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Cheap flights from Key West to Chicago Midway Airport from $143

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 Midway Airport departing on 4/2. 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 - 10:20 pmEYW-MDW
5h 04m1 stop
6:00 am - 2:08 pmMDW-EYW
7h 08m1 stop
$424Delta
Find Deal
Fri, Jan 31 - Sun, Feb 9
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
6:00 am - 2:08 pmMDW-EYW
7h 08m1 stop
$754Delta
Find Deal
Sat, Feb 8 - Sat, Feb 15
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
9:33 am - 8:11 pmMDW-EYW
9h 38m2 stops
$852Delta
Find Deal
Fri, Jan 31 - Sun, Feb 9
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
9:33 am - 8:11 pmMDW-EYW
9h 38m2 stops
$1,046Delta
Find Deal
Mon, Feb 10 - Fri, Feb 28
7:00 am - 4:09 pmEYW-MDW
10h 09m2 stops
6:00 am - 2:08 pmMDW-EYW
7h 08m1 stop
$1,236Delta
Find Deal
Sat, Feb 8 - Sat, Feb 15
7:00 am - 4:09 pmEYW-MDW
10h 09m2 stops
9:33 am - 8:11 pmMDW-EYW
9h 38m2 stops
$1,734Delta
Find Deal
Sat, Feb 8 - Sat, Feb 15
7:00 am - 5:43 pmEYW-MDW
11h 43m2 stops
10:19 am - 8:11 pmMDW-EYW
8h 52m2 stops
$2,015Delta
Find Deal
Mon, Feb 10 - Fri, Feb 28
12:33 pm - 6:14 pmEYW-MDW
6h 41m2 stops
9:33 am - 8:11 pmMDW-EYW
9h 38m2 stops
$2,545Delta
Find Deal
Fri, Jan 31 - Sun, Feb 9
2:00 pm - 9:33 pmEYW-MDW
8h 33m1 stop
Wed, Apr 2
10:00 am - 9:25 pmEYW-MDW
12h 25m1 stop
Fri, Feb 21
3:05 pm - 11:24 pmEYW-MDW
9h 19m1 stop
Tue, Apr 1
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
$314Delta
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Fri, Feb 7
7:00 am - 6:11 pmEYW-MDW
12h 11m2 stops
$383Delta
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Wed, Feb 12
6:14 pm - 11:59 amEYW-MDW
18h 45m1 stop
$432Delta
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Mon, Feb 17
7:00 am - 2:53 pmEYW-MDW
8h 53m1 stop
$437Delta
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Sun, Feb 16
7:00 am - 11:59 amEYW-MDW
5h 59m1 stop
$460Delta
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Sun, Feb 23
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
$479Delta
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Fri, Jan 17
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
$574Delta
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Mon, Jan 13
7:00 am - 5:47 pmEYW-MDW
11h 47m2 stops
6:00 am - 2:08 pmMDW-EYW
7h 08m1 stop
$1,010Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
6:00 am - 2:08 pmMDW-EYW
7h 08m1 stop
$1,119Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:00 am - 5:47 pmEYW-MDW
11h 47m2 stops
9:34 am - 8:11 pmMDW-EYW
9h 37m2 stops
$1,422Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:00 am - 5:47 pmEYW-MDW
11h 47m2 stops
10:19 am - 8:11 pmMDW-EYW
8h 52m2 stops
$3,639Delta
Find Deal
Thu, Jan 9 - Fri, Jan 17
12:33 pm - 6:14 pmEYW-MDW
6h 41m2 stops
9:34 am - 8:11 pmMDW-EYW
9h 37m2 stops
$3,676Delta
Find Deal
Thu, Jan 9 - Sun, Jan 12

Delta flights from Key West to Chicago Midway Airport

Our best Delta deals on Key West to Chicago Midway Airport flight tickets
Delta
Jan 31
EYW6:16 pmKey West
5h 04m
1 stop
MDW10:20 pmChicago Midway
Feb 9
MDW6:00 amChicago Midway
7h 08m
1 stop
EYW2:08 pmKey West
Delta
Feb 8
EYW6:16 pmKey West
5h 04m
1 stop
MDW10:20 pmChicago Midway
Feb 15
MDW6:00 amChicago Midway
7h 08m
1 stop
EYW2:08 pmKey West
Delta
Jan 31
EYW6:16 pmKey West
5h 04m
1 stop
MDW10:20 pmChicago Midway
Feb 9
MDW9:33 amChicago Midway
9h 38m
2 stops
EYW8:11 pmKey West

See travel insights to Chicago from

How to get the cheapest flight ticket from Key West to Chicago Midway 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 airline that flies from Key West to Chicago Midway?

Delta is the most popular carrier operating from Key West to Chicago Midway

When to book flights from Key West to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Key West to Chicago Midway 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 Midway Airport (EYW to MDW) flight deals and tips

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

Best Price Found

$143

Fastest flight time

4h 46m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Key West in the past 72 hours is $143. The best round-trip flight deal from Key West to Chicago Midway Airport found on momondo in the last 72 hours is $424.
The fastest flight from Key West to Chicago Midway Airport takes 4h 46m
There are no direct flights from Key West to Chicago Midway Airport. Popular non-direct route for this connection is Key West Airport - Chicago Midway Airport.

  • How far is Key West to Chicago Midway by plane?

    There are 1237.6 mi between Key West and Chicago Midway. A reasonable flight in good conditions will take 5h 04m.

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

    Prices for flights from Key West Airport to Chicago Midway Airport were last updated today.

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

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

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.


Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Key West to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo allows you to filter the results for Key West to Chicago flights to just show those with flexible booking policies.

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

Once all potential Key West to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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 not ready to book a flight from Key West to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.


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