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Cheap flights from Fort Myers to Chicago from $143

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Fort Myers to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:48 pm - 12:53 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
8h 05m1 stop Denver Intl
Frontier Logo
1:58 pm - 5:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
$285Frontier
Sat, Nov 21 - Sat, Nov 28
Frontier Logo
6:52 pm - 9:10 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 18mnonstop
Frontier Logo
1:58 pm - 5:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
$285Frontier
Tue, Nov 24 - Sat, Nov 28
Multiple Airlines Logo
12:55 pm - 6:30 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
6h 35m1 stop Minneapolis St Paul
Multiple Airlines Logo
1:58 pm - 5:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
$285Multiple Airlines
Thu, Nov 19 - Mon, Nov 23
Multiple Airlines Logo
12:55 pm - 6:30 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
6h 35m1 stop Minneapolis St Paul
Multiple Airlines Logo
1:58 pm - 5:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
$292Multiple Airlines
Thu, Nov 19 - Mon, Nov 23
United Airlines Logo
2:14 pm - 4:33 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 19mnonstop
United Airlines Logo
8:41 am - 12:44 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 03mnonstop
$297United Airlines
Sat, Dec 5 - Tue, Dec 8
United Airlines Logo
12:17 pm - 2:31 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 14mnonstop
United Airlines Logo
4:30 pm - 8:36 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 06mnonstop
$297United Airlines
Thu, Oct 8 - Sat, Oct 10
American Airlines Logo
11:52 am - 2:15 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 23mnonstop
American Airlines Logo
6:57 am - 11:02 amORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 05mnonstop
$297American Airlines
Thu, Feb 4 - Mon, Feb 8
American Airlines Logo
7:40 pm - 10:00 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 20mnonstop
American Airlines Logo
6:50 pm - 10:43 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 53mnonstop
$297American Airlines
Wed, Dec 2 - Wed, Dec 9
JetBlue Logo
6:32 am - 8:47 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
27h 15m1 stop Boston Logan Intl
JetBlue Logo
12:38 pm - 9:21 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
7h 43m1 stop New York John F Kennedy Intl
$496JetBlue
Tue, Oct 13 - Sat, Oct 24
JetBlue Logo
8:20 pm - 8:47 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
13h 27m1 stop Boston Logan Intl
JetBlue Logo
6:10 am - 9:21 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
14h 11m1 stop New York John F Kennedy Intl
$520JetBlue
Tue, Oct 13 - Mon, Oct 19

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American Airlines flights from Fort Myers to Chicago O'Hare Intl Airport

Our best American Airlines deals on Fort Myers to Chicago O'Hare Intl Airport flight tickets
American Airlines
Oct 8
RSW7:51 pmFort Myers SW Florida Intl
5h 17m
1 stop
ORD12:08 amChicago O'Hare Intl
Oct 15
ORD6:50 pmChicago O'Hare Intl
3h 02m
RSW10:52 pmFort Myers SW Florida Intl
$321
American Airlines
Nov 23
RSW8:17 amFort Myers SW Florida Intl
3h 27m
ORD10:44 amChicago O'Hare Intl
Dec 1
ORD9:00 amChicago O'Hare Intl
4h 36m
1 stop
RSW2:36 pmFort Myers SW Florida Intl
$329
American Airlines
Nov 21
RSW11:48 amFort Myers SW Florida Intl
5h 28m
1 stop
ORD4:16 pmChicago O'Hare Intl
Nov 23
ORD5:19 amChicago O'Hare Intl
7h 16m
1 stop
RSW1:35 pmFort Myers SW Florida Intl
$331

Frontier flights from Fort Myers to Chicago O'Hare Intl Airport

Our best Frontier deals on Fort Myers to Chicago O'Hare Intl Airport flight tickets
Frontier
Nov 20
RSW6:52 pmFort Myers SW Florida Intl
3h 18m
ORD9:10 pmChicago O'Hare Intl
Nov 30
ORD1:58 pmChicago O'Hare Intl
2h 56m
RSW5:54 pmFort Myers SW Florida Intl
$286
Frontier
Nov 25
RSW1:21 pmFort Myers SW Florida Intl
7h 54m
1 stop
ORD8:15 pmChicago O'Hare Intl
Nov 27
ORD1:58 pmChicago O'Hare Intl
2h 56m
RSW5:54 pmFort Myers SW Florida Intl
$287
Frontier
Nov 25
RSW5:48 pmFort Myers SW Florida Intl
8h 05m
1 stop
ORD12:53 amChicago O'Hare Intl
Nov 28
ORD1:58 pmChicago O'Hare Intl
2h 56m
RSW5:54 pmFort Myers SW Florida Intl
$288

momondo Fare Finder

 
Use the filters below to find and compare flights from Fort Myers to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Sat 11/21

5:48 pm-12:53 am

1 stop8h 05m

Chicago O'Hare Intl

Sat 11/28

1:58 pm-5:54 pm

Nonstop2h 56m

$285

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Tue 11/24

6:52 pm-9:10 pm

Nonstop3h 18m

Chicago O'Hare Intl

Sat 11/28

1:58 pm-5:54 pm

Nonstop2h 56m

$285

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Thu 11/19

12:55 pm-6:30 pm

1 stop6h 35m

Chicago O'Hare Intl

Mon 11/23

1:58 pm-5:54 pm

Nonstop2h 56m

$285

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Thu 11/19

12:55 pm-6:30 pm

1 stop6h 35m

Chicago O'Hare Intl

Mon 11/23

1:58 pm-5:54 pm

Nonstop2h 56m

$292

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Sat 12/5

2:14 pm-4:33 pm

Nonstop3h 19m

Chicago O'Hare Intl

Tue 12/8

8:41 am-12:44 pm

Nonstop3h 03m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Thu 10/8

12:17 pm-2:31 pm

Nonstop3h 14m

Chicago O'Hare Intl

Sat 10/10

4:30 pm-8:36 pm

Nonstop3h 06m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Thu 2/4

11:52 am-2:15 pm

Nonstop3h 23m

Chicago O'Hare Intl

Mon 2/8

6:57 am-11:02 am

Nonstop3h 05m

$297
Quickest round-trip

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Wed 12/2

7:40 pm-10:00 pm

Nonstop3h 20m

Chicago O'Hare Intl

Wed 12/9

6:50 pm-10:43 pm

Nonstop2h 53m

$297

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Tue 10/13

6:32 am-8:47 am

1 stop27h 15m

Chicago O'Hare Intl

Sat 10/24

12:38 pm-9:21 pm

1 stop7h 43m

$496

Fort MyersChicago

RSW Fort Myers SW Florida Intl - ORD Chicago O'Hare Intl

RSWORD

Fort Myers SW Florida Intl

Tue 10/13

8:20 pm-8:47 am

1 stop13h 27m

Chicago O'Hare Intl

Mon 10/19

6:10 am-9:21 pm

1 stop14h 11m

$520

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 O'Hare Intl 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 typical price of a round-trip flight between Fort Myers and Chicago O'Hare Intl Airport?

Prices are currently typical for flights on this route.

Typical prices usually range from $270 to $353.
The lowest price recently found on this route was $285.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Fort Myers averaging around $189.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $373. This is often the case because there is less demand to fly during this day of the week. 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 $523.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Fort Myers in the evening is the least expensive time of day to depart. momondo users have found prices as low as $336 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $408. 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 O'Hare Intl flight route?

Fly from Fort Myers SW Florida Intl to Chicago O'Hare Intl for the best Fort Myers SW Florida Intl - Chicago O'Hare Intl flight prices

How far in advance should I book a flight from Fort Myers to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Fort Myers when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $287 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Fort Myers for as low as $271 on momondo.

What cabin class options are available on Fort Myers to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Fort Myers to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flight prices changed over time?

As of September 2026, prices for Fort Myers to Chicago O'Hare Intl Airport flights are approximately 1% more expensive when compared to flights at the same time last year.

When to book flights from Fort Myers to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Fort Myers to Chicago O'Hare Intl 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 O'Hare Intl Airport (RSW to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Fort Myers to Chicago O'Hare Intl Airport

Best Price Found

$143

Fastest flight time

3h 06m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Fort Myers in the past 72 hours is $143. The best round-trip flight deal from Fort Myers to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $285.
The fastest flight from Fort Myers to Chicago O'Hare Intl Airport takes 3h 06m
Direct flights go from Fort Myers to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Fort Myers to Chicago O'Hare Intl Airport

  • How far is Fort Myers SW Florida Intl to Chicago O'Hare Intl by plane?

    There are 1112.7 mi between Fort Myers SW Florida Intl and Chicago O'Hare Intl. Typically, this will take 3h 06m by plane in normal conditions.

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

    Prices for flights from Fort Myers SW Florida Intl Airport to Chicago O'Hare Intl Airport are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Fort Myers SW Florida Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents required for your trip to Chicago O'Hare Intl 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 O'Hare Intl 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 O'Hare Intl Airport?

  • What is the most popular airline from Fort Myers to Chicago O'Hare Intl Airport?

Best airlines flying from Fort Myers to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Fort Myers to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $43Free CancellationRating
5.6
2,601 reviews
Search Frontier flights
United AirlinesPriceFrom $160Free CancellationRating
7.4
10,213 reviews
Search United Airlines flights
American AirlinesPriceFrom $178Free CancellationRating
7.1
12,050 reviews
Search American Airlines flights
SouthwestPriceFrom $199Free CancellationRating
8.0
4,189 reviews
Search Southwest flights
JetBluePriceFrom $255Free CancellationRating
7.1
3,035 reviews
Search JetBlue flights

  • United Airlines Flights From Fort Myers to Chicago O'Hare Intl Airport

    United Airlines flight deals from Fort Myers to Chicago O'Hare Intl Airport start from $160 round-trip. Over the 17 United Airlines flights for this route in a normal week, average airfare is usually $334 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Fort Myers to Chicago O'Hare Intl Airport

    American Airlines (7.1/10 from 12,050 reviews) operates around 19 flights from Fort Myers to Chicago O'Hare Intl Airport in any given week. The average American Airlines airfare for this route is around $316, with deals from around $178 rare but found on momondo. Referenced prices are for round-trip Fort Myers to Chicago O'Hare Intl Airport 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
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Rosemont
Gurnee
Oak Brook
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Evanston
Skokie

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Fort Myers to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Fort Myers to Chicago with flexible booking policies on momondo?

Flights from Fort Myers to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Fort Myers to Chicago?

momondo helps you find the best flight between Fort Myers and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Fort Myers and alert you when they change.

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