CHI - RSW

$143 Find Cheap Flights from Chicago to Fort Myers - Compare and Save

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Everything you should know

Cheapest round-trip
$276
Typical prices: $209-$420
Frontier
Thu 12/6Mon 12/10
ORD - RSW • Non-stop
Cheapest non-stop
$277
Typical prices: $208-$417
Frontier
Thu 11/29Thu 12/6
ORD - RSW • Non-stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and others. Average duration is 2h 58m.
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 13% 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 26% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 28% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $226 (round-trip)
Shortest trip • 4h 39m (one-way)
Insights
Insights
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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

Sun, Dec 6 - Thu, Dec 10
Frontier Logo
10:52 am - 2:58 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 06mnonstop
Frontier Logo
10:57 am - 8:16 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
10h 19m2 stops Cleveland Hopkins Intl Atlanta Hartsfield-Jackson
$276Frontier
Sun, Nov 29 - Sun, Dec 6
Frontier Logo
1:58 pm - 5:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
Frontier Logo
3:53 pm - 6:14 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 21mnonstop
$277Frontier
Fri, Oct 23 - Tue, Oct 27
Southwest Logo
6:50 pm - 10:40 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 50mnonstop
Southwest Logo
8:15 am - 1:20 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
6h 05m1 stop Nashville Intl
$277Southwest
Tue, Oct 27 - Fri, Oct 30
Southwest Logo
6:35 pm - 10:25 pmMDW  Chicago Midway-RSW Fort Myers SW Florida Intl
2h 50mnonstop
Southwest Logo
2:50 pm - 9:25 pmRSW  Fort Myers SW Florida Intl-MDW Chicago Midway
7h 35m1 stop Nashville Intl
$277Southwest
Sun, Dec 13 - Fri, Dec 18
Multiple Airlines Logo
10:52 am - 2:58 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 06mnonstop
Multiple Airlines Logo
6:30 am - 6:40 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
13h 10m1 stop Minneapolis St Paul
$277Multiple Airlines
Tue, Nov 17 - Mon, Nov 23
Multiple Airlines Logo
7:15 am - 10:08 amORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
25h 53m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
Multiple Airlines Logo
6:52 pm - 9:10 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 18mnonstop
$296Multiple Airlines
Sat, Oct 31 - Tue, Nov 3
United Airlines Logo
7:15 am - 11:18 amORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 03mnonstop
United Airlines Logo
4:45 pm - 7:04 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 19mnonstop
$297United Airlines
Tue, Oct 20 - Tue, Oct 27
United Airlines Logo
9:02 am - 1:08 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 06mnonstop
United Airlines Logo
9:10 am - 11:24 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 14mnonstop
$297United Airlines
Thu, Nov 12 - Thu, Nov 19
American Airlines Logo
2:50 pm - 6:50 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 00mnonstop
American Airlines Logo
7:26 pm - 9:55 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 29mnonstop
$297American Airlines
Sat, Nov 7 - Tue, Nov 17
American Airlines Logo
6:50 pm - 10:43 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 53mnonstop
American Airlines Logo
11:52 am - 2:16 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 24mnonstop
$297American Airlines
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 from Chicago to Fort Myers with more confidence.

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

Round-trip flights from Chicago to Fort Myers start at $276. Prices are typical for this route right now, with typical round-trip fares ranging from $209 to $420. The lowest price found in the past 5 days was $276 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 $297 round-trip. Other Chicago to Fort Myers routes average $387, based on KAYAK data over the past 12 months.

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

Wednesday is the cheapest day of the week to fly from Chicago to Fort Myers, it is 6% cheaper than the average day. Sunday is the most expensive day with flight prices 12% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • January is the cheapest month to fly from Chicago to Fort Myers at $219 round-trip.
  • June ($378) and July ($362) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 72% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices 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 26% 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

$143
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 13% increase in price.
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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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.

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

    Among airlines operating Chicago to Fort Myers flights:

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

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

  • What airlines are available 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

  • 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).

  • 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:

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

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

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

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

    • Economy Class
    • First Class

  • 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 $226 round-trip via New York John F Kennedy Intl (JFK), compared to $301 for nonstop.

  • 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.

  • 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) - 51% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 29% of one-stop connections
    • New York John F Kennedy Intl (JFK) - 3% of one-stop connections
    • Boston Logan Intl (BOS) - 2% of one-stop connections

    Chicago O'Hare Intl (ORD) handles the largest share of one-stop connections on this route.

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

    Yes. Being flexible with your travel dates can save you up to 16% on the Chicago to Fort Myers route. Wednesday is the cheapest departure day at $286 round-trip on average, while Sunday is the most expensive at $340, a difference of $54. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • 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 2 hours 43 minutes.

  • 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 46% of flights leaving in that window. Afternoon departures account for 36%, evening flights for 18%, and night flights for 0%.

  • 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 Edison Mall. These are among the most viewed places in Fort Myers on KAYAK.

  • 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 8:03 am
    • Latest: departs at 8:55 pm and lands at 11:53 pm.

    The flight takes about 2h 58m.

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

    Last-minute fares on this route - booked within 2 weeks of departure - run 18% above the route average of $303. Book 7 weeks before departure for the lowest fares.

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

    A nonstop flight from Chicago to Fort Myers takes 2h 58m, 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 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 $149, which is 16% below the typical average for this route.

  • How does United Airlines’s on-time performance compare to other airlines on Chicago to Fort Myers flights?

    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 on time 79% of the time on average.

  • How do delay rates compare for morning and evening flights from Chicago to Fort Myers?

    Night flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

  • 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 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 starting from around $20 for economy cars. Top options include:
    • Hertz
    • Dollar
    • Thrifty
    • Fox
    • Budget

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

    Round-trip flights from Chicago to Fort Myers range from $209 to $420, with an average of $303 over the past 12 months. Anything below $209 counts as a good deal.

  • 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.

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 can be flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average $286 - about $54 less than Sunday (16% 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 26% 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 January. Fares historically average $219 round-trip in that month - typically $159 less than the most expensive month, which is June (based on the last 12 months).
  • If arriving on time is high on your priority list, United Airlines is the strongest pick on this route. 85% of United Airlines flights from Chicago to Fort Myers arrived on time in the past 3 months, slightly above the route's average on-time arrival rate of 79%. When flights on this route do arrive late, the average delay is 2 hours 43 minutes, so choosing a carrier with strong on-time performance can make a difference on tight schedules.
  • 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 $226 round-trip on this route - about $75 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,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Tuesday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Wednesday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Saturday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Sunday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

See more direct flights

Direct returns

Fort Myers SW Florida Intl to Chicago

Monday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Tuesday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Wednesday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Saturday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Sunday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +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