Cheap flights from Chicago (CHI) to Key West (EYW)

CHI — EYW
Dec 3 — Dec 101

The best prices from Chicago to Key West are usually found in January or September, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Friday

How to find the cheapest flight from Chicago (CHI) to Key West (EYW)

All the information you need to plan the best CHI to EYW flight in 2022: compare Chicago to Key West flight prices with the expected peak season, weather and rainfall in Key West.

CHI - EYW

Price

$409 - $537

EYW

Temperature

69.8 - 84.2 °F

EYW

Rainfall

1.5 - 6.7 inches

Popular inMarchHigh demand for flights, 13% potential price rise
Cheapest inJanuaryBest time to find cheap flights, 12% potential price drop
Round-trip from$409From Chicago (CHI) to Key West
One-way from$101One-way flight from Chicago (CHI) to Key West

What is the cheapest day to fly round-trip from Chicago to Key West?

Tuesday is generally a great day to depart. Flying on this day could help you save up to 26%.

How far in advance should I book a flight from Chicago to Key West?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 61 days in advance, which can save you up to 39% on flights from Chicago to Key West compared to booking the week you need them. Waiting 61 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $567. For sooner than that we have options available in the next 3 days from $685.

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

Our data shows that January tends to be the cheapest month to fly to Key West from Chicago. Users have commonly found prices around $467 for the month, but tickets can be as low as $277. Due to multiple factors, prepare for potentially higher prices in March.

When is the cheapest time to fly from Chicago to Key West (CHI - EYW)?

It’s optimal to fly from Chicago to Key West in the evening. By choosing this option you can save up to 19% on the cost of your flight, compared to a flight in the morning.

Cheap flights from Chicago to Key West in November, December 2022

The best prices found for CHI to EYW flights for November, December
Dec 9 - Dec 15
MDW

Chicago Midway

EYW

Key West

2 stops

18h 22m
EYW

Key West

MDW

Chicago Midway

1 stop

9h 07m
$192

Multiple Airlines

Pick Dates

Deal found 11/27

Dec 2 - Dec 4
MDW

Chicago Midway

EYW

Key West

2 stops

18h 35m
EYW

Key West

MDW

Chicago Midway

1 stop

27h 15m
$230

Allegiant Air

Pick Dates

Deal found 11/26

Dec 16 - Dec 20
MDW

Chicago Midway

EYW

Key West

1 stop

26h 04m
EYW

Key West

MDW

Chicago Midway

1 stop

8h 53m
$234

Multiple Airlines

Pick Dates

Deal found 11/27

Chicago to Key West 2022 flight deals

Cheap flights to Key West from Chicago found for this year
Dec 9 - Dec 15
MDW

Chicago Midway

EYW

Key West

2 stops

18h 22m
EYW

Key West

MDW

Chicago Midway

1 stop

9h 07m
$192

Multiple Airlines

Pick Dates

Deal found 11/27

Dec 2 - Dec 4
MDW

Chicago Midway

EYW

Key West

2 stops

18h 35m
EYW

Key West

MDW

Chicago Midway

1 stop

27h 15m
$230

Allegiant Air

Pick Dates

Deal found 11/26

Dec 16 - Dec 20
MDW

Chicago Midway

EYW

Key West

1 stop

26h 04m
EYW

Key West

MDW

Chicago Midway

1 stop

8h 53m
$234

Multiple Airlines

Pick Dates

Deal found 11/27

Cheap American Airlines flights from Chicago to Key West

May 13 - May 20
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 48m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 30m
$248

American Airlines

Pick Dates

Deal found 11/26

Mar 29 - Apr 12
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

7h 07m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 30m
$255

American Airlines

Pick Dates

Deal found 11/27

Dec 21 - Dec 28
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

6h 48m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

5h 30m
$263

American Airlines

Pick Dates

Deal found 11/26

Cheap United Airlines flights from Chicago to Key West

Jan 7 - Jan 12
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 22m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

6h 50m
$257

United Airlines

Pick Dates

Deal found 11/26

Jan 8 - Jan 14
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

6h 54m
EYW

Key West

ORD

Chicago O'Hare Intl

1 stop

7h 00m
$266

United Airlines

Pick Dates

Deal found 11/26

Jan 10 - Feb 14
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 22m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 33m
$274

United Airlines

Pick Dates

Deal found 11/28

Non-stop flights to Key West from Chicago

Save time with Chicago to Key West direct flight deals
May 13 - May 20
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 48m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 30m
$248

American Airlines

Pick Dates

Deal found 11/26

Jan 10 - Feb 14
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 22m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 33m
$274

United Airlines

Pick Dates

Deal found 11/28

Feb 14 - Feb 22
ORD

Chicago O'Hare Intl

EYW

Key West

Nonstop

3h 25m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 33m
$300

United Airlines

Pick Dates

Deal found 11/27

Last minute flights from Chicago to Key West

Late deals on return flights to Key West from Chicago, departing today and this week
Dec 5 - Dec 8
MDW

Chicago Midway

EYW

Key West

1 stop

7h 20m
EYW

Key West

MDW

Chicago Midway

1 stop

27h 19m
$295

Multiple Airlines

Pick Dates

Deal found 11/28

Dec 4 - Dec 27
MDW

Chicago Midway

EYW

Key West

2 stops

17h 28m
EYW

Key West

MDW

Chicago Midway

1 stop

15h 06m
$361

Multiple Airlines

Pick Dates

Deal found 11/27

Dec 4 - Dec 27
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

6h 14m
EYW

Key West

ORD

Chicago O'Hare Intl

Nonstop

3h 27m
$362

United Airlines

Pick Dates

Deal found 11/27

One-way flights to Key West from Chicago

The cheapest one-way flights from Chicago to Key West
Dec 19
ORD

Chicago O'Hare Intl

EYW

Key West

2 stops

26h 31m
$93

Multiple Airlines

Pick Dates

Deal found 11/25

Jan 6
ORD

Chicago O'Hare Intl

EYW

Key West

1 stop

14h 08m
$101

Multiple Airlines

Pick Dates

Deal found 11/27

Dec 19
MDW

Chicago Midway

EYW

Key West

2 stops

25h 26m
$105

Multiple Airlines

Pick Dates

Deal found 11/25

Related info for your journey

Useful info, stats and facts about Chicago to Key West flights.

What airport do you fly into for flights to Key West from Chicago?

Located just 2.6 mi from the city center, Key West is the airport most travelers will use when flying to Key West from Chicago. Booking flights from Chicago to Key West (EYW) should be relatively easy as there are 0 daily inbound flights from Chicago from 6 different airlines.

Which airlines flying from Chicago to Key West have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Key West that may be offering flexible cancellation policies are American Airlines, United Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Key West for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Key West for under $200. The cheapest flight booked recently is on Multiple Airlines for just $192, but on average you can expect to pay $250.

Are there nonstop flights from Chicago to Key West for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Key West under $300. A good price for a nonstop flight from Chicago to Key West is less than $379.

Are there last-minute flights available from Chicago to Key West for under $300?

There are currently 20+ open flights from Chicago to Key West within the next 7 days for less than $300.

What days are nonstop flights available from Chicago to Key West?

Nonstop flights are available for this route on the following days: Tuesday, Wednesday, Thursday, Friday.

How many flights depart from Chicago to Key West on average per day?

4 flight departures from Chicago to Key West per day on average.
Morning (6am - Noon) - 100% of flight departures

How long is the flight from Chicago to Key West?

Airlines like American Airlines, United Airlines, and Delta fly from Chicago to Key West in about 3h 22m. The time it takes to get you to your destination can typically vary by up to 5h 31m. Chicago and Key West are separated by a distance of 1261 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Chicago to Key West round-trip?

Our cheapest airline available from Chicago to Key West is American Airlines. Our recent data shows that you can find tickets from as low as $248 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $257 and $270 round-trip. American Airlines is currently priced 46% below the average price you’ll pay for this route.

What are the most popular airlines that fly from Chicago to Key West?

The most popular airlines flying from Chicago to Key West are American Airlines, Alaska Airlines and Delta. Something to consider prior to booking your flight.

What are the cheapest flights from Chicago to Key West?

Looking for the cheapest flight from Chicago to Key West? While on average our users pay $1,249, our data indicates the cheapest price to be $226. The most popular route (Chicago O'Hare Intl - Key West), is priced around $245.

Alternative routes for Chicago to Key West

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Chicago to Key West

The chart below displays the airlines Cheapflights users traveling from Chicago to Key West choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$10Average$22FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
DeltaCheapest$245Average$513FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$247Average$461FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$254Average$468FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights

Hourly flight availability from Chicago to Key West

See what time of day planes typically take off from Chicago to Key West
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chicago to Key West

See how many times per day planes take to the skies headed from Chicago to Key West
Sunday1daily flight
Monday1daily flight
Tuesday1daily flight
Wednesday0daily flights
Thursday0daily flights
Friday0daily flights
Saturday1daily flight