Nonstop flights from Fort Myers to Chicago

3 airlines fly from Fort Myers (RSW) to 2 Chicago airports (ORD and MDW), with up to 9 flights a day.

RSWORD

Routes

2 airport pairs

When they leave

Fort Myers time

6:07a5:40pFirst departure 6:07 AM, last 5:40 PM

Six in the morning, 6:07 AM to 11:55 AM, then three in the afternoon, 12:27 PM to 4:40 PM, then two in the evening, 5:25 PM to 5:40 PM.

Every flight

Earliest first

6:07 AM→8:30 AMRSW to ORDAmerican AirlinesBoeing 737Daily
6:50 AM→8:40 AMRSW to MDWSouthwest AirlinesBoeing 737Mon, Thu, Fri
7:10 AM→8:55 AMRSW to MDWSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sat, Sun
9:15 AM→11:29 AMRSW to ORDUnited AirlinesBoeing 737Daily
11:27 AM→1:50 PMRSW to ORDAmerican AirlinesBoeing 737Daily
11:55 AM→1:45 PMRSW to MDWSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
12:27 PM→2:41 PMRSW to ORDUnited AirlinesBoeing 737 MAX 9Daily
4:39 PM→7:10 PMRSW to ORDAmerican AirlinesBoeing 737 MAX 8Daily
4:40 PM→6:59 PMRSW to ORDUnited AirlinesAirbus A321neoDaily
5:25 PM→7:15 PMRSW to MDWSouthwest AirlinesBoeing 737 MAX 8Mon, Thu, Fri
5:40 PM→7:30 PMRSW to MDWSouthwest AirlinesBoeing 737 MAX 8Tue, Wed, Sat, Sun

Schedules last checked Sep 21, 2026. Times are local.

Flying from Fort Myers to Chicago

American Airlines flies 3 times a day on the Boeing 737 and Boeing 737 MAX 8. United Airlines flies 3 times a day on the Airbus A321neo, Boeing 737 and Boeing 737 MAX 9. Southwest Airlines flies 2 to 3 times a day on the Boeing 737 MAX 8 and Boeing 737.

Flights run every day of the week, 9 on Mondays, Thursdays and Fridays and 8 on the other days. The first arrival in Chicago is at 8:30 AM and the last at 7:30 PM.

RSW to ORD is the busiest airport pair, with 42 flights a week, then RSW to MDW with 17.

Flying back, Chicago to Fort Myers has 24 nonstop flights a week.

Return flights

Chicago to Fort MyersView

Find the cheapest day to fly from Fort Myers to Chicago.

Schedules as of Oct 9, 2026.