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How to get from Fort Myers to Chicago

No nonstop flights. The fastest way is via Indianapolis: about 6h 59m including the connection. Other options: via Atlanta, Orlando, Columbus and St Louis. Two tickets from $303.

Flights from Fort Myers to Chicago

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Prices by day: Fort Myers to Chicago

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

Filters

Best fares from Fort Myers to Chicago

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $111 4 December 2026, nonstop Cheapest nonstop $111 4 December 2026, F9 Cheapest in the next 7 days $216 15 November, Sun Cheapest weekend departure $111 Fri, 4 December 2026 Cheapest month December 2026 tickets from $111

Where to connect

Options with one connection, fastest first

fastest, via Indianapolis
6h 59m
two tickets, via Orlando
$303
connection options
5
straight-line distance
1,102 mi (1,774 km)
fastest
Via Indianapolis
6h 59m
with the connection
Fort Myers to Indianapolis flight 2h 38m
Connection of about 3h
Indianapolis to Chicago flight 1h 21m
Via Atlanta
7h 3m
with the connection
Fort Myers to Atlanta flight 1h 52m
Connection of about 3h
Atlanta to Chicago flight 2h 11m
Via Orlando
7h 8m
with the connection
Fort Myers to Orlando flight 1h
Connection of about 3h Arrival: Orlando International. Departure to Chicago: Orlando International, Orlando Sanford International.
Orlando to Chicago flight 3h 8m
two ticketsfrom $303
Via Columbus
7h 11m
with the connection
Fort Myers to Columbus flight 2h 30m
Connection of about 3h
Columbus to Chicago flight 1h 41m
Via St Louis
7h 13m
with the connection
Fort Myers to St Louis flight 2h 45m
Connection of about 3h
St Louis to Chicago flight 1h 28m

One ticket or two

How the options are calculated and what to keep in mind at the connection

Flight times come from the nonstop schedule (estimated from the distance where there is no schedule), with 3h allowed for the connection. The price of an option is the sum of the lowest known fares for each leg; their dates may not match, so treat it as a guide. The search shows tickets for your dates, including connections on a single ticket.

When to visit Chicago

Weather by month

Best time to visit: May, June, July, August, September and October, +18° to +27° by day. In November it is +10° by day and +2° at night, with 7 rainy days.

Jan
0° −7° 10 days
Feb
+2° −6° 7 days
Mar
+9° 0° 12 days
Apr
+14° +5° 13 days
May
+19° +10° 11 days
Jun
+27° +17° 9 days
Jul
+27° +19° 12 days
Aug
+27° +19° 10 days
Sep
+24° +16° 7 days
Oct
+18° +10° 11 days
Nov
+10° +2° 7 days
Dec
+4° −3° 10 days

Daytime and night temperatures in °C, rainy days. Months with the most comfortable weather are in green. Long-term averages.

Nearest nonstop flights

The closest you can get without a connection

Frequently asked questions

Is there a nonstop flight from Fort Myers to Chicago?
There are no nonstop flights in the schedule. You will need a connection, the fastest is via Indianapolis.
What is the fastest way to fly from Fort Myers to Chicago?
Via Indianapolis: 2h 38m to the connection, 1h 21m after it, about 6h 59m in total with 3h for the connection.
How much does a flight from Fort Myers to Chicago with a connection cost?
Two nonstop tickets via Orlando from $303. This is the sum of the lowest known prices for each leg, and their dates may not match.
Which cities can you connect in between Fort Myers and Chicago?
Indianapolis (6h 59m total), Atlanta (7h 3m total), Orlando (7h 8m total), Columbus (7h 11m total) and St Louis (7h 13m total).
How far is Chicago from Fort Myers?
1,102 mi (1,774 km) in a straight line between the cities.
How much time should I allow for the connection?
The options allow 3h. On a single ticket the carrier is responsible for the connection; on separate tickets you set the margin yourself, allowing time to collect and re-check your bags.