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Cheap flights from Fort Myers to Chicago from $47

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 4/8. 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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Find the cheapest flights from Fort Myers to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Fort Myers to Chicago.
Frontier Logo
6:00 am - 8:21 amRSW-ORD
3h 21mnonstop
Frontier Logo
8:50 pm - 12:59 amORD-RSW
3h 09mnonstop
$98Frontier
Find Deal
Thu, Apr 17 - Sun, Apr 20
 Logo
6:00 am - 8:21 amRSW-ORD
3h 21mnonstop
 Logo
11:54 am - 3:45 pmORD-RSW
2h 51mnonstop
Thu, Apr 17 - Mon, May 5
Spirit Airlines Logo
3:15 pm - 5:25 pmRSW-ORD
3h 10mnonstop
Spirit Airlines Logo
11:54 am - 3:45 pmORD-RSW
2h 51mnonstop
$117Spirit Airlines
Find Deal
Thu, Apr 24 - Tue, Apr 29
Spirit Airlines Logo
8:52 am - 10:59 amRSW-ORD
3h 07mnonstop
Spirit Airlines Logo
10:24 am - 2:16 pmORD-RSW
2h 52mnonstop
$118Spirit Airlines
Find Deal
Fri, Apr 25 - Sun, Apr 27
American Airlines Logo
6:05 am - 8:22 amRSW-ORD
3h 17mnonstop
American Airlines Logo
12:49 pm - 4:41 pmORD-RSW
2h 52mnonstop
$177American Airlines
Find Deal
Wed, Apr 30 - Wed, Apr 30
American Airlines Logo
6:05 am - 8:22 amRSW-ORD
3h 17mnonstop
American Airlines Logo
12:51 pm - 4:45 pmORD-RSW
2h 54mnonstop
$179American Airlines
Find Deal
Wed, Apr 30 - Wed, May 7
United Airlines Logo
7:30 am - 9:50 amRSW-ORD
3h 20mnonstop
United Airlines Logo
4:07 pm - 8:11 pmORD-RSW
3h 04mnonstop
$184United Airlines
Find Deal
Tue, May 6 - Tue, May 6
United Airlines Logo
4:30 pm - 6:49 pmRSW-ORD
3h 19mnonstop
United Airlines Logo
4:07 pm - 8:11 pmORD-RSW
3h 04mnonstop
$198United Airlines
Find Deal
Fri, May 16 - Tue, May 20
Southwest Logo
5:10 am - 7:10 amRSW-MDW
3h 00mnonstop
Southwest Logo
6:25 am - 1:55 pmMDW-RSW
6h 30m1 stop
$208Southwest
Find Deal
Fri, May 16 - Tue, May 20
Southwest Logo
7:15 am - 9:10 amRSW-MDW
2h 55mnonstop
Southwest Logo
10:10 am - 3:40 pmMDW-RSW
4h 30m1 stop
$228Southwest
Find Deal
Wed, May 14 - Tue, May 20

Frontier flights from Fort Myers to Chicago

Our best Frontier deals on Fort Myers to Chicago flight tickets
Frontier
Apr 10
RSW6:00 amFort Myers SW Florida Intl
3h 21m
ORD8:21 amChicago O'Hare Intl
Apr 13
ORD8:50 pmChicago O'Hare Intl
3h 09m
RSW12:59 amFort Myers SW Florida Intl
Frontier
Apr 8
RSW6:15 amFort Myers SW Florida Intl
3h 21m
ORD8:36 amChicago O'Hare Intl
Apr 15
ORD7:59 pmChicago O'Hare Intl
3h 00m
RSW11:59 pmFort Myers SW Florida Intl
Frontier
Apr 17
RSW6:00 amFort Myers SW Florida Intl
3h 21m
ORD8:21 amChicago O'Hare Intl
Apr 20
ORD8:50 pmChicago O'Hare Intl
3h 09m
RSW12:59 amFort Myers SW Florida Intl

American Airlines flights from Fort Myers to Chicago

Our best American Airlines deals on Fort Myers to Chicago flight tickets
American Airlines
Apr 30
RSW6:05 amFort Myers SW Florida Intl
3h 17m
ORD8:22 amChicago O'Hare Intl
Apr 30
ORD12:49 pmChicago O'Hare Intl
2h 52m
RSW4:41 pmFort Myers SW Florida Intl
American Airlines
Apr 30
RSW6:05 amFort Myers SW Florida Intl
3h 17m
ORD8:22 amChicago O'Hare Intl
May 7
ORD12:51 pmChicago O'Hare Intl
2h 54m
RSW4:45 pmFort Myers SW Florida Intl
American Airlines
Jul 8
RSW4:26 pmFort Myers SW Florida Intl
3h 15m
ORD6:41 pmChicago O'Hare Intl
Jul 29
ORD11:40 amChicago O'Hare Intl
2h 56m
RSW3:36 pmFort 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 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 $184. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Fort Myers to Chicago during February average around $204.

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 Thursday when prices can be found for as low as $293. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Fort Myers to Chicago for around $399.

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 $189. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $348.

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?

You are more likely to see cheaper flights to Chicago from Fort Myers when booking 9 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $266 when searching 9 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Fort Myers for as low as $193 on momondo.

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.

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

As of April 2025, prices for Fort Myers to Chicago flights are approximately 29% cheaper 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

$47

Fastest flight time

2h 50m

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 $47. The best round-trip flight deal from Fort Myers to Chicago found on momondo in the last 72 hours is $98.
The fastest flight from Fort Myers to Chicago takes 2h 50m
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 50m, 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 $46Free CancellationRating
5.9
3,277 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $66Free CancellationRating
6.3
7,886 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $159Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $167Free CancellationRating
7.4
8,615 reviews
Search United Airlines flights
DeltaPriceFrom $216Free CancellationRating
8.0
7,899 reviews
Search Delta flights
SouthwestPriceFrom $219Free CancellationRating
8.0
4,275 reviews
Search Southwest flights
  • Southwest Flights From Fort Myers to Chicago

    Southwest flight deals from Fort Myers to Chicago start from $219 round-trip. Over the 29 Southwest flights for this route in a normal week, average airfare is usually $424 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 8,615 reviews) operates around 27 flights from Fort Myers to Chicago in any given week. The average United Airlines airfare for this route is around $324, with deals from around $167 rare but found on momondo. Referenced prices are for round-trip Fort Myers to Chicago flight searches in the last 72 hours.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
Saint John

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago