EYW - MDW

$128 Find Cheap Flights from Key West to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$339
Typical prices: $236-$236
Delta
Tue 9/11Fri 9/14
EYW - MDW • 1 stop
Cheapest one-way
$128
Typical prices: $100-$263
Multiple Airlines
Sun 10/7
EYW - MDW • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Key West and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

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

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

Recent round-trip flight deals from Key West to Midway

Fri, Sep 11 - Mon, Sep 14
Delta Logo
6:19 pm - 10:44 pmEYW  Key West-MDW Chicago Midway
5h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:53 pmMDW  Chicago Midway-EYW Key West
5h 48m1 stop Atlanta Hartsfield-Jackson
$339Delta
Tue, Sep 1 - Sat, Sep 5
Delta Logo
6:15 pm - 10:36 pmEYW  Key West-MDW Chicago Midway
5h 21m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 2:52 pmMDW  Chicago Midway-EYW Key West
7h 47m1 stop Atlanta Hartsfield-Jackson
$482Delta
Fri, Sep 4 - Tue, Sep 8
Delta Logo
7:40 am - 11:51 amEYW  Key West-MDW Chicago Midway
5h 11m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:53 pmMDW  Chicago Midway-EYW Key West
5h 48m1 stop Atlanta Hartsfield-Jackson
$484Delta
Tue, Sep 1 - Sat, Sep 5
Delta Logo
11:48 am - 3:44 pmEYW  Key West-MDW Chicago Midway
4h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:24 am - 7:57 pmMDW  Chicago Midway-EYW Key West
9h 33m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$727Delta
Fri, Sep 4 - Tue, Sep 8
Delta Logo
7:40 am - 11:51 amEYW  Key West-MDW Chicago Midway
5h 11m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:29 am - 8:00 pmMDW  Chicago Midway-EYW Key West
9h 31m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$763Delta
Fri, Sep 11 - Mon, Sep 14
Delta Logo
7:40 am - 4:17 pmEYW  Key West-MDW Chicago Midway
9h 37m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:05 am - 12:53 pmMDW  Chicago Midway-EYW Key West
5h 48m1 stop Atlanta Hartsfield-Jackson
$769Delta
Fri, Sep 11 - Mon, Sep 14
Delta Logo
6:19 pm - 10:44 pmEYW  Key West-MDW Chicago Midway
5h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:24 am - 8:00 pmMDW  Chicago Midway-EYW Key West
9h 36m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$859Delta
Fri, Sep 4 - Tue, Sep 8
Delta Logo
11:48 am - 6:33 pmEYW  Key West-MDW Chicago Midway
7h 45m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 5:23 pmMDW  Chicago Midway-EYW Key West
6h 54m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$1,018Delta
Tue, Sep 1 - Sat, Sep 5
Delta Logo
7:40 am - 4:59 pmEYW  Key West-MDW Chicago Midway
10h 19m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
9:24 am - 7:57 pmMDW  Chicago Midway-EYW Key West
9h 33m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$1,097Delta
Booking Insights

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

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Key West to Chicago Midway Airport with more confidence.

What is the cheapest airline to fly from Key West to Chicago Midway Airport?

Delta ($339) offered the cheapest round-trip ticket from Key West to Chicago Midway Airport in the last 5 days.

Find deals

Key details for Key West to Chicago Midway Airport flights

Cheapest flight

$128
Flight from Key West to Chicago Midway Airport

When to book flights from Key West to Midway

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

Your Key West to Chicago Midway Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

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

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

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

    A nonstop flight from Key West to Chicago Midway Airport takes 0h 00m, covering 1,238 miles.

  • What are the earliest and latest flights from Key West to Chicago Midway Airport?

    These are the earliest and latest flight times available from Key West to Chicago Midway Airport:

    • Earliest: departs at 12:00 am and lands at 12:00 am
    • Latest: departs at 12:00 am and lands at 12:00 am.

    The flight takes about 0h 00m.

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

    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.

  • Have flight prices from Key West to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $339 to $1,097. That means the highest observed fare was about 3x higher than the lowest one.

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

    One-way fares from Key West to Chicago Midway Airport are currently higher than usual. Average one-way flight prices are about $159, which is 12% above the typical average for this route.

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

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

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    · Hertz
    · Dollar
    · Budget
    · Alamo
    · Rent-A-Wreck

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

    Round-trip flights from Key West to Chicago Midway Airport range from $236 to $236, with an average of $236 over the past 12 months. Anything below $236 counts as a good deal.

Your guide to booking Key West to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.

Everything you need to know for your flight from Key West to Midway

Information on your arrival and departure airports

Key West (EYW)
Midway (MDW)