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Cheap flights from Fort Myers to Chicago Midway Airport from $53

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 Midway Airport departing on 2/15. 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.
8:50 pm - 10:45 pmRSW-MDW
2h 55mnonstop
7:00 pm - 10:50 pmMDW-RSW
2h 50mnonstop
$190Southwest
Find Deal
Fri, Jan 17 - Mon, Jan 20
6:20 am - 8:20 amRSW-MDW
3h 00mnonstop
7:00 pm - 10:50 pmMDW-RSW
2h 50mnonstop
$198Southwest
Find Deal
Sat, Feb 8 - Mon, Feb 10
11:15 am - 1:20 pmRSW-MDW
3h 05mnonstop
6:05 am - 10:05 amMDW-RSW
3h 00mnonstop
$204Southwest
Find Deal
Fri, Feb 7 - Mon, Feb 10
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
6:25 pm - 10:15 pmMDW-RSW
2h 50mnonstop
$214Southwest
Find Deal
Wed, Jan 15 - Sun, Jan 19
5:40 am - 10:12 amRSW-MDW
5h 32m1 stop
2:08 pm - 9:13 pmMDW-RSW
6h 05m1 stop
$216Delta
Find Deal
Thu, Feb 6 - Mon, Feb 10
8:00 am - 1:08 pmRSW-MDW
6h 08m1 stop
1:26 pm - 11:32 pmMDW-RSW
9h 06m1 stop
$236Delta
Find Deal
Tue, Jan 7 - Mon, Jan 20
5:40 pm - 7:40 pmRSW-MDW
3h 00mnonstop
6:05 am - 10:05 amMDW-RSW
3h 00mnonstop
$249Southwest
Find Deal
Thu, Jan 9 - Sun, Jan 12
8:55 am - 1:35 pmRSW-MDW
5h 40m1 stop
7:00 pm - 10:50 pmMDW-RSW
2h 50mnonstop
$253Southwest
Find Deal
Tue, Jan 7 - Mon, Jan 20
6:40 am - 12:46 pmRSW-MDW
7h 06m1 stop
6:00 am - 12:15 pmMDW-RSW
5h 15m1 stop
$256Delta
Find Deal
Wed, Jan 8 - Sat, Jan 11
6:20 am - 8:20 amRSW-MDW
3h 00mnonstop
8:35 am - 6:10 pmMDW-RSW
8h 35m1 stop
$257Southwest
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Sat, Feb 8 - Mon, Feb 10
5:17 pm - 12:17 amRSW-MDW
8h 00m1 stop
$53Frontier
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Sat, Feb 15
5:17 pm - 12:17 amRSW-MDW
8h 00m1 stop
$54Frontier
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Sat, Feb 15
6:20 am - 8:20 amRSW-MDW
3h 00mnonstop
$79Southwest
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Sat, Feb 8
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
$85Southwest
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Thu, Jan 23
5:40 am - 11:59 amRSW-MDW
7h 19m1 stop
$108Delta
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Tue, Jan 21
6:56 pm - 8:49 amRSW-MDW
14h 53m1 stop
$112Avelo Airlines
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Mon, Jan 6
8:00 am - 1:08 pmRSW-MDW
6h 08m1 stop
$128Delta
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Mon, Jan 27
10:17 am - 7:50 amRSW-MDW
22h 33m2 stops
Thu, Mar 13
6:56 pm - 8:49 amRSW-MDW
14h 53m1 stop
$215Avelo Airlines
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Mon, Dec 30
10:17 am - 7:45 amRSW-MDW
22h 28m2 stops
Sun, Apr 6
7:05 am - 9:00 amRSW-MDW
2h 55mnonstop
6:50 pm - 10:35 pmMDW-RSW
2h 45mnonstop
$699Southwest
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Fri, Dec 27 - Wed, Jan 1
10:45 am - 2:05 pmRSW-MDW
4h 20m1 stop
6:50 pm - 10:35 pmMDW-RSW
2h 45mnonstop
$704Southwest
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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
12:45 pm - 2:40 pmRSW-MDW
2h 55mnonstop
8:00 pm - 11:50 pmMDW-RSW
2h 50mnonstop
$838Southwest
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Fri, Dec 27 - Mon, Dec 30
10:45 am - 2:05 pmRSW-MDW
4h 20m1 stop
8:00 pm - 11:50 pmMDW-RSW
2h 50mnonstop
$843Southwest
Find Deal
Fri, Dec 27 - Mon, Dec 30
9:40 pm - 11:35 pmRSW-MDW
2h 55mnonstop
2:25 pm - 10:40 pmMDW-RSW
7h 15m1 stop
$847Southwest
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Fri, Dec 27 - Sun, Dec 29
10:45 am - 2:05 pmRSW-MDW
4h 20m1 stop
4:30 pm - 10:40 pmMDW-RSW
5h 10m1 stop
$852Southwest
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Fri, Dec 27 - Sun, Dec 29
11:27 am - 4:24 pmRSW-MDW
5h 57m1 stop
6:25 pm - 12:22 amMDW-RSW
4h 57m1 stop
$856Delta
Find Deal
Fri, Dec 27 - Sun, Dec 29
5:45 am - 9:23 amRSW-MDW
4h 38m1 stop
6:25 pm - 12:22 amMDW-RSW
4h 57m1 stop
$896Delta
Find Deal
Wed, Dec 25 - Thu, Dec 26
7:15 am - 9:10 amRSW-MDW
2h 55mnonstop
5:10 pm - 12:30 amMDW-RSW
6h 20m1 stop
$1,012Southwest
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Wed, Dec 25 - Fri, Dec 27
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
1:50 pm - 5:40 pmMDW-RSW
2h 50mnonstop
$170Southwest
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Thu, Jan 23 - Sun, Jan 26
8:50 pm - 10:45 pmRSW-MDW
2h 55mnonstop
7:00 pm - 10:50 pmMDW-RSW
2h 50mnonstop
$190Southwest
Find Deal
Fri, Jan 17 - Mon, Jan 20
6:20 am - 8:20 amRSW-MDW
3h 00mnonstop
7:00 pm - 10:50 pmMDW-RSW
2h 50mnonstop
$198Southwest
Find Deal
Sat, Feb 8 - Mon, Feb 10
11:15 am - 1:20 pmRSW-MDW
3h 05mnonstop
6:05 am - 10:05 amMDW-RSW
3h 00mnonstop
$204Southwest
Find Deal
Fri, Feb 7 - Mon, Feb 10
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
6:25 pm - 10:15 pmMDW-RSW
2h 50mnonstop
$214Southwest
Find Deal
Wed, Jan 15 - Sun, Jan 19
5:40 pm - 7:40 pmRSW-MDW
3h 00mnonstop
6:05 am - 10:05 amMDW-RSW
3h 00mnonstop
$249Southwest
Find Deal
Thu, Jan 9 - Sun, Jan 12
5:40 pm - 7:40 pmRSW-MDW
3h 00mnonstop
7:00 pm - 10:50 pmMDW-RSW
2h 50mnonstop
$313Southwest
Find Deal
Mon, Feb 3 - Mon, Feb 10
6:50 am - 8:50 amRSW-MDW
3h 00mnonstop
6:25 pm - 10:15 pmMDW-RSW
2h 50mnonstop
$332Southwest
Find Deal
Mon, Jan 20 - Mon, Jan 27
7:00 am - 9:00 amRSW-MDW
3h 00mnonstop
5:00 am - 8:50 amMDW-RSW
2h 50mnonstop
$373Southwest
Find Deal
Wed, Mar 5 - Mon, Mar 10
6:15 am - 8:15 amRSW-MDW
3h 00mnonstop
9:05 pm - 12:50 amMDW-RSW
2h 45mnonstop
$493Southwest
Find Deal
Fri, Mar 21 - Mon, Mar 24

Delta flights from Fort Myers to Chicago Midway Airport

Our best Delta deals on Fort Myers to Chicago Midway Airport flight tickets
Delta
Feb 6
RSW5:40 amFort Myers SW Florida Intl
5h 32m
1 stop
MDW10:12 amChicago Midway
Feb 10
MDW2:08 pmChicago Midway
6h 05m
1 stop
RSW9:13 pmFort Myers SW Florida Intl
Delta
Jan 7
RSW8:00 amFort Myers SW Florida Intl
6h 08m
1 stop
MDW1:08 pmChicago Midway
Jan 20
MDW1:26 pmChicago Midway
9h 06m
1 stop
RSW11:32 pmFort Myers SW Florida Intl
Delta
Jan 8
RSW6:40 amFort Myers SW Florida Intl
7h 06m
1 stop
MDW12:46 pmChicago Midway
Jan 11
MDW6:00 amChicago Midway
5h 15m
1 stop
RSW12:15 pmFort Myers SW Florida Intl

Southwest flights from Fort Myers to Chicago Midway Airport

Our best Southwest deals on Fort Myers to Chicago Midway Airport flight tickets
Southwest
Jan 17
RSW8:50 pmFort Myers SW Florida Intl
2h 55m
MDW10:45 pmChicago Midway
Jan 20
MDW7:00 pmChicago Midway
2h 50m
RSW10:50 pmFort Myers SW Florida Intl
Southwest
Feb 8
RSW6:20 amFort Myers SW Florida Intl
3h 00m
MDW8:20 amChicago Midway
Feb 10
MDW7:00 pmChicago Midway
2h 50m
RSW10:50 pmFort Myers SW Florida Intl
Southwest
Feb 7
RSW11:15 amFort Myers SW Florida Intl
3h 05m
MDW1:20 pmChicago Midway
Feb 10
MDW6:05 amChicago Midway
3h 00m
RSW10:05 amFort Myers SW Florida Intl

See travel insights to Chicago from

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

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 Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Fort Myers, with most prices found around $238. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Fort Myers during the month February is also very affordable. Most momondo users find prices during this month for around $279.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Fort Myers. The lowest ticket price found for a Wednesday departure recently was $278. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Fort Myers because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $457.

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

Flying to Chicago Midway Airport from Fort Myers in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $371 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $448. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Fly from Fort Myers SW Florida Intl to Chicago Midway for the best Fort Myers SW Florida Intl - Chicago Midway flight prices

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

There are 1 cabin classes available to choose from on Fort Myers SW Florida Intl to Chicago Midway 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 Midway Airport flights?

You could potentially save up to 32% on your flight if you consider stops on a Fort Myers to Chicago Midway Airport flight.

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


When to book flights from Fort Myers to Chicago Midway Airport

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

Cheap Fort Myers to Chicago Midway Airport (RSW to MDW) flight deals and tips

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

Best Price Found

$53

Fastest flight time

2h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Fort Myers in the past 72 hours is $53. The best round-trip flight deal from Fort Myers to Chicago Midway Airport found on momondo in the last 72 hours is $190.
The fastest flight from Fort Myers to Chicago Midway Airport takes 2h 55m
Direct flights go from Fort Myers to Chicago Midway Airport every day.

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

    A flight from Fort Myers SW Florida Intl to Chicago Midway will travel around 1097.4 mi. Typically, this will take 2h 55m by plane in normal conditions.

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

    Prices for flights from Fort Myers SW Florida Intl Airport to Chicago Midway Airport were last updated today.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Fort Myers SW Florida Intl Airport to Chicago Midway Airport.

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

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

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


Best airlines flying from Fort Myers to Chicago Midway Airport

Compare and see reviews for airlines that fly from Fort Myers to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
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 Midway Airport

    Southwest flight deals from Fort Myers to Chicago Midway Airport 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.


Why use momondo?

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

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 Chicago from Fort Myers.

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?

momondo provides multiple filters to help you find the best flight to Chicago from Fort Myers. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Of course. momondo tracks the price of Fort Myers to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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