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Cheap flights from Chicago to Fort Myers from $74

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 10/20. 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

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Spirit Airlines Logo
7:00 am - 10:51 amORD-RSW
2h 51mnonstop
Spirit Airlines Logo
11:56 am - 2:06 pmRSW-ORD
3h 10mnonstop
$130Spirit Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Spirit Airlines Logo
5:28 pm - 9:17 pmORD-RSW
2h 49mnonstop
Spirit Airlines Logo
10:59 am - 1:03 pmRSW-ORD
3h 04mnonstop
$131Spirit Airlines
Find Deal
Sun, Oct 26 - Sun, Nov 2
Frontier Logo
5:11 am - 12:12 pmORD-RSW
6h 01m1 stop
Frontier Logo
9:28 pm - 7:26 amRSW-ORD
10h 58m1 stop
$150Frontier
Find Deal
Thu, Oct 30 - Sun, Nov 2
Frontier Logo
5:20 am - 11:19 amMDW-RSW
4h 59m1 stop
Frontier Logo
1:13 pm - 6:39 pmRSW-MDW
6h 26m1 stop
$150Frontier
Find Deal
Sun, Nov 2 - Thu, Nov 6
American Airlines Logo
8:05 am - 12:05 pmORD-RSW
3h 00mnonstop
American Airlines Logo
6:10 am - 8:29 amRSW-ORD
3h 19mnonstop
$157American Airlines
Find Deal
Wed, Dec 10 - Tue, Dec 16
Southwest Logo
6:05 pm - 9:50 pmMDW-RSW
2h 45mnonstop
Southwest Logo
7:25 am - 9:20 amRSW-MDW
2h 55mnonstop
$157Southwest
Find Deal
Sat, Jan 17 - Tue, Jan 20
United Airlines Logo
7:25 am - 11:26 amORD-RSW
3h 01mnonstop
United Airlines Logo
4:38 pm - 6:50 pmRSW-ORD
3h 12mnonstop
$158United Airlines
Find Deal
Wed, Nov 19 - Mon, Nov 24
Southwest Logo
4:50 pm - 8:30 pmMDW-RSW
2h 40mnonstop
Southwest Logo
6:30 am - 8:25 amRSW-MDW
2h 55mnonstop
$158Southwest
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
$159United Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
American Airlines Logo
8:05 am - 12:00 pmORD-RSW
2h 55mnonstop
American Airlines Logo
1:50 pm - 4:13 pmRSW-ORD
3h 23mnonstop
$168American Airlines
Find Deal
Wed, Nov 5 - Wed, Nov 12

Frontier flights from Chicago to Fort Myers

Our best Frontier deals on Chicago to Fort Myers flight tickets
Frontier
Oct 30
ORD5:11 amChicago O'Hare Intl
6h 01m
1 stop
RSW12:12 pmFort Myers SW Florida Intl
Nov 2
RSW9:28 pmFort Myers SW Florida Intl
10h 58m
1 stop
ORD7:26 amChicago O'Hare Intl
$150
Find similar
Frontier
Nov 2
MDW5:20 amChicago Midway
4h 59m
1 stop
RSW11:19 amFort Myers SW Florida Intl
Nov 6
RSW1:13 pmFort Myers SW Florida Intl
9h 50m
1 stop
MDW10:03 pmChicago Midway
$161
Find similar
Frontier
Oct 26
MDW6:20 amChicago Midway
4h 56m
1 stop
RSW12:16 pmFort Myers SW Florida Intl
Oct 30
RSW1:13 pmFort Myers SW Florida Intl
6h 26m
1 stop
MDW6:39 pmChicago Midway
$176
Find similar

American Airlines flights from Chicago to Fort Myers

Our best American Airlines deals on Chicago to Fort Myers flight tickets
American Airlines
Dec 10
ORD8:05 amChicago O'Hare Intl
3h 00m
RSW12:05 pmFort Myers SW Florida Intl
Dec 16
RSW6:10 amFort Myers SW Florida Intl
3h 19m
ORD8:29 amChicago O'Hare Intl
$157
Find similar
American Airlines
Nov 5
ORD8:05 amChicago O'Hare Intl
2h 55m
RSW12:00 pmFort Myers SW Florida Intl
Nov 12
RSW1:50 pmFort Myers SW Florida Intl
3h 23m
ORD4:13 pmChicago O'Hare Intl
$168
Find similar
American Airlines
Nov 5
ORD8:05 amChicago O'Hare Intl
2h 55m
RSW12:00 pmFort Myers SW Florida Intl
Nov 11
RSW6:00 amFort Myers SW Florida Intl
3h 19m
ORD8:19 amChicago O'Hare Intl
$175
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 7, 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

Fri 12/5

7:00 am-10:51 am

Nonstop2h 51m

Fort Myers SW Florida Intl

Mon 12/8

11:56 am-2:06 pm

Nonstop3h 10m

$130

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sun 10/26

5:28 pm-9:17 pm

Nonstop2h 49m

Fort Myers SW Florida Intl

Sun 11/2

10:59 am-1:03 pm

Nonstop3h 04m

$131

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

Sun 11/2

9:28 pm-7:26 am

1 stop10h 58m

$150

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sun 11/2

5:20 am-11:19 am

1 stop4h 59m

Fort Myers SW Florida Intl

Thu 11/6

1:13 pm-6:39 pm

1 stop6h 26m

$150

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 12/10

8:05 am-12:05 pm

Nonstop3h 00m

Fort Myers SW Florida Intl

Tue 12/16

6:10 am-8:29 am

Nonstop3h 19m

$157

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 1/17

6:05 pm-9:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

Tue 1/20

7:25 am-9:20 am

Nonstop2h 55m

$157

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 11/19

7:25 am-11:26 am

Nonstop3h 01m

Fort Myers SW Florida Intl

Mon 11/24

4:38 pm-6:50 pm

Nonstop3h 12m

$158

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Fri 10/31

4:50 pm-8:30 pm

Nonstop2h 40m

Fort Myers SW Florida Intl

Tue 11/4

6:30 am-8:25 am

Nonstop2h 55m

$158

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

$159

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 11/5

8:05 am-12:00 pm

Nonstop2h 55m

Fort Myers SW Florida Intl

Wed 11/12

1:50 pm-4:13 pm

Nonstop3h 23m

$168

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 $266. Flights at noon are often more expensive with an average ticket price of $301.

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 $260 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 $216 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 7% 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 $200.
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
3,146 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $85Free CancellationRating
6.3
8,077 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
United AirlinesPriceFrom $169Free CancellationRating
7.4
8,957 reviews
Search United Airlines flights
SouthwestPriceFrom $171Free CancellationRating
8.0
4,232 reviews
Search Southwest flights
DeltaPriceFrom $178Free CancellationRating
7.9
7,967 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 $430, but momondo users have found Southwest deals from Chicago to Fort Myers from as low as $171 round-trip. Southwest has been scored 8.0/10 in 4,232 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 $169, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $343 round-trip. United Airlines operates 27 flights out of Chicago into Fort Myers in an average week, so prices vary by time and availability. 8,957 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

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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