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How to get from Key West to Chicago

No nonstop flights. The fastest way is via Tampa: about 7h 11m including the connection. Other options: via Miami, Orlando, Washington and Philadelphia. Two tickets from $96.

Flights from Key West 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.

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Where to connect

Options with one connection, fastest first

fastest, via Tampa
7h 11m
two tickets, via Orlando
$96
connection options
5
straight-line distance
1,243 mi (2,000 km)
fastest
Via Tampa
7h 11m
with the connection
Key West to Tampa flight 1h 6m
Connection of about 3h Arrival: St. Petersburg-Clearwater International, Tampa International. Departure to Chicago: St. Petersburg-Clearwater International, Tampa International.
Tampa to Chicago flight 3h 5m
two ticketsfrom $177
Via Miami
7h 14m
with the connection
Key West to Miami flight 54m
Connection of about 3h Arrival: Miami International. Departure to Chicago: Fort Lauderdale-Hollywood International, Miami International.
Miami to Chicago flight 3h 20m
two ticketsfrom $515
Via Orlando
7h 21m
with the connection
Key West to Orlando flight 1h 13m
Connection of about 3h Arrival: Orlando International, Orlando Sanford International. Departure to Chicago: Orlando International, Orlando Sanford International.
Orlando to Chicago flight 3h 8m
two ticketsfrom $96
Via Washington
8h 10m
with the connection
Key West to Washington flight 2h 51m
Connection of about 3h Arrival: Ronald Reagan National, Washington Dulles International. Departure to Chicago: Baltimore/Wash International Thurgood Marshall, Ronald Reagan National, Washington Dulles International.
Washington to Chicago flight 2h 19m
Via Philadelphia
8h 41m
with the connection
Key West to Philadelphia flight 3h 5m
Connection of about 3h
Philadelphia to Chicago flight 2h 36m

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 Key West to Chicago?
There are no nonstop flights in the schedule. You will need a connection, the fastest is via Tampa.
What is the fastest way to fly from Key West to Chicago?
Via Tampa: 1h 6m to the connection, 3h 5m after it, about 7h 11m in total with 3h for the connection.
How much does a flight from Key West to Chicago with a connection cost?
Two nonstop tickets via Orlando from $96. 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 Key West and Chicago?
Tampa (7h 11m total), Miami (7h 14m total), Orlando (7h 21m total), Washington (8h 10m total) and Philadelphia (8h 41m total).
How far is Chicago from Key West?
1,243 mi (2,000 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.