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 $94 round trip and CA $42 one way. Prices and availability subject to change. Additional terms may apply.

Sun, Feb 22 - Wed, Feb 25
ORD
Chicago
RSW
Fort Myers
CA $94 Roundtrip, found 2 days ago
CA $94
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Feb 22 from Chicago to Fort Myers, returning Wed, Feb 25, priced at CA $94 found 2 days ago
Sun, Mar 1 - Thu, Mar 5
ORD
Chicago
RSW
Fort Myers
CA $156 Roundtrip, found 2 days ago
CA $156
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Mar 1 from Chicago to Fort Myers, returning Thu, Mar 5, priced at CA $156 found 2 days ago
Sun, Feb 22 - Wed, Feb 25
ORD
Chicago
RSW
Fort Myers
CA $161 Roundtrip, found 2 days ago
CA $161
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Feb 22 from Chicago to Fort Myers, returning Wed, Feb 25, priced at CA $161 found 2 days ago
Sun, Feb 22 - Wed, Feb 25
ORD
Chicago
RSW
Fort Myers
CA $165 Roundtrip, found 2 days ago
CA $165
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Feb 22 from Chicago to Fort Myers, returning Wed, Feb 25, priced at CA $165 found 2 days ago
Sun, Mar 1 - Wed, Mar 4
ORD
Chicago
RSW
Fort Myers
CA $176 Roundtrip, found 2 days ago
CA $176
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Mar 1 from Chicago to Fort Myers, returning Wed, Mar 4, priced at CA $176 found 2 days ago
Sun, Feb 22 - Wed, Feb 25
ORD
Chicago
RSW
Fort Myers
CA $227 Roundtrip, found 2 days ago
CA $227
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Feb 22 from Chicago to Fort Myers, returning Wed, Feb 25, priced at CA $227 found 2 days ago
Sun, Feb 22 - Wed, Feb 25
ORD
Chicago
RSW
Fort Myers
CA $232 Roundtrip, found 2 days ago
CA $232
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Feb 22 from Chicago to Fort Myers, returning Wed, Feb 25, priced at CA $232 found 2 days ago
Sun, Mar 1 - Thu, Mar 5
ORD
Chicago
RSW
Fort Myers
CA $239 Roundtrip, found 2 days ago
CA $239
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Mar 1 from Chicago to Fort Myers, returning Thu, Mar 5, priced at CA $239 found 2 days ago
Sun, Feb 22 - Wed, Feb 25
ORD
Chicago
RSW
Fort Myers
CA $247 Roundtrip, found 2 days ago
CA $247
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Feb 22 from Chicago to Fort Myers, returning Wed, Feb 25, priced at CA $247 found 2 days ago
Sun, Mar 1 - Wed, Mar 4
ORD
Chicago
RSW
Fort Myers
CA $249 Roundtrip, found 2 days ago
CA $249
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Mar 1 from Chicago to Fort Myers, returning Wed, Mar 4, priced at CA $249 found 2 days 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.