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Cheap flights from Key West to Chicago O'Hare Intl Airport from $109

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 O'Hare Intl Airport departing on 4/23. 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 from Key West to Chicago

The cheapest plane tickets from Key West to Chicago found on KAYAK recently.
4:07 pm - 6:49 pmEYW-ORD
3h 42mnonstop
10:51 am - 3:03 pmORD-EYW
3h 12mnonstop
$179United Airlines
Find Deal
Wed, Mar 5 - Wed, Mar 12
6:14 pm - 11:49 pmEYW-ORD
6h 35m1 stop
2:55 pm - 8:30 pmORD-EYW
4h 35m1 stop
$217Delta
Find Deal
Wed, Mar 5 - Wed, Mar 12
12:12 pm - 6:52 pmEYW-ORD
7h 40m1 stop
10:51 am - 3:03 pmORD-EYW
3h 12mnonstop
$224United Airlines
Find Deal
Wed, Mar 5 - Wed, Mar 12
6:14 pm - 11:49 pmEYW-ORD
6h 35m1 stop
9:47 am - 5:20 pmORD-EYW
6h 33m1 stop
$243Delta
Find Deal
Thu, Mar 6 - Tue, Mar 11
6:14 pm - 11:49 pmEYW-ORD
6h 35m1 stop
9:35 am - 5:19 pmORD-EYW
6h 44m1 stop
$269Delta
Find Deal
Thu, Feb 13 - Mon, Feb 17
12:21 pm - 8:08 pmEYW-ORD
8h 47m1 stop
8:06 am - 12:28 pmORD-EYW
3h 22mnonstop
$279American Airlines
Find Deal
Thu, Feb 13 - Mon, Feb 17
4:59 pm - 11:52 pmEYW-ORD
7h 53m1 stop
5:10 am - 12:06 pmORD-EYW
5h 56m1 stop
$309American Airlines
Find Deal
Wed, Feb 19 - Wed, Feb 26
1:01 pm - 3:29 pmEYW-ORD
3h 28mnonstop
8:06 am - 12:28 pmORD-EYW
3h 22mnonstop
$319American Airlines
Find Deal
Thu, Feb 13 - Mon, Feb 17
5:08 pm - 7:40 amEYW-ORD
15h 32m1 stop
8:53 pm - 9:36 amORD-EYW
11h 43m1 stop
Mon, Mar 24 - Wed, Mar 26
5:08 pm - 9:29 amEYW-ORD
17h 21m2 stops
7:21 pm - 8:03 amORD-EYW
11h 42m1 stop
Fri, Mar 7 - Sat, Mar 15
6:00 pm - 12:06 amEYW-ORD
7h 06m1 stop
$109Delta
Find Deal
Wed, Apr 23
10:19 am - 1:09 pmEYW-ORD
3h 50mnonstop
$130United Airlines
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Tue, Mar 18
6:15 pm - 11:56 pmEYW-ORD
6h 41m1 stop
$140Delta
Find Deal
Wed, Mar 19
5:06 pm - 7:40 amEYW-ORD
15h 34m1 stop
Mon, Apr 7
7:00 am - 12:09 pmEYW-ORD
6h 09m1 stop
$170Delta
Find Deal
Tue, Apr 15
5:52 pm - 12:39 pmEYW-ORD
19h 47m2 stops
Sun, Feb 9
1:01 pm - 3:29 pmEYW-ORD
3h 28mnonstop
$250American Airlines
Find Deal
Sat, Feb 15
1:50 pm - 4:15 pmEYW-ORD
3h 25mnonstop
$254American Airlines
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Tue, May 6
11:20 am - 1:04 pmEYW-ORD
26h 44m3 stops
$819Alaska Airlines
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Sat, Feb 15
12:05 pm - 2:14 pmEYW-ORD
27h 09m3 stops
$839Alaska Airlines
Find Deal
Sat, Jun 7
4:07 pm - 6:49 pmEYW-ORD
3h 42mnonstop
10:51 am - 3:03 pmORD-EYW
3h 12mnonstop
$179United Airlines
Find Deal
Wed, Mar 5 - Wed, Mar 12
1:01 pm - 3:29 pmEYW-ORD
3h 28mnonstop
8:06 am - 12:28 pmORD-EYW
3h 22mnonstop
$319American Airlines
Find Deal
Thu, Feb 13 - Mon, Feb 17
12:55 pm - 3:23 pmEYW-ORD
3h 28mnonstop
8:04 am - 12:20 pmORD-EYW
3h 16mnonstop
$384American Airlines
Find Deal
Thu, Mar 6 - Tue, Mar 11
3:59 pm - 6:40 pmEYW-ORD
3h 41mnonstop
4:42 pm - 9:03 pmORD-EYW
3h 21mnonstop
$423United Airlines
Find Deal
Fri, Mar 7 - Sat, Mar 15
4:07 pm - 6:49 pmEYW-ORD
3h 42mnonstop
10:59 am - 3:11 pmORD-EYW
3h 12mnonstop
$464United Airlines
Find Deal
Wed, Feb 19 - Wed, Feb 26
10:19 am - 1:09 pmEYW-ORD
3h 50mnonstop
4:42 pm - 9:03 pmORD-EYW
3h 21mnonstop
$528United Airlines
Find Deal
Mon, Mar 24 - Wed, Mar 26
1:01 pm - 3:29 pmEYW-ORD
3h 28mnonstop
8:06 am - 12:28 pmORD-EYW
3h 22mnonstop
$654American Airlines
Find Deal
Sun, Feb 16 - Sun, Feb 23
3:59 pm - 6:40 pmEYW-ORD
3h 41mnonstop
10:51 am - 3:03 pmORD-EYW
3h 12mnonstop
$657United Airlines
Find Deal
Mon, Mar 24 - Thu, Mar 27
10:19 am - 1:09 pmEYW-ORD
3h 50mnonstop
4:42 pm - 9:03 pmORD-EYW
3h 21mnonstop
$693United Airlines
Find Deal
Thu, Mar 20 - Sun, Mar 23
1:01 pm - 3:29 pmEYW-ORD
3h 28mnonstop
8:06 am - 12:28 pmORD-EYW
3h 22mnonstop
$703American Airlines
Find Deal
Sun, Feb 16 - Sun, Feb 23

Delta flights from Key West to Chicago O'Hare Intl Airport

Our best Delta deals on Key West to Chicago O'Hare Intl Airport flight tickets
Delta
Mar 5
EYW6:14 pmKey West
6h 35m
1 stop
ORD11:49 pmChicago O'Hare Intl
Mar 12
ORD2:55 pmChicago O'Hare Intl
4h 35m
1 stop
EYW8:30 pmKey West
Delta
Mar 6
EYW6:14 pmKey West
6h 35m
1 stop
ORD11:49 pmChicago O'Hare Intl
Mar 11
ORD9:47 amChicago O'Hare Intl
6h 33m
1 stop
EYW5:20 pmKey West
Delta
Feb 13
EYW6:14 pmKey West
6h 35m
1 stop
ORD11:49 pmChicago O'Hare Intl
Feb 17
ORD9:35 amChicago O'Hare Intl
6h 44m
1 stop
EYW5:19 pmKey West

United Airlines flights from Key West to Chicago O'Hare Intl Airport

Our best United Airlines deals on Key West to Chicago O'Hare Intl Airport flight tickets
United Airlines
Mar 5
EYW4:07 pmKey West
3h 42m
ORD6:49 pmChicago O'Hare Intl
Mar 12
ORD10:51 amChicago O'Hare Intl
3h 12m
EYW3:03 pmKey West
United Airlines
Mar 5
EYW12:12 pmKey West
7h 40m
1 stop
ORD6:52 pmChicago O'Hare Intl
Mar 12
ORD10:51 amChicago O'Hare Intl
3h 12m
EYW3:03 pmKey West
United Airlines
Mar 6
EYW10:00 amKey West
11h 00m
1 stop
ORD8:00 pmChicago O'Hare Intl
Mar 11
ORD10:51 amChicago O'Hare Intl
3h 12m
EYW3:03 pmKey West

See travel insights to Chicago from

How to get the cheapest flight ticket from Key West to Chicago O'Hare Intl Airport

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 O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Key West averaging around $240.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $366. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Key West because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $978.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Key West at noon is the least expensive time of day to depart. momondo users have found prices as low as $349 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $437. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Key West to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Key West to Chicago O'Hare Intl flights?

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

How have Key West to Chicago O'Hare Intl Airport flight prices changed over time?

As of January 2025, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 52% cheaper when compared to flights at the same time last year.

When to book flights from Key West to Chicago O'Hare Intl Airport

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

Cheap Key West to Chicago O'Hare Intl Airport (EYW to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Key West to Chicago O'Hare Intl Airport

Best Price Found

$109

Fastest flight time

3h 25m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Key West in the past 72 hours is $109. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $179.
The fastest flight from Key West to Chicago O'Hare Intl Airport takes 3h 25m
Direct flights go from Key West to Chicago O'Hare Intl Airport every day.

  • How far is Key West to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 1252.7 mi away from Key West. Typically, this will take 3h 28m by plane in normal conditions.

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

    Prices for flights from Key West Airport to Chicago O'Hare Intl Airport refresh daily.

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

  • How old do you have to be to fly from Key West Airport to Chicago O'Hare Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Key West Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Key West to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Key West to Chicago O'Hare Intl Airport?


Best airlines flying from Key West to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Key West to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $211Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $224Free CancellationRating
7.4
8,984 reviews
Search United Airlines flights
  • United Airlines Flights From Key West to Chicago O'Hare Intl Airport

    Across 7 United Airlines flights from Key West to Chicago O'Hare Intl Airport this week, the average price was $394, with the best United Airlines deals starting from $224 round-trip. 8,985 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • American Airlines Flights From Key West to Chicago O'Hare Intl Airport

    $211 is the best American Airlines flight deal from Key West to Chicago O'Hare Intl Airport found on momondo over the last 72 hours. The average American Airlines ticket price found was closer to $392, however, with flight time and availability significantly affecting the price. American Airlines (7.2/10 from 10,000 user reviews) flies into Chicago O'Hare Intl Airport from Key West 3 times in an average week so prices can vary.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Rockford
Lake Geneva
Schaumburg
Merrillville
Rosemont
Gurnee
Naperville
Kenosha
Joliet
South Haven
Racine
Hammond
Oak Brook
South Holland
Tinley Park
New Buffalo
Elk Grove Village
Aurora
Elgin
Waukegan

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Key West to Chicago for you.

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

Flights from Key West to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Key West.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Key West and alert you when they change.


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