Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Fort Myers to Chicago from $30

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 7/29. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from Fort Myers to Chicago

Cheap round-trip flights

Spirit Airlines Logo
7:00 am - 9:13 amRSW-ORD
3h 13mnonstop
Spirit Airlines Logo
5:31 pm - 9:24 pmORD-RSW
2h 53mnonstop
$78Spirit Airlines
Find Deal
Thu, Sep 18 - Sun, Sep 21
Spirit Airlines Logo
8:17 pm - 10:32 pmRSW-ORD
3h 15mnonstop
Spirit Airlines Logo
4:34 pm - 8:29 pmORD-RSW
2h 55mnonstop
$80Spirit Airlines
Find Deal
Wed, Jul 16 - Tue, Jul 29
Spirit Airlines Logo
7:00 am - 9:13 amRSW-ORD
3h 13mnonstop
Spirit Airlines Logo
5:31 pm - 9:24 pmORD-RSW
2h 53mnonstop
$81Spirit Airlines
Find Deal
Thu, Sep 18 - Sun, Sep 21
American Airlines Logo
3:38 pm - 5:55 pmRSW-ORD
3h 17mnonstop
American Airlines Logo
8:40 am - 12:43 pmORD-RSW
3h 03mnonstop
$157American Airlines
Find Deal
Tue, Aug 26 - Tue, Sep 16
Southwest Logo
5:40 pm - 7:30 pmRSW-MDW
2h 50mnonstop
Southwest Logo
7:00 pm - 10:45 pmMDW-RSW
2h 45mnonstop
$157Southwest
Find Deal
Thu, Aug 14 - Mon, Aug 18
Southwest Logo
12:10 pm - 2:05 pmRSW-MDW
2h 55mnonstop
Southwest Logo
8:30 pm - 12:10 amMDW-RSW
2h 40mnonstop
$158Southwest
Find Deal
Thu, Oct 9 - Sun, Oct 12
Frontier Logo
7:24 pm - 11:20 pmRSW-MDW
4h 56m1 stop
Frontier Logo
6:20 am - 6:29 pmMDW-RSW
11h 09m1 stop
$194Frontier
Find Deal
Thu, Sep 4 - Sun, Sep 7
Frontier Logo
7:15 pm - 11:17 pmRSW-MDW
5h 02m1 stop
Frontier Logo
6:20 am - 6:21 pmMDW-RSW
11h 01m1 stop
$215Frontier
Find Deal
Thu, Aug 14 - Sun, Aug 17
Delta Logo
5:35 am - 11:48 amRSW-MDW
7h 13m1 stop
Delta Logo
6:00 am - 2:16 pmMDW-RSW
7h 16m1 stop
$217Delta
Find Deal
Thu, Sep 25 - Mon, Sep 29
Delta Logo
12:24 pm - 6:40 pmRSW-MDW
7h 16m1 stop
Delta Logo
5:05 pm - 12:45 amMDW-RSW
6h 40m1 stop
$233Delta
Find Deal
Wed, Jul 16 - Tue, Jul 29

Spirit Airlines flights from Fort Myers to Chicago

Our best Spirit Airlines deals on Fort Myers to Chicago flight tickets
Spirit Airlines
Sep 18
RSW7:00 amFort Myers SW Florida Intl
3h 13m
ORD9:13 amChicago O'Hare Intl
Sep 21
ORD5:31 pmChicago O'Hare Intl
2h 53m
RSW9:24 pmFort Myers SW Florida Intl
Spirit Airlines
Jul 16
RSW8:17 pmFort Myers SW Florida Intl
3h 15m
ORD10:32 pmChicago O'Hare Intl
Jul 29
ORD4:34 pmChicago O'Hare Intl
2h 55m
RSW8:29 pmFort Myers SW Florida Intl
Spirit Airlines
Sep 18
RSW7:00 amFort Myers SW Florida Intl
3h 13m
ORD9:13 amChicago O'Hare Intl
Sep 21
ORD5:31 pmChicago O'Hare Intl
2h 53m
RSW9:24 pmFort Myers SW Florida Intl

Frontier flights from Fort Myers to Chicago

Our best Frontier deals on Fort Myers to Chicago flight tickets
Frontier
Sep 4
RSW7:24 pmFort Myers SW Florida Intl
4h 56m
1 stop
MDW11:20 pmChicago Midway
Sep 7
MDW6:20 amChicago Midway
11h 09m
1 stop
RSW6:29 pmFort Myers SW Florida Intl
Frontier
Jul 10
RSW7:15 pmFort Myers SW Florida Intl
6h 07m
1 stop
ORD12:22 amChicago O'Hare Intl
Jul 12
ORD5:07 pmChicago O'Hare Intl
24h 14m
1 stop
RSW6:21 pmFort Myers SW Florida Intl
Frontier
Aug 14
RSW7:15 pmFort Myers SW Florida Intl
5h 02m
1 stop
MDW11:17 pmChicago Midway
Aug 17
MDW6:20 amChicago Midway
11h 01m
1 stop
RSW6:21 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 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 $184. If you’re not able to fly to Chicago in January, then August is your next best option. Flight prices from Fort Myers to Chicago during August average around $197.

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 $292. 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 $421.

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 $223. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $338.

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 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $250 when searching 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 $197 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.

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

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

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

As of June 2025, prices for Fort Myers to Chicago flights are approximately 0% 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

$30

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 $30. The best round-trip flight deal from Fort Myers to Chicago found on momondo in the last 72 hours is $78.
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
3,293 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $68Free CancellationRating
6.3
8,096 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $159Free CancellationRating
7.4
8,852 reviews
Search United Airlines flights
American AirlinesPriceFrom $159Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $210Free CancellationRating
8.0
4,278 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
8.0
7,969 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 14 Southwest flights for this route in a normal week, average airfare is usually $393 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 8,852 reviews) operates around 11 flights from Fort Myers to Chicago in any given week. The average United Airlines airfare for this route is around $332, with deals from around $159 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
Saint Joseph
Lansing
Schererville
Valparaiso
Crown Point
Munster
Monticello
Chesterton
Porter
Griffith
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.


An easier way to manage your Chicago 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 7/5
Sat 7/12

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