Cheap Flights from Fort Myers, FL to Chicago, IL from $64

Return flight: Chicago – Fort Myers

On Cheapflightsplus.com you will find 21 direct and 406 connecting flights from Fort Myers to Chicago. You can compare airfare deals from 6 airlines and multiple travel sites from $64, book and save on cheap plane tickets and last minute offers. Also check out RSW-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Fort Myers to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $64 (one-way), $110 (round-trip).
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights
Full flight schedule will help you in detecting at what time planes fly from Fort Myers to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
07:15 — 09:29
07:15 — 09:29 UA2189 United Airlines
Fort Myers — Chicago
3h 14m
Find flight
from$124
08:30 — 10:43
08:30 — 10:43 AS6294 Alaska Airlines
Fort Myers — Chicago
3h 13m
Find flight
from$6330
09:04 — 11:13
09:04 — 11:13 NK2605 Spirit Airlines
Fort Myers — Chicago
3h 9m
Find flight
from$72
09:15 — 11:30
09:15 — 11:30 UA1811 United Airlines
Fort Myers — Chicago
3h 15m
Find flight
from$124
09:15 — 11:30
09:15 — 11:30 UA752 United Airlines
Fort Myers — Chicago
3h 15m
Find flight
from$149
09:30 — 11:44
09:30 — 11:44 UA1864 United Airlines
Fort Myers — Chicago
3h 14m
Find flight
from$228
11:26 — 13:42
11:26 — 13:42 AS6756 Alaska Airlines
Fort Myers — Chicago
3h 16m
Find flight
from$6325
11:26 — 13:42
11:26 — 13:42 AS4363 Alaska Airlines
Fort Myers — Chicago
3h 16m
Find flight
from$6340
12:14 — 14:27
12:14 — 14:27 UA1863 United Airlines
Fort Myers — Chicago
3h 13m
Find flight
from$168
12:20 — 14:35
12:20 — 14:35 UA2494 United Airlines
Fort Myers — Chicago
3h 15m
Find flight
from$124
12:26 — 14:39
12:26 — 14:39 UA310 United Airlines
Fort Myers — Chicago
3h 13m
Find flight
from$124
13:10 — 15:22
13:10 — 15:22 AS6706 Alaska Airlines
Fort Myers — Chicago
3h 12m
Find flight
from$6343
13:30 — 15:43
13:30 — 15:43 NK2930 Spirit Airlines
Fort Myers — Chicago
3h 13m
Find flight
from$64
13:38 — 15:53
13:38 — 15:53 NK2607 Spirit Airlines
Fort Myers — Chicago
3h 15m
Find flight
from$64
14:30 — 16:45
14:30 — 16:45 UA1967 United Airlines
Fort Myers — Chicago
3h 15m
Find flight
from$149
16:26 — 18:41
16:26 — 18:41 AS6450 Alaska Airlines
Fort Myers — Chicago
3h 15m
Find flight
from$6325
16:30 — 18:43
16:30 — 18:43 AS6817 Alaska Airlines
Fort Myers — Chicago
3h 13m
Find flight
from$6351
16:39 — 18:55
16:39 — 18:55 UA2211 United Airlines
Fort Myers — Chicago
3h 16m
Find flight
from$124
16:39 — 18:54
16:39 — 18:54 UA2738 United Airlines
Fort Myers — Chicago
3h 15m
Find flight
from$215
19:30 — 21:52
19:30 — 21:52 UA637 United Airlines
Fort Myers — Chicago
3h 22m
Find flight
from$228
21:57 — 00:07
+1 day
21:57 — 00:07 NK1872 Spirit Airlines
Fort Myers — Chicago
3h 10m
Find flight
from$64
06:30 — 11:58
06:00 — 08:54 UA1254 United Airlines
Fort Myers — Newark
54m stop
10:26 — 12:05 UA1525 United Airlines
Newark — Chicago
6h 28m
including layover
Find flight
from$235
11:43 — 20:39
12:03 — 14:49 SY384 Sun Country Airlines
Fort Myers — Minneapolis
4h 42m stop
10:48 — 12:27 SY1629 Sun Country Airlines
Minneapolis — Chicago
9h 56m
including layover
Find flight
from$147
11:43 — 17:15
11:49 — 14:24 SY384 Sun Country Airlines
Fort Myers — Minneapolis
1h 18m stop
15:42 — 17:21 SY259 Sun Country Airlines
Minneapolis — Chicago
6h 32m
including layover
Find flight
from$168
18:25 — 23:15
18:25 — 20:50 UA1361 United Airlines
Fort Myers — Washington D.C.
1h 20m stop
22:10 — 23:15 UA1738 United Airlines
Washington D.C. — Chicago
5h 50m
including layover
Find flight
from$232
18:50 — 17:33
+1 day
18:50 — 21:26 SY1982 Sun Country Airlines
Fort Myers — Minneapolis
18h 28m stop
15:54 — 17:33 SY261 Sun Country Airlines
Minneapolis — Chicago
23h 43m
including layover
Find flight
from$196
19:16 — 23:17
19:16 — 21:11 F92217 Frontier Airlines
Fort Myers — Atlanta
1h 4m stop
22:15 — 23:18 F92779 Frontier Airlines
Atlanta — Chicago
5h 1m
including layover
Find flight
from$116
19:16 — 00:14
+1 day
19:16 — 21:11 F92217 Frontier Airlines
Fort Myers — Atlanta
1h 47m stop
22:58 — 00:14 F93397 Frontier Airlines
Atlanta — Chicago
5h 58m
including layover
Find flight
from$116
06:00 — 09:41
+1 day
06:00 — 08:35 SY390 Sun Country Airlines
Fort Myers — Minneapolis
11h 15m stop
19:50 — 23:08 G4246 Allegiant Air
Minneapolis — Fletcher
9h 52m stop
09:00 — 09:41 G41848 Allegiant Air
Fletcher — Chicago
28h 41m
including layover
Find flight
from$220
07:05 — 20:48
07:05 — 09:06 MX744 Mexicana
Fort Myers — Raleigh
6h 20m stop
15:26 — 16:38 NK1592 Spirit Airlines
Raleigh — Baltimore
2h 47m stop
19:25 — 20:48 NK1187 Spirit Airlines
Baltimore — Chicago
14h 43m
including layover
Find flight
from$240
17:09 — 08:55
+1 day
17:09 — 20:04 NK2495 Spirit Airlines
Fort Myers — Detroit
1h 5m stop
21:09 — 23:11 NK2493 Spirit Airlines
Detroit — Atlanta
8h 37m stop
07:48 — 08:55 NK2707 Spirit Airlines
Atlanta — Chicago
16h 46m
including layover
Find flight
from$140
17:09 — 20:03
+1 day
17:09 — 20:04 NK2495 Spirit Airlines
Fort Myers — Detroit
14h 23m stop
10:27 — 13:03 NK2739 Spirit Airlines
Detroit — Orlando
4h 52m stop
17:55 — 20:03 NK2541 Spirit Airlines
Orlando — Chicago
27h 54m
including layover
Find flight
from$183
20:09 — 09:38
+1 day
20:09 — 23:02 NK2495 Spirit Airlines
Fort Myers — Detroit
6h 13m stop
05:15 — 07:22 NK2350 Spirit Airlines
Detroit — Atlanta
1h 8m stop
08:30 — 09:38 NK2707 Spirit Airlines
Atlanta — Chicago
14h 29m
including layover
Find flight
from$155
20:09 — 20:05
+1 day
17:09 — 20:04 NK2495 Spirit Airlines
Fort Myers — Detroit
7h 8m stop
06:00 — 07:40 NK2496 Spirit Airlines
Detroit — New York
10h 40m stop
18:30 — 20:07 NK2178 Spirit Airlines
New York — Chicago
24h 56m
including layover
Find flight
from$190
*Departure and arrival times - local. Updated on July 30, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Fort Myers to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Fort Myers and Chicago is 1789 miles. Time difference between the cities is 1h. Airplanes depart 06:00 to 21:57 from 2 Fort Myers airports and arrive 06:00 to 21:57 to 7 Chicago airports. Average flight time is 3h 15m.

  • The fastest flight 3h 9m
  • Average flight time 3h 15m
  • The earliest flight 06:00
  • The latest flight 21:57
  • Distance 1112 ml

The cheapest months to travel to Chicago are july (from 64 $), june (from 64 $), august (from 64 $).

The most expensive months are may (from 85 $), october (from 72 $), september (from 68 $).

What is the lowest airfare Fort Myers to Chicago?

The cheapest plane ticket found by our users is $64. This airfare is for economy class on one-way NK2607 flight by Spirit Airlines for July 5, 2025 which leaves Southwest Florida Reg in Fort Myers at 13:38 am and arrives at Chicago O'Hare International at 15:53.

Economy class
$64
Find
Business class
?
Find
First class
?
Find

Popular Airlines on the Route

The flight Fort Myers — Chicago is served by 6 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 6 departures per week at the price of from $ 6325 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 6351.

Direct flights

There are 21 nonstop flights on the route. The fastest direct flight is NK2605 by Spirit Airlines takes 3h 9m and the cheapest is NK2607 by Spirit Airlines for $64.

  • AS - Alaska Airlines
    from $6325
    Find
  • UA - United Airlines
    from $124
    Find
  • NK - Spirit Airlines
    from $64
    Find
See more direct flights

Connecting Flights

There are 406 flights with layovers on the route. The fastest connecting flight is F92217 by Frontier Airlines takes 5h 1m and the cheapest is NK2607 by Spirit Airlines for $116.

  • F9 - Frontier Airlines
    from $116
    Find
  • SY - Sun Country Airlines
    from $147
    Find
  • MX - Mexicana
    from $240
    Find
  • UA - United Airlines
    from $215
    Find
  • NK - Spirit Airlines
    from $140
    Find
See more connecting flights

Airports

You can fly from Fort Myers to Chicago from 2 airports (Southwest Florida Reg, Page Field).

Fort Myers airports

  • Southwest Florida Reg-RSW
    from $64
    Find
  • Page Field-FMY
    Find

Chicago airports

  • O'Hare International-ORD
    Find
  • Midway-MDW
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

Back