App
Customer Support
NZD
Find Bookings
Trip.com
>
Cheap Flights
>
United States
>
Illinois
>
Chicago
>
Flights from Fort Myers to Chicago
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Flights from Fort Myers to Chicago Starting at NZD 31

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

  • One way
  • Round-trip
      • Cheapest nonstop
        RSW06:00
        3h 20m
        Nonstop
        ORD08:20
        Thu, Mar 6|Fort Myers - Chicago|Frontier Airlines
        NZD 31NZD 124
        75% OFF
        75% OFF
        NZD 124NZD 31

        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, Mar 6, arriving at O'Hare International Airport. One-way Prices start from NZD 31 including taxes and charges.

      • RSW06:00
        3h 20m
        Nonstop
        ORD08:20
        Tue, Mar 11|Fort Myers - Chicago|Frontier Airlines
        NZD 31NZD 124
        75% OFF
        75% OFF
        NZD 124NZD 31

        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, Mar 11, arriving at O'Hare International Airport. One-way Prices start from NZD 31 including taxes and charges.

      • RSW06:00
        3h 20m
        Nonstop
        ORD08:20
        Tue, Mar 18|Fort Myers - Chicago|Frontier Airlines
        NZD 50NZD 124
        59% OFF
        59% OFF
        NZD 124NZD 50

        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, Mar 18, arriving at O'Hare International Airport. One-way Prices start from NZD 50 including taxes and charges.

      • RSW14:57
        3h 20m
        Nonstop
        ORD17:17
        Sat, Feb 8|Fort Myers - Chicago|Frontier Airlines
        NZD 53
        NZD 53

        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 8, arriving at O'Hare International Airport. One-way Prices start from NZD 53 including taxes and charges.

      • RSW15:53
        3h 20m
        Nonstop
        ORD18:13
        Fri, Feb 28|Fort Myers - Chicago|Frontier Airlines
        NZD 65
        NZD 65

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Fri, Feb 28, arriving at O'Hare International Airport. One-way Prices start from NZD 65 including taxes and charges.

      • RSW15:53
        3h 20m
        Nonstop
        ORD18:13
        Wed, Feb 26|Fort Myers - Chicago|Frontier Airlines
        NZD 71
        NZD 71

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Wed, Feb 26, arriving at O'Hare International Airport. One-way Prices start from NZD 71 including taxes and charges.

      • RSW15:53
        3h 20m
        Nonstop
        ORD18:13
        Wed, Mar 5|Fort Myers - Chicago|Frontier Airlines
        NZD 75
        NZD 75

        Choose Frontier Airlines flights from Fort Myers to Chicago. The one-way direct flight with Frontier Airlines departs from Southwest Florida International Airport on Wed, Mar 5, arriving at O'Hare International Airport. One-way Prices start from NZD 75 including taxes and charges.

      • RSW20:16
        3h 20m
        Nonstop
        ORD22:36
        Sat, Mar 1|Fort Myers - Chicago|Frontier Airlines
        NZD 78
        NZD 78

        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, Mar 1, arriving at O'Hare International Airport. One-way Prices start from NZD 78 including taxes and charges.

      • RSW06:00
        3h 20m
        Nonstop
        ORD08:20
        Tue, Mar 25|Fort Myers - Chicago|Frontier Airlines
        NZD 80
        NZD 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 Tue, Mar 25, arriving at O'Hare International Airport. One-way Prices start from NZD 80 including taxes and charges.

      • RSW06:00
        3h 21m
        Nonstop
        ORD08:21
        Sat, Apr 19|Fort Myers - Chicago|Frontier Airlines
        NZD 85
        NZD 85

        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, Apr 19, arriving at O'Hare International Airport. One-way Prices start from NZD 85 including taxes and charges.

      • FMY01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Sat, Feb 15|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.

Fort Myers to Chicago flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. F93799

    Frontier Airlines

    06:00

    RSW

    3.4h

    Nonstop

    08:21

    ORD

    --TWTFS
    Search

  2. AA2088

    American Airlines

    06:05

    RSW

    3.2h

    Nonstop

    08:17

    ORD

    ----T--
    Search

  3. NK712

    Spirit Airlines

    10:52

    RSW

    3.1h

    Nonstop

    12:57

    ORD

    SMTWTFS
    Search

  4. F92026

    Frontier Airlines

    11:23

    RSW

    2.9h

    14:14

    PHL

    --TWT--
    Search

  5. F94367

    Frontier Airlines

    20:23

    PHL

    2.3h

    21:40

    MDW

    ---W---

  6. F94981

    Frontier Airlines

    17:17

    RSW

    4.5h

    19:47

    DEN

    -M-W--S
    Search

  7. F92210

    Frontier Airlines

    15:42

    DEN

    2.4h

    19:08

    MDW

    SMTWTFS

  8. F91744

    Frontier Airlines

    20:51

    RSW

    2.8h

    23:39

    TTN

    --TWTF-
    Search

  9. F94367

    Frontier Airlines

    20:23

    PHL

    2.3h

    21:40

    MDW

    ---W---
Find more flights and airlines

Find the best 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.

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 logoFrontier AirlinesUnited Airlines logoUnited AirlinesAmerican Airlines logoAmerican Airlines

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 departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

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

    According to Trip.com's data, the lowest price is around NZD 609.

  • How long does it take to fly from Fort Myers (FMY) to Chicago (CHI) and what is the distance?

    It takes around 3 hours 30 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 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • 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): Emirates, United Airlines, Southwest Airlines, Alaska Airlines, American Airlines, Air New Zealand, Air Canada and Qatar Airways.

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 from Fort Myers to Chicago

Cheapest nonstop flight priceNZD 30
Cheapest round-trip ticket priceNZD 84
Off-season for travelDecember
Peak season for travelMay
Flight distance1,780.05 km
Average flight time3 hours 30 minutes
Popular airlineJetblue Airways

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.