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Cheap flights from Chicago to Key West from $162

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Key West departing on 4/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to Key West

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Key West.
10:35 am - 5:15 pmMDW-EYW
5h 40m1 stop
11:45 am - 6:03 pmEYW-MDW
7h 18m1 stop
$269Delta
Find Deal
Sat, Jul 19 - Fri, Jul 25
9:39 am - 5:30 pmORD-EYW
6h 51m1 stop
6:25 pm - 11:58 pmEYW-ORD
6h 33m1 stop
$269Delta
Find Deal
Wed, May 7 - Wed, May 14
8:10 am - 4:52 pmORD-EYW
7h 42m1 stop
12:49 pm - 3:28 pmEYW-ORD
3h 39mnonstop
$276American Airlines
Find Deal
Wed, May 7 - Wed, May 14
11:44 am - 6:49 pmORD-EYW
6h 05m1 stop
12:49 pm - 3:28 pmEYW-ORD
3h 39mnonstop
$279American Airlines
Find Deal
Wed, May 7 - Wed, May 14
7:00 am - 1:39 pmORD-EYW
5h 39m1 stop
12:49 pm - 3:28 pmEYW-ORD
3h 39mnonstop
$282American Airlines
Find Deal
Wed, May 7 - Wed, May 14
10:00 am - 4:52 pmORD-EYW
5h 52m1 stop
12:49 pm - 3:28 pmEYW-ORD
3h 39mnonstop
$284American Airlines
Find Deal
Wed, May 7 - Wed, May 14
6:30 am - 8:03 amORD-EYW
24h 33m1 stop
8:53 am - 4:55 pmEYW-ORD
33h 02m2 stops
Wed, Jun 11 - Sun, Jun 15
4:35 pm - 9:40 amORD-EYW
16h 05m1 stop
3:52 pm - 11:50 amEYW-ORD
20h 58m3 stops
Sat, May 17 - Sat, May 24
10:59 am - 3:04 pmORD-EYW
3h 05mnonstop
8:45 am - 9:35 amEYW-ORD
25h 50m1 stop
$366United Airlines
Find Deal
Tue, Apr 22 - Mon, Apr 28
7:10 am - 11:15 amORD-EYW
3h 05mnonstop
8:45 am - 9:58 pmEYW-ORD
14h 13m1 stop
$386United Airlines
Find Deal
Sat, Apr 19 - Wed, Apr 30

Delta flights from Chicago to Key West

Our best Delta deals on Chicago to Key West flight tickets
Delta
Jul 19
MDW10:35 amChicago Midway
5h 40m
1 stop
EYW5:15 pmKey West
Jul 25
EYW11:45 amKey West
7h 18m
1 stop
MDW6:03 pmChicago Midway
Delta
May 14
MDW10:25 amChicago Midway
6h 05m
1 stop
EYW5:30 pmKey West
May 21
EYW7:00 amKey West
5h 53m
1 stop
MDW11:53 amChicago Midway
Delta
Apr 15
ORD7:05 amChicago O'Hare Intl
6h 00m
1 stop
EYW2:05 pmKey West
Apr 30
EYW5:15 pmKey West
7h 44m
1 stop
ORD11:59 pmChicago O'Hare Intl

American Airlines flights from Chicago to Key West

Our best American Airlines deals on Chicago to Key West flight tickets
American Airlines
May 7
ORD8:10 amChicago O'Hare Intl
7h 42m
1 stop
EYW4:52 pmKey West
May 14
EYW12:49 pmKey West
3h 39m
ORD3:28 pmChicago O'Hare Intl
American Airlines
May 7
ORD11:44 amChicago O'Hare Intl
6h 05m
1 stop
EYW6:49 pmKey West
May 14
EYW12:49 pmKey West
3h 39m
ORD3:28 pmChicago O'Hare Intl
American Airlines
May 7
ORD7:00 amChicago O'Hare Intl
5h 39m
1 stop
EYW1:39 pmKey West
May 14
EYW12:49 pmKey West
3h 39m
ORD3:28 pmChicago O'Hare Intl

See travel insights to Key West from

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 to Key West?

In general, August is the cheapest month to fly from Chicago to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $358. If you are unable to visit Key West during the month of August, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $378.

What is the cheapest day to depart on your flight to Key West?

On average, the least expensive day to fly to Key West from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $362. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Key West for around $561.

What is the cheapest time of day to depart on your flight to Key West?

According to our data, the cheapest time of day to fly to Key West is at noon. momondo users have found flights departing from Chicago to Key West at noon for as low as $338. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly in the evening, with an average ticket price of $822. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Key West flight route?

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

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

You are more likely to see cheaper flights to Key West from Chicago when booking 7 weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $429 when searching 7 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Chicago for as low as $381 on momondo.

What cabin class options are available on Chicago to Key West flights?

There are 3 cabin classes available to choose from on Chicago to Key West flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Key West flight prices changed over time?

As of March 2025, prices for Chicago to Key West flights are approximately 13% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Key West

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Key West according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Key West (CHI to EYW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Key West

Best Price Found

$162

Fastest flight time

3h 05m

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 $162. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $269.
The fastest flight from Chicago to Key West takes 3h 05m
Direct flights go from Chicago to Key West every day.
There is 1 airport near Key West: Key West (EYW)

  • How far is Chicago to Key West by plane?

    The distance between Chicago and Key West is about 1241.6 mi. 3h 05m 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.

  • What is the most popular plane model from Chicago to Key West?

  • What is the most popular airline from Chicago to Key West?


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
DeltaPriceFrom $216Free CancellationRating
8.0
7,899 reviews
Search Delta flights
American AirlinesPriceFrom $256Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $261Free CancellationRating
7.4
8,614 reviews
Search United Airlines flights
  • United Airlines Flights From Chicago to Key West

    United Airlines flight deals from Chicago to Key West start from $261 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $467 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to Key West

    Across 10,000 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago to Key West about 4 times each week, with ticket deals ranging from $256 to $432. Price data is based on momondo searches in the last 72 hours.


Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

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.

I’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.


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