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Cheap flights from Chicago to Fort Myers from $79

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 12/16. 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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Cheap round-trip flights

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Spirit Airlines Logo
5:28 pm - 9:17 pmORD-RSW
2h 49mnonstop
Spirit Airlines Logo
10:59 am - 1:03 pmRSW-ORD
3h 04mnonstop
$149Spirit Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Spirit Airlines Logo
7:00 am - 10:51 amORD-RSW
2h 51mnonstop
Spirit Airlines Logo
11:56 am - 2:06 pmRSW-ORD
3h 10mnonstop
$155Spirit Airlines
Find Deal
Sat, Jan 10 - Sat, Jan 17
American Airlines Logo
8:05 am - 12:05 pmORD-RSW
3h 00mnonstop
American Airlines Logo
1:51 pm - 4:20 pmRSW-ORD
3h 29mnonstop
$157American Airlines
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Wed, Dec 3 - Wed, Dec 10
Frontier Logo
5:11 am - 12:12 pmORD-RSW
6h 01m1 stop
Frontier Logo
1:13 pm - 12:11 amRSW-ORD
11h 58m1 stop
$160Frontier
Find Deal
Thu, Oct 30 - Thu, Nov 6
Frontier Logo
6:20 am - 12:12 pmMDW-RSW
4h 52m1 stop
Frontier Logo
1:13 pm - 6:39 pmRSW-MDW
6h 26m1 stop
$160Frontier
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Thu, Oct 30 - Thu, Nov 6
United Airlines Logo
4:15 pm - 8:16 pmORD-RSW
3h 01mnonstop
United Airlines Logo
9:10 am - 11:22 amRSW-ORD
3h 12mnonstop
$168United Airlines
Find Deal
Fri, Oct 31 - Tue, Nov 4
United Airlines Logo
4:15 pm - 8:16 pmORD-RSW
3h 01mnonstop
United Airlines Logo
9:10 am - 11:22 amRSW-ORD
3h 12mnonstop
$169United Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
American Airlines Logo
7:34 pm - 11:35 pmORD-RSW
3h 01mnonstop
American Airlines Logo
4:55 pm - 7:18 pmRSW-ORD
3h 23mnonstop
$179American Airlines
Find Deal
Sat, Nov 8 - Tue, Nov 11
Southwest Logo
5:45 pm - 9:30 pmMDW-RSW
2h 45mnonstop
Southwest Logo
1:05 pm - 7:00 pmRSW-MDW
6h 55m1 stop
$179Southwest
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Fri, Jan 23 - Mon, Jan 26
Southwest Logo
5:35 am - 9:20 amMDW-RSW
2h 45mnonstop
Southwest Logo
9:05 am - 12:45 pmRSW-MDW
4h 40m1 stop
$183Southwest
Find Deal
Fri, Dec 12 - Sun, Jan 18

Southwest flights from Chicago to Fort Myers

Our best Southwest deals on Chicago to Fort Myers flight tickets
Southwest
Jan 23
MDW5:45 pmChicago Midway
2h 45m
RSW9:30 pmFort Myers SW Florida Intl
Jan 26
RSW1:05 pmFort Myers SW Florida Intl
6h 55m
1 stop
MDW7:00 pmChicago Midway
$179
Find similar
Southwest
Dec 12
MDW5:35 amChicago Midway
2h 45m
RSW9:20 amFort Myers SW Florida Intl
Jan 18
RSW9:05 amFort Myers SW Florida Intl
4h 40m
1 stop
MDW12:45 pmChicago Midway
$183
Find similar
Southwest
Jan 23
MDW5:45 pmChicago Midway
2h 45m
RSW9:30 pmFort Myers SW Florida Intl
Jan 26
RSW1:05 pmFort Myers SW Florida Intl
6h 30m
2 stops
MDW6:35 pmChicago Midway
$184
Find similar

Delta flights from Chicago to Fort Myers

Our best Delta deals on Chicago to Fort Myers flight tickets
Delta
Nov 10
MDW1:15 pmChicago Midway
7h 28m
1 stop
RSW9:43 pmFort Myers SW Florida Intl
Nov 15
RSW5:35 amFort Myers SW Florida Intl
5h 18m
1 stop
MDW9:53 amChicago Midway
$217
Find similar
Delta
Oct 29
MDW6:00 amChicago Midway
4h 50m
1 stop
RSW11:50 amFort Myers SW Florida Intl
Oct 31
RSW5:38 amFort Myers SW Florida Intl
5h 07m
1 stop
MDW9:45 amChicago Midway
$233
Find similar
Delta
Nov 3
MDW5:09 pmChicago Midway
6h 30m
1 stop
RSW12:39 amFort Myers SW Florida Intl
Nov 10
RSW7:49 pmFort Myers SW Florida Intl
4h 51m
1 stop
MDW11:40 pmChicago Midway
$246
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 October 16, 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 10/30

5:28 pm-9:17 pm

Nonstop2h 49m

Fort Myers SW Florida Intl

Sun 11/2

10:59 am-1:03 pm

Nonstop3h 04m

$149

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/10

7:00 am-10:51 am

Nonstop2h 51m

Fort Myers SW Florida Intl

Sat 1/17

11:56 am-2:06 pm

Nonstop3h 10m

$155

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 12/3

8:05 am-12:05 pm

Nonstop3h 00m

Fort Myers SW Florida Intl

Wed 12/10

1:51 pm-4:20 pm

Nonstop3h 29m

$157

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Thu 10/30

5:11 am-12:12 pm

1 stop6h 01m

Fort Myers SW Florida Intl

Thu 11/6

1:13 pm-12:11 am

1 stop11h 58m

$160

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Thu 10/30

6:20 am-12:12 pm

1 stop4h 52m

Fort Myers SW Florida Intl

Thu 11/6

1:13 pm-6:39 pm

1 stop6h 26m

$160

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Fri 10/31

4:15 pm-8:16 pm

Nonstop3h 01m

Fort Myers SW Florida Intl

Tue 11/4

9:10 am-11:22 am

Nonstop3h 12m

$168

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 11/8

4:15 pm-8:16 pm

Nonstop3h 01m

Fort Myers SW Florida Intl

Sat 11/15

9:10 am-11:22 am

Nonstop3h 12m

$169

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 11/8

7:34 pm-11:35 pm

Nonstop3h 01m

Fort Myers SW Florida Intl

Tue 11/11

4:55 pm-7:18 pm

Nonstop3h 23m

$179

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Fri 1/23

5:45 pm-9:30 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Mon 1/26

1:05 pm-7:00 pm

1 stop6h 55m

$179

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Fri 12/12

5:35 am-9:20 am

Nonstop2h 45m

Fort Myers SW Florida Intl

Sun 1/18

9:05 am-12:45 pm

1 stop4h 40m

$183

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 $189. If you are unable to visit Fort Myers during the month of August, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $198.

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 $251. Flights from Chicago to Fort Myers on a Friday will generally be more expensive and average around $296. 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 $265. Flights at noon are often more expensive with an average ticket price of $299.

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 $259 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 $217 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.

Can stopping save me money on Chicago to Fort Myers flights?

No. A direct flight is the cheapest option for a flight between Chicago to Fort Myers.

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

As of October 2025, prices for Chicago to Fort Myers flights are approximately 3% 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

$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 $196.
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 45m 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
3,137 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $85Free CancellationRating
6.3
8,098 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $159Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
United AirlinesPriceFrom $168Free CancellationRating
7.4
8,982 reviews
Search United Airlines flights
SouthwestPriceFrom $175Free CancellationRating
8.0
4,241 reviews
Search Southwest flights
DeltaPriceFrom $178Free CancellationRating
7.9
7,984 reviews
Search Delta flights

  • Southwest Flights From Chicago to Fort Myers

    Southwest operates around 17 flights from Chicago to Fort Myers every week. The average price of these flights found in the last 72 hours has been $427, but momondo users have found Southwest deals from Chicago to Fort Myers from as low as $175 round-trip. Southwest has been scored 8.0/10 in 4,241 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 $168, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $339 round-trip. United Airlines operates 20 flights out of Chicago into Fort Myers in an average week, so prices vary by time and availability. 8,982 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
Fort Myers Beach
Sanibel
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

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