Chicago to Key West, Florida (& vice versa) for only $176 roundtrip

Cheap flights from Chicago to Key West, Florida for only $176 roundtrip with American Airlines.

Also works in reverse.

 

DEPART:
Chicago, USA

 

ARRIVE:
Key West, USA

 

RETURN:
Chicago, USA

 

DATES:
Limited availability from October to December 2023

Example dates:

 

Chicago – Key West
2nd-9th Dec
5th-12th Dec
6th-13th Dec
9th-13th Dec

 

Key West – Chicago
31st Oct – 7th Nov
2nd-9th Dec
5th-12th Dec

possibly more…

 

STOPS:
Charlotte
(outgoing only)

 

AIRLINES:
American Airlines

 

 

Non-stop from Boston to Key West, Florida (& vice versa) for only $157 roundtrip

Non-stop flights from Boston to Key West, Florida for only $157 roundtrip with JetBlue.

Also works in reverse.

 

DEPART:
Boston, USA

 

ARRIVE:
Key West, USA

 

RETURN:
Boston, USA

 

DATES:
Limited availability from December 2022 to January 2023 (excluding Christmas)

Example dates:

 

Boston – Key West
10th-25th Dec
19th-25th Dec

 

Key West – Boston
25th Dec – 9th Jan

possibly more…

 

STOPS:

 

AIRLINES:
JetBlue

 

 

Non-stop from New York to Key West, Florida (& vice versa) for only $168 roundtrip

Non-stop flights from New York to Key West, Florida for only $168 roundtrip with United Airlines.

Also works in reverse.

 

DEPART:
New York, USA

 

ARRIVE:
Key West, USA

 

RETURN:
New York, USA

 

DATES:
Availability from November 2022 to February 2023 (excluding Christmas/New Year)

Example dates:

 

New York – Key West
24th Nov – 1st Dec
7th-14th Jan
11th-18th Jan
17th-24th Jan
21st-28th Jan
25th Jan – 1st Feb

 

Key West – New York
11th-18th Jan
13th-20th Jan
21st-28th Jan
25th Jan – 1st Feb
31st Jan – 7th Feb

and more…

 

STOPS:

 

AIRLINES:
United Airlines

 

 

Boston to Key West, Florida (& vice versa) for only $179 roundtrip

Cheap flights from Boston to Key West, Florida for only $179 roundtrip with American Airlines.

Also works in reverse.

 

DEPART:
Boston, USA

 

ARRIVE:
Key West, USA

 

RETURN:
Boston, USA

 

DATES:
Availability from November 2022 to February 2023 (excluding Christmas/New Year)

Example dates:

 

Boston – Key West
2nd-9th Dec
3rd-10th Dec
7th-14th Dec
11th-18th Jan
18th-25th Jan
20th-27th Jan
24th-31st Jan
25th Jan – 1st Feb
27th Jan – 3rd Feb

 

Key West – Boston
30th Nov – 7th Dec
2nd-9th Dec
3rd-10th Dec
6th-13th Dec
7th-14th Dec
10th-17th Jan
11th-18th Jan
18th-25th Jan
19th-26th Jan
20th-27th Jan
24th-31st Jan
25th Jan – 1st Feb
27th Jan – 3rd Feb

and more…

 

STOPS:
Charlotte

 

AIRLINES:
American Airlines

 

 

Non-stop from New York to Key West, Florida (& vice versa) for only $136 roundtrip

Non-stop flights from New York to Key West, Florida for only $136 roundtrip with United Airlines.

Also works in reverse.

 

DEPART:
New York, USA

 

ARRIVE:
Key West, USA

 

RETURN:
New York, USA

 

DATES:
Availability from November 2021 to March 2022 (excluding Christmas/New Year)

Example dates:

 

New York – Key West
7th-12th Nov
14th-19th Nov
5th-10th Dec
12th-17th Dec
13th-18th Dec
14th-19th Dec
8th-13th Jan
9th-14th Jan
16th-21st Jan
22nd-27th Jan
23rd-28th Jan
30th Jan – 4th Feb
26th Feb – 3rd Mar

 

Key West – New York
2nd-7th Nov
3rd-8th Nov
4th-9th Nov
10th-15th Nov
11th-16th Nov
25th-30th Nov
2nd-7th Dec
3rd-8th Dec
9th-14th Dec
10th-15th Dec
6th-11th Jan
12th-17th Jan
13th-18th Jan
19th-24th Jan
20th-25th Jan
26th-31st Jan
27th Jan – 1st Feb
2nd-7th Feb
3rd-8th Feb
9th-14th Feb
10th-15th Feb
17th-22nd Feb
24th Feb – 1st Mar
3rd-8th Mar
10th-15th Mar
17th-22nd Mar

and more…

 

STOPS:

 

AIRLINES:
United Airlines

 

 

Nashville to Key West, Florida (& vice versa) for only $174 roundtrip

Cheap flights from Nashville to Key West, Florida for only $174 roundtrip with American Airlines.

Also works in reverse.

 

DEPART:
Nashville, USA

 

ARRIVE:
Key West, USA

 

RETURN:
Nashville, USA

 

DATES:
Limited availability in September 2021

Example dates:

 

Nashville – Key West: $174-$176
15th-21st Sep
15th-22nd Sep
15th-23rd Sep
18th-24th Sep

 

Key West – Nashville: $174-$176
14th-21st Sep
14th-22nd Sep
15th-22nd Sep
21st-28th Sep
21st-29th Sep

possibly more…

 

STOPS:
Miami/Charlotte

 

AIRLINES:
American Airlines

 

 

New York to Key West, Florida (& vice versa) for only $145 roundtrip

Cheap flights from New York to Key West, Florida for only $145 roundtrip with JetBlue and Delta Air Lines.

Also works in reverse.

 

DEPART:
New York, USA

 

ARRIVE:
Key West, USA

 

RETURN:
New York, USA

 

DATES:
Availability from September to October 2021

Example dates:

 

New York – Key West: $145-$154
15th-21st Sep
15th-22nd Sep
15th-23rd Sep
18th-24th Sep
18th-25th Sep
25th-29th Sep
13th-19th Oct

 

Key West – New York: $149-$154
14th-21st Sep
14th-22nd Sep
21st-28th Sep
21st-29th Sep
19th-26th Oct

and more…

 

STOPS:
Atlanta
(incoming only)

 

AIRLINES:
JetBlue
Delta Air Lines

 

 

Nashville to Key West, Florida (& vice versa) for only $176 roundtrip

Cheap flights from Nashville to Key West, Florida for only $176 roundtrip with American Airlines.

Also works in reverse.

 

DEPART:
Nashville, USA

 

ARRIVE:
Key West, USA

 

RETURN:
Nashville, USA

 

DATES:
Limited availability from August to October 2021

Example dates:

 

Nashville – Key West
28th Aug – 5th Sep
23rd Sep – 1st Oct

 

Key West – Nashville
5th-13th Sep
11th-19th Sep

possibly more…

 

STOPS:
Miami

 

AIRLINES:
American Airlines

 

 

SUMMER: New York to Key West, Florida (& vice versa) for only $153 roundtrip

Summer flights from New York to Key West, Florida for only $153 roundtrip with American Airlines.

Also works in reverse.

 

DEPART:
New York, USA

 

ARRIVE:
Key West, USA

 

RETURN:
New York, USA

 

DATES:
Availability from August to October 2021

Example dates:

 

New York – Key West
4th-12th Aug
11th-19th Aug
16th-24th Aug
24th Aug – 1st Sep
1st-9th Sep
7th-15th Sep
14th-22nd Sep
17th-25th Sep
21st-29th Sep
28th Sep – 6th Oct
29th Sep – 7th Oct
5th-13th Oct
12th-20th Oct
18th-26th Oct
19th-27th Oct

 

Key West – New York
2nd-10th Aug
24th Aug – 1st Sep
31st Aug – 8th Sep
9th-17th Sep
24th Sep – 2nd Oct

and more…

 

STOPS:
Charlotte/Washington DC

 

AIRLINES:
American Airlines

 

 

Atlanta to Key West, Florida (& vice versa) for only $136 roundtrip

Cheap flights from Atlanta to Key West, Florida for only $136 roundtrip with Delta Air Lines.

Also works in reverse.

 

DEPART:
Atlanta, USA

 

ARRIVE:
Key West, USA

 

RETURN:
Atlanta, USA

 

DATES:
Availability in September 2021

Example dates:

 

Atlanta – Key West
7th-14th Sep
7th-15th Sep
7th-16th Sep
8th-14th Sep
8th-15th Sep
8th-16th Sep
8th-17th Sep
13th-22nd Sep
14th-22nd Sep
14th-23rd Sep
19th-28th Sep
20th-28th Sep
20th-29th Sep
21st-28th Sep
21st-29th Sep

 

Key West – Atlanta
8th-14th Sep
10th-19th Sep
14th-20th Sep
14th-21st Sep
15th-21st Sep
17th-26th Sep
22nd-28th Sep
22nd-29th Sep
23rd-29th Sep

and more…

 

STOPS:

 

AIRLINES:
Delta Air Lines