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MDW - EYW

$127 Find Cheap Flights from Chicago Midway Airport to Key West - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$245
Typical prices: $319-$588
Multiple Airlines
Tue 10/30Tue 11/6
MDW - EYW • 2 stops
Cheapest one-way
$127
Typical prices: $192-$323
Multiple Airlines
Wed 10/24
MDW - EYW • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and Key West. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
January
Cheapest • 32% price drop
September
Most popular
Good to know
+1
Good to know
+1
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We hope you love your trip to Key West!
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Flight Deals

Cheap Flights from Midway to Key West (MDW-EYW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Key West

Fri, Oct 30 - Fri, Nov 6
Multiple Airlines Logo
6:16 am - 9:24 amMDW  Chicago Midway-EYW Key West
26h 08m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
10:14 am - 7:19 pmEYW  Key West-MDW Chicago Midway
10h 05m1 stop Knoxville McGhee Tyson
$245Multiple Airlines
Wed, Dec 2 - Sun, Dec 6
Multiple Airlines Logo
12:28 pm - 11:20 amMDW  Chicago Midway-EYW Key West
21h 52m2 stops Atlanta Hartsfield-Jackson Orlando
Multiple Airlines Logo
10:59 am - 8:42 pmEYW  Key West-MDW Chicago Midway
10h 43m1 stop Orlando
$356Multiple Airlines
Tue, Nov 17 - Sun, Nov 22
Multiple Airlines Logo
6:16 am - 9:24 amMDW  Chicago Midway-EYW Key West
26h 08m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
10:59 am - 7:47 pmEYW  Key West-MDW Chicago Midway
9h 48m1 stop Orlando
$372Multiple Airlines
Mon, Nov 16 - Mon, Nov 23
Multiple Airlines Logo
6:42 pm - 9:24 amMDW  Chicago Midway-EYW Key West
37h 42m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
10:59 am - 7:47 pmEYW  Key West-MDW Chicago Midway
9h 48m1 stop Orlando
$373Multiple Airlines
Sat, Nov 14 - Wed, Nov 18
Delta Logo
11:27 am - 5:10 pmMDW  Chicago Midway-EYW Key West
4h 43m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:08 pm - 10:54 pmEYW  Key West-MDW Chicago Midway
5h 46m1 stop Atlanta Hartsfield-Jackson
$379Delta
Tue, Dec 15 - Sun, Dec 20
Delta Logo
11:28 am - 8:01 pmMDW  Chicago Midway-EYW Key West
7h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:20 pm - 10:22 pmEYW  Key West-MDW Chicago Midway
5h 02m1 stop Atlanta Hartsfield-Jackson
$379Delta
Mon, Dec 7 - Sat, Dec 12
Multiple Airlines Logo
9:37 pm - 10:19 amMDW  Chicago Midway-EYW Key West
11h 42m1 stop Orlando
Multiple Airlines Logo
6:26 pm - 2:55 pmEYW  Key West-MDW Chicago Midway
21h 29m2 stops Tampa St. Petersburg Atlanta Hartsfield-Jackson
$379Multiple Airlines
Thu, Dec 24 - Tue, Dec 29
Multiple Airlines Logo
9:23 pm - 12:19 pmMDW  Chicago Midway-EYW Key West
13h 56m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
10:59 am - 7:02 pmEYW  Key West-MDW Chicago Midway
9h 03m1 stop Orlando
$379Multiple Airlines
Mon, Nov 16 - Sun, Nov 22
Multiple Airlines Logo
6:42 pm - 9:24 amMDW  Chicago Midway-EYW Key West
37h 42m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
10:59 am - 7:47 pmEYW  Key West-MDW Chicago Midway
9h 48m1 stop Orlando
$379Multiple Airlines
Sat, Jan 2 - Wed, Jan 6
Multiple Airlines Logo
8:07 pm - 10:18 amMDW  Chicago Midway-EYW Key West
13h 11m1 stop Orlando
Multiple Airlines Logo
11:19 am - 11:46 pmEYW  Key West-MDW Chicago Midway
13h 27m2 stops Orlando Atlanta Hartsfield-Jackson
$379Multiple Airlines
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Key West flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What's the cheapest day of the week to fly from Chicago Midway Airport to Key West?

Based on deals KAYAK users found in the last 12 months, Sunday is the cheapest day of the week to fly from Chicago Midway Airport to Key West. It’s 38% cheaper than the average day, while Monday is the most expensive, with prices 32% higher.

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Key details for Chicago Midway Airport to Key West flights

Low season

June

Cheapest flight

$127
The most popular month to fly with an average 39% increase in travelers.
One-way flight from Chicago Midway Airport to Key West

When to book flights from Midway to Key West

Are your dates flexible? Find out the best times to travel from Midway to Key West based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Key West flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Chicago Midway Airport to Key West?

    Only Economy Class is available on flights from Chicago Midway Airport to Key West.

  • How long is a flight from Chicago Midway Airport to Key West?

    A nonstop flight from Chicago Midway Airport to Key West takes 00m, covering 1,238 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Key West?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to Key West flight?

    Round-trip flights from Chicago Midway Airport to Key West range from $319 to $588, with an average of $469 over the past 12 months. Anything below $319 counts as a good deal.

  • How are flight prices from Chicago Midway Airport to Key West looking right now?

    One-way fares from Chicago Midway Airport to Key West are currently lower than usual. Average one-way flight prices are about $187, which is 15% below the typical average for this route.

  • What car rental options are available at Key West Airport (EYW)?

    Key West Airport (EYW) hosts 5 major car rental companies, with daily rates starting from around $29 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Budget
    • Enterprise Rent-A-Car
    • Alamo

  • Which airports can I use when flying from Chicago Midway Airport to Key West?

    Flights from Chicago Midway Airport to Key West usually depart from Chicago Midway (MDW) and arrive at Key West (EYW).

  • Which airports do connecting flights from Chicago Midway Airport to Key West pass through?

    Most connecting flights from Chicago Midway Airport to Key West pass through Atlanta Hartsfield-Jackson (ATL), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Key West?

    Yes. Flexible dates can save you up to 53% on flights from Chicago Midway Airport to Key West. Sunday is the cheapest departure day at $293 round-trip on average, while Monday is the most expensive at $622, a difference of $329.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What is the time difference between Chicago Midway Airport and Key West?

    Key West is 1 hour ahead of Chicago Midway Airport (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Key West?

    Some of the most popular sights in Key West are Duval Street, Key West Historic District and Mallory Square. These are among the most viewed places in Key West on KAYAK.

Your guide to booking Chicago Midway Airport to Key West flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Sunday departure and avoid flying on Monday. On this route, Sunday flights average $293, about $329 less than Monday fares (53% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago Midway Airport to Key West trip for January. Fares historically average $318 round-trip in that month - typically $510 less than the most expensive month, which is February (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Key West Airport.

    • Havana Cabana at Key West
    • Parrot Key Hotel & Villas
    • Margaritaville Beach House Key West

More options for your flight from Midway to Key West

Complete your trip to Key West with a hotel stay or car rental

Car rentals in Key West
Hotels in Key West
Vacations in Key West