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Cheap flights from Fort Myers to Chicago from $36

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Fort Myers to Chicago departing on 1/23. 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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Find the cheapest flights from Fort Myers to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Fort Myers to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Fort Myers to Chicago.

Cheap last minute flights

Planning a quick getaway from Fort Myers to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Fort Myers to Chicago

Find recent round-trip train or bus tickets from Fort Myers to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
12:32 pm - 2:52 pmRSW-ORD
3h 20mnonstop
5:37 pm - 9:38 pmORD-RSW
3h 01mnonstop
$58Frontier
Find Deal
Thu, Jan 23 - Sun, Jan 26
12:32 pm - 2:52 pmRSW-ORD
3h 20mnonstop
5:37 pm - 9:38 pmORD-RSW
3h 01mnonstop
$65Frontier
Find Deal
Thu, Jan 23 - Sun, Jan 26
10:52 am - 12:57 pmRSW-ORD
3h 05mnonstop
5:35 am - 9:29 amORD-RSW
2h 54mnonstop
$102Spirit Airlines
Find Deal
Wed, Feb 5 - Tue, Feb 11
7:30 am - 9:39 amRSW-ORD
3h 09mnonstop
5:35 am - 9:29 amORD-RSW
2h 54mnonstop
$104Spirit Airlines
Find Deal
Fri, Jan 17 - Sun, Jan 19
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
1:50 pm - 5:40 pmMDW-RSW
2h 50mnonstop
$170Southwest
Find Deal
Thu, Jan 23 - Sun, Jan 26
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
6:25 pm - 10:15 pmMDW-RSW
2h 50mnonstop
$180Southwest
Find Deal
Fri, Jan 24 - Tue, Jan 28
5:29 pm - 7:45 pmRSW-ORD
3h 16mnonstop
7:00 am - 1:04 pmORD-RSW
5h 04m1 stop
$183American Airlines
Find Deal
Wed, Feb 5 - Tue, Feb 11
3:40 pm - 9:53 pmRSW-ORD
7h 13m1 stop
12:42 pm - 4:39 pmORD-RSW
2h 57mnonstop
$187American Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
6:05 pm - 8:22 pmRSW-ORD
3h 17mnonstop
8:50 am - 4:07 pmORD-RSW
6h 17m1 stop
$189United Airlines
Find Deal
Thu, Jan 23 - Sun, Jan 26
6:05 pm - 8:22 pmRSW-ORD
3h 17mnonstop
8:50 am - 4:07 pmORD-RSW
6h 17m1 stop
$234United Airlines
Find Deal
Fri, Jan 10 - Mon, Jan 13
12:32 pm - 2:52 pmRSW-ORD
3h 20mnonstop
$36Frontier
Find Deal
Thu, Jan 23
12:32 pm - 2:52 pmRSW-ORD
3h 20mnonstop
$44Frontier
Find Deal
Thu, Feb 6
10:45 pm - 12:47 amRSW-ORD
3h 02mnonstop
$51Spirit Airlines
Find Deal
Tue, Jan 7
7:30 am - 9:39 amRSW-ORD
3h 09mnonstop
$57Spirit Airlines
Find Deal
Fri, Jan 24
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
$79Southwest
Find Deal
Wed, Feb 5
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
$85Southwest
Find Deal
Thu, Jan 23
12:05 pm - 6:54 pmRSW-ORD
7h 49m1 stop
$95United Airlines
Find Deal
Fri, Jan 31
12:04 pm - 6:54 pmRSW-ORD
7h 50m1 stop
$103United Airlines
Find Deal
Sat, Jan 25
6:00 am - 10:38 amRSW-ORD
5h 38m1 stop
$105American Airlines
Find Deal
Thu, Feb 6
11:50 am - 2:04 pmRSW-ORD
3h 14mnonstop
$149American Airlines
Find Deal
Wed, Jan 1
10:45 pm - 12:47 amRSW-ORD
3h 02mnonstop
6:05 am - 10:04 amORD-RSW
2h 59mnonstop
$175Spirit Airlines
Find Deal
Thu, Dec 26 - Wed, Jan 1
10:45 pm - 12:47 amRSW-ORD
3h 02mnonstop
6:05 am - 10:04 amORD-RSW
2h 59mnonstop
$181Spirit Airlines
Find Deal
Fri, Dec 27 - Fri, Jan 3
9:57 am - 12:12 pmRSW-ORD
3h 15mnonstop
6:45 am - 10:40 amORD-RSW
2h 55mnonstop
$291Frontier
Find Deal
Thu, Dec 26 - Sat, Dec 28
9:57 am - 12:12 pmRSW-ORD
3h 15mnonstop
10:14 pm - 8:20 amORD-RSW
9h 06m1 stop
$470Frontier
Find Deal
Thu, Dec 26 - Sun, Dec 29
4:30 pm - 10:52 pmRSW-ORD
7h 22m1 stop
5:57 pm - 12:21 amORD-RSW
5h 24m1 stop
$646Delta
Find Deal
Fri, Dec 27 - Wed, Jan 1
7:05 am - 9:00 amRSW-MDW
2h 55mnonstop
6:50 pm - 10:35 pmMDW-RSW
2h 45mnonstop
$699Southwest
Find Deal
Fri, Dec 27 - Wed, Jan 1
1:33 pm - 7:48 amRSW-ORD
19h 15m2 stops
11:02 am - 3:08 pmORD-RSW
3h 06mnonstop
$703United Airlines
Find Deal
Tue, Dec 24 - Wed, Dec 25
10:45 am - 2:05 pmRSW-MDW
4h 20m1 stop
6:50 pm - 10:35 pmMDW-RSW
2h 45mnonstop
$704Southwest
Find Deal
Fri, Dec 27 - Wed, Jan 1
11:10 am - 4:17 pmRSW-MDW
6h 07m1 stop
5:51 pm - 12:22 amMDW-RSW
5h 31m1 stop
$727Delta
Find Deal
Fri, Dec 27 - Wed, Jan 1
1:02 pm - 6:42 pmRSW-ORD
6h 40m1 stop
2:32 pm - 12:47 pmORD-RSW
21h 15m2 stops
$806United Airlines
Find Deal
Fri, Dec 27 - Wed, Jan 1
12:32 pm - 2:52 pmRSW-ORD
3h 20mnonstop
5:37 pm - 9:38 pmORD-RSW
3h 01mnonstop
$58Frontier
Find Deal
Thu, Jan 23 - Sun, Jan 26
12:32 pm - 2:52 pmRSW-ORD
3h 20mnonstop
5:37 pm - 9:38 pmORD-RSW
3h 01mnonstop
$65Frontier
Find Deal
Thu, Jan 23 - Sun, Jan 26
10:52 am - 12:57 pmRSW-ORD
3h 05mnonstop
5:35 am - 9:29 amORD-RSW
2h 54mnonstop
$102Spirit Airlines
Find Deal
Wed, Feb 5 - Tue, Feb 11
7:30 am - 9:39 amRSW-ORD
3h 09mnonstop
5:35 am - 9:29 amORD-RSW
2h 54mnonstop
$104Spirit Airlines
Find Deal
Fri, Jan 17 - Sun, Jan 19
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
6:05 am - 10:05 amMDW-RSW
3h 00mnonstop
$170Southwest
Find Deal
Thu, Jan 23 - Sun, Jan 26
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
6:25 pm - 10:15 pmMDW-RSW
2h 50mnonstop
$180Southwest
Find Deal
Fri, Jan 24 - Tue, Jan 28
7:20 am - 9:37 amRSW-ORD
3h 17mnonstop
2:00 pm - 6:05 pmORD-RSW
3h 05mnonstop
$237United Airlines
Find Deal
Sat, Jan 25 - Sat, Jan 25
10:55 am - 1:14 pmRSW-ORD
3h 19mnonstop
6:00 am - 9:59 amORD-RSW
2h 59mnonstop
$277United Airlines
Find Deal
Thu, Feb 13 - Thu, Feb 27
3:34 pm - 5:45 pmRSW-ORD
3h 11mnonstop
7:00 am - 10:49 amORD-RSW
2h 49mnonstop
$457American Airlines
Find Deal
Fri, May 23 - Wed, May 28
12:09 pm - 2:20 pmRSW-ORD
3h 11mnonstop
9:55 am - 1:47 pmORD-RSW
2h 52mnonstop
$467American Airlines
Find Deal
Fri, May 30 - Sun, Jun 1

Spirit Airlines flights from Fort Myers to Chicago

Our best Spirit Airlines deals on Fort Myers to Chicago flight tickets
Spirit Airlines
Feb 5
RSW10:52 amFort Myers SW Florida Intl
3h 05m
ORD12:57 pmChicago O'Hare Intl
Feb 11
ORD5:35 amChicago O'Hare Intl
2h 54m
RSW9:29 amFort Myers SW Florida Intl
Spirit Airlines
Jan 17
RSW7:30 amFort Myers SW Florida Intl
3h 09m
ORD9:39 amChicago O'Hare Intl
Jan 19
ORD5:35 amChicago O'Hare Intl
2h 54m
RSW9:29 amFort Myers SW Florida Intl
Spirit Airlines
Jan 10
RSW7:30 amFort Myers SW Florida Intl
3h 09m
ORD9:39 amChicago O'Hare Intl
Jan 11
ORD5:35 amChicago O'Hare Intl
2h 54m
RSW9:29 amFort Myers SW Florida Intl

Sun Country Air flights from Fort Myers to Chicago

Our best Sun Country Air deals on Fort Myers to Chicago flight tickets
Sun Country Air
Apr 10
RSW9:15 amFort Myers SW Florida Intl
9h 51m
1 stop
ORD6:06 pmChicago O'Hare Intl
Apr 25
ORD7:35 pmChicago O'Hare Intl
23h 43m
1 stop
RSW8:18 pmFort Myers SW Florida Intl
Sun Country Air
Dec 27
RSW12:17 pmFort Myers SW Florida Intl
7h 21m
1 stop
ORD6:38 pmChicago O'Hare Intl
Dec 30
ORD7:30 pmChicago O'Hare Intl
13h 22m
1 stop
RSW9:52 amFort Myers SW Florida Intl
Sun Country Air
Dec 24
RSW6:00 pmFort Myers SW Florida Intl
16h 03m
1 stop
ORD9:03 amChicago O'Hare Intl
Dec 26
ORD7:50 pmChicago O'Hare Intl
12h 55m
1 stop
RSW9:45 amFort Myers SW Florida Intl

See travel insights to Chicago from

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

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 Fort Myers and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Fort Myers, with most prices found around $158. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Fort Myers to Chicago during May average around $218.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $229. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Fort Myers to Chicago for around $353.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Fort Myers to Chicago during this time can be as low as $185. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $278.

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

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

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Fort Myers is 52 days out, which is when prices tend to be around $269. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $142.

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

There are 4 cabin classes available to choose from on Fort Myers SW Florida Intl to Chicago 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 Fort Myers to Chicago flights?

You could potentially save up to 86% on your flight if you consider stops on a Fort Myers to Chicago flight.

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

As of December 2024, prices for Fort Myers to Chicago flights are approximately 12% more expensive when compared to flights at the same time last year.

When to book flights from Fort Myers to Chicago

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

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

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

Best Price Found

$36

Fastest flight time

2h 55m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Fort Myers in the past 72 hours is $36. The best round-trip flight deal from Fort Myers to Chicago found on momondo in the last 72 hours is $58.
The fastest flight from Fort Myers to Chicago takes 2h 55m
Direct flights go from Fort Myers to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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

    Fort Myers SW Florida Intl and Chicago are 1101.2 mi apart from one another. Flights usually cover this in 2h 55m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Fort Myers SW Florida Intl Airport to Chicago refresh daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Fort Myers SW Florida Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago 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 Chicago. 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 Fort Myers to Chicago?

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


Best airlines flying from Fort Myers to Chicago

Compare and see reviews for airlines that fly from Fort Myers to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $35Free CancellationRating
6.1
3,469 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $63Free CancellationRating
6.3
8,113 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $166Free CancellationRating
7.4
9,020 reviews
Search United Airlines flights
SouthwestPriceFrom $210Free CancellationRating
8.1
4,780 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
8.0
8,588 reviews
Search Delta flights
  • Southwest Flights From Fort Myers to Chicago

    Southwest flight deals from Fort Myers to Chicago start from $210 round-trip. Over the 20 Southwest flights for this route in a normal week, average airfare is usually $410 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From Fort Myers to Chicago

    United Airlines (7.4/10 from 9,022 reviews) operates around 46 flights from Fort Myers to Chicago in any given week. The average United Airlines airfare for this route is around $327, with deals from around $166 rare but found on momondo. Referenced prices are for round-trip Fort Myers to Chicago flight searches in the last 72 hours.


Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Fort Myers to Chicago for you.

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

Yes. momondo allows you to filter the results for Fort Myers to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Fort Myers.

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

Yes momondo offers price alerts on flights to Chicago from Fort Myers. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago