$39 Cheap flights from O'Hare Intl. to Southwest Florida Intl. (ORD to RSW)

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Find The Best Dates To Fly from O'Hare Intl. to Southwest Florida Intl.

Amazing ORD to RSW Flight Deals

The cheapest flights to Southwest Florida Intl. found within the past 7 days were $87 round trip and $39 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Dec 3 - Thu, Dec 5
ORD
Chicago
RSW
Fort Myers
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Dec 3 from Chicago to Fort Myers, returning Thu, Dec 5, priced at $87 just found
Sat, Jan 25 - Sat, Jan 25
ORD
Chicago
RSW
Fort Myers
$95 Roundtrip, found 3 days ago
$95
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jan 25 from Chicago to Fort Myers, returning Sat, Jan 25, priced at $95 found 3 days ago
Mon, Nov 25 - Thu, Nov 28
ORD
Chicago
RSW
Fort Myers
$96 Roundtrip, just found
$96
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Nov 25 from Chicago to Fort Myers, returning Thu, Nov 28, priced at $96 just found
Tue, Jan 7 - Sat, Jan 25
ORD
Chicago
RSW
Fort Myers
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Jan 7 from Chicago to Fort Myers, returning Sat, Jan 25, priced at $100 found 2 days ago
Sun, Jan 12 - Sun, Jan 12
ORD
Chicago
RSW
Fort Myers
$101 Roundtrip, found 2 hours ago
$101
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Jan 12 from Chicago to Fort Myers, returning Sun, Jan 12, priced at $101 found 2 hours ago
Wed, Jan 15 - Thu, Jan 23
ORD
Chicago
RSW
Fort Myers
$101 Roundtrip, found 16 hours ago
$101
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Jan 15 from Chicago to Fort Myers, returning Thu, Jan 23, priced at $101 found 16 hours ago
Sat, Jan 11 - Sun, Jan 19
ORD
Chicago
RSW
Fort Myers
$102 Roundtrip, found 5 hours ago
$102
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Jan 11 from Chicago to Fort Myers, returning Sun, Jan 19, priced at $102 found 5 hours ago
Sun, Jan 19 - Sat, Jan 25
ORD
Chicago
RSW
Fort Myers
$103 Roundtrip, found 14 hours ago
$103
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sun, Jan 19 from Chicago to Fort Myers, returning Sat, Jan 25, priced at $103 found 14 hours ago
Sat, Jan 11 - Sat, Jan 25
ORD
Chicago
RSW
Fort Myers
$104 Roundtrip, found 2 days ago
$104
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jan 11 from Chicago to Fort Myers, returning Sat, Jan 25, priced at $104 found 2 days ago
Sun, Jan 12 - Thu, Jan 16
ORD
Chicago
RSW
Fort Myers
$106 Roundtrip, found 1 hour ago
$106
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Jan 12 from Chicago to Fort Myers, returning Thu, Jan 16, priced at $106 found 1 hour ago

Best Southwest Florida Intl. Flight and Hotel Packages

Southwest Florida Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
SpringHill Suites by Marriott Fort Myers Estero

SpringHill Suites by Marriott Fort Myers Estero

2.5 out of 5
per person
Dec 7 - Dec 9
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
THE Palmview AND Sandpiper Inns

THE Palmview AND Sandpiper Inns

3.5 out of 5
Save 100% on your flight
per person
Dec 22 - Dec 29
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
Save 100% on your flight
per person
Dec 22 - Dec 29
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Fort Myers (RSW)
Fairfield Inn & Suites by Marriott Cape Coral/North Fort Myers

Fairfield Inn & Suites by Marriott Cape Coral/North Fort Myers

3 out of 5
per person
Dec 7 - Dec 9
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
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Frequently asked questions

Can I catch a flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport right now?
For info on any current Southwest Florida Intl. Airport travel advice and quarantine requirements, go to the Covid-19 Travel Advisor. Look before you book your flight, so you don’t get caught up en route.
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.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to RSW, please visit our Customer Service Portal.
How long is the flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
On average, flying from ORD to Southwest Florida Intl. Airport takes a mere 2 hours and 55 minutes. Use the short flight to rest your eyelids or listen to a quick podcast before the next part of your journey begins.
What is the flight distance from O'Hare Airport to Southwest Florida Intl. Airport?
With a flight distance of 1,100 mi between ORD and Southwest Florida Intl. Airport (RSW), you’ll be cruising at altitude for a reasonable length of time. It’s a great chance to get engrossed in a movie, get some work done or just relax with a novel.
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 airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you’re flying with Southwest Airlines, United Airlines or Delta you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity 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 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

 

Traveling From
O'Hare Intl.
Traveling To
Southwest Florida Intl.
Shortest Flight Time
 hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price
$87

Route Info

Flight path for flights from O'Hare International Airport to Southwest Florida International Airport


Origin:
ORD - O'Hare International Airport
Destination:
RSW - Southwest Florida International Airport
Distance:
1,129.00 miles


Airlines & Aircraft Used on ORD to RSW Flight Routes


Airline Carrier
Aircraft
American Airlines
Airbus A320-100/200
American Airlines
Boeing 737-300 pax
American Airlines
Boeing 737-800 pax
United Airlines
Airbus A319
United Airlines
Airbus A320-100/200

Discover our best flights from Chicago ORD to Fort Myers RSW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Chicago ORD to Fort Myers RSW at the right price  

Airfares to Fort Myers RSW from Chicago ORD currently cost between $87 and $106. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Chicago ORD to Fort Myers RSW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Chicago ORD to Fort Myers RSW on Travelocity starting at $39. Prices and availability subject to change. Additional terms may apply. 

 

Get to Fort Myers RSW from Chicago ORD quicker with direct flights. 

Get to Fort Myers faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to RSW from ORD to take around hour(s) min(s).  

 

Find our cheapest airfares for flights from Chicago ORD to Fort Myers RSW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to RSW from ORD. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Chicago ORD to Fort Myers RSW today 

If you’re flexible about when you travel, December is usually the cheapest month to fly from Chicago ORD to Fort Myers RSW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Fort Myers RSW from Chicago ORD 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to RSW from ORD have this option.  

 

Travel with confidence when you book flights to Fort Myers RSW from Chicago ORD with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*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.