Cheap Flights from Chicago to Fort Myers
Cheap Flights from Chicago to Fort Myers
Looking for cheap flights from Chicago to Fort Myers? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Fort Myers vary by season, cabin, and date, but available award flights can start around 7,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Fort Myers for specific travel dates.
2026-11-05
ORD - RSW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-06
ORD - RSW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-07
ORD - RSW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-08
ORD - RSW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-09
ORD - RSW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
2026-11-10
ORD - RSW
Economy | Non stop | 9+ left
From 7,500 Pts + $25.6
Chicago to Fort Myers flight facts
Distance
1,118 mi
1,799 km in a straight line
Estimated flight time
about 2h 45m
In the air, for the straight-line distance
Time difference
+1h
Fort Myers is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Fort Myers
RSW · Southwest Florida Intl
Nearby airport alternatives
Flights Milwaukee - Fort Myers · Milwaukee is 73 mi from Chicago
Flights Chicago - Sarasota · Sarasota is 77 mi from Fort Myers
Flights South Bend - Fort Myers · South Bend is 86 mi from Chicago
Flights Chicago - Fort Lauderdale · Fort Lauderdale is 104 mi from Fort Myers
Flights Chicago - Miami · Miami is 104 mi from Fort Myers
Flights Bloomington - Fort Myers · Bloomington is 109 mi from Chicago
Premium cabin flights from Chicago to Fort Myers
Premium cabin
2026-11-13
ORD - RSW
First | Non stop | 6 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-14
ORD - RSW
First | Non stop | 6 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-15
ORD - RSW
First | Non stop | 8 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-16
ORD - RSW
First | Non stop | 1 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-17
ORD - RSW
First | Non stop | 1 left
From 15,000 Pts + $25.6
Premium cabin
2026-11-11
ORD - RSW
First | 1 Stop | 5 left
From 25,000 Pts + $25.6
Selected hotels for your next stay
Marco Island, FL (USA)
JW Marriott Marco Island Beach Resort
From Pts or $797
Fort Myers, FL (USA)
Luminary Hotel & Co., Autograph Collection
From Pts or $282
Naples (USA)
The Ritz-Carlton, Naples
From Pts or $1253
Frequently Asked Questions
The cheapest route from Chicago to Fort Myers depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Fort Myers.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Fort Myers.
Chicago and Fort Myers are about 1,118 miles (1,799 km) apart in a straight line.
Flying the 1,118-mile straight-line distance takes about 2h 45m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Fort Myers is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Fort Myers: Southwest Florida Intl (RSW).
Travelers searching this route also look at other popular routes into Fort Myers, plus the return trip when we track it. Fares and award space change daily.
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