Cheap Flights From O'Hare Intl. (ORD) To Southwest Florida Intl. (RSW)

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Cheapest Flights from Chicago (ORD) to Fort Myers (RSW)

The cheapest flights to Southwest Florida Intl. found within the past 7 days were CA $104 round trip and CA $56 one way. Prices and availability subject to change. Additional terms may apply.

Sat, Aug. 30 - Sun, Aug. 31
ORD
Chicago
RSW
Fort Myers
CA $104 Roundtrip, found 1 day ago
CA $104
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Aug. 30 from Chicago to Fort Myers, returning Sun, Aug. 31, priced at CA $104 found 1 day ago
Sun, Aug. 24 - Thu, Aug. 28
ORD
Chicago
RSW
Fort Myers
CA $119 Roundtrip, found 1 day ago
CA $119
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Aug. 24 from Chicago to Fort Myers, returning Thu, Aug. 28, priced at CA $119 found 1 day ago
Fri, Nov. 7 - Sun, Nov. 9
ORD
Chicago
RSW
Fort Myers
CA $161 Roundtrip, found 1 day ago
CA $161
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Nov. 7 from Chicago to Fort Myers, returning Sun, Nov. 9, priced at CA $161 found 1 day ago
Sun, Aug. 24 - Thu, Aug. 28
ORD
Chicago
RSW
Fort Myers
CA $297 Roundtrip, found 1 day ago
CA $297
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Aug. 24 from Chicago to Fort Myers, returning Thu, Aug. 28, priced at CA $297 found 1 day ago
Sun, Aug. 24 - Thu, Aug. 28
ORD
Chicago
RSW
Fort Myers
CA $307 Roundtrip, found 1 day ago
CA $307
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, Aug. 24 from Chicago to Fort Myers, returning Thu, Aug. 28, priced at CA $307 found 1 day ago
Sun, Aug. 24 - Thu, Aug. 28
ORD
Chicago
RSW
Fort Myers
CA $434 Roundtrip, found 1 day ago
CA $434
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Aug. 24 from Chicago to Fort Myers, returning Thu, Aug. 28, priced at CA $434 found 1 day ago
Fri, Nov. 7 - Sun, Nov. 9
ORD
Chicago
RSW
Fort Myers
CA $448 Roundtrip, found 1 day ago
CA $448
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Nov. 7 from Chicago to Fort Myers, returning Sun, Nov. 9, priced at CA $448 found 1 day ago
Sun, Aug. 24 - Thu, Aug. 28
ORD
Chicago
RSW
Fort Myers
CA $461 Roundtrip, found 1 day ago
CA $461
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Aug. 24 from Chicago to Fort Myers, returning Thu, Aug. 28, priced at CA $461 found 1 day ago
Sun, Aug. 24 - Thu, Aug. 28
ORD
Chicago
RSW
Fort Myers
CA $484 Roundtrip, found 1 day ago
CA $484
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, Aug. 24 from Chicago to Fort Myers, returning Thu, Aug. 28, priced at CA $484 found 1 day ago
Fri, Nov. 7 - Sun, Nov. 9
ORD
Chicago
RSW
Fort Myers
CA $16,033 Roundtrip, found 1 day ago
CA $16,033
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, Nov. 7 from Chicago to Fort Myers, returning Sun, Nov. 9, priced at CA $16,033 found 1 day ago

Frequently asked questions

Are there direct flights from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport?
Kick off your escape relaxed and calm and fly straight to Southwest Florida Intl. Airport (RSW) from O'Hare Intl. Airport (ORD). United Airlines and American Airlines are among the airlines that offer direct services on this route.
What airlines fly from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport?
If you'd prefer to fly direct from O'Hare Intl. Airport (ORD) to RSW, you don't have to worry about choice. We've listed some of the most popular airlines that advertise nonstop services on this route:

  • United Airlines - (UA) with 117 flights every month
  • American Airlines - (AA) with 47 flights every month
  • Spirit Airlines - (NK) with 30 flights every month
  • Southwest Airlines - (WN) with 8 flights every month

What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Chicago (ORD)

Travelers at ORD love to visit these top cities. Roam to the top destinations from Chicago (ORD) today with the cheap prices from Travelocity!

Popular Flight Routes from Fort Myers (RSW)

Travelers at RSW love to visit these top cities. Roam to the top destinations from Fort Myers(RSW) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.