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Flights from Chicago to Fort Myers

Book direct flights from Chicago to Fort Myers: One way flights from $138, round trip flights from $294. Find flight deals for the next 3 months below.

      • Cheapest nonstop
        MDW 6:55 PM
        2h 50m
        Nonstop
        RSW 10:45 PM
        Chicago - Fort Myers | Tue, Jul 28 | Hahn Air
        RSW 5:10 AM
        2h 50m
        Nonstop
        MDW 7:00 AM
        Fort Myers - Chicago | Mon, Aug 3 |
        $294 $343
        14% off
        14% off
        $343 $294
      • ORD 5:30 AM
        5h 41m
        1 stop
        RSW 12:11 PM
        Chicago - Fort Myers | Sat, Jul 25 | Delta Air Lines
        RSW 6:27 PM
        6h 26m
        1 stop
        ORD 11:53 PM
        Fort Myers - Chicago | Sat, Aug 1 | Delta Air Lines
        $265 $343
        23% off
        23% off
        $343 $265
      • MDW 6:00 AM
        7h 35m
        1 stop
        RSW 2:35 PM
        Chicago - Fort Myers | Tue, Jul 28 | Delta Air Lines
        RSW 6:27 PM
        6h 26m
        1 stop
        ORD 11:53 PM
        Fort Myers - Chicago | Sat, Aug 1 | Delta Air Lines
        $265 $343
        23% off
        23% off
        $343 $265
      • MDW 6:05 AM
        5h 8m
        1 stop
        RSW 12:13 PM
        Chicago - Fort Myers | Wed, Aug 12 | Delta Air Lines
        RSW 6:29 PM
        6h 28m
        1 stop
        ORD 11:57 PM
        Fort Myers - Chicago | Mon, Aug 17 | Delta Air Lines
        $283
        17% off
        $343 $283
      • MDW 9:29 AM
        6h 50m
        1 stop
        RSW 5:19 PM
        Chicago - Fort Myers | Thu, Sep 10 | Delta Air Lines
        RSW 6:24 PM
        5h 21m
        1 stop
        MDW 10:45 PM
        Fort Myers - Chicago | Tue, Sep 15 | Delta Air Lines
        $284
        17% off
        $343 $284
      • MDW 9:29 AM
        6h 50m
        1 stop
        RSW 5:19 PM
        Chicago - Fort Myers | Tue, Sep 8 | Delta Air Lines
        RSW 6:24 PM
        6h 35m
        1 stop
        ORD 11:59 PM
        Fort Myers - Chicago | Mon, Sep 14 | Delta Air Lines
        $289
        16% off
        $343 $289
      • MDW 6:05 AM
        7h 19m
        1 stop
        RSW 2:24 PM
        Chicago - Fort Myers | Mon, Aug 17 | Delta Air Lines
        RSW 6:46 AM
        6h 54m
        1 stop
        ORD 12:40 PM
        Fort Myers - Chicago | Mon, Aug 24 | Delta Air Lines
        $296
        14% off
        $343 $296
      • ORD 4:26 PM
        3h 8m
        Nonstop
        RSW 8:34 PM
        Chicago - Fort Myers | Tue, Jul 28 | United Airlines
        RSW 12:36 PM
        6h 31m
        1 stop
        MDW 6:07 PM
        Fort Myers - Chicago | Sat, Aug 1 | Delta Air Lines
        $301
        12% off
        $343 $301
      • ORD 12:41 PM
        2h 53m
        Nonstop
        RSW 4:34 PM
        Chicago - Fort Myers | Tue, Jul 28 | American Airlines
        RSW 6:27 PM
        4h 48m
        1 stop
        MDW 10:15 PM
        Fort Myers - Chicago | Sat, Aug 1 | Delta Air Lines
        $305
        11% off
        $343 $305
      • ORD 7:29 PM
        3h
        Nonstop
        RSW 11:29 PM
        Chicago - Fort Myers | Sat, Jul 25 | American Airlines
        RSW 2:00 PM
        5h 7m
        1 stop
        MDW 6:07 PM
        Fort Myers - Chicago | Sat, Aug 1 | Delta Air Lines
        $305
        11% off
        $343 $305
      • CHI 1:00 PM
        17h 25m
        1 stop
        FMY 2:00 PM
        Chicago - Fort Myers | Sun, Jul 19 | Normal Airline
        FMY 3:00 PM
        6h
        Nonstop
        CHI 4:00 PM
        Fort Myers - Chicago | Tue, Jul 21 | Normal Airline
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      • Cheapest nonstop
        ORD 7:15 AM
        3h 6m
        Nonstop
        RSW 11:21 AM
        Chicago - Fort Myers | Tue, Sep 1 | United Airlines
        $138 $156
        12% off
        12% off
        $156 $138
      • MDW 6:05 AM
        5h 8m
        1 stop
        RSW 12:13 PM
        Chicago - Fort Myers | Tue, Sep 1 | Delta Air Lines
        $101 $156
        35% off
        35% off
        $156 $101
      • ORD 6:30 PM
        5h 10m
        1 stop
        RSW 12:40 AM
        Chicago - Fort Myers | Sat, Aug 29 | Delta Air Lines
        $103 $156
        34% off
        34% off
        $156 $103
      • MDW 12:46 PM
        7h 32m
        1 stop
        RSW 9:18 PM
        Chicago - Fort Myers | Thu, Aug 20 | Delta Air Lines
        $103
        34% off
        $156 $103
      • MDW 5:10 PM
        6h 30m
        1 stop
        RSW 12:40 AM
        Chicago - Fort Myers | Wed, Aug 19 | Delta Air Lines
        $110
        28% off
        $156 $110
      • ORD 5:30 AM
        5h 43m
        1 stop
        RSW 12:13 PM
        Chicago - Fort Myers | Wed, Aug 12 | Delta Air Lines
        $132
        15% off
        $156 $132
      • ORD 6:40 AM
        6h 44m
        1 stop
        RSW 2:24 PM
        Chicago - Fort Myers | Mon, Aug 17 | Delta Air Lines
        $133
        15% off
        $156 $133
      • MDW 5:10 PM
        6h 30m
        1 stop
        RSW 12:40 AM
        Chicago - Fort Myers | Fri, Aug 28 | Delta Air Lines
        $133
        15% off
        $156 $133
      • ORD 5:30 AM
        5h 43m
        1 stop
        RSW 12:13 PM
        Chicago - Fort Myers | Tue, Aug 11 | Delta Air Lines
        $135
        13% off
        $156 $135
      • MDW 4:30 PM
        7h 6m
        1 stop
        RSW 12:36 AM
        Chicago - Fort Myers | Wed, Sep 9 | Delta Air Lines
        $137
        12% off
        $156 $137
      • CHI 1:00 PM
        17h 25m
        1 stop
        FMY 2:00 PM
        Chicago - Fort Myers | Sun, Jul 19 | Normal Airline
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Find cheap airlines flights from Chicago to Fort Myers

You can choose from 3 airlines that fly from Chicago to Fort Myers, including Frontier Airlines, Delta Air Lines, and American Airlines. United Airlines has lowest fares on this route.
Frontier Airlines logo Frontier Airlines
Delta Air Lines logo Delta Air Lines
American Airlines logo American Airlines
Airlines are determined based on actual purchased flight tickets from Chicago to Fort Myers according to previous 12 months data from Trip.com.

Flight Info | Chicago to Fort Myers

The distance between Chicago and Fort Myers is approximately 1,780.05 km. It takes around 2 hours 57 minutes on average to fly from Chicago to Fort Myers. Based on Trip.com's data travel demand peaks in July. The off-season for travel is August.

Cheapest one-way flight price$101
Cheapest round-trip ticket price$265
Off-season for travelAugust
Peak season for travelJuly
Flight distance1,780.05 km
Average flight time2 hours 57 minutes
Popular airlineFrontier Airlines
Flight statistics for the Chicago–Fort Myers route are based on aggregated booking data from Trip.com over the past 12 months.

Frequently Asked Questions

  • What are the cheapest flights from Chicago to Fort Myers (CHI-FMY)?

    Based on Trip.com data, Delta Air Lines offers one-way fares as low as $101 on Cheapest nonstop routes (e.g. MDW to RSW on Tue, Sep 1), while Delta Air Lines offers Cheapest nonstop round-trips from $265 departing on Sat, Jul 25 and returning on Sat, Aug 1.
  • At the moment, you can catch a nonstop flight from Chicago to Fort Myers with the following airlines, including: Frontier Airlines American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes around 2 hours 57 minutes to fly from Chicago (CHI) to Fort Myers (FMY).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Fort Myers is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • Based on Trip.com data in the past 4 weeks, there is 18 flight per week flying from Chicago to Fort Myers. You can check the weekly schedule for popular airlines on this route below: American Airlines: S/M/T/W/T/F/S -- AA3238 (09:25)
  • To find best deals on flights from Chicago to Fort Myers, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Tue, Sep 1, with one-way flights priced at just $101.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Fort Myers travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Chicago to Fort Myers is August, when demand for travel is lower.
  • After crunching the numbers on our July flight calendar, it's currently cheapest to fly from Chicago to Fort Myers on July 28, 2026 with Delta Air Lines, with prices starting at $264.
  • You can land at any one of the following hubs in Fort Myers, with O'Hare International Airport to Southwest Florida International Airport (ORD-RSW) is by far the most common option on this route: Southwest Florida International Airport (RSW).
  • The time difference between Fort Myers and Chicago is 1h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

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Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.