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Cheap flights from Key West to Chicago O'Hare Intl Airport from $110

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 1/8. 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.
6:16 pm - 11:59 pmEYW-ORD
6h 43m1 stop
11:05 am - 5:21 pmORD-EYW
5h 16m1 stop
$268Delta
Find Deal
Wed, Jan 22 - Tue, Jan 28
3:09 pm - 7:26 pmEYW-ORD
5h 17m1 stop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$279American Airlines
Find Deal
Wed, Jan 22 - Wed, Jan 29
1:45 pm - 7:19 pmEYW-ORD
6h 34m1 stop
10:10 am - 4:37 pmORD-EYW
5h 27m1 stop
$308American Airlines
Find Deal
Wed, Jan 8 - Sat, Jan 11
4:50 pm - 12:15 amEYW-ORD
8h 25m1 stop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$314United Airlines
Find Deal
Sun, Jan 19 - Mon, Jan 27
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$329United Airlines
Find Deal
Thu, Jan 23 - Mon, Jan 27
1:50 pm - 8:25 pmEYW-ORD
7h 35m1 stop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$339United Airlines
Find Deal
Wed, Jan 22 - Mon, Jan 27
3:09 pm - 9:42 pmEYW-ORD
7h 33m1 stop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$344American Airlines
Find Deal
Wed, Jan 8 - Sat, Jan 11
4:50 pm - 12:15 amEYW-ORD
8h 25m1 stop
7:00 am - 6:55 pmORD-EYW
10h 55m1 stop
$346United Airlines
Find Deal
Sun, Jan 19 - Mon, Jan 27
4:50 pm - 12:15 amEYW-ORD
8h 25m1 stop
8:45 am - 6:55 pmORD-EYW
9h 10m1 stop
$350United Airlines
Find Deal
Sun, Jan 19 - Thu, Jan 30
6:16 pm - 8:35 amEYW-ORD
15h 19m1 stop
11:05 am - 5:21 pmORD-EYW
5h 16m1 stop
$397Delta
Find Deal
Tue, Jan 21 - Mon, Jan 27
10:52 am - 8:49 pmEYW-ORD
10h 57m1 stop
Wed, Jan 8
4:07 pm - 6:49 pmEYW-ORD
3h 42mnonstop
$140United Airlines
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Wed, Feb 19
4:50 pm - 10:45 pmEYW-ORD
6h 55m1 stop
$149United Airlines
Find Deal
Sat, Jan 18
2:00 pm - 10:16 pmEYW-ORD
9h 16m1 stop
Mon, Feb 3
3:03 pm - 6:49 pmEYW-ORD
4h 46m1 stop
$178Delta
Find Deal
Sat, Feb 1
2:54 pm - 9:57 pmEYW-ORD
8h 03m1 stop
$278American Airlines
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Sat, Dec 28
2:35 pm - 9:15 pmEYW-ORD
7h 40m1 stop
$283Delta
Find Deal
Wed, Mar 19
5:01 pm - 10:58 pmEYW-ORD
6h 57m1 stop
$358American Airlines
Find Deal
Thu, Jan 2
11:20 am - 5:59 pmEYW-ORD
31h 39m3 stops
$705Alaska Airlines
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Tue, Feb 25
12:17 pm - 5:55 pmEYW-ORD
30h 38m3 stops
$755Alaska Airlines
Find Deal
Wed, Mar 12
4:19 pm - 6:50 pmEYW-ORD
3h 31mnonstop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$429United Airlines
Find Deal
Thu, Dec 19 - Wed, Jan 1
4:19 pm - 6:50 pmEYW-ORD
3h 31mnonstop
6:00 am - 4:09 pmORD-EYW
9h 09m1 stop
$439United Airlines
Find Deal
Fri, Dec 20 - Wed, Jan 1
10:55 am - 4:31 pmEYW-ORD
6h 36m1 stop
7:25 am - 4:09 pmORD-EYW
7h 44m1 stop
$448United Airlines
Find Deal
Mon, Dec 23 - Wed, Jan 1
4:10 pm - 11:37 pmEYW-ORD
8h 27m1 stop
12:15 pm - 7:01 pmORD-EYW
5h 46m1 stop
$458American Airlines
Find Deal
Sun, Dec 22 - Mon, Dec 30
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
7:00 am - 3:30 pmORD-EYW
7h 30m1 stop
$484American Airlines
Find Deal
Thu, Dec 19 - Tue, Dec 31
8:01 am - 12:12 pmEYW-ORD
5h 11m1 stop
5:02 am - 11:41 amORD-EYW
5h 39m1 stop
$493American Airlines
Find Deal
Thu, Dec 19 - Tue, Dec 31
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
8:05 am - 5:11 pmORD-EYW
8h 06m1 stop
$509American Airlines
Find Deal
Sat, Dec 21 - Mon, Dec 23
7:25 am - 11:26 amEYW-ORD
5h 01m1 stop
5:45 am - 12:07 pmORD-EYW
5h 22m1 stop
$628Delta
Find Deal
Thu, Dec 19 - Wed, Jan 1
6:02 pm - 11:53 pmEYW-ORD
6h 51m1 stop
5:57 pm - 10:52 amORD-EYW
15h 55m1 stop
$953Delta
Find Deal
Fri, Dec 20 - Tue, Dec 31
1:02 pm - 10:52 pmEYW-ORD
10h 50m2 stops
5:40 am - 12:07 pmORD-EYW
5h 27m1 stop
$1,430Delta
Find Deal
Sun, Dec 22 - Mon, Dec 30
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$329United Airlines
Find Deal
Thu, Jan 23 - Tue, Jan 28
1:06 pm - 3:37 pmEYW-ORD
3h 31mnonstop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$364American Airlines
Find Deal
Wed, Jan 22 - Wed, Jan 29
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:36 am - 2:50 pmORD-EYW
3h 14mnonstop
$388United Airlines
Find Deal
Wed, Jan 8 - Sat, Jan 11
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$424United Airlines
Find Deal
Sun, Jan 19 - Wed, Jan 29
1:06 pm - 3:37 pmEYW-ORD
3h 31mnonstop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$513American Airlines
Find Deal
Tue, Jan 7 - Fri, Jan 31
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$535United Airlines
Find Deal
Wed, Jan 22 - Tue, Jan 28
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$555United Airlines
Find Deal
Thu, Jan 23 - Wed, Jan 29
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$600United Airlines
Find Deal
Wed, Jan 22 - Fri, Jan 31
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$630United Airlines
Find Deal
Sat, Jan 25 - Mon, Jan 27
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$650United Airlines
Find Deal
Sun, Jan 19 - Wed, Jan 29

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
Dec 24
EYW12:26 pmKey West
3h 29m
ORD2:55 pmChicago O'Hare Intl
Dec 31
ORD11:02 amChicago O'Hare Intl
3h 11m
EYW3:13 pmKey West
United Airlines
Dec 24
EYW12:26 pmKey West
3h 29m
ORD2:55 pmChicago O'Hare Intl
Jan 1
ORD7:25 amChicago O'Hare Intl
7h 44m
1 stop
EYW4:09 pmKey West
United Airlines
Dec 24
EYW4:50 pmKey West
7h 30m
1 stop
ORD11:20 pmChicago O'Hare Intl
Jan 1
ORD6:00 amChicago O'Hare Intl
9h 09m
1 stop
EYW4:09 pmKey West

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

Our best American Airlines deals on Key West to Chicago O'Hare Intl Airport flight tickets
American Airlines
Dec 24
EYW1:07 pmKey West
3h 31m
ORD3:38 pmChicago O'Hare Intl
Jan 11
ORD10:28 amChicago O'Hare Intl
7h 39m
1 stop
EYW7:07 pmKey West
American Airlines
Jan 22
EYW3:09 pmKey West
5h 17m
1 stop
ORD7:26 pmChicago O'Hare Intl
Jan 29
ORD8:10 amChicago O'Hare Intl
3h 24m
EYW12:34 pmKey West
American Airlines
Jan 8
EYW1:45 pmKey West
6h 34m
1 stop
ORD7:19 pmChicago O'Hare Intl
Jan 11
ORD10:10 amChicago O'Hare Intl
5h 27m
1 stop
EYW4:37 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 August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Key West averaging around $278.

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.

Can stopping save me money on Key West to Chicago O'Hare Intl Airport flights?

You could potentially save up to 21% on your flight if you consider stops on a Key West to Chicago O'Hare Intl Airport flight.

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

As of December 2024, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 13% 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

$110

Fastest flight time

3h 29m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Key West in the past 72 hours is $110. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $268.
The fastest flight from Key West to Chicago O'Hare Intl Airport takes 3h 29m
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 31m 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
9,059 reviews
Search United Airlines flights
  • United Airlines Flights From Key West to Chicago O'Hare Intl Airport

    Across 3 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. 9,055 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 $419, 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.


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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