Cheap flights from Chicago to Key West

Round-trip
Economy
Chicago (CHI)
Key West (EYW)
Mon 8/23
Mon 8/30
Any month
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Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from Chicago to Key West.
View current United States travel restrictions

Flight information for Chicago to Key West
(CHI to EYW)

Find info about flight duration, direct flights, and airports for your flight from Chicago to Key West
Best Price Found$305The best flight deal from Chicago to Key West found on momondo in the last 72 hours is $305
Fastest flight time3h 25mThe fastest flight from Chicago to Key West takes 3h 25m
Direct flightsMoDirect flights go from Chicago to Key West on Monday. Airlines offering direct flights are: American Airlines and Qatar Airways.
Airports in Key West1 airportThere is 1 airport near Key West: Key West (EYW)

How to get the cheapest flight ticket from Chicago to Key West

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Chicago to Key West?

August
The cheapest time of year to fly to Key West from Chicago is August. Most expensive is December

What is the cheapest day to depart Chicago for Key West?

Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Thursday

When is the cheapest time to fly from Chicago to Key West?

in the evening
Chicago to Key West flights are approximately 55% more expensive in the morning than in the evening

What is the cheapest airline that flies to Key West from Chicago?

JetBlue
JetBlue, American Airlines, and Delta are the most popular carriers operating from Chicago to Key West

What is the cheapest Chicago to Key West flight route?

Chicago O'Hare Intl - Key West
Fly from Chicago O'Hare Intl to Key West for the best Chicago - Key West flight prices

How far in advance should you book Chicago to Key West flights?

57 days before
The cheapest time to buy a flight from Chicago to Key West is approximately 57 days to departure
60
Days before departure
0

Easily compare round-trip flights from Chicago to Key West

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Key West by changing tabs
Multiple Airlines
Aug 29
ORD3:45 amChicago O'Hare Intl
6h 05m
1 stop
EYW9:50 amKey West
Sep 1
EYW7:45 amKey West
9h 32m
1 stop
ORD5:17 pmChicago O'Hare Intl
Multiple Airlines
Aug 28
ORD3:45 amChicago O'Hare Intl
7h 50m
1 stop
EYW11:35 amKey West
Sep 4
EYW1:20 pmKey West
7h 59m
1 stop
ORD9:19 pmChicago O'Hare Intl
Multiple Airlines
Aug 10
ORD3:30 amChicago O'Hare Intl
6h 00m
1 stop
EYW9:30 amKey West
Aug 12
EYW11:25 amKey West
9h 54m
1 stop
ORD9:19 pmChicago O'Hare Intl

Find the cheapest one-way flights from Chicago to Key West

If you're looking for one-way flights from Chicago to Key West, view some of our deals below provided by American Airlines
American Airlines
Oct 9
ORD9:35 amChicago O'Hare Intl
8h 22m
1 stop
EYW5:57 pmKey West
Multiple Airlines
Sep 17
ORD1:25 amChicago O'Hare Intl
8h 25m
1 stop
EYW9:50 amKey West
Multiple Airlines
Aug 21
ORD1:25 amChicago O'Hare Intl
10h 10m
1 stop
EYW11:35 amKey West

Best airlines flying from Chicago to Key West

Compare and see reviews for airlines that fly from Chicago to Key West with momondo
AirlineRatingFree CancellationPrice
JetBlue
PriceFrom $148
Free Cancellation
Rating
7.1
7.4

Boarding

7.6

Comfort

8.0

Crew

7.3

Entertainment

6.9

Food

Reviews

Cons: Boarding at a tourist location is tough but cabin space is prestigious nowadays. Passengers need to be given clear guidance for carry-on baggage since it delays the onboarding process.

1 / 10
American Airlines
PriceFrom $185
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.8

Crew

7.0

Entertainment

6.8

Food

Reviews

Pros: Delayed flight no reasons seems like American Airlines don’t know what to do in these situations

Cons: I believe this airlines should have figured the answer to this question by now.

1 / 10
Delta
PriceFrom $222
Free Cancellation
Rating
8.2
8.3

Boarding

8.5

Comfort

8.3

Crew

7.9

Entertainment

8.0

Food

Reviews

Cons: Wouldn't let us on the flight when there was plenty of time to get there. Manager was arrogant and slow - didn't care. Poor policies at that airport.

1 / 10
United Airlines
PriceFrom $223
Free Cancellation
Rating
6.8
7.2

Boarding

6.6

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Pros: Everything! From ticketing agent to all the crew on our flight back were awesome. Thank you!

1 / 10

Are airlines flying from Chicago to Key West offering flexible cancellation due to COVID-19?

Due to the global impact of COVID-19, some of our airline partners operating flights from Chicago to Key West, such as American Airlines, United Airlines, and Delta may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.

How far is Chicago to Key West by plane?

The distance between Chicago and Key West is about 1241.6 mi. 8h 22m is a normal flight duration for this route.

Can I fly to Key West from Chicago right now?

Information is based on travel restrictions for travel to Key West within the United States

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Key West.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Key West.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Key West.

Can I fly back to Chicago from Key West?

Returning to Chicago from Key West

COVID-19 testing requirements
Visitors from Key West must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Key West are not required to quarantine after entering Chicago.

If you are planning to travel to Key West at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

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