CHI - RSW

$124 Find Cheap Flights from Chicago to Fort Myers - Compare and Save

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Everything you should know

Cheapest round-trip
$235
Typical prices: $219-$433
Frontier
Tue 1/2Sun 1/7
ORD - RSW • Non-stop
Cheapest one-way
$124
Typical prices: $128-$272
Frontier
Thu 11/22
ORD - RSW • Non-stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and others. Average duration is 3h.
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 14% average savings
Most popular
Insights
Insights
Avoid delays
Most punctual • 85% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 27% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $257 (round-trip)
Shortest trip • 4h 39m (one-way)
Insights
Insights
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We hope you love your trip to Fort Myers!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Fort Myers

Sat, Jan 2 - Thu, Jan 7
Frontier Logo
4:55 pm - 8:57 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 02mnonstop
Frontier Logo
9:41 pm - 12:02 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 21mnonstop
$235Frontier
Mon, Dec 21 - Mon, Dec 28
Frontier Logo
4:55 pm - 8:57 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 02mnonstop
Frontier Logo
9:57 pm - 12:18 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 21mnonstop
$236Frontier
Wed, Nov 18 - Tue, Nov 24
Multiple Airlines Logo
6:30 am - 10:13 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
14h 43m2 stops Denver Intl Raleigh-Durham
Multiple Airlines Logo
6:07 pm - 8:25 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 18mnonstop
$242Multiple Airlines
Fri, Dec 18 - Wed, Dec 23
Multiple Airlines Logo
7:40 pm - 9:42 amORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
13h 02m1 stop Minneapolis St Paul
Multiple Airlines Logo
9:57 pm - 12:18 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 21mnonstop
$244Multiple Airlines
Tue, Dec 8 - Sat, Dec 12
United Airlines Logo
12:55 pm - 4:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 59mnonstop
United Airlines Logo
10:40 am - 12:56 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 16mnonstop
$253United Airlines
Sat, Dec 5 - Tue, Dec 15
United Airlines Logo
11:30 am - 3:35 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 05mnonstop
United Airlines Logo
10:40 am - 12:56 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 16mnonstop
$253United Airlines
Tue, Dec 1 - Tue, Dec 8
American Airlines Logo
2:40 pm - 6:36 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
American Airlines Logo
7:37 pm - 9:55 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 18mnonstop
$253American Airlines
Sat, Dec 5 - Wed, Dec 9
American Airlines Logo
6:59 pm - 11:06 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 07mnonstop
American Airlines Logo
7:37 pm - 9:55 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 18mnonstop
$253American Airlines
Sat, Dec 5 - Tue, Dec 15
Southwest Logo
11:35 am - 3:15 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 40mnonstop
Southwest Logo
7:00 am - 8:55 amRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
2h 55mnonstop
$253Southwest
Tue, Nov 17 - Tue, Nov 24
Southwest Logo
6:45 am - 10:30 amMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 45mnonstop
Southwest Logo
9:45 pm - 11:45 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
3h 00mnonstop
$253Southwest
Booking Insights

Price, demand and travel trends for Chicago to Fort Myers flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Chicago to Fort Myers typically range from $219 to $433. The lowest price found in the past 5 days was $235, on Frontier.

What is the cheapest Chicago to Fort Myers flight route?

Chicago O'Hare Intl Airport (ORD) to Fort Myers (RSW) is the cheapest Chicago to Fort Myers route, averaging $307 round-trip. Other Chicago to Fort Myers routes average $407, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago to Fort Myers. It’s 4% cheaper than the average day, while Sunday is the most expensive, with prices 12% higher.

What’s the cheapest month to fly from Chicago to Fort Myers?

•February is the cheapest month to fly from Chicago to Fort Myers at $221 round-trip.
•June ($379) and December ($363) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 71% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago to Fort Myers the cheapest?

Flights from Chicago to Fort Myers are cheapest 7 weeks before departure. Booking in this window typically costs about 27% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Chicago to Fort Myers

 
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.

Key details for Chicago to Fort Myers flights

Low season

August

Cheapest flight

$124
Beat the crowds with an average 61% drop in travelers.
The most popular month to fly with an average 101% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Fort Myers

When to book flights from Chicago to Fort Myers

Are your dates flexible? Find out the best times to travel from Chicago to Fort Myers based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago to Fort Myers flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago to Fort Myers?

    These are the earliest and latest flight times available from Chicago to Fort Myers:

    • Earliest: departs at 5:05 am and lands at 8:05 am
    • Latest: departs at 8:55 pm and lands at 11:55 pm.

    The flight takes about 3h.

  • What cabin classes can I book on flights from Chicago to Fort Myers?

    Three cabin classes are available on flights from Chicago to Fort Myers:

    • Economy Class
    • Premium Economy Class
    • First Class

  • How long is a flight from Chicago to Fort Myers?

    A nonstop flight from Chicago to Fort Myers takes 3h, covering 1,110 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago to Fort Myers flight?

    Round-trip flights from Chicago to Fort Myers range from $219 to $433, with an average of $313 over the past 12 months. Anything below $219 counts as a good deal.

  • How expensive are last-minute Chicago to Fort Myers flights?

    Last-minute fares on this route (booked within two weeks of departure) run 20% above the $313 route average. Book 7 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago to Fort Myers?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $257 round-trip via New York John F Kennedy Intl (JFK), compared to $311 for nonstop.

  • How does on-time performance compare across airlines flying from Chicago to Fort Myers?

    United Airlines is slightly above the route average for timely arrivals, while Frontier has a lower on-time arrival rate. On-time arrival rates on Chicago to Fort Myers flights are:

    • United Airlines: 85% on time
    • Frontier: 84% on time
    • Southwest: 76% on time

    Overall, flights on this route are punctual 80% of the time on average.

  • What is the standard checked-bag allowance on flights from Chicago to Fort Myers?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Chicago to Fort Myers spread across the day?

    Morning is the busiest departure period on Chicago to Fort Myers flights, with 43% of flights leaving in that window. Afternoon departures account for 36%, evening flights for 21%, and night flights for 0%.

  • Which airlines offer Wi-Fi on Chicago to Fort Myers flights?

    Two airlines offer in-flight Wi-Fi on Chicago to Fort Myers flights:

    • American Airlines
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from Chicago to Fort Myers looking right now?

    One-way fares from Chicago to Fort Myers are currently lower than usual. Average one-way flight prices are about $128, which is 32% below the typical average for this route.

  • What car rental options are available at Fort Myers SW Florida Intl Airport (RSW)?

    Fort Myers SW Florida Intl Airport (RSW) hosts 5 major car rental companies, with daily rates averaging $49 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Thrifty
    • Fox
    • Budget

  • Which airports can I use when flying from Chicago to Fort Myers?

    Flights from Chicago to Fort Myers may depart from several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Flights usually arrive at Fort Myers SW Florida Intl (RSW).

  • What time of day has the fewest delays on flights from Chicago to Fort Myers?

    Morning flights have the fewest delays on this route, while evening departures tend to have the most.

  • At what point is a flight considered delayed from Chicago to Fort Myers?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago to Fort Myers route, 21% of flights were delayed in the past 3 months, with delays averaging 2h 43m.

  • Which airports do connecting flights from Chicago to Fort Myers pass through?

    One-stop flights from Chicago to Fort Myers most commonly connect through:

    • Chicago O'Hare Intl (ORD) - 48% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 28% of one-stop connections
    • Charlotte Douglas (CLT) - 4% of one-stop connections
    • Minneapolis St Paul (MSP) - 3% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago to Fort Myers?

    Yes. Flexible dates can save you up to 15% on flights from Chicago to Fort Myers. Wednesday is the cheapest departure day at $301 round-trip on average, while Sunday is the most expensive at $351, a difference of $50.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago to Fort Myers?

    4 airlines operate flights between Chicago and Fort Myers. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Southwest
    • Frontier

  • How much time can I save by choosing a different layover airport from Chicago to Fort Myers?

    Flying via Columbus (CMH) gives the shortest average 1-stop total travel time at 4h 39m, compared with 4h 43m via Orlando (MCO) and 4h 49m via Lambert-St Louis (STL).

  • What is the time difference between Chicago and Fort Myers?

    Fort Myers is 1 hour ahead of Chicago (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Fort Myers?

    Some of the most popular sights in Fort Myers are Lee Memorial Hospital, Terry Park Ballfield and Red Sox Stadium. These are among the most viewed places in Fort Myers on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago to Fort Myers flights?

    Among airlines operating Chicago to Fort Myers flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Frontier: offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago to Fort Myers flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Frontier: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

  • What amenities does O'Hare International Airport offer children?

    In addition to several private nursing and changing rooms that are placed in every terminal of O’Hare International Airport, there is also a Kids On The Fly interactive exhibit that is in Terminal 2. This indoor playground features aviation themed activities and toys, making it popular amongst kids of all ages.

  • Where can I grab a bite to eat at Chicago Midway International Airport?

    Go Go White Sox Bar and Grill is in the Central Market of Chicago Midway International Airport and has beers, sandwiches, burgers, and steaks, while Porkchop is in Concourse B and specializes in BBQ. Tabo Sushi is also in the Central Market and sells to-go Japanese food.

  • What are some nice hotels near Southwest Airport?

    The Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park is an affordable hotel that is only a 5m drive from the airport and 15m drive from Lakes Park. To stay somewhere stylish, select the Hilton Garden Inn, which is a 4m drive from the airport and a 15m drive from the Koreshan State Park.

  • Where can I rent a car from Southwest Florida International Airport?

    To find the rental car desks, go to the baggage claim of the Arrivals terminal in Southwest Florida International Airport. There are 7 different companies that have on-site locations at the airport, including Budget, Hertz, and National. Payless does not have an office in this area, but they do provide a free shuttle service near the airport parking garage for guests to get to their car storage facility.

Your guide to booking Chicago to Fort Myers flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average $301, about $50 less than Sunday fares (14% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 7 weeks before you fly. On this route, that window historically saves about 27% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago to Fort Myers trip for February. Fares historically average $221 round-trip in that month - typically $158 less than the most expensive month, which is June (based on the last 12 months).
  • For the best chance of arriving on time, fly with United Airlines. Over the past three months, 85% of United Airlines flights from Chicago to Fort Myers arrived on time, slightly above the route average of 79%. When flights on this route arrive late, they're delayed by an average of 2h 43m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • If you have the time, taking a 1-stop flight through New York John F Kennedy Intl Airport (JFK) can be cheaper than flying direct. The cheapest layover option averages $257 round-trip on this route - about $54 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Fort Myers SW Florida Intl Airport.

    • Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park
    • Holiday Inn Express & Suites Fort Myers Airport By IHG
  • When booking flights from Chicago to Fort Myers, there are two major airports that you can depart from. Chicago Midway International Airport (MDW) is a convenient option for travelers coming from the southern part of the city, while O'Hare International Airport (ORD) is located in the north.
  • To have a non-stop flight from Chicago to Fort Myers, book your trip with either Spirit or American Airlines. If you will be traveling with a lot of luggage, fly with Southwest Airlines, as they allow customers to check up to two suitcases for free.
  • If you find flying to be stressful, drop by the yoga room that is in Concourse C of Chicago Midway International Airport. In addition to complimentary exercise mats, this room also has TVs that display common yoga poses and play tranquil music.
  • For those that are traveling to Fort Myers for work, consider having your meeting or workshop in the Business Center that can be found in Concourse B of Southwest Florida International Airport (RSW). There is a private room that can be rented for a small fee as well as a video projector, Internet access, and photocopy machines.
  • If you have a large amount of cash but would feel more comfortable having a debit card, go to one of the Cash-to-Card Kiosks in Southwest Florida International Airport. These machines allow you to turn your cash into a prepaid Visa debit card for a $5 fee, and their maximum value is $1,000.

Prefer to fly direct from Chicago to Fort Myers?

 
Find which airlines fly direct from Chicago to Fort Myers SW Florida Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago to Fort Myers SW Florida Intl

Monday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Tuesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Wednesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Thursday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Direct returns

Fort Myers SW Florida Intl to Chicago

Monday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Tuesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Wednesday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Thursday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Friday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

More options for your flight from Chicago to Fort Myers

Complete your trip to Fort Myers with a hotel stay or car rental