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Cheap flights from Fort Myers to Chicago from $80

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 11/24. 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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Find the cheapest flights from Fort Myers to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:15 am - 8:24 amRSW-ORD
3h 09mnonstop
Multiple Airlines Logo
12:32 pm - 6:18 pmORD-RSW
28h 46m1 stop
$141Multiple Airlines
Find Deal
lun., dic. 22 - mar., dic. 30
Frontier Logo
5:41 pm - 12:12 amRSW-ORD
7h 31m1 stop
Frontier Logo
6:10 am - 6:43 pmORD-RSW
11h 33m1 stop
$144Frontier
Find Deal
dom., dic. 21 - sáb., ene. 3
Frontier Logo
9:28 am - 7:04 pmRSW-MDW
10h 36m1 stop
Frontier Logo
8:41 pm - 8:33 amMDW-RSW
10h 52m1 stop
$144Frontier
Find Deal
mar., nov. 25 - vie., nov. 28
Multiple Airlines Logo
11:16 am - 10:24 pmRSW-ORD
12h 08m2 stops
Multiple Airlines Logo
8:15 am - 12:20 pmORD-RSW
3h 05mnonstop
$145Multiple Airlines
Find Deal
jue., dic. 11 - lun., dic. 15
Spirit Airlines Logo
11:09 am - 1:18 pmRSW-ORD
3h 09mnonstop
Spirit Airlines Logo
12:29 pm - 4:17 pmORD-RSW
2h 48mnonstop
$149Spirit Airlines
Find Deal
mar., nov. 25 - vie., nov. 28
Frontier Logo
11:36 am - 6:20 pmRSW-MDW
7h 44m1 stop
Frontier Logo
8:41 pm - 8:33 amMDW-RSW
10h 52m1 stop
$149Frontier
Find Deal
mié., nov. 26 - vie., nov. 28
Multiple Airlines Logo
11:09 am - 1:18 pmRSW-ORD
3h 09mnonstop
Multiple Airlines Logo
6:11 am - 6:19 pmORD-RSW
11h 08m1 stop
$150Multiple Airlines
Find Deal
mar., nov. 25 - vie., dic. 5
Multiple Airlines Logo
4:06 pm - 12:08 amRSW-ORD
9h 02m1 stop
Multiple Airlines Logo
12:29 pm - 4:17 pmORD-RSW
2h 48mnonstop
$153Multiple Airlines
Find Deal
mié., nov. 26 - vie., nov. 28
Southwest Logo
6:30 am - 8:25 amRSW-MDW
2h 55mnonstop
Southwest Logo
5:35 am - 9:20 amMDW-RSW
2h 45mnonstop
$159Southwest
Find Deal
jue., dic. 11 - dom., dic. 14
Southwest Logo
7:25 am - 9:20 amRSW-MDW
2h 55mnonstop
Southwest Logo
6:15 pm - 10:05 pmMDW-RSW
2h 50mnonstop
$163Southwest
Find Deal
mar., ene. 20 - dom., ene. 25

American Airlines flights from Fort Myers to Chicago

Our best American Airlines deals on Fort Myers to Chicago flight tickets
American Airlines
Dec 13
RSW6:16 amFort Myers SW Florida Intl
3h 19m
ORD8:35 amChicago O'Hare Intl
Dec 14
ORD7:15 pmChicago O'Hare Intl
3h 01m
RSW11:16 pmFort Myers SW Florida Intl
$158
Find similar
American Airlines
Dec 11
RSW6:16 amFort Myers SW Florida Intl
3h 19m
ORD8:35 amChicago O'Hare Intl
Dec 14
ORD6:45 amChicago O'Hare Intl
2h 54m
RSW10:39 amFort Myers SW Florida Intl
$159
Find similar
American Airlines
Dec 10
RSW6:10 amFort Myers SW Florida Intl
3h 19m
ORD8:29 amChicago O'Hare Intl
Dec 17
ORD1:28 pmChicago O'Hare Intl
3h 02m
RSW5:30 pmFort Myers SW Florida Intl
$168
Find similar

Spirit Airlines flights from Fort Myers to Chicago

Our best Spirit Airlines deals on Fort Myers to Chicago flight tickets
Spirit Airlines
Nov 25
RSW11:09 amFort Myers SW Florida Intl
3h 09m
ORD1:18 pmChicago O'Hare Intl
Nov 28
ORD12:29 pmChicago O'Hare Intl
2h 48m
RSW4:17 pmFort Myers SW Florida Intl
$149
Find similar
Spirit Airlines
Nov 23
RSW1:38 pmFort Myers SW Florida Intl
3h 08m
ORD3:46 pmChicago O'Hare Intl
Nov 28
ORD12:29 pmChicago O'Hare Intl
2h 48m
RSW4:17 pmFort Myers SW Florida Intl
$174
Find similar
Spirit Airlines
Nov 25
RSW11:09 amFort Myers SW Florida Intl
3h 09m
ORD1:18 pmChicago O'Hare Intl
Nov 27
ORD2:01 pmChicago O'Hare Intl
2h 57m
RSW5:58 pmFort Myers SW Florida Intl
$175
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 noviembre 13, 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

lun. 12/22

6:15 am-8:24 am

Nonstop3h 09m

Chicago O'Hare Intl

mar. 12/30

12:32 pm-6:18 pm

1 stop28h 46m

$141

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

dom. 12/21

5:41 pm-12:12 am

1 stop7h 31m

Chicago O'Hare Intl

sáb. 1/3

6:10 am-6:43 pm

1 stop11h 33m

$144

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

mar. 11/25

9:28 am-7:04 pm

1 stop10h 36m

Chicago Midway

vie. 11/28

8:41 pm-8:33 am

1 stop10h 52m

$144

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

jue. 12/11

11:16 am-10:24 pm

2 stops12h 08m

Chicago O'Hare Intl

lun. 12/15

8:15 am-12:20 pm

Nonstop3h 05m

$145

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

mar. 11/25

11:09 am-1:18 pm

Nonstop3h 09m

Chicago O'Hare Intl

vie. 11/28

12:29 pm-4:17 pm

Nonstop2h 48m

$149

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

mié. 11/26

11:36 am-6:20 pm

1 stop7h 44m

Chicago Midway

vie. 11/28

8:41 pm-8:33 am

1 stop10h 52m

$149

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

mar. 11/25

11:09 am-1:18 pm

Nonstop3h 09m

Chicago O'Hare Intl

vie. 12/5

6:11 am-6:19 pm

1 stop11h 08m

$150

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

mié. 11/26

4:06 pm-12:08 am

1 stop9h 02m

Chicago O'Hare Intl

vie. 11/28

12:29 pm-4:17 pm

Nonstop2h 48m

$153

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

jue. 12/11

6:30 am-8:25 am

Nonstop2h 55m

Chicago Midway

dom. 12/14

5:35 am-9:20 am

Nonstop2h 45m

$159

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

mar. 1/20

7:25 am-9:20 am

Nonstop2h 55m

Chicago Midway

dom. 1/25

6:15 pm-10:05 pm

Nonstop2h 50m

$163

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 $185.

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 30% 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 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 $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 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)
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
3,114 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $71Free CancellationRating
6.3
8,139 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
United AirlinesPriceFrom $159Free CancellationRating
7.4
9,015 reviews
Search United Airlines flights
SouthwestPriceFrom $179Free CancellationRating
8.0
4,236 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
8,007 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 21 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 9,015 reviews) operates around 23 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