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Cheap flights from Key West to Chicago from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Key West to Chicago departing on 12/25. 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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Find the cheapest flights from Key West to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Key West to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Key West to Chicago.

Cheap last minute flights

Planning a quick getaway from Key West to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Key West to Chicago

Find recent round-trip train or bus tickets from Key West to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:36 am - 2:50 pmORD-EYW
3h 14mnonstop
$224United Airlines
Find Deal
Sat, Jan 18 - Sun, Jan 26
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
5:45 am - 4:01 pmORD-EYW
9h 16m1 stop
$234United Airlines
Find Deal
Sat, Jan 18 - Sun, Jan 26
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
10:57 am - 5:21 pmMDW-EYW
5h 24m1 stop
$243Delta
Find Deal
Sat, Jan 18 - Sun, Jan 26
4:50 pm - 10:45 pmEYW-ORD
6h 55m1 stop
5:45 am - 4:01 pmORD-EYW
9h 16m1 stop
$243United Airlines
Find Deal
Sat, Jan 18 - Sun, Jan 26
1:06 pm - 3:43 pmEYW-ORD
3h 37mnonstop
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
$244American Airlines
Find Deal
Thu, Dec 12 - Tue, Dec 17
11:09 am - 4:09 pmEYW-ORD
6h 00m1 stop
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
$254American Airlines
Find Deal
Sat, Dec 14 - Tue, Dec 17
2:19 pm - 9:05 pmEYW-ORD
7h 46m1 stop
9:30 am - 5:24 pmORD-EYW
6h 54m1 stop
$263Delta
Find Deal
Thu, Dec 12 - Tue, Dec 17
1:45 pm - 7:59 pmEYW-ORD
7h 14m1 stop
9:45 am - 5:21 pmORD-EYW
6h 36m1 stop
$288Delta
Find Deal
Sat, Jan 18 - Sun, Jan 26
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$289American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
10:02 am - 10:07 amEYW-ORD
25h 05m3 stops
1:44 pm - 5:05 pmORD-EYW
26h 21m3 stops
Sat, Jan 18 - Sun, Jan 26
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
$100American Airlines
Find Deal
Wed, Dec 25
3:03 pm - 8:48 pmEYW-ORD
6h 45m1 stop
$109Delta
Find Deal
Tue, Jan 28
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
$109Delta
Find Deal
Wed, Feb 5
1:02 pm - 7:14 pmEYW-ORD
7h 12m1 stop
$118Delta
Find Deal
Tue, Dec 24
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
$124United Airlines
Find Deal
Sat, Jan 18
6:16 pm - 11:59 pmEYW-ORD
6h 43m1 stop
$139Delta
Find Deal
Wed, Feb 26
4:19 pm - 6:50 pmEYW-ORD
3h 31mnonstop
$140United Airlines
Find Deal
Tue, Dec 24
4:50 pm - 10:45 pmEYW-ORD
6h 55m1 stop
$144United Airlines
Find Deal
Sat, Jan 11
10:52 am - 11:32 pmEYW-ORD
13h 40m2 stops
Wed, Feb 5
11:24 am - 4:16 pmEYW-ORD
5h 52m1 stop
$159American Airlines
Find Deal
Wed, Jan 1
5:06 pm - 10:53 pmEYW-ORD
6h 47m1 stop
5:02 am - 12:00 pmORD-EYW
5h 58m1 stop
$413American Airlines
Find Deal
Sat, Nov 30 - Tue, Dec 24
8:01 am - 12:11 pmEYW-ORD
5h 10m1 stop
12:15 pm - 7:01 pmORD-EYW
5h 46m1 stop
$458American Airlines
Find Deal
Sat, Nov 30 - Mon, Dec 23
12:10 pm - 8:04 pmEYW-ORD
8h 54m1 stop
8:00 am - 12:37 pmORD-EYW
3h 37mnonstop
$489American Airlines
Find Deal
Sat, Nov 30 - Tue, Dec 24
2:13 pm - 6:50 pmEYW-ORD
5h 37m1 stop
6:00 am - 11:38 amORD-EYW
4h 38m1 stop
$498Delta
Find Deal
Thu, Nov 28 - Sun, Dec 1
11:57 am - 5:59 pmEYW-ORD
7h 02m1 stop
8:09 am - 12:25 pmORD-EYW
3h 16mnonstop
$499American Airlines
Find Deal
Thu, Nov 28 - Sun, Dec 1
2:13 pm - 6:50 pmEYW-ORD
5h 37m1 stop
6:00 am - 11:38 amORD-EYW
4h 38m1 stop
$518Delta
Find Deal
Thu, Nov 28 - Sun, Dec 1
12:12 pm - 2:33 pmEYW-ORD
3h 21mnonstop
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
$579United Airlines
Find Deal
Thu, Nov 28 - Sun, Dec 1
5:59 pm - 2:31 pmEYW-ORD
21h 32m2 stops
7:53 pm - 8:03 amORD-EYW
11h 10m1 stop
Sun, Dec 1 - Mon, Dec 23
5:59 pm - 2:31 pmEYW-ORD
21h 32m2 stops
7:53 pm - 9:13 amORD-EYW
12h 20m1 stop
Sun, Dec 1 - Sun, Dec 22
1:55 pm - 9:22 pmEYW-ORD
8h 27m1 stop
7:25 am - 6:55 pmORD-EYW
10h 30m2 stops
$772United Airlines
Find Deal
Sat, Nov 30 - Tue, Dec 24
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:36 am - 2:50 pmORD-EYW
3h 14mnonstop
$224United Airlines
Find Deal
Sat, Jan 18 - Sun, Jan 26
1:06 pm - 3:43 pmEYW-ORD
3h 37mnonstop
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
$244American Airlines
Find Deal
Thu, Dec 12 - Tue, Dec 17
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$289American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$339American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
$369United Airlines
Find Deal
Sat, Dec 14 - Tue, Dec 17
1:05 pm - 3:42 pmEYW-ORD
3h 37mnonstop
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
$518American Airlines
Find Deal
Mon, Dec 16 - Wed, Dec 18
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$679United Airlines
Find Deal
Thu, Jan 9 - Fri, Jan 17
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
$788United Airlines
Find Deal
Sun, Dec 15 - Tue, Dec 17
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
$838United Airlines
Find Deal
Sun, Dec 15 - Wed, Dec 18

American Airlines flights from Key West to Chicago

Our best American Airlines deals on Key West to Chicago flight tickets
American Airlines
Dec 12
EYW1:06 pmKey West
3h 37m
ORD3:43 pmChicago O'Hare Intl
Dec 17
ORD8:10 amChicago O'Hare Intl
3h 25m
EYW12:35 pmKey West
American Airlines
Dec 14
EYW11:09 amKey West
6h 00m
1 stop
ORD4:09 pmChicago O'Hare Intl
Dec 17
ORD8:10 amChicago O'Hare Intl
3h 25m
EYW12:35 pmKey West
American Airlines
Dec 24
EYW1:07 pmKey West
3h 31m
ORD3:38 pmChicago O'Hare Intl
Jan 11
ORD8:10 amChicago O'Hare Intl
3h 24m
EYW12:34 pmKey West

Delta flights from Key West to Chicago

Our best Delta deals on Key West to Chicago flight tickets
Delta
Jan 18
EYW6:16 pmKey West
5h 04m
1 stop
MDW10:20 pmChicago Midway
Jan 26
MDW10:57 amChicago Midway
5h 24m
1 stop
EYW5:21 pmKey West
Delta
Dec 12
EYW2:19 pmKey West
7h 46m
1 stop
ORD9:05 pmChicago O'Hare Intl
Dec 17
ORD9:30 amChicago O'Hare Intl
6h 54m
1 stop
EYW5:24 pmKey West
Delta
Jan 18
EYW1:45 pmKey West
7h 14m
1 stop
ORD7:59 pmChicago O'Hare Intl
Jan 26
ORD9:45 amChicago O'Hare Intl
6h 36m
1 stop
EYW5:21 pmKey West

See travel insights to Chicago from

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

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 Chicago?

The month of August is, on average, the cheapest month to fly to Chicago from Key West, with most prices found around $294. If you’re not able to fly to Chicago in August, then June is your next best option. Flight prices from Key West to Chicago during June average around $322.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $0. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Key West to Chicago for around $453.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Key West to Chicago during this time can be as low as $0. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $412.

What is the cheapest Key West to Chicago flight route?

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

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

There are 4 cabin classes available to choose from on Key West to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

You could potentially save up to 9% on your flight if you consider stops on a Key West to Chicago flight.

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


When to book flights from Key West to Chicago

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

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

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

Best Price Found

$100

Fastest flight time

3h 21m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Key West in the past 72 hours is $100. The best round-trip flight deal from Key West to Chicago found on momondo in the last 72 hours is $224.
The fastest flight from Key West to Chicago takes 3h 21m
Direct flights go from Key West to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Key West to Chicago by plane?

    Chicago is 1241.6 mi away from Key West. In terms of flight time, this usually takes a little over 3h 21m.

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

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

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

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

    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 Key West Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 Key West to Chicago?

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


Best airlines flying from Key West to Chicago

Compare and see reviews for airlines that fly from Key West to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $211Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $313Free CancellationRating
7.4
9,153 reviews
Search United Airlines flights
  • United Airlines Flights From Key West to Chicago

    Across 1 United Airlines flight from Key West to Chicago this week, the average price was $464, with the best United Airlines deals starting from $313 round-trip. 9,153 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Key West to Chicago

    Another popular option for Key West to Chicago flights is American Airlines (7.2/10, 10,000 ratings). American Airlines flies from Key West to Chicago around 3 times per week, with deals starting from $211 round-trip and rising to an average price of around $428.


Why use momondo?

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

It is quick and easy to find Key West to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. All flights to Chicago from Key West on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

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

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

Yes momondo offers price alerts on flights to Chicago from Key West. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago