Cheap flights from Chicago to Key West from $72

1 adult
Economy
0 bags
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Sun 10/8
Sun 10/15
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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

$72

Fastest flight time

3h 03m

Direct flights

Every day

Airports in Key West

1 airport
The best one-way flight to Key West from Chicago in the past 72 hours is $72. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $217.
The fastest flight from Chicago to Key West takes 3h 03m
Direct flights go from Chicago to Key West every day.
There 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?

September. The cheapest time of year to fly to Key West from Chicago is September. Most expensive is March

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?

At noon. Chicago to Key West flights are approximately 33% more expensive in the morning than at noon

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

American Airlines. Alaska Airlines, 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?

40 days before. The cheapest time to buy a flight from Chicago to Key West is approximately 40 days to departure

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

The number of flights available between Chicago and Key West is 14 per week as of October 2023. The most frequent departure day is Sunday, with 14% of weekly flights leaving on this day.

Can stopping save me money on Chicago to Key West flights?

No. A direct flight is the cheapest option for a flight between Chicago to Key West.

When traveling from Chicago to Key West, the most popular airport to fly into is Key West Airport. The majority of travelers flying into Key West Airport from Chicago are departing from Chicago O'Hare Intl Airport. You may be looking for an airport near Chicago O'Hare Intl Airport to depart from when traveling to Key West and Chicago Midway Airport, located in Chicago is a great option. The least expensive flight option from Chicago to Key West will typically be ORD ā€” EYW during the month of October with an average price of $225 RT.

Chicago O'Hare Intl Airport (ORD) to Key West Airport (EYW)$225
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Chicago Midway Airport (MDW) to Key West Airport (EYW)$247
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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 six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Key West by changing tabs
United Airlines
Jan 5
ORD10:35 amChicago O'Hare Intl
3h 12m
EYW2:47 pmKey West
Jan 10
EYW3:52 pmKey West
3h 20m
ORD6:12 pmChicago O'Hare Intl
American Airlines
Jan 27
ORD1:15 pmChicago O'Hare Intl
6h 39m
1 stop
EYW8:54 pmKey West
Jan 31
EYW3:14 pmKey West
3h 33m
ORD5:47 pmChicago O'Hare Intl
Multiple Airlines
Oct 17
ORD12:25 pmChicago O'Hare Intl
19h 44m
1 stop
EYW9:09 amKey West
Oct 22
EYW2:44 pmKey West
18h 40m
1 stop
ORD8:24 amChicago O'Hare Intl
Delta
Jan 3
ORD6:00 amChicago O'Hare Intl
5h 10m
1 stop
EYW12:10 pmKey West
Jan 10
EYW3:00 pmKey West
8h 44m
1 stop
ORD10:44 pmChicago O'Hare Intl
Spirit Airlines
Nov 18
MDW12:40 pmChicago Midway
5h 48m
1 stop
EYW7:28 pmKey West
Nov 25
EYW5:54 pmKey West
4h 38m
1 stop
MDW9:32 pmChicago Midway
United Airlines
Jan 9
ORD10:35 amChicago O'Hare Intl
3h 03m
EYW2:38 pmKey West
Jan 17
EYW3:52 pmKey West
3h 20m
ORD6:12 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, Delta and United Airlines
Multiple Airlines
Nov 4
ORD7:23 pmChicago O'Hare Intl
12h 45m
1 stop
EYW9:08 amKey West
Delta
Dec 13
ORD6:00 amChicago O'Hare Intl
7h 32m
1 stop
EYW2:32 pmKey West
United Airlines
Dec 8
ORD2:05 pmChicago O'Hare Intl
27h 55m
1 stop
EYW7:00 pmKey West

Search last-minute flights to Key West from Chicago

Find and compare round-trip flight prices for your last-minute flight from Chicago to Key West
Multiple Airlines
Oct 9
ORD8:22 pmChicago O'Hare Intl
35h 47m
2 stops
EYW9:09 amKey West
Oct 12
EYW2:54 pmKey West
18h 30m
1 stop
ORD8:24 amChicago O'Hare Intl
Delta
Oct 13
ORD9:30 amChicago O'Hare Intl
6h 30m
1 stop
EYW5:00 pmKey West
Oct 16
EYW6:02 pmKey West
6h 56m
1 stop
ORD11:58 pmChicago O'Hare Intl
United Airlines
Oct 11
ORD11:10 amChicago O'Hare Intl
6h 20m
1 stop
EYW6:30 pmKey West
Oct 15
EYW8:40 amKey West
26h 11m
1 stop
ORD9:51 amChicago O'Hare Intl
American Airlines
Oct 13
ORD5:34 amChicago O'Hare Intl
6h 37m
1 stop
EYW1:11 pmKey West
Oct 16
EYW11:57 amKey West
8h 35m
2 stops
ORD7:32 pmChicago O'Hare Intl
Multiple Airlines
Oct 13
ORD8:22 pmChicago O'Hare Intl
18h 48m
2 stops
EYW4:10 pmKey West
Oct 16
EYW7:10 pmKey West
27h 32m
3 stops
ORD9:42 pmChicago O'Hare Intl
Multiple Airlines
Oct 9
ORD8:22 pmChicago O'Hare Intl
17h 23m
1 stop
EYW2:45 pmKey West
Oct 12
EYW2:54 pmKey West
18h 30m
1 stop
ORD8:24 amChicago O'Hare Intl

Best airlines flying from Chicago to Key West

Compare and see reviews for airlines that fly from Chicago to Key West with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $226Free CancellationRating
7.1
2,893 reviews
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DeltaPriceFrom $226Free CancellationRating
7.8
1,565 reviews
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United AirlinesPriceFrom $239Free CancellationRating
7.2
2,719 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $438Free CancellationRating
7.9
3,001 reviews
Search Alaska Airlines flights
  • United Airlines Flights From Chicago to Key West

    United Airlines flight deals from Chicago to Key West start from $239 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $546 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to Key West

    Across 2,893 American Airlines reviews on momondo, the average score is 7.1/10. American Airlines flies from Chicago to Key West about 7 times each week, with ticket deals ranging from $226 to $426. Price data is based on momondo searches in the last 72 hours.


American Airlines flights from Chicago to Key West

Our best American Airlines deals on Chicago to Key West flight tickets
American Airlines
Jan 27
ORD1:15 pmChicago O'Hare Intl
6h 39m
1 stop
EYW8:54 pmKey West
Jan 31
EYW3:14 pmKey West
3h 33m
ORD5:47 pmChicago O'Hare Intl
American Airlines
Dec 7
ORD1:41 pmChicago O'Hare Intl
6h 12m
1 stop
EYW8:53 pmKey West
Dec 13
EYW3:09 pmKey West
3h 33m
ORD5:42 pmChicago O'Hare Intl
American Airlines
Dec 19
ORD1:41 pmChicago O'Hare Intl
6h 12m
1 stop
EYW8:53 pmKey West
Dec 26
EYW1:25 pmKey West
3h 31m
ORD3:56 pmChicago O'Hare Intl

Delta flights from Chicago to Key West

Our best Delta deals on Chicago to Key West flight tickets
Delta
Jan 3
ORD6:00 amChicago O'Hare Intl
5h 10m
1 stop
EYW12:10 pmKey West
Jan 10
EYW3:00 pmKey West
8h 44m
1 stop
ORD10:44 pmChicago O'Hare Intl
Delta
Jan 29
ORD6:00 amChicago O'Hare Intl
7h 05m
1 stop
EYW2:05 pmKey West
Feb 7
EYW3:00 pmKey West
6h 46m
1 stop
ORD8:46 pmChicago O'Hare Intl
Delta
Nov 7
ORD6:00 amChicago O'Hare Intl
7h 29m
1 stop
EYW2:29 pmKey West
Nov 11
EYW3:21 pmKey West
7h 10m
1 stop
ORD9:31 pmChicago O'Hare Intl

  • How far is Chicago to Key West by plane?

    The distance between Chicago and Key West is about 1241.6 mi. 3h 03m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to Key West Airport?

    Prices for flights from Chicago to Key West Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Key West Airport?

  • How old do you have to be to fly from Chicago to Key West Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The travel and health documents you'll need for your trip to Key West Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Key West Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.


Alternative routes for Chicago to Key West

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Chicago to Fort Lauderdale Flights
Fastest flight time2h 56m
Cheapest price$52
Chicago to Tampa Flights
Fastest flight time2h 35m
Cheapest price$33
Chicago to Orlando Flights
Fastest flight time2h 35m
Cheapest price$48
Chicago to Fort Myers Flights
Fastest flight time2h 42m
Cheapest price$63
Chicago to Miami Flights
Fastest flight time2h 57m
Cheapest price$48
St. Louis to Miami Flights
Fastest flight time2h 39m
Cheapest price$124
St. Louis to Orlando Flights
Fastest flight time2h 23m
Cheapest price$54
Chicago to West Palm Beach Flights
Fastest flight time4h 29m
Cheapest price$165
St. Louis to Fort Lauderdale Flights
Fastest flight time4h 21m
Cheapest price$124
Chicago to Pensacola Flights
Fastest flight time2h 18m
Cheapest price$121
Chicago to Jacksonville Flights
Fastest flight time2h 10m
Cheapest price$163
Chicago to Daytona Beach Flights
Fastest flight time4h 10m
Cheapest price$297

Similar Chicago to Key West flights

Flexible with your destination? Broaden your search and find flights similar to your Chicago to Key West route

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Key West?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Key West. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Key West with flexible booking policies on momondo?

momondo does allow users to show only those flights to Key West from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Key West?

momondo provides multiple filters to help you find the best flight to Key West from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

Iā€™m not ready to book a flight from Chicago to Key West right now. Can momondo alert me if prices change?

Price alerts on flights to Key West from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


An easier way to manage your Key West trip

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