RSW - CHI

$147 Find Cheap Flights from Fort Myers to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Fort Myers to Chicago departing on 11/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$275
Typical prices: $148-$289
American Airlines
Sat 9/5Thu 9/10
RSW - ORD • Non-stop
Cheapest one-way
$145
Typical prices: $129-$341
JetBlue
Sun 11/1
RSW - ORD • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds legroom; AA Main Cabin Extra adds early boarding.
Southwest keeps a free carry-on; United Priority Boarding helps avoid gate checks.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 3h 09m
Direct flights
Direct flights
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+1
Direct flights
Direct flights
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Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $210 (round-trip)
Shortest trip • 4h 48m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
Good to know
+1
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Flight Deals

Cheap Flights from Fort Myers to Chicago (RSW-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Fort Myers to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Fort Myers to Chicago

Sat, Sep 5 - Thu, Sep 10
American Airlines Logo
4:39 pm - 7:10 pm
RSW
-
ORD
3h 31mnonstop
American Airlines Logo
7:07 pm - 11:09 pm
ORD
-
RSW
3h 02mnonstop
$275American Airlines
Sat, Sep 5 - Mon, Sep 14
American Airlines Logo
11:27 am - 1:50 pm
RSW
-
ORD
3h 23mnonstop
American Airlines Logo
6:50 am - 10:51 am
ORD
-
RSW
3h 01mnonstop
$275American Airlines
Thu, Oct 22 - Mon, Oct 26
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
Mon, Oct 5 - Mon, Oct 12
United Airlines Logo
12:17 pm - 2:31 pm
RSW
-
ORD
3h 14mnonstop
United Airlines Logo
7:05 am - 11:11 am
ORD
-
RSW
3h 06mnonstop
$283United Airlines
Thu, Aug 20 - Sat, Aug 22
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 - Wed, Aug 19
Southwest Logo
7:10 am - 8:55 am
RSW
-
MDW
2h 45mnonstop
Southwest Logo
6:00 pm - 9:45 pm
MDW
-
RSW
2h 45mnonstop
$283Southwest
Sat, Nov 7 - Mon, Nov 9
Southwest Logo
3:20 pm - 5:15 pm
RSW
-
MDW
2h 55mnonstop
Southwest Logo
5:05 am - 8:50 am
MDW
-
RSW
2h 45mnonstop
$283Southwest
Thu, Oct 22 - Mon, Oct 26
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
Sun, Dec 6 - Sun, Dec 13
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
Thu, Dec 10 - Sun, Dec 13
Frontier Logo
3:53 pm - 6:14 pm
RSW
-
ORD
3h 21mnonstop
Frontier Logo
10:52 am - 2:58 pm
ORD
-
RSW
3h 06mnonstop
$286Frontier
Booking Insights

KAYAK's insights & trends for Fort Myers to Chicago flights

Get data-powered insights and trends into flights from Fort Myers to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Fort Myers to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Fort Myers to Chicago departing in August.

Flight prices are typical for this route right now.

Flights to Chicago from Fort Myers usually cost between $182 and $298 in August.
The lowest price found in the past 5 days was $275 on American Airlines (Aug 13-Aug 17).

What is the cheapest Fort Myers to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Fort Myers to Chicago costs $255 on the route between Fort Myers (RSW) and Chicago Midway Airport (MDW). This is also the most popular route.

What’s the cheapest day of the week to fly from Fort Myers to Chicago?

The average price of all round-trip flights from Fort Myers to Chicago clicked on KAYAK for each day over the last 12 months.

For Fort Myers to Chicago, Thursday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to Fort Myers, the best deals are generally found on Wednesday, with Friday being the most expensive.

What is the cheapest month to fly from Fort Myers to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Fort Myers to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Fort Myers to Chicago is February, where tickets cost $194 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $356 and $349 respectively.

Can I save money by flying with a layover from Fort Myers to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $364, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Fort Myers to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Fort Myers to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Fort Myers to Chicago, you should book around 2 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Expert advice

Expert advice for your flight from Fort Myers to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Marisa Garcia

Marisa Garcia

Expert on RSW

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Good to know

Low season

February

Cheapest flight

$147
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Fort Myers to Chicago O'Hare Airport

When to book flights from Fort Myers to Chicago

Are your dates flexible? Find out the best times to travel from Fort Myers to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Fort Myers to Chicago

  • Are there hotels near the airport that offer park and sleep packages?

    Hotels near airports that offer parking packages have grown to be popular with frequent travelers. These packages provide convenient parking and hotel room options when you depart or arrive from the airport and are frequently less expensive than airport parking alone. Instead of leaving your house early in the morning if you have an early departure, you can reserve a room at an airport hotel that provides Park, Sleep, and Fly packages.

  • Where can you dine at Southwest Florida Airport?

    You will undoubtedly find something that works for you at Southwest Florida Airport, whether in a hurry or have time to look through the available dining and retail alternatives. Many airport eateries offer take-away food to be brought on board and provide sit-down table service for guests' convenience.

  • Which kid's services are available at the arrival airport?

    Passengers with kids at Chicago Midway airport can take advantage of the family services offered. Breastfeeding mothers can use the baby care room located next to the yoga room in concourse C. Diaper changing stations are also available in most washrooms in the airport. Some of the restaurants in the airport are also children-friendly and provide kid's menus and high chairs.

  • Are there ATMs at the departure and arrival airports?

    For passengers who want to withdraw before traveling at Southwest Florida Airport, ATMs are available at the upper level of the main terminal and the baggage claim area. ATMs are also available at Chicago Midway airport. The machines can be found on the landside and airside. Seaway National Bank provides ATM services and is located on concourse A.

  • What is the cheapest flight from Fort Myers to Chicago?

    In the last 5 days, the lowest price for a flight from Fort Myers to Chicago was $145 for a one-way ticket and $275 for a round-trip.

  • Do I need a passport to fly between Fort Myers and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Fort Myers to Chicago?

    Fort Myers is served by only 1 airport and there are 2 airports in Chicago. You will leave Fort Myers from Fort Myers SW Florida Intl and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Fort Myers to Chicago?

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Fort Myers to Chicago flight route.

  • Which aircraft models fly most regularly from Fort Myers to Chicago?

    The Airbus A321neo is the aircraft model that flies most regularly on the Fort Myers to Chicago flight route.

  • Which airline alliances offer flights from Fort Myers to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Fort Myers and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Fort Myers to Chicago?

    There are nonstop flights from Fort Myers to Chicago on a daily basis.

  • Which is the best airline for flights from Fort Myers to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Fort Myers to Chicago are Southwest and United Airlines. With an average price for the route of $341 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $313 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Fort Myers to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Fort Myers to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Fort Myers to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Fort Myers is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Fort Myers to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Fort Myers with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Fort Myers to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Fort Myers up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Fort Myers to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $216 or less one-way and $337 or less round-trip.
  • Passengers who wish to leave their vehicle at Southwest Florida International Airport (RSW) can reserve a parking lot by booking online. RSW airport offers both short-term and long-term parking services. The short-term parking lot is located in front of the terminal, while the long-term parking garage is found beyond the short-term parking lot.
  • Passengers can get gift ideas or buy newspapers, magazines or novels from the stores at the airport. Both in the main terminal and each of the Concourses, there are stores. Beachwear, souvenirs and everyday things are the main items sold in stores.
  • Passengers traveling with breastfeeding kids at Southwest Florida Airport can use the baby care room. The airport offers a space for mothers to breast pump, breastfeed and change their baby diapers. The room is located on the landside of the main terminal, near airline counters.
  • If you are a military officer, on arrival at Chicago Midway airport (MDW), relax and unwind at the USO lounge. This lounge offers free services to active members of the military and their families. It is located on the airside of concourse C.
  • When traveling from Southwest Florida Airport to Chicago, there are many flight options you can consider. The journey from RSW to CHI is often not long. If you want to fly directly, you can use Southwest American Airlines, Air Canada, American Airlines, Alaska Airlines, Swiss, Spirit Airlines, Qatar Airways or United Airlines. We recommend passengers research and compare the prices and services offered by different airlines.

Prefer to fly direct from Fort Myers to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Fort Myers SW Florida Intl to Chicago.
Find which airlines fly direct from Fort Myers SW Florida Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Fort Myers SW Florida Intl to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Fort Myers SW Florida Intl

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Everything you need to know for your flight from Fort Myers to Chicago

Information on your arrival and departure airports