Find the Cheapest Flight from Fort Myers (RSW) to Chicago (CHI)
Find the ideal departure and return dates from to Chicago and the cheapest flights of the month. We already found out the best options for you.
| Departure at | Return at | Airline | Find tickets |
|---|---|---|---|
| August 15, 2026 | August 17, 2026 | United Airlines | Tickets from 411 |
How Much is a Flight from Fort Myers?
What is the Best Airline to Fly from Fort Myers?
At cheapfly365 we give you all the available options from our reputable partners. We give you every one of the accessible choices from our legitimate accomplices. Select the aircraft that best suits your inclinations and participation loyalties.
| Airline | Destination | Find tickets |
|---|---|---|
| United Airlines | Chicago | Tickets from 411 |
| Sun Country Airlines | Minneapolis | Tickets from 351 |
| Southwest Airlines | St Louis | Tickets from 224 |
| Breeze Airways | Indianapolis | Tickets from 363 |
| jetBlue | Moscow | Tickets from 1 538 |
| Turkish Airlines | Barcelona | Tickets from 850 |
| Porter Airlines Canada | Berlin | Tickets from 1 006 |
| jetBlue | Batumi | Tickets from 1 355 |
| United Airlines | Cortez | Tickets from 1 108 |
| Southwest Airlines | Dallas | Tickets from 256 |
| Frontier Airlines | Detroit | Tickets from 326 |
| Air Canada | Dublin | Tickets from 766 |
| United Airlines | Istanbul | Tickets from 960 |
| Southwest Airlines | Las Vegas | Tickets from 149 |
| Breeze Airways | Norfolk | Tickets from 290 |
| American Airlines | Rochester | Tickets from 334 |
| Southwest Airlines | Seattle | Tickets from 314 |
| Air Canada | Podgorica | Tickets from 1 024 |
| Discover Airlines | Warsaw | Tickets from 607 |
Non-stop Flights from Fort Myers to Chicago – Leaving Soon
We have collected for you the flight ticket prices from to Chicago for the entire current month. Find the flight you're interested in with one-way. Don't forget to book a hotel and rental car before you travel.
| Departure at | Trip class | Distance | Find tickets |
|---|---|---|---|
| August 17, 2026 | Economy | 1122 ml | Tickets from 249 |
| August 16, 2026 | Economy | 1122 ml | Tickets from 252 |
Find Flights from Fort Myers to Chicago within your Budget
Easily find the cheapest day or month for your trip. You can choose direct or return flights but also you can choose one-way or the holiday duration system (choose from 1 to 30 days and you will be informed about the cheapest flights).
Fort Myers to Chicago Flight Deals
Are you looking to travel to Chicago in the coming months? The cheapest tickets we have for you.
| Departure at | Return at | Airline | Flight number | Find tickets |
|---|---|---|---|---|
| August 15, 2026 | August 17, 2026 | United Airlines | UA 2628 | Tickets from 411 |
The Cheapest Return Flights from Fort Myers to Chicago
It is time to travel from to Chicago and you are looking for the cheapest round trip airfare. Well good for you! In the table below you can check the lowest prices from to Chicago.
| Departure at | Return at | Airline | Find tickets |
|---|---|---|---|
| August 15, 2026 | August 17, 2026 | United Airlines | Tickets from 411 |
Fly your Favorite Airline from Chicago
Looking for direct flight destinations from Chicago? We searched and found the best options for you.
| Origin - Destination | Departure at | Return at | Airline | Find tickets |
|---|---|---|---|---|
ChicagoAddis Ababa | August 31, 2026 | September 30, 2026 | Ethiopian Airlines | Tickets from 1 453 |
ChicagoAthens | August 25, 2026 | September 9, 2026 | United Airlines | Tickets from 1 088 |
ChicagoAtlanta | August 20, 2026 | August 22, 2026 | Frontier Airlines | Tickets from 245 |
ChicagoAbu Dhabi | October 25, 2026 | November 11, 2026 | Etihad Airways | Tickets from 937 |
ChicagoAustin | November 5, 2026 | November 9, 2026 | Southwest Airlines | Tickets from 195 |
Cheap Flights to Chicago Airport
Book the next cheap ticket to Chicago immediately. The table below shows from which cities you can find a cheap flight to Chicago airport.
| Origin - Destination | Departure at | Return at | Find tickets |
|---|---|---|---|
Fort LauderdaleChicago | September 10, 2026 | September 14, 2026 | Tickets from 55 |
AtlantaChicago | September 7, 2026 | September 17, 2026 | Tickets from 83 |
OrlandoChicago | September 12, 2026 | September 16, 2026 | Tickets from 105 |
Las VegasChicago | September 10, 2026 | September 14, 2026 | Tickets from 112 |
PhiladelphiaChicago | September 29, 2026 | October 1, 2026 | Tickets from 120 |
Direct Flights from Fort Myers
Find cheap flights from to top destinations. Start your next trip now!
| Origin - Destination | Departure at | Return at | Find tickets |
|---|---|---|---|
Fort MyersLas Vegas | October 8, 2026 | October 12, 2026 | Tickets from 151 |
Fort MyersSt Louis | October 17, 2026 | October 24, 2026 | Tickets from 226 |
Fort MyersSan Francisco | December 23, 2026 | December 27, 2026 | Tickets from 256 |
Fort MyersDallas | September 3, 2026 | September 8, 2026 | Tickets from 259 |
Fort MyersChattanooga | November 23, 2026 | November 27, 2026 | Tickets from 274 |
Useful Information Before the Fort Myers – Chicago Flight
Found more than 56 flights every day. The average flight duration is 2h 45m. Below is the flight schedule with departures and arrivals of the day. The airline, the airports of the flight and the schedule of the week are also displayed.
Fort Myers, United StatesChicago, United States
| Time and stops | Airline | Route | Schedule | Find tickets |
|---|---|---|---|---|
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06:5008:40 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
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11:2713:50 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
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15:2017:10 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
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15:3020:27 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3020:55 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3020:55 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3020:55 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3020:55 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3020:55 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3020:55 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3021:35 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3021:35 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3021:35 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3021:35 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:3021:35 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
15:4020:10 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
16:1518:05 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
16:1520:45 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
16:2020:30 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
16:3919:10 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
16:3919:10 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
16:3919:10 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
16:3919:10 Direct | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
16:4018:59 Direct | United Airlines | RSW — ORD | S M T W T F S | Pick Dates |
17:0021:00 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:0022:00 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
17:0022:36 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
17:0521:30 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:0522:40 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:1020:55 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:2519:15 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
17:4019:30 Direct | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
18:1022:25 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
18:1521:50 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
18:2521:55 1 Stop | Southwest Airlines | RSW — MDW | S M T W T F S | Pick Dates |
18:2922:36 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
18:2922:36 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
18:2922:36 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
18:2922:36 1 Stop | Delta | RSW — MDW | S M T W T F S | Pick Dates |
18:2923:57 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
18:2923:57 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
18:2923:57 1 Stop | Delta | RSW — ORD | S M T W T F S | Pick Dates |
18:3423:52 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
19:3523:56 1 Stop | American Airlines | RSW — ORD | S M T W T F S | Pick Dates |
