What airlines fly to Chicago?

United Airlines, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Fort Myers according to our data. United Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Fort Myers SW Florida Intl to Chicago?

Spirit Airlines, United Airlines, and Southwest are the most popular carriers operating from Fort Myers SW Florida Intl to Chicago

How many flights depart from Fort Myers to Chicago on average per day?

The number of flights available between Fort Myers and Chicago is 7 per day as of December 2025. The most frequent departure time is 12:00PM, with 61% of daily flights leaving in the afternoon.

How many flights depart from Fort Myers to Chicago on average per week?

As of December 2025, 54 flights take off from Fort Myers and land in Chicago each week. The most common flight departure day for this route is Tue, with 43% of weekly flights taking off on this day.

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?

As of December 2025, there are 6 operators available to choose from 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.

$60 Cheap Flights from Fort Myers to Chicago in 2025/26

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:31 am - 9:43 am

RSW

ORD

3h 12mnonstop

7:21 pm - 11:24 pm

ORD

RSW

3h 03mnonstop

$112Spirit Airlines

Mon, Jan 12 - Mon, Jan 19

7:45 pm - 10:04 pm

RSW

ORD

3h 19mnonstop

7:00 am - 11:01 am

ORD

RSW

3h 01mnonstop

$113Spirit Airlines

Thu, Jan 8 - Thu, Jan 15

7:31 am - 9:43 am

RSW

ORD

3h 12mnonstop

7:35 pm - 9:07 am

ORD

RSW

12h 32m1 stop

$118Multiple Airlines

Fri, Jan 16 - Sun, Jan 18

9:55 pm - 11:56 pm

RSW

ORD

3h 01mnonstop

5:50 am - 12:18 pm

ORD

RSW

5h 28m1 stop

$120Multiple Airlines

Wed, Jan 7 - Mon, Jan 12

7:45 pm - 10:04 pm

RSW

ORD

3h 19mnonstop

8:45 am - 6:30 pm

ORD

RSW

8h 45m1 stop

$121Multiple Airlines

Thu, Feb 5 - Sun, Feb 8

1:02 pm - 10:39 pm

RSW

ORD

10h 37m1 stop

6:30 am - 10:39 am

ORD

RSW

3h 09mnonstop

$125Frontier

Sat, Feb 14 - Sun, Feb 22

12:40 pm - 2:45 pm

RSW

MDW

3h 05mnonstop

10:05 am - 4:20 pm

MDW

RSW

5h 15m1 stop

$167Southwest

Tue, Jan 13 - Tue, Jan 20

7:36 pm - 11:45 am

RSW

MDW

17h 09m1 stop

6:20 am - 6:41 pm

MDW

RSW

11h 21m1 stop

$174Frontier

Thu, Feb 5 - Sun, Feb 8

8:00 pm - 10:00 pm

RSW

MDW

3h 00mnonstop

6:15 pm - 10:05 pm

MDW

RSW

2h 50mnonstop

$179Southwest

Thu, Jan 15 - Mon, Jan 19

6:25 pm - 10:42 pm

RSW

MDW

5h 17m1 stop

10:53 am - 5:18 pm

MDW

RSW

5h 25m1 stop

$217Delta

Fri, Feb 27 - Mon, Mar 2

United Airlines flights from Fort Myers to Chicago

Our best United Airlines deals on Fort Myers to Chicago flight tickets

United Airlines

Jan 16

RSW2:35 pmFort Myers SW Florida Intl

3h 23m

ORD4:58 pmChicago O'Hare Intl

Jan 19

ORD12:50 pmChicago O'Hare Intl

3h 02m

RSW4:52 pmFort Myers SW Florida Intl

$179

Find similar

United Airlines

Jan 13

RSW12:30 pmFort Myers SW Florida Intl

3h 24m

ORD2:54 pmChicago O'Hare Intl

Jan 20

ORD10:52 amChicago O'Hare Intl

8h 10m

1 stop

RSW8:02 pmFort Myers SW Florida Intl

$187

Find similar

United Airlines

Dec 24

RSW7:00 amFort Myers SW Florida Intl

3h 15m

ORD9:15 amChicago O'Hare Intl

Jan 1

ORD6:00 amChicago O'Hare Intl

2h 58m

RSW9:58 amFort Myers SW Florida Intl

$237

Find similar

Frontier flights from Fort Myers to Chicago

Our best Frontier deals on Fort Myers to Chicago flight tickets

Frontier

Feb 12

RSW9:31 pmFort Myers SW Florida Intl

10h 35m

1 stop

ORD7:06 amChicago O'Hare Intl

Feb 14

ORD1:37 pmChicago O'Hare Intl

3h 14m

RSW5:51 pmFort Myers SW Florida Intl

$120

Find similar

Frontier

Feb 14

RSW1:02 pmFort Myers SW Florida Intl

10h 37m

1 stop

ORD10:39 pmChicago O'Hare Intl

Feb 22

ORD6:30 amChicago O'Hare Intl

3h 09m

RSW10:39 amFort Myers SW Florida Intl

$125

Find similar

Frontier

Feb 14

RSW1:02 pmFort Myers SW Florida Intl

10h 37m

1 stop

ORD10:39 pmChicago O'Hare Intl

Feb 21

ORD5:05 amChicago O'Hare Intl

5h 56m

1 stop

RSW12:01 pmFort Myers SW Florida Intl

$155

Find similar

Fly from

Fly to

Route

Depart

Return

Price

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Mon 1/12

7:31 am-9:43 am

Nonstop3h 12m

Chicago O'Hare Intl

Mon 1/19

7:21 pm-11:24 pm

Nonstop3h 03m

$112

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 1/8

7:45 pm-10:04 pm

Nonstop3h 19m

Chicago O'Hare Intl

Thu 1/15

7:00 am-11:01 am

Nonstop3h 01m

$113

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 1/16

7:31 am-9:43 am

Nonstop3h 12m

Chicago O'Hare Intl

Sun 1/18

7:35 pm-9:07 am

1 stop12h 32m

$118

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 1/7

9:55 pm-11:56 pm

Nonstop3h 01m

Chicago O'Hare Intl

Mon 1/12

5:50 am-12:18 pm

1 stop5h 28m

$120

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 2/5

7:45 pm-10:04 pm

Nonstop3h 19m

Chicago O'Hare Intl

Sun 2/8

8:45 am-6:30 pm

1 stop8h 45m

$121

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 2/14

1:02 pm-10:39 pm

1 stop10h 37m

Chicago O'Hare Intl

Sun 2/22

6:30 am-10:39 am

Nonstop3h 09m

$125

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Tue 1/13

12:40 pm-2:45 pm

Nonstop3h 05m

Chicago Midway

Tue 1/20

10:05 am-4:20 pm

1 stop5h 15m

$167

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 2/5

7:36 pm-11:45 am

1 stop17h 09m

Chicago Midway

Sun 2/8

6:20 am-6:41 pm

1 stop11h 21m

$174

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 1/15

8:00 pm-10:00 pm

Nonstop3h 00m

Chicago Midway

Mon 1/19

6:15 pm-10:05 pm

Nonstop2h 50m

$179

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 2/27

6:25 pm-10:42 pm

1 stop5h 17m

Chicago Midway

Mon 3/2

10:53 am-5:18 pm

1 stop5h 25m

$217

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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

Prices

Airlines

Other information

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 $168. 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 $179.

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 $428.

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 $188. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $348.

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 $226 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 $174 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 December 2025, prices for Fort Myers to Chicago flights are approximately 8% 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	$126
Fastest flight time	2h 55m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Fort Myers in the past 72 hours is $126. The best round-trip flight deal from Fort Myers to Chicago found on momondo in the last 72 hours is $196.

The fastest flight from Fort Myers to Chicago takes 2h 55m

Direct flights go from Fort Myers to Chicago every day.

There are 3 airports in Chicago. From Fort Myers there are direct flights to 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?
As of December 2025, there are 6 operators available to choose from 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?
momondo data reveals that the most frequently booked plane model on the route from Fort Myers to Chicago is Boeing 737-800, representing 30.07% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 12.20%, Boeing 737 MAX 9 at 10.43%, and Airbus A321neo at 8.57%.
What is the most popular airline from Fort Myers to Chicago?
momondo data reveals that the most frequently booked airline on the route from Fort Myers to Chicago is Spirit Airlines, representing 36% of all bookings. The subsequent popular airlines are American Airlines at 27%, United Airlines at 20%, and Southwest at 14%.

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
Frontier	PriceFrom $52	Free Cancellation	Rating 5.8 3,082 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $61	Free Cancellation	Rating 6.3 8,188 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $157	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
United Airlines	PriceFrom $158	Free Cancellation	Rating 7.4 9,094 reviews	Search United Airlines flights
Southwest	PriceFrom $179	Free Cancellation	Rating 7.9 4,250 reviews	Search Southwest flights
Delta	PriceFrom $216	Free Cancellation	Rating 7.9 8,009 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 9 Southwest flights for this route in a normal week, average airfare is usually $374 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 9,094 reviews) operates around 8 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 $158 rare but found on momondo. Referenced prices are for round-trip Fort Myers to Chicago flight searches in the last 72 hours.

Merrillville

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Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Cheap flights from Fort Myers to Chicago from $74

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 1/1. 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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Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Find the cheapest flights from Fort Myers to Chicago

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United Airlines flights from Fort Myers to Chicago

Our best United Airlines deals on Fort Myers to Chicago flight tickets

Frontier flights from Fort Myers to Chicago

Our best Frontier deals on Fort Myers to Chicago flight tickets

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Use the filters below to find and compare flights from Fort Myers to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Fort Myers to 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 $168. 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 $179.

What is the cheapest day to depart on your flight to Chicago?

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 $188. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $348.

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?

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 December 2025, prices for Fort Myers to Chicago flights are approximately 8% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Fort Myers SW Florida Intl to Chicago?

Spirit Airlines, United Airlines, and Southwest are the most popular carriers operating from Fort Myers SW Florida Intl to Chicago

What airlines fly to Chicago?

How many flights depart from Fort Myers to Chicago on average per day?

The number of flights available between Fort Myers and Chicago is 7 per day as of December 2025. The most frequent departure time is 12:00PM, with 61% of daily flights leaving in the afternoon.

How many flights depart from Fort Myers to Chicago on average per week?

As of December 2025, 54 flights take off from Fort Myers and land in Chicago each week. The most common flight departure day for this route is Tue, with 43% of weekly flights taking off on this day.

When to book flights from Fort Myers to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

How far is Fort Myers SW Florida Intl to Chicago by plane?

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

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?

What documentation or ID do you need to fly to Chicago?

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

Southwest Flights From Fort Myers to Chicago

United Airlines Flights From Fort Myers to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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