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Cheap flights from Key West to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport departing on 12/18. 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.
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$224American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
1:06 pm - 3:43 pmEYW-ORD
3h 37mnonstop
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
$249American Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
10:28 am - 7:07 pmORD-EYW
7h 39m1 stop
$254American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
2:19 pm - 9:05 pmEYW-ORD
7h 46m1 stop
9:30 am - 5:24 pmORD-EYW
6h 54m1 stop
$268Delta
Find Deal
Thu, Dec 12 - Mon, Dec 16
11:55 am - 6:50 pmEYW-ORD
7h 55m1 stop
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
$279American Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
12:26 pm - 2:55 pmEYW-ORD
3h 29mnonstop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$304United Airlines
Find Deal
Tue, Dec 24 - Mon, Dec 30
10:55 am - 11:46 amEYW-ORD
25h 51m1 stop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$324United Airlines
Find Deal
Tue, Dec 17 - Tue, Dec 24
10:31 am - 8:49 pmEYW-ORD
11h 18m2 stops
3:31 pm - 4:56 pmORD-EYW
24h 25m3 stops
Tue, Dec 24 - Mon, Dec 30
10:31 am - 8:49 pmEYW-ORD
11h 18m2 stops
8:14 pm - 4:56 pmORD-EYW
19h 42m2 stops
Tue, Dec 24 - Mon, Dec 30
6:20 pm - 11:59 pmEYW-ORD
6h 39m1 stop
8:35 am - 8:11 pmORD-EYW
10h 36m2 stops
$975Delta
Find Deal
Thu, Jan 9 - Fri, Jan 17
1:05 pm - 3:42 pmEYW-ORD
3h 37mnonstop
$100American Airlines
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Wed, Dec 18
6:30 pm - 11:58 pmEYW-ORD
6h 28m1 stop
$109Delta
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Wed, Dec 18
9:03 am - 5:20 pmEYW-ORD
9h 17m1 stop
Sun, Jan 12
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
$140United Airlines
Find Deal
Tue, Dec 17
4:50 pm - 10:56 pmEYW-ORD
7h 06m1 stop
$149United Airlines
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Wed, Dec 25
1:01 pm - 3:29 pmEYW-ORD
3h 28mnonstop
$150American Airlines
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Wed, Feb 19
4:50 pm - 10:58 pmEYW-ORD
7h 08m1 stop
$154United Airlines
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Sat, Feb 15
8:53 am - 10:29 pmEYW-ORD
14h 36m1 stop
Sun, Feb 23
11:30 am - 1:07 pmEYW-ORD
26h 37m3 stops
$678Alaska Airlines
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Sat, Jan 11
11:30 am - 5:05 pmEYW-ORD
30h 35m3 stops
$978Alaska Airlines
Find Deal
Sun, Jan 12
12:55 pm - 3:26 pmEYW-ORD
3h 31mnonstop
8:09 am - 12:25 pmORD-EYW
3h 16mnonstop
$349American Airlines
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Fri, Nov 22 - Mon, Nov 25
5:13 pm - 10:05 pmEYW-ORD
5h 52m1 stop
8:04 am - 12:20 pmORD-EYW
3h 16mnonstop
$359American Airlines
Find Deal
Fri, Nov 22 - Sun, Nov 24
6:13 pm - 11:59 pmEYW-ORD
6h 46m1 stop
7:10 am - 1:18 pmORD-EYW
5h 08m1 stop
$377Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
12:55 pm - 3:26 pmEYW-ORD
3h 31mnonstop
12:15 pm - 6:48 pmORD-EYW
5h 33m1 stop
$409American Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
10:55 am - 9:37 amEYW-ORD
23h 42m1 stop
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
$419United Airlines
Find Deal
Sun, Nov 24 - Fri, Nov 29
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
$429United Airlines
Find Deal
Sun, Nov 24 - Fri, Nov 29
2:25 pm - 8:32 pmEYW-ORD
7h 07m1 stop
10:06 am - 4:35 pmORD-EYW
5h 29m1 stop
$448American Airlines
Find Deal
Fri, Nov 22 - Sun, Nov 24
2:13 pm - 9:15 pmEYW-ORD
8h 02m1 stop
1:30 pm - 8:30 pmORD-EYW
6h 00m1 stop
$488Delta
Find Deal
Sun, Nov 24 - Thu, Nov 28
11:57 am - 7:22 pmEYW-ORD
8h 25m2 stops
12:15 pm - 6:48 pmORD-EYW
5h 33m1 stop
$533American Airlines
Find Deal
Sun, Nov 24 - Fri, Nov 29
10:11 am - 9:20 amEYW-ORD
24h 09m2 stops
11:51 am - 4:25 pmORD-EYW
27h 34m3 stops
Fri, Nov 22 - Mon, Nov 25
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
8:10 am - 12:34 pmORD-EYW
3h 24mnonstop
$224American Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 11
1:06 pm - 3:43 pmEYW-ORD
3h 37mnonstop
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
$249American Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$279United Airlines
Find Deal
Tue, Dec 17 - Tue, Dec 24
12:26 pm - 2:55 pmEYW-ORD
3h 29mnonstop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$304United Airlines
Find Deal
Tue, Dec 24 - Mon, Dec 30
4:19 pm - 6:50 pmEYW-ORD
3h 31mnonstop
7:10 am - 11:30 amORD-EYW
3h 20mnonstop
$329United Airlines
Find Deal
Mon, Dec 23 - Mon, Dec 30
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
11:02 am - 3:13 pmORD-EYW
3h 11mnonstop
$627United Airlines
Find Deal
Mon, Dec 16 - Thu, Dec 19
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
$649United Airlines
Find Deal
Thu, Jan 9 - Fri, Jan 17
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
8:00 am - 12:37 pmORD-EYW
3h 37mnonstop
$664American Airlines
Find Deal
Mon, Dec 23 - Mon, Dec 30
4:05 pm - 6:26 pmEYW-ORD
3h 21mnonstop
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
$834United Airlines
Find Deal
Sun, Dec 1 - Thu, Dec 5

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
ORD8:10 amChicago O'Hare Intl
3h 24m
EYW12:34 pmKey West
American Airlines
Dec 12
EYW1:06 pmKey West
3h 37m
ORD3:43 pmChicago O'Hare Intl
Dec 16
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
ORD10:28 amChicago O'Hare Intl
7h 39m
1 stop
EYW7:07 pmKey West

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
Dec 12
EYW2:19 pmKey West
7h 46m
1 stop
ORD9:05 pmChicago O'Hare Intl
Dec 16
ORD9:30 amChicago O'Hare Intl
6h 54m
1 stop
EYW5:24 pmKey West
Delta
Nov 28
EYW12:33 pmKey West
7h 17m
1 stop
ORD6:50 pmChicago O'Hare Intl
Dec 1
ORD12:00 pmChicago O'Hare Intl
7h 30m
1 stop
EYW8:30 pmKey West
Delta
Nov 24
EYW2:13 pmKey West
8h 02m
1 stop
ORD9:15 pmChicago O'Hare Intl
Nov 28
ORD1:30 pmChicago O'Hare Intl
6h 00m
1 stop
EYW8:30 pmKey West

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 from Key West to Chicago O'Hare Intl Airport?

April. The cheapest time of year to fly to Chicago O'Hare Intl Airport from Key West is April. Most expensive is January

What is the cheapest day to depart Key West for Chicago O'Hare Intl Airport?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday

When is the cheapest time to fly from Key West to Chicago O'Hare Intl Airport?

At noon. Key West to Chicago O'Hare Intl Airport flights are approximately 16% more expensive in the morning than at noon

What is the cheapest airline that flies to Chicago O'Hare Intl Airport from Key West?

United Airlines. United Airlines and American Airlines are the most popular carriers operating from Key West to Chicago O'Hare Intl Airport

How many flights depart from Key West to Chicago O'Hare Intl Airport on average per day?

The number of flights available between Key West and Chicago O'Hare Intl Airport is 3 per day as of November 2024. The most frequent departure time is 4:00PM, with 100% of daily flights leaving in the afternoon.

How many flights depart from Key West to Chicago O'Hare Intl Airport on average per week?

24 flights are operational weekly from Key West to Chicago O'Hare Intl Airport as of November 2024. The most popular departure day for this route is Fri, with 21% of flights per week taking off on this day.

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

No. A direct flight is the cheapest option for a flight between Key West to Chicago O'Hare Intl Airport.

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

As of November 2024, prices for Key West to Chicago O'Hare Intl Airport flights are approximately 43% 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

$100

Fastest flight time

3h 21m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Key West in the past 72 hours is $100. The best round-trip flight deal from Key West to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $224.
The fastest flight from Key West to Chicago O'Hare Intl Airport takes 3h 21m
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 21m 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 $313Free CancellationRating
7.4
9,168 reviews
Search United Airlines flights
  • United Airlines Flights From Key West to Chicago O'Hare Intl Airport

    Across 5 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 $313 round-trip. 9,168 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 $434, 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 6 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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