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Cheap flights from Fort Myers to Chicago from $145

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 10/28. 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
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.
Multiple Airlines Logo
12:45 pm - 6:24 pm
RSW
-
ORD
6h 39m
1 stop
Multiple Airlines Logo
2:15 pm - 11:37 pm
ORD
-
RSW
8h 22m
1 stop
$279Multiple Airlines
Thu, Oct 22 - Mon, Oct 26
American Airlines Logo
7:12 pm - 9:44 pm
RSW
-
ORD
3h 32mnonstop
American Airlines Logo
7:07 pm - 11:09 pm
ORD
-
RSW
3h 02mnonstop
$283American Airlines
Wed, Sep 16 - Sat, Sep 19
United Airlines Logo
9:15 am - 11:29 am
RSW
-
ORD
3h 14mnonstop
United Airlines Logo
7:15 am - 11:21 am
ORD
-
RSW
3h 06mnonstop
$283United Airlines
Tue, Aug 18 - Thu, Aug 20
United Airlines Logo
4:40 pm - 6:59 pm
RSW
-
ORD
3h 19mnonstop
United Airlines Logo
10:30 am - 2:36 pm
ORD
-
RSW
3h 06mnonstop
$283United Airlines
Tue, Aug 18 - Mon, Aug 24
American Airlines Logo
8:18 am - 10:40 am
RSW
-
ORD
3h 22mnonstop
American Airlines Logo
6:50 pm - 10:46 pm
ORD
-
RSW
2h 56mnonstop
$283American Airlines
Sat, Oct 31 - Mon, Nov 2
Frontier Logo
3:53 pm - 6:14 pm
RSW
-
ORD
3h 21mnonstop
Frontier Logo
10:52 am - 2:58 pm
ORD
-
RSW
3h 06mnonstop
$284Frontier
Sun, Dec 6 - Sun, Dec 13
Multiple Airlines Logo
12:45 pm - 6:24 pm
RSW
-
ORD
6h 39m
1 stop
Multiple Airlines Logo
2:15 pm - 11:37 pm
ORD
-
RSW
8h 22m
1 stop
$284Multiple Airlines
Thu, Oct 22 - Mon, Oct 26
Frontier Logo
3:53 pm - 6:14 pm
RSW
-
ORD
3h 21mnonstop
Frontier Logo
10:52 am - 2:58 pm
ORD
-
RSW
3h 06mnonstop
$285Frontier
Sun, Dec 6 - Sun, Dec 13
JetBlue Logo
6:00 am - 1:20 pm
RSW
-
ORD
8h 20m
1 stop
JetBlue Logo
2:15 pm - 11:37 pm
ORD
-
RSW
8h 22m
1 stop
$289JetBlue
Sat, Oct 31 - Mon, Nov 2
JetBlue Logo
11:08 am - 7:22 pm
RSW
-
ORD
9h 14m
1 stop
JetBlue Logo
2:15 pm - 11:37 pm
ORD
-
RSW
8h 22m
1 stop
$289JetBlue
Thu, Oct 22 - Mon, Oct 26

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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
Dec 6
RSW3:53 pmFort Myers SW Florida Intl
3h 21m
ORD6:14 pmChicago O'Hare Intl
Dec 13
ORD10:52 amChicago O'Hare Intl
3h 06m
RSW2:58 pmFort Myers SW Florida Intl
$285
Frontier
Dec 10
RSW3:53 pmFort Myers SW Florida Intl
3h 21m
ORD6:14 pmChicago O'Hare Intl
Dec 13
ORD10:52 amChicago O'Hare Intl
3h 06m
RSW2:58 pmFort Myers SW Florida Intl
$286
Frontier
Sep 7
RSW8:09 pmFort Myers SW Florida Intl
24h 59m
2 stops
ORD8:08 pmChicago O'Hare Intl
Sep 27
ORD7:25 amChicago O'Hare Intl
8h 20m
1 stop
RSW4:45 pmFort Myers SW Florida Intl
$318

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
Sep 9
RSW11:42 amFort Myers SW Florida Intl
3h 18m
ORD2:00 pmChicago O'Hare Intl
Sep 11
ORD12:11 pmChicago O'Hare Intl
2h 56m
RSW4:07 pmFort Myers SW Florida Intl
$284
American Airlines
Sep 2
RSW11:04 amFort Myers SW Florida Intl
5h 56m
1 stop
ORD4:00 pmChicago O'Hare Intl
Sep 3
ORD6:45 amChicago O'Hare Intl
2h 52m
RSW10:37 amFort Myers SW Florida Intl
$293
American Airlines
Sep 9
RSW11:14 amFort Myers SW Florida Intl
7h 24m
1 stop
ORD5:38 pmChicago O'Hare Intl
Sep 11
ORD7:07 pmChicago O'Hare Intl
3h 02m
RSW11:09 pmFort Myers SW Florida Intl
$294

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 July 30, 2026.
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 - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/22

12:45 pm-6:24 pm

1 stop6h 39m

Chicago O'Hare Intl

Mon 10/26

2:15 pm-11:37 pm

1 stop8h 22m

$279

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 9/16

7:12 pm-9:44 pm

Nonstop3h 32m

Chicago O'Hare Intl

Sat 9/19

7:07 pm-11:09 pm

Nonstop3h 02m

$283

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 8/18

9:15 am-11:29 am

Nonstop3h 14m

Chicago O'Hare Intl

Thu 8/20

7:15 am-11:21 am

Nonstop3h 06m

$283

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 8/18

4:40 pm-6:59 pm

Nonstop3h 19m

Chicago O'Hare Intl

Mon 8/24

10:30 am-2:36 pm

Nonstop3h 06m

$283
Quickest round-trip

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 10/31

8:18 am-10:40 am

Nonstop3h 22m

Chicago O'Hare Intl

Mon 11/2

6:50 pm-10:46 pm

Nonstop2h 56m

$283

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sun 12/6

3:53 pm-6:14 pm

Nonstop3h 21m

Chicago O'Hare Intl

Sun 12/13

10:52 am-2:58 pm

Nonstop3h 06m

$284

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/22

12:45 pm-6:24 pm

1 stop6h 39m

Chicago O'Hare Intl

Mon 10/26

2:15 pm-11:37 pm

1 stop8h 22m

$284

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sun 12/6

3:53 pm-6:14 pm

Nonstop3h 21m

Chicago O'Hare Intl

Sun 12/13

10:52 am-2:58 pm

Nonstop3h 06m

$285

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 10/31

6:00 am-1:20 pm

1 stop8h 20m

Chicago O'Hare Intl

Mon 11/2

2:15 pm-11:37 pm

1 stop8h 22m

$289

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 10/22

11:08 am-7:22 pm

1 stop9h 14m

Chicago O'Hare Intl

Mon 10/26

2:15 pm-11:37 pm

1 stop8h 22m

$289

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 $200 to $320.
The lowest price recently found on this route was $279.

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 $187.

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 $352. 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 $529.

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 $343 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $396. 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 $269 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 $233 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 July 2026, prices for Fort Myers to Chicago O'Hare Intl Airport 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 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

$196

Fastest flight time

3h 10m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Fort Myers in the past 72 hours is $196. The best round-trip flight deal from Fort Myers to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $335.
The fastest flight from Fort Myers to Chicago O'Hare Intl Airport takes 3h 10m
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 10m 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
2,748 reviews
Search Frontier flights
JetBluePriceFrom $105Free CancellationRating
7.1
3,028 reviews
Search JetBlue flights
United AirlinesPriceFrom $159Free CancellationRating
7.4
10,047 reviews
Search United Airlines flights
American AirlinesPriceFrom $161Free CancellationRating
7.1
11,842 reviews
Search American Airlines flights
SouthwestPriceFrom $199Free CancellationRating
8.0
4,227 reviews
Search Southwest 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 $159 round-trip. Over the 19 United Airlines flights for this route in a normal week, average airfare is usually $315 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 11,842 reviews) operates around 7 flights from Fort Myers to Chicago O'Hare Intl Airport in any given week. The average American Airlines airfare for this route is around $304, with deals from around $161 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
South Haven
Merrillville
Rockford
Gurnee
Rosemont
Orland Park
Oak Brook
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Aurora
Racine
Janesville
Elgin
Evanston
South Holland

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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