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Cheap flights from Fort Myers to Chicago from $60

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 10/2. 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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Cheap round-trip flights

Spirit Airlines Logo
11:56 am - 2:06 pmRSW-ORD
3h 10mnonstop
Spirit Airlines Logo
7:00 am - 10:51 amORD-RSW
2h 51mnonstop
$99Spirit Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Spirit Airlines Logo
7:00 am - 9:13 amRSW-ORD
3h 13mnonstop
Spirit Airlines Logo
5:01 pm - 8:50 pmORD-RSW
2h 49mnonstop
$105Spirit Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Spirit Airlines Logo
7:00 am - 9:13 amRSW-ORD
3h 13mnonstop
Spirit Airlines Logo
5:23 pm - 9:16 pmORD-RSW
2h 53mnonstop
$106Spirit Airlines
Find Deal
Thu, Oct 2 - Fri, Oct 3
Logo
7:24 pm - 12:10 amRSW-ORD
5h 46m1 stop
Logo
5:23 pm - 9:16 pmORD-RSW
2h 53mnonstop
$123
Find Deal
Thu, Sep 25 - Mon, Sep 29
Logo
6:40 am - 8:34 amRSW-ORD
2h 54mnonstop
Logo
5:05 am - 12:16 pmORD-RSW
6h 11m1 stop
$125
Find Deal
Thu, Oct 16 - Sun, Oct 19
Frontier Logo
1:01 pm - 11:39 pmRSW-ORD
11h 38m1 stop
Frontier Logo
5:05 am - 12:16 pmORD-RSW
6h 11m1 stop
$155Frontier
Find Deal
Thu, Oct 16 - Sun, Oct 19
Frontier Logo
7:24 pm - 10:31 amRSW-ORD
16h 07m1 stop
Frontier Logo
5:10 am - 6:29 pmORD-RSW
12h 19m1 stop
$163Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5
American Airlines Logo
6:55 am - 9:05 amRSW-ORD
3h 10mnonstop
American Airlines Logo
2:44 pm - 6:50 pmORD-RSW
3h 06mnonstop
$177American Airlines
Find Deal
Sat, Oct 4 - Sat, Oct 4
American Airlines Logo
3:48 pm - 6:14 pmRSW-ORD
3h 26mnonstop
American Airlines Logo
7:34 pm - 11:35 pmORD-RSW
3h 01mnonstop
$178American Airlines
Find Deal
Thu, Nov 6 - Sat, Nov 8
United Airlines Logo
9:10 am - 11:22 amRSW-ORD
3h 12mnonstop
United Airlines Logo
4:15 pm - 8:16 pmORD-RSW
3h 01mnonstop
$191United Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 1

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 4
RSW6:55 amFort Myers SW Florida Intl
3h 10m
ORD9:05 amChicago O'Hare Intl
Oct 4
ORD2:44 pmChicago O'Hare Intl
3h 06m
RSW6:50 pmFort Myers SW Florida Intl
$177
Find similar
American Airlines
Nov 6
RSW3:48 pmFort Myers SW Florida Intl
3h 26m
ORD6:14 pmChicago O'Hare Intl
Nov 8
ORD7:34 pmChicago O'Hare Intl
3h 01m
RSW11:35 pmFort Myers SW Florida Intl
$178
Find similar
American Airlines
Oct 2
RSW8:00 amFort Myers SW Florida Intl
3h 09m
ORD10:09 amChicago O'Hare Intl
Oct 5
ORD7:05 amChicago O'Hare Intl
2h 51m
RSW10:56 amFort Myers SW Florida Intl
$179
Find similar

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

Our best Spirit Airlines deals on Fort Myers to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines
Dec 5
RSW11:56 amFort Myers SW Florida Intl
3h 10m
ORD2:06 pmChicago O'Hare Intl
Dec 7
ORD7:00 amChicago O'Hare Intl
2h 51m
RSW10:51 amFort Myers SW Florida Intl
$99
Find similar
Spirit Airlines
Oct 2
RSW7:00 amFort Myers SW Florida Intl
3h 13m
ORD9:13 amChicago O'Hare Intl
Oct 5
ORD5:01 pmChicago O'Hare Intl
2h 49m
RSW8:50 pmFort Myers SW Florida Intl
$105
Find similar
Spirit Airlines
Oct 2
RSW7:00 amFort Myers SW Florida Intl
3h 13m
ORD9:13 amChicago O'Hare Intl
Oct 3
ORD5:23 pmChicago O'Hare Intl
2h 53m
RSW9:16 pmFort Myers SW Florida Intl
$106
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Fort Myers to Chicago O'Hare Intl Airport 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 September 3, 2025.
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

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 12/5

11:56 am-2:06 pm

Nonstop3h 10m

Chicago O'Hare Intl

Sun 12/7

7:00 am-10:51 am

Nonstop2h 51m

$99

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/2

7:00 am-9:13 am

Nonstop3h 13m

Chicago O'Hare Intl

Sun 10/5

5:01 pm-8:50 pm

Nonstop2h 49m

$105

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/2

7:00 am-9:13 am

Nonstop3h 13m

Chicago O'Hare Intl

Fri 10/3

5:23 pm-9:16 pm

Nonstop2h 53m

$106

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 9/25

7:24 pm-12:10 am

1 stop5h 46m

Chicago O'Hare Intl

Mon 9/29

5:23 pm-9:16 pm

Nonstop2h 53m

$123

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/16

6:40 am-8:34 am

Nonstop2h 54m

Chicago O'Hare Intl

Sun 10/19

5:05 am-12:16 pm

1 stop6h 11m

$125

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/16

1:01 pm-11:39 pm

1 stop11h 38m

Chicago O'Hare Intl

Sun 10/19

5:05 am-12:16 pm

1 stop6h 11m

$155

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/2

7:24 pm-10:31 am

1 stop16h 07m

Chicago O'Hare Intl

Sun 10/5

5:10 am-6:29 pm

1 stop12h 19m

$163

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 10/4

6:55 am-9:05 am

Nonstop3h 10m

Chicago O'Hare Intl

Sat 10/4

2:44 pm-6:50 pm

Nonstop3h 06m

$177

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 11/6

3:48 pm-6:14 pm

Nonstop3h 26m

Chicago O'Hare Intl

Sat 11/8

7:34 pm-11:35 pm

Nonstop3h 01m

$178

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 11/1

9:10 am-11:22 am

Nonstop3h 12m

Chicago O'Hare Intl

Sat 11/1

4:15 pm-8:16 pm

Nonstop3h 01m

$191

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of July is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Fort Myers averaging around $207.

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 $271. 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 $416.

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 $163 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $343. 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 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 $243 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 $191 on momondo.

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

There are 4 cabin classes available to choose from on Fort Myers SW Florida Intl to Chicago O'Hare Intl 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 2025, prices for Fort Myers to Chicago O'Hare Intl Airport flights are approximately 13% 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

$112

Fastest flight time

2h 54m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Fort Myers in the past 72 hours is $112. The best round-trip flight deal from Fort Myers to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $175.
The fastest flight from Fort Myers to Chicago O'Hare Intl Airport takes 2h 54m
Direct flights go from Fort Myers to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 2h 54m 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 $46Free CancellationRating
5.8
3,196 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $66Free CancellationRating
6.3
8,012 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $159Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $177Free CancellationRating
7.4
8,937 reviews
Search United Airlines 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 $177 round-trip. Over the 19 United Airlines flights for this route in a normal week, average airfare is usually $345 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 (7.2/10 from 10,000 reviews) operates around 3 flights from Fort Myers to Chicago O'Hare Intl Airport in any given week. The average American Airlines airfare for this route is around $264, with deals from around $159 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
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

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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