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Cheap flights from Chicago to Fort Myers from $55

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Fort Myers departing on 6/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Spirit Airlines Logo
12:08 pm - 4:01 pmORD-RSW
2h 53mnonstop
Spirit Airlines Logo
9:04 am - 11:13 amRSW-ORD
3h 09mnonstop
$112Spirit Airlines
Find Deal
jue., jun. 12 - dom., jun. 15
Spirit Airlines Logo
12:26 pm - 4:13 pmORD-RSW
2h 47mnonstop
Spirit Airlines Logo
9:04 am - 11:13 amRSW-ORD
3h 09mnonstop
$114Spirit Airlines
Find Deal
jue., jun. 5 - jue., jun. 12
American Airlines Logo
6:55 am - 10:42 amORD-RSW
2h 47mnonstop
American Airlines Logo
11:26 am - 1:42 pmRSW-ORD
3h 16mnonstop
$133American Airlines
Find Deal
mar., jun. 17 - mar., jul. 15
American Airlines Logo
6:45 am - 10:38 amORD-RSW
2h 53mnonstop
American Airlines Logo
8:30 am - 10:43 amRSW-ORD
3h 13mnonstop
$135American Airlines
Find Deal
mar., may. 27 - sáb., may. 31
Southwest Logo
1:05 pm - 4:50 pmMDW-RSW
2h 45mnonstop
Southwest Logo
5:55 am - 7:50 amRSW-MDW
2h 55mnonstop
$167Southwest
Find Deal
mar., may. 27 - sáb., may. 31
Southwest Logo
5:45 am - 9:25 amMDW-RSW
2h 40mnonstop
Southwest Logo
6:45 pm - 8:40 pmRSW-MDW
2h 55mnonstop
$170Southwest
Find Deal
mar., jun. 17 - mar., jul. 15
Frontier Logo
6:20 am - 6:20 pmMDW-RSW
11h 00m1 stop
Frontier Logo
7:16 pm - 11:17 pmRSW-MDW
5h 01m1 stop
$200Frontier
Find Deal
jue., ago. 14 - dom., ago. 17
United Airlines Logo
10:52 am - 2:57 pmORD-RSW
3h 05mnonstop
United Airlines Logo
7:30 pm - 9:52 pmRSW-ORD
3h 22mnonstop
$215United Airlines
Find Deal
mar., jun. 3 - sáb., jun. 7
United Airlines Logo
7:30 am - 11:35 amORD-RSW
3h 05mnonstop
United Airlines Logo
7:30 pm - 9:52 pmRSW-ORD
3h 22mnonstop
$228United Airlines
Find Deal
vie., jun. 6 - sáb., jun. 7
Frontier Logo
6:15 am - 6:09 pmMDW-RSW
10h 54m1 stop
Frontier Logo
7:13 pm - 11:25 pmRSW-MDW
5h 12m1 stop
$261Frontier
Find Deal
jue., sep. 11 - dom., sep. 14

Spirit Airlines flights from Chicago to Fort Myers

Our best Spirit Airlines deals on Chicago to Fort Myers flight tickets
Spirit Airlines
Jun 12
ORD12:08 pmChicago O'Hare Intl
2h 53m
RSW4:01 pmFort Myers SW Florida Intl
Jun 15
RSW9:04 amFort Myers SW Florida Intl
3h 09m
ORD11:13 amChicago O'Hare Intl
Spirit Airlines
Jun 5
ORD12:26 pmChicago O'Hare Intl
2h 47m
RSW4:13 pmFort Myers SW Florida Intl
Jun 12
RSW9:04 amFort Myers SW Florida Intl
3h 09m
ORD11:13 amChicago O'Hare Intl
Spirit Airlines
Jun 2
ORD12:26 pmChicago O'Hare Intl
2h 47m
RSW4:13 pmFort Myers SW Florida Intl
Jun 6
RSW9:15 amFort Myers SW Florida Intl
3h 16m
ORD11:31 amChicago O'Hare Intl

Delta flights from Chicago to Fort Myers

Our best Delta deals on Chicago to Fort Myers flight tickets
Delta
Jun 4
ORD3:33 pmChicago O'Hare Intl
6h 40m
1 stop
RSW11:13 pmFort Myers SW Florida Intl
Jun 18
RSW11:17 amFort Myers SW Florida Intl
7h 29m
1 stop
ORD5:46 pmChicago O'Hare Intl
Delta
May 27
ORD8:40 amChicago O'Hare Intl
7h 29m
1 stop
RSW5:09 pmFort Myers SW Florida Intl
Jun 3
RSW7:40 amFort Myers SW Florida Intl
7h 48m
1 stop
ORD2:28 pmChicago O'Hare Intl
Delta
Jun 5
ORD3:57 pmChicago O'Hare Intl
7h 40m
1 stop
RSW12:37 amFort Myers SW Florida Intl
Jun 10
RSW5:49 pmFort Myers SW Florida Intl
7h 08m
1 stop
ORD11:57 pmChicago O'Hare Intl

See travel insights to Fort Myers from

How to get the cheapest flight ticket from Chicago to Fort Myers

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Fort Myers?

In general, January is the cheapest month to fly from Chicago to Fort Myers. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $224. If you are unable to visit Fort Myers during the month of January, then departing from Chicago during the month August is also very affordable. Most momondo users find prices during this month for around $227.

What is the cheapest day to depart on your flight to Fort Myers?

The cheapest day to depart from Chicago to Fort Myers is on a Tuesday when prices can be found for as low as $254. Flights from Chicago to Fort Myers on a Friday will generally be more expensive and average around $314. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Fort Myers?

The cheapest time of day to fly to Fort Myers is in the morning when flights can be purchased for as low as $289. Flights at noon are often more expensive with an average ticket price of $338.

What is the cheapest Chicago to Fort Myers SW Florida Intl flight route?

Fly from Chicago O'Hare Intl to Fort Myers SW Florida Intl for the best Chicago - Fort Myers SW Florida Intl flight prices

How far in advance should I book a flight to Fort Myers?

You are more likely to see cheaper flights to Fort Myers from Chicago when booking 4 weeks ahead of your departure date. In general, you can expect to find flights to Fort Myers for around $275 when searching 4 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Fort Myers from Chicago for as low as $232 on momondo.

What cabin class options are available on Chicago to Fort Myers SW Florida Intl flights?

There are 4 cabin classes available to choose from on Chicago to Fort Myers SW Florida Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Fort Myers flight prices changed over time?

As of May 2025, prices for Chicago to Fort Myers flights are approximately 33% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Fort Myers

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Fort Myers according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Fort Myers (CHI to RSW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Fort Myers

Best Price Found

$55

Fastest flight time

2h 40m

Direct flights

Every day

Airports in Fort Myers

1 airport
The best one-way flight to Fort Myers from Chicago in the past 72 hours is $55. The best round-trip flight deal from Chicago to Fort Myers found on momondo in the last 72 hours is $112.
The fastest flight from Chicago to Fort Myers takes 2h 40m
Direct flights go from Chicago to Fort Myers every day.
There is 1 airport near Fort Myers: Fort Myers SW Florida Intl (RSW)

  • How far is Chicago to Fort Myers SW Florida Intl by plane?

    There are 1101.2 mi between Chicago and Fort Myers SW Florida Intl. 2h 40m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to Fort Myers SW Florida Intl Airport?

    Prices for flights from Chicago to Fort Myers SW Florida Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Fort Myers SW Florida Intl Airport?

  • How old do you have to be to fly from Chicago to Fort Myers SW Florida Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Fort Myers SW Florida Intl Airport.

  • What documentation or ID do you need to fly to Fort Myers SW Florida Intl Airport?

    The required travel and health documents for your Fort Myers SW Florida Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Fort Myers SW Florida Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to Fort Myers?

  • What is the most popular airline from Chicago to Fort Myers?


Best airlines flying from Chicago to Fort Myers

Compare and see reviews for airlines that fly from Chicago to Fort Myers with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $54Free CancellationRating
5.9
3,289 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $84Free CancellationRating
6.3
7,974 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $95Free CancellationRating
7.4
8,710 reviews
Search United Airlines flights
Sun Country AirPriceFrom $134Free CancellationRating
6.9
346 reviews
Search Sun Country Air flights
American AirlinesPriceFrom $175Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $216Free CancellationRating
8.0
7,944 reviews
Search Delta flights
SouthwestPriceFrom $235Free CancellationRating
8.0
4,293 reviews
Search Southwest flights
  • Southwest Flights From Chicago to Fort Myers

    Southwest operates around 15 flights from Chicago to Fort Myers every week. The average price of these flights found in the last 72 hours has been $476, but momondo users have found Southwest deals from Chicago to Fort Myers from as low as $235 round-trip. Southwest has been scored 8.0/10 in 4,293 reviews.

  • United Airlines Flights From Chicago to Fort Myers

    The best United Airlines deal for Chicago to Fort Myers flight tickets found on momondo in the last 72 hours was $95, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $381 round-trip. United Airlines operates 21 flights out of Chicago into Fort Myers in an average week, so prices vary by time and availability. 8,710 United Airlines reviews by users on momondo have scored the airline at 7.4/10.


Traveling to a place near Fort Myers?

Book flights to Fort Myers if you plan to visit one of these locations
Sanibel
Fort Myers Beach
Cape Coral
Estero
North Fort Myers
Captiva
Lehigh Acres
Boca Grande

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Fort Myers?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Fort Myers from Chicago.

Can I find flights from Chicago to Fort Myers with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Fort Myers from Chicago with this policy.

How can momondo help me find flights from Chicago to Fort Myers?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Fort Myers.

I’m not ready to book a flight from Chicago to Fort Myers right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Fort Myers now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Fort Myers and let you know when they change.


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1 adult
lun. 5/12
lun. 5/19

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