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Cheap flights from Chicago to Fort Myers from $65

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 9/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to Fort Myers (CHI-RSW)

Cheap round-trip flights

Spirit Airlines Logo
5:01 pm - 8:50 pmORD-RSW
2h 49mnonstop
Spirit Airlines Logo
6:40 am - 8:34 amRSW-ORD
2h 54mnonstop
$88Spirit Airlines
Find Deal
Thu, Oct 16 - Mon, Oct 20
Spirit Airlines Logo
5:23 pm - 9:16 pmORD-RSW
2h 53mnonstop
Spirit Airlines Logo
7:00 am - 9:13 amRSW-ORD
3h 13mnonstop
$92Spirit Airlines
Find Deal
Mon, Sep 8 - Mon, Sep 15
Frontier Logo
6:20 am - 6:29 pmMDW-RSW
11h 09m1 stop
Frontier Logo
7:24 pm - 11:20 pmRSW-MDW
4h 56m1 stop
$143Frontier
Find Deal
Thu, Sep 18 - Sun, Sep 21
Frontier Logo
6:20 am - 6:29 pmMDW-RSW
11h 09m1 stop
Frontier Logo
7:24 pm - 11:20 pmRSW-MDW
4h 56m1 stop
$144Frontier
Find Deal
Thu, Sep 25 - Thu, Oct 2
American Airlines Logo
2:44 pm - 6:50 pmORD-RSW
3h 06mnonstop
American Airlines Logo
1:36 pm - 3:52 pmRSW-ORD
3h 16mnonstop
$157American Airlines
Find Deal
Sat, Sep 20 - Wed, Sep 24
Southwest Logo
9:05 am - 12:50 pmMDW-RSW
2h 45mnonstop
Southwest Logo
4:25 pm - 6:15 pmRSW-MDW
2h 50mnonstop
$157Southwest
Find Deal
Tue, Sep 23 - Sat, Sep 27
American Airlines Logo
7:05 am - 10:56 amORD-RSW
2h 51mnonstop
American Airlines Logo
1:36 pm - 3:52 pmRSW-ORD
3h 16mnonstop
$158American Airlines
Find Deal
Mon, Sep 29 - Sat, Oct 4
Southwest Logo
9:05 am - 12:50 pmMDW-RSW
2h 45mnonstop
Southwest Logo
1:20 pm - 3:15 pmRSW-MDW
2h 55mnonstop
$158Southwest
Find Deal
Tue, Sep 23 - Fri, Sep 26
Delta Logo
5:04 pm - 12:39 amMDW-RSW
6h 35m1 stop
Delta Logo
4:11 pm - 10:14 pmRSW-MDW
7h 03m1 stop
$217Delta
Find Deal
Tue, Oct 21 - Fri, Oct 24
Delta Logo
6:00 am - 12:33 pmMDW-RSW
5h 33m1 stop
Delta Logo
6:10 am - 1:03 pmRSW-MDW
7h 53m1 stop
$220Delta
Find Deal
Wed, Sep 10 - Sun, Sep 14

American Airlines flights from Chicago to Fort Myers

Our best American Airlines deals on Chicago to Fort Myers flight tickets
American Airlines
Sep 20
ORD2:44 pmChicago O'Hare Intl
3h 06m
RSW6:50 pmFort Myers SW Florida Intl
Sep 24
RSW1:36 pmFort Myers SW Florida Intl
3h 16m
ORD3:52 pmChicago O'Hare Intl
$157
Find similar
American Airlines
Sep 29
ORD7:05 amChicago O'Hare Intl
2h 51m
RSW10:56 amFort Myers SW Florida Intl
Oct 4
RSW1:36 pmFort Myers SW Florida Intl
3h 16m
ORD3:52 pmChicago O'Hare Intl
$158
Find similar
American Airlines
Sep 28
ORD7:05 amChicago O'Hare Intl
2h 51m
RSW10:56 amFort Myers SW Florida Intl
Oct 3
RSW8:00 amFort Myers SW Florida Intl
3h 09m
ORD10:09 amChicago O'Hare Intl
$159
Find similar

Spirit Airlines flights from Chicago to Fort Myers

Our best Spirit Airlines deals on Chicago to Fort Myers flight tickets
Spirit Airlines
Oct 16
ORD5:01 pmChicago O'Hare Intl
2h 49m
RSW8:50 pmFort Myers SW Florida Intl
Oct 20
RSW6:40 amFort Myers SW Florida Intl
2h 54m
ORD8:34 amChicago O'Hare Intl
$88
Find similar
Spirit Airlines
Sep 8
ORD5:23 pmChicago O'Hare Intl
2h 53m
RSW9:16 pmFort Myers SW Florida Intl
Sep 15
RSW7:00 amFort Myers SW Florida Intl
3h 13m
ORD9:13 amChicago O'Hare Intl
$92
Find similar
Spirit Airlines
Sep 8
ORD5:23 pmChicago O'Hare Intl
2h 53m
RSW9:16 pmFort Myers SW Florida Intl
Sep 12
RSW7:00 amFort Myers SW Florida Intl
3h 13m
ORD9:13 amChicago O'Hare Intl
$93
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Fort Myers that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 21, 2025.
Use the filters below to find and compare flights from Chicago to Fort Myers that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 10/16

5:01 pm-8:50 pm

Nonstop2h 49m

Fort Myers SW Florida Intl

Mon 10/20

6:40 am-8:34 am

Nonstop2h 54m

$88

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 9/8

5:23 pm-9:16 pm

Nonstop2h 53m

Fort Myers SW Florida Intl

Mon 9/15

7:00 am-9:13 am

Nonstop3h 13m

$92

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 9/18

6:20 am-6:29 pm

1 stop11h 09m

Fort Myers SW Florida Intl

Sun 9/21

7:24 pm-11:20 pm

1 stop4h 56m

$143

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 9/25

6:20 am-6:29 pm

1 stop11h 09m

Fort Myers SW Florida Intl

Thu 10/2

7:24 pm-11:20 pm

1 stop4h 56m

$144

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 9/20

2:44 pm-6:50 pm

Nonstop3h 06m

Fort Myers SW Florida Intl

Wed 9/24

1:36 pm-3:52 pm

Nonstop3h 16m

$157

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 9/23

9:05 am-12:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Sat 9/27

4:25 pm-6:15 pm

Nonstop2h 50m

$157

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Mon 9/29

7:05 am-10:56 am

Nonstop2h 51m

Fort Myers SW Florida Intl

Sat 10/4

1:36 pm-3:52 pm

Nonstop3h 16m

$158

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 9/23

9:05 am-12:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Fri 9/26

1:20 pm-3:15 pm

Nonstop2h 55m

$158

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Tue 10/21

5:04 pm-12:39 am

1 stop6h 35m

Fort Myers SW Florida Intl

Fri 10/24

4:11 pm-10:14 pm

1 stop7h 03m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Wed 9/10

6:00 am-12:33 pm

1 stop5h 33m

Fort Myers SW Florida Intl

Sun 9/14

6:10 am-1:03 pm

1 stop7h 53m

$220

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Chicago and Fort Myers?

What is the cheapest month to fly to Fort Myers?

In general, August 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 $209. If you are unable to visit Fort Myers during the month of August, then departing from Chicago during the month July is also very affordable. Most momondo users find prices during this month for around $217.

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 Wednesday when prices can be found for as low as $261. Flights from Chicago to Fort Myers on a Friday will generally be more expensive and average around $307. 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 afternoon when flights can be purchased for as low as $275. Flights at noon are often more expensive with an average ticket price of $321.

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 weeks ahead of your departure date. In general, you can expect to find flights to Fort Myers for around $267 when searching 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 $230 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 August 2025, prices for Chicago to Fort Myers flights are approximately 1% more expensive 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

$92

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 $92. The best round-trip flight deal from Chicago to Fort Myers found on momondo in the last 72 hours is $126.
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)
Search flight deals

  • 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
5.8
3,207 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $82Free CancellationRating
6.3
8,035 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $160Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $177Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,245 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
7,981 reviews
Search Delta flights

  • Southwest Flights From Chicago to Fort Myers

    Southwest operates around 13 flights from Chicago to Fort Myers every week. The average price of these flights found in the last 72 hours has been $466, but momondo users have found Southwest deals from Chicago to Fort Myers from as low as $177 round-trip. Southwest has been scored 8.0/10 in 4,245 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 $177, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $366 round-trip. United Airlines operates 19 flights out of Chicago into Fort Myers in an average week, so prices vary by time and availability. 8,930 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
Captiva
Estero
North Fort Myers
Boca Grande
Lehigh Acres

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.

An easier way to manage your Fort Myers trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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