (F9) with 13 monthly flights ### Are Southwest Florida Intl. Airport (RSW) to ORD flight tickets cheaper when they're purchased at the last minute? > Booking your trip from Southwest Florida Intl. Airport (RSW) to ORD at the last minute could be your ticket to an awesome deal. However, it could end up costing a good deal more! If you'd rather not take any chances, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to 12 months in advance. If your preferred carrier hasn't released tickets yet, check back often as deals are updated all the time on Expedia. ## Explore a world of travel with Expedia - Flights ### Flights - [Flights from Calgary to Rosemont](https://www.expedia.ca/lp/flights/178245/7581/calgary-to-rosemont) - [Flights from Denver to Northwest Chicago](https://www.expedia.ca/lp/flights/178254/6350697/denver-to-northwest-chicago) - [Flights from Los Angeles to Evanston](https://www.expedia.ca/lp/flights/178280/8049/los-angeles-to-evanston) - [Flights from Mexico City to Northwest Chicago](https://www.expedia.ca/lp/flights/178285/6350697/mexico-city-to-northwest-chicago) - [Flights from New York to Evanston](https://www.expedia.ca/lp/flights/178293/8049/new-york-to-evanston) - [Flights from Ottawa to Evanston](https://www.expedia.ca/lp/flights/178296/8049/ottawa-to-evanston) - [Flights from Philadelphia to Rosemont](https://www.expedia.ca/lp/flights/178297/7581/philadelphia-to-rosemont) - [Flights from Portland to Rosemont](https://www.expedia.ca/lp/flights/178299/7581/portland-to-rosemont) - 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