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Flights from Fort Myers to Chicago
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Find Fort Myers to Chicago flights starting at CAD 62.

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        RSW09:57
        3h 15m
        Nonstop
        ORD12:12
        Thu, Dec 26|Fort Myers - Chicago|Frontier Airlines
        CAD 62CAD 106
        41% OFF
        41% OFF
        CAD 106CAD 62

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Thu, Dec 26, arriving at O'Hare International Airport. One-way Prices start from CAD 62 including taxes and charges.

      • RSW22:28
        3h 20m
        Nonstop
        ORD00:48
        Sun, Jan 19|Fort Myers - Chicago|Frontier Airlines
        CAD 64CAD 106
        39% OFF
        39% OFF
        CAD 106CAD 64

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Sun, Jan 19, arriving at O'Hare International Airport. One-way Prices start from CAD 64 including taxes and charges.

      • RSW12:32
        3h 20m
        Nonstop
        ORD14:52
        Thu, Feb 6|Fort Myers - Chicago|Frontier Airlines
        CAD 64CAD 106
        39% OFF
        39% OFF
        CAD 106CAD 64

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Thu, Feb 6, arriving at O'Hare International Airport. One-way Prices start from CAD 64 including taxes and charges.

      • RSW22:21
        3h 25m
        Nonstop
        ORD00:46
        Sun, Jan 12|Fort Myers - Chicago|Frontier Airlines
        CAD 64
        CAD 64

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Sun, Jan 12, arriving at O'Hare International Airport. One-way Prices start from CAD 64 including taxes and charges.

      • RSW22:28
        3h 20m
        Nonstop
        ORD00:48
        Sun, Feb 2|Fort Myers - Chicago|Frontier Airlines
        CAD 67
        CAD 67

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Sun, Feb 2, arriving at O'Hare International Airport. One-way Prices start from CAD 67 including taxes and charges.

      • RSW22:28
        3h 20m
        Nonstop
        ORD00:48
        Sun, Feb 9|Fort Myers - Chicago|Frontier Airlines
        CAD 70
        CAD 70

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Sun, Feb 9, arriving at O'Hare International Airport. One-way Prices start from CAD 70 including taxes and charges.

      • RSW20:16
        3h 20m
        Nonstop
        ORD22:36
        Sat, Feb 15|Fort Myers - Chicago|Frontier Airlines
        CAD 73
        CAD 73

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Sat, Feb 15, arriving at O'Hare International Airport. One-way Prices start from CAD 73 including taxes and charges.

      • RSW22:28
        3h 20m
        Nonstop
        ORD00:48
        Sun, Jan 26|Fort Myers - Chicago|Frontier Airlines
        CAD 74
        CAD 74

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Sun, Jan 26, arriving at O'Hare International Airport. One-way Prices start from CAD 74 including taxes and charges.

      • RSW21:32
        3h 25m
        Nonstop
        ORD23:57
        Tue, Dec 24|Fort Myers - Chicago|Frontier Airlines
        CAD 76
        CAD 76

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Tue, Dec 24, arriving at O'Hare International Airport. One-way Prices start from CAD 76 including taxes and charges.

      • RSW09:57
        3h 15m
        Nonstop
        ORD12:12
        Thu, Dec 19|Fort Myers - Chicago|Frontier Airlines
        CAD 80
        CAD 80

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Thu, Dec 19, arriving at O'Hare International Airport. One-way Prices start from CAD 80 including taxes and charges.

      • FMY13:00
        3h 5m
        Nonstop
        CHI14:00
        Sat, Nov 30|Fort Myers - Chicago|Frontier Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Fort Myers to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from Fort Myers to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From CAD 62
American Airlines
From CAD 106
Jetblue Airways
From CAD 132
Delta Air Lines
From CAD 139
Spirit Airlines
From CAD 150
United Airlines
From CAD 150
Sun Country Airlines
From CAD 195
Avelo Airlines
From CAD 267
Alaska Airlines
From CAD 300
Southwest Airlines
From CAD 902

Find more flights and airlines

Alternative Routes for Fort Myers to Chicago Flights

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Fort Myers to Chicago.

  • Cheapest
    Frontier Airlines
    RSW
    09:57
    3h 15m
    Nonstop
    ORD
    12:12
    Southwest Florida International Airport - O'Hare International Airport
    Thu, Dec 26Frontier Airlines
    CAD 62
  • Frontier Airlines
    RSW
    21:58
    9h 41m
    1 transfer
    MDW
    06:39
    Southwest Florida International Airport - Midway International Airport
    Wed, Dec 18Frontier Airlines
    CAD 84
  • Frontier Airlines
    RSW
    21:58
    9h 41m
    1 transfer
    MDW
    06:39
    Southwest Florida International Airport - Midway International Airport
    Wed, Dec 18Frontier Airlines
    CAD 84
    Find More Flights

FAQ

  • When are flight tickets from Fort Myers (FMY) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Fort Myers to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from Fort Myers (FMY) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around CAD 485.

  • How long is the flight from Fort Myers (FMY) to Chicago (CHI)?

    It takes about 3 hours 25 minutes to fly from Fort Myers (FMY) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Fort Myers (FMY) to Chicago (CHI)?

    Airlines with flights from Fort Myers (FMY) to Chicago (CHI): Southwest Airlines, Emirates, Alaska Airlines, United Airlines, Spirit Airlines, American Airlines, Air New Zealand and Qatar Airways.

  • What's the most popular airline for direct flights from Fort Myers (FMY) to Chicago (CHI)?

    United Airlines operates 2 direct flights from Fort Myers (FMY) to Chicago (CHI).

  • How many airports in Chicago (CHI)?

How to find a cheap flight from Fort Myers to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Fort Myers to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information for Fort Myers to Chicago Flights

Cheapest direct flight priceCAD 61
Cheapest return ticket priceCAD 133
Off-season travel monthNovember
Peak season for travelAugust
Flight distance1,780.05km
Average flight time3 hours 25 minutes
Popular airlineAmerican Airlines

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