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Cheap flights from Fort Myers to Chicago from $79

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 1/17. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
1:15 pm - 3:23 pmRSW-ORD
3h 08mnonstop
Spirit Airlines Logo
8:15 am - 12:20 pmORD-RSW
3h 05mnonstop
$130Spirit Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Spirit Airlines Logo
7:00 am - 9:12 amRSW-ORD
3h 12mnonstop
Spirit Airlines Logo
7:20 pm - 11:23 pmORD-RSW
3h 03mnonstop
$131Spirit Airlines
Find Deal
Wed, Mar 25 - Mon, Apr 6
Multiple Airlines Logo
6:00 am - 10:53 amRSW-ORD
5h 53m1 stop
Multiple Airlines Logo
7:45 pm - 11:48 pmORD-RSW
3h 03mnonstop
$132Multiple Airlines
Find Deal
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
7:20 pm - 9:39 pmRSW-ORD
3h 19mnonstop
Multiple Airlines Logo
6:00 pm - 11:16 amORD-RSW
16h 16m2 stops
$133Multiple Airlines
Find Deal
Thu, Feb 19 - Mon, Feb 23
Spirit Airlines Logo
1:15 pm - 3:23 pmRSW-ORD
3h 08mnonstop
Spirit Airlines Logo
8:15 am - 12:20 pmORD-RSW
3h 05mnonstop
$134Spirit Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
Spirit Airlines Logo
1:15 pm - 3:23 pmRSW-ORD
3h 08mnonstop
Spirit Airlines Logo
8:15 am - 12:20 pmORD-RSW
3h 05mnonstop
$135Spirit Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
Southwest Logo
6:15 am - 8:15 amRSW-MDW
3h 00mnonstop
Southwest Logo
6:15 pm - 10:05 pmMDW-RSW
2h 50mnonstop
$169Southwest
Find Deal
Sat, Jan 10 - Sun, Jan 11
Frontier Logo
5:45 pm - 10:12 pmRSW-MDW
5h 27m1 stop
Frontier Logo
6:15 am - 4:50 pmMDW-RSW
9h 35m1 stop
$171Frontier
Find Deal
Mon, Dec 8 - Mon, Dec 15
Southwest Logo
6:30 am - 8:25 amRSW-MDW
2h 55mnonstop
Southwest Logo
8:20 am - 12:10 pmMDW-RSW
2h 50mnonstop
$179Southwest
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Thu, Dec 11 - Mon, Dec 15
Frontier Logo
4:09 pm - 10:43 pmRSW-MDW
7h 34m1 stop
Frontier Logo
6:12 am - 6:43 pmMDW-RSW
11h 31m1 stop
$210Frontier
Find Deal
Mon, Dec 1 - Sat, Jan 3

Spirit Airlines flights from Fort Myers to Chicago

Our best Spirit Airlines deals on Fort Myers to Chicago flight tickets
Spirit Airlines
Dec 5
RSW1:15 pmFort Myers SW Florida Intl
3h 08m
ORD3:23 pmChicago O'Hare Intl
Dec 8
ORD8:15 amChicago O'Hare Intl
3h 05m
RSW12:20 pmFort Myers SW Florida Intl
$130
Find similar
Spirit Airlines
Mar 25
RSW7:00 amFort Myers SW Florida Intl
3h 12m
ORD9:12 amChicago O'Hare Intl
Apr 6
ORD7:20 pmChicago O'Hare Intl
3h 03m
RSW11:23 pmFort Myers SW Florida Intl
$131
Find similar
Spirit Airlines
Dec 11
RSW1:15 pmFort Myers SW Florida Intl
3h 08m
ORD3:23 pmChicago O'Hare Intl
Dec 15
ORD8:15 amChicago O'Hare Intl
3h 05m
RSW12:20 pmFort Myers SW Florida Intl
$134
Find similar

American Airlines flights from Fort Myers to Chicago

Our best American Airlines deals on Fort Myers to Chicago flight tickets
American Airlines
Jan 8
RSW6:28 amFort Myers SW Florida Intl
3h 16m
ORD8:44 amChicago O'Hare Intl
Jan 11
ORD5:59 pmChicago O'Hare Intl
3h 04m
RSW10:03 pmFort Myers SW Florida Intl
$169
Find similar
American Airlines
Dec 4
RSW5:00 pmFort Myers SW Florida Intl
3h 24m
ORD7:24 pmChicago O'Hare Intl
Dec 12
ORD1:28 pmChicago O'Hare Intl
3h 02m
RSW5:30 pmFort Myers SW Florida Intl
$236
Find similar
American Airlines
Dec 4
RSW10:01 amFort Myers SW Florida Intl
7h 50m
1 stop
ORD4:51 pmChicago O'Hare Intl
Dec 12
ORD6:45 amChicago O'Hare Intl
2h 54m
RSW10:39 amFort Myers SW Florida Intl
$270
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Fort Myers to Chicago 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 November 20, 2025.
Use the filters below to find and compare flights from Fort Myers to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 12/5

1:15 pm-3:23 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 12/8

8:15 am-12:20 pm

Nonstop3h 05m

$130

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 3/25

7:00 am-9:12 am

Nonstop3h 12m

Chicago O'Hare Intl

Mon 4/6

7:20 pm-11:23 pm

Nonstop3h 03m

$131

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 1/9

6:00 am-10:53 am

1 stop5h 53m

Chicago O'Hare Intl

Mon 1/12

7:45 pm-11:48 pm

Nonstop3h 03m

$132

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 2/19

7:20 pm-9:39 pm

Nonstop3h 19m

Chicago O'Hare Intl

Mon 2/23

6:00 pm-11:16 am

2 stops16h 16m

$133

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 12/11

1:15 pm-3:23 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 12/15

8:15 am-12:20 pm

Nonstop3h 05m

$134

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 12/11

1:15 pm-3:23 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 12/14

8:15 am-12:20 pm

Nonstop3h 05m

$135

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 1/10

6:15 am-8:15 am

Nonstop3h 00m

Chicago Midway

Sun 1/11

6:15 pm-10:05 pm

Nonstop2h 50m

$169

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 12/8

5:45 pm-10:12 pm

1 stop5h 27m

Chicago Midway

Mon 12/15

6:15 am-4:50 pm

1 stop9h 35m

$171

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 12/11

6:30 am-8:25 am

Nonstop2h 55m

Chicago Midway

Mon 12/15

8:20 am-12:10 pm

Nonstop2h 50m

$179

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Mon 12/1

4:09 pm-10:43 pm

1 stop7h 34m

Chicago Midway

Sat 1/3

6:12 am-6:43 pm

1 stop11h 31m

$210

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 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 September is, on average, the cheapest month to fly to Chicago from Fort Myers, with most prices found around $159. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Fort Myers to Chicago during January average around $183.

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 Friday when prices can be found for as low as $272. 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 $400.

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 $183. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $336.

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 $227 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 $178 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 November 2025, prices for Fort Myers to Chicago flights are approximately 32% 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

$113

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 $113. The best round-trip flight deal from Fort Myers to Chicago found on momondo in the last 72 hours is $203.
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)
Search flight deals

  • 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 $46Free CancellationRating
5.8
3,106 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $71Free CancellationRating
6.3
8,156 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
11,045 reviews
Search American Airlines flights
United AirlinesPriceFrom $159Free CancellationRating
7.4
9,029 reviews
Search United Airlines flights
SouthwestPriceFrom $179Free CancellationRating
8.0
4,249 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
8,002 reviews
Search Delta flights

  • Southwest Flights From Fort Myers to Chicago

    Southwest flight deals from Fort Myers to Chicago start from $179 round-trip. Over the 6 Southwest flights for this route in a normal week, average airfare is usually $377 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 9,029 reviews) operates around 24 flights from Fort Myers to Chicago in any given week. The average United Airlines airfare for this route is around $305, 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
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport