RSW - ORD

$143 Find Cheap Flights from Fort Myers to Chicago O'Hare Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$285
Typical prices: $195-$370
Frontier
Sat 11/24Wed 11/28
RSW - ORD • Non-stop
Cheapest one-way
$143
Typical prices: $124-$261
Frontier
Mon 10/29
RSW - ORD • 1 stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and Frontier. Average duration is 3h 21m
Direct flights
+1
Direct flights
+1
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 38% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $210 (round-trip)
Shortest trip • 4h 50m (one-way)
Insights
Insights
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We hope you love your trip to Chicago O'Hare Intl Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Fort Myers to O'Hare Intl (RSW-ORD)

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

Recent round-trip flight deals from Fort Myers to O'Hare Intl

Sat, Nov 21 - Sat, Nov 28
Frontier Logo
5:48 pm - 12:53 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
8h 05m1 stop Denver Intl
Frontier Logo
1:58 pm - 5:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
$285Frontier
Tue, Nov 24 - Sat, Nov 28
Frontier Logo
6:52 pm - 9:10 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 18mnonstop
Frontier Logo
1:58 pm - 5:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
$285Frontier
Thu, Nov 19 - Mon, Nov 23
Multiple Airlines Logo
12:55 pm - 6:30 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
6h 35m1 stop Minneapolis St Paul
Multiple Airlines Logo
1:58 pm - 5:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
$285Multiple Airlines
Thu, Nov 19 - Mon, Nov 23
Multiple Airlines Logo
12:55 pm - 6:30 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
6h 35m1 stop Minneapolis St Paul
Multiple Airlines Logo
1:58 pm - 5:54 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 56mnonstop
$292Multiple Airlines
Sat, Dec 5 - Tue, Dec 8
United Airlines Logo
2:14 pm - 4:33 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 19mnonstop
United Airlines Logo
8:41 am - 12:44 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 03mnonstop
$297United Airlines
Thu, Oct 8 - Sat, Oct 10
United Airlines Logo
12:17 pm - 2:31 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 14mnonstop
United Airlines Logo
4:30 pm - 8:36 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 06mnonstop
$297United Airlines
Thu, Feb 4 - Mon, Feb 8
American Airlines Logo
11:52 am - 2:15 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 23mnonstop
American Airlines Logo
6:57 am - 11:02 amORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
3h 05mnonstop
$297American Airlines
Wed, Dec 2 - Wed, Dec 9
American Airlines Logo
7:40 pm - 10:00 pmRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
3h 20mnonstop
American Airlines Logo
6:50 pm - 10:43 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
2h 53mnonstop
$297American Airlines
Tue, Oct 13 - Sat, Oct 24
JetBlue Logo
6:32 am - 8:47 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
27h 15m1 stop Boston Logan Intl
JetBlue Logo
12:38 pm - 9:21 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
7h 43m1 stop New York John F Kennedy Intl
$496JetBlue
Tue, Oct 13 - Mon, Oct 19
JetBlue Logo
8:20 pm - 8:47 amRSW  Fort Myers SW Florida Intl-ORD Chicago O'Hare Intl
13h 27m1 stop Boston Logan Intl
JetBlue Logo
6:10 am - 9:21 pmORD  Chicago O'Hare Intl-RSW Fort Myers SW Florida Intl
14h 11m1 stop New York John F Kennedy Intl
$520JetBlue
Booking Insights

Price, demand and travel trends for Fort Myers to Chicago O'Hare Intl Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Fort Myers to Chicago O'Hare Intl Airport with more confidence.

How much is a round-trip flight from Fort Myers to Chicago O'Hare Intl Airport?

Round-trip flights from Fort Myers to Chicago O'Hare Intl Airport start at $285. Prices are typical for this route right now, with typical round-trip fares ranging from $195 to $370. The lowest price found in the past 5 days was $285 on Frontier.

What's the cheapest day of the week to fly from Fort Myers to Chicago O'Hare Intl Airport?

Friday is the cheapest day of the week to fly from Fort Myers to Chicago O'Hare Intl Airport, it is 10% cheaper than the average day. Sunday is the most expensive day with flight prices 25% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Fort Myers to Chicago O'Hare Intl Airport?

  • January and February are the cheapest months to fly from Fort Myers to Chicago O'Hare Intl Airport at $179 round-trip.
  • July ($352) and June ($350) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 96% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Fort Myers to Chicago O'Hare Intl Airport the cheapest?

Flights from Fort Myers to Chicago O'Hare Intl Airport are cheapest 4 weeks before departure. Booking in this window typically costs about 30% 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 Fort Myers to O'Hare Intl

 
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.

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 Fort Myers to Chicago O'Hare Intl Airport flights

Low season

February

Cheapest flight

$143
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Fort Myers to Chicago O'Hare Intl Airport

When to book flights from Fort Myers to O'Hare Intl

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

Your Fort Myers to Chicago O'Hare Intl Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines have lounges at Chicago O'Hare International Airport?

    ORD has several airline lounges such as Admiral Club, United Club, American Flagship Lounge, Sky Club, Swissport Lounge, British Airways Lounge, and SAS Lounge. Flyers from any airline club can find a quiet place to sit back, use the wireless Internet, work, or recharge their smart devices at ORD. Flyers who don't own membership to the airline clubs in ORD can buy a day's pass for most of the airline clubs.

  • Where are car rental facilities located at Chicago O’Hare International Airport?

    ORD has a car rental center on its complex in the Multi-Modal Facility with several different car rental companies. ORD’s Airport Transit System provides transport from the terminals to the Multi-Modal Facility and vice versa. Alamo, ACD Rent A Car, Budget, Avis, Enterprise, Dollar, Fox, Hertz, Routes Car Rental, National, SIXT, Thrifty, and Payless are ORD’s on site car rental agencies.

  • Where is the business center located at Chicago O'Hare International Airport?

    For business people, if you have important business to tend to while at ORD, you can use the Chicago Hilton Airport Hotel's business center. The business center is at the lower arcade level of the hotel. The center facilitates full-service services such as photocopying, printing, packaging and shipping, Internet, and faxing. The hotel is adjacent to the three Domestic Terminals. You can get there through underground footways.

  • Where is Chicago O'Hare International Airport's service animal/pet relief area?

    ORD is a pet and service animal welcoming airport. The Airport has outdoor and indoor pet/service animal relief areas near the terminals, and they are accessible to flyers traveling with their pets or service animals round the clock. At O'Hare Airport, you'll find the pet/service animal relief areas in Terminal 3 Rotunda, Terminal 1 C Concourse next to gate 10, and Terminal 5, 2, and 1 outside the arrivals at gates 5B, 2A, and 2A, respectively.

  • Which airlines offer extra legroom and free seat selection on Fort Myers to Chicago O'Hare Intl Airport flights?

    Among airlines operating Fort Myers to Chicago O'Hare Intl Airport flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; 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 Fort Myers to Chicago O'Hare Intl Airport?

    3 airlines operate flights between Fort Myers and Chicago O'Hare Intl Airport. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Frontier

  • Which airports can I use when flying from Fort Myers to Chicago O'Hare Intl Airport?

    Flights from Fort Myers to Chicago O'Hare Intl Airport usually depart from Fort Myers SW Florida Intl (RSW) and arrive at Chicago O'Hare Intl (ORD).

  • Which airlines include bags at no extra cost on Fort Myers to Chicago O'Hare Intl Airport 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 and a checked bag in Business 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 Fort Myers to Chicago O'Hare Intl Airport?

    Three cabin classes are available on flights from Fort Myers to Chicago O'Hare Intl Airport:

    • Economy Class
    • Business Class
    • First Class

  • How much can I save by taking a layover when flying from Fort Myers to Chicago O'Hare Intl Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $210 round-trip via Boston Logan Intl (BOS), compared to $291 for nonstop.

  • What is the standard checked-bag allowance on flights from Fort Myers to Chicago O'Hare Intl Airport?

    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 aircraft model is used most often on flights from Fort Myers to Chicago O'Hare Intl Airport?

    The Airbus A321neo family is used most often on this route, operated mainly by United Airlines and Spirit Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

  • Which airports do connecting flights from Fort Myers to Chicago O'Hare Intl Airport pass through?

    One-stop flights from Fort Myers to Chicago O'Hare Intl Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 45% of one-stop connections
    • Minneapolis St Paul (MSP) - 15% of one-stop connections
    • Denver Intl (DEN) - 10% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 10% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Fort Myers to Chicago O'Hare Intl Airport?

    Yes. Being flexible with your travel dates can save you up to 29% on the Fort Myers to Chicago O'Hare Intl Airport route. Friday is the cheapest departure day at $262 round-trip on average, while Sunday is the most expensive at $366, a difference of $104. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How are flight departures from Fort Myers to Chicago O'Hare Intl Airport spread across the day?

    Morning is the busiest departure period on Fort Myers to Chicago O'Hare Intl Airport flights, with 38% of flights leaving in that window. Afternoon departures account for 37%, evening flights for 25%, and night flights for 0%.

  • What popular places can I visit in Chicago O'Hare Intl Airport?

    Some of the most popular sights in Chicago O'Hare Intl Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago O'Hare Intl Airport on KAYAK.

  • What are the earliest and latest flights from Fort Myers to Chicago O'Hare Intl Airport?

    These are the earliest and latest flight times available from Fort Myers to Chicago O'Hare Intl Airport:

    • Earliest: departs at 6:02 am and lands at 9:23 am
    • Latest: departs at 8:44 pm and lands at 12:05 am.

    The flight takes about 3h 21m.

  • How expensive are last-minute Fort Myers to Chicago O'Hare Intl Airport flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 15% above the route average of $291. Book 4 weeks before departure for the lowest fares.

  • How long is a flight from Fort Myers to Chicago O'Hare Intl Airport?

    A nonstop flight from Fort Myers to Chicago O'Hare Intl Airport takes 3h 21m, covering 1,122 miles.

  • Do I need a passport to fly from Fort Myers to Chicago O'Hare Intl Airport?

    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 Fort Myers to Chicago O'Hare Intl Airport looking right now?

    One-way fares from Fort Myers to Chicago O'Hare Intl Airport are currently higher than usual. Average one-way flight prices are about $225, which is 25% above the typical average for this route.

  • How much time can I save by choosing a different layover airport from Fort Myers to Chicago O'Hare Intl Airport?

    Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 4h 50m, compared with 5h 59m via Detroit Metropolitan Wayne County (DTW) and 6h 00m via Atlanta Hartsfield-Jackson (ATL).

  • What is the time difference between Fort Myers and Chicago O'Hare Intl Airport?

    Chicago O'Hare Intl Airport is 1 hour behind Fort Myers (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Chicago O'Hare Intl Airport (ORD)?

    Chicago O'Hare Intl Airport (ORD) hosts 5 major car rental companies, with daily rates starting from around $17 for economy cars. Top options include:
    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Dollar
    • Ace

  • How much should I expect to pay for a Fort Myers to Chicago O'Hare Intl Airport flight?

    Round-trip flights from Fort Myers to Chicago O'Hare Intl Airport range from $195 to $370, with an average of $291 over the past 12 months. Anything below $195 counts as a good deal.

  • Which airlines offer Wi-Fi on Fort Myers to Chicago O'Hare Intl Airport flights?

    Two airlines offer in-flight Wi-Fi on Fort Myers to Chicago O'Hare Intl Airport 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 Fort Myers to Chicago O'Hare Intl Airport 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 Friday departure instead of Sunday. On this route, Friday flights average $262 - about $104 less than Sunday (28% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 4 weeks before you fly. On this route, that window historically saves about 30% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Fort Myers to Chicago O'Hare Intl Airport trip for January. Fares historically average $179 round-trip in that month - typically $173 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Boston Logan Intl Airport (BOS) can be cheaper than flying direct. The cheapest layover option averages $210 round-trip on this route - about $81 less than direct flights (based on the last 12 months).
  • On the day you're flying to Chicago from Fort Myers, you should arrive at Southwest Florida International Airport (RSW) approximately 2h before your flight's departure time. It will allow you time to smoothly check in at RSW, walk through the busy TSA security checkpoint, and get to your aircraft in time.
  • Chicago O'Hare International Airport (ORD) is one of Chicago's major airports. ORD includes four terminals; Terminals 3, 2, and 1 are for local flights, while Terminal 4 is for international flights. The three Domestic Terminals on the secured side are within walking distance through walkways following the signage. You must use the Airport Transit System to reach the International Terminal from any of the three Domestic Terminals.
  • If you're connecting to ORD from Fort Myers, you can distract yourself on the flight with movies and TV shows on Netflix and live TV on the plane through the personal entertainment device. United Airlines, American Airlines, and Delta provide an entertainment feature for the route.
  • Flights connecting to ORD from Fort Myers may include at least one layover. The most common layover cities are Charlotte, Detroit, Philadelphia, Washington D.C, New York, Dallas, Atlanta, Newark, and Minneapolis.
  • If someone is picking you up at ORD, they can park temporarily for free and wait at the Cell Phone Lot. And pick you up at the front curb once you call them.

Prefer to fly direct from Fort Myers to Chicago O'Hare Airport?

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

Direct departures

Fort Myers SW Florida Intl to Chicago O'Hare Intl

Monday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Fort Myers SW Florida Intl

Monday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

See more direct flights

More options for your flight from Fort Myers to O'Hare Intl

Complete your trip to Chicago with a hotel stay or car rental