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

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

How to find the cheapest flight from
Key West (EYW) to Midway (MDW)

All the information you need to plan the best EYW to MDW flight in 2022: compare Key West to Midway flight prices with the expected peak season, weather and rainfall in Midway.
When is the cheapest time to fly from Key West to Chicago Midway Airport (EYW - MDW)?

When flying from Key West to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

April is one of the best times of the year to fly to Chicago Midway Airport from Key West. Prices for April average $408 per person but you can even find prices for as low as $188. The most expensive prices can be found in the month of March. Opting for a April flight can save you 52% on your journey compared to booking in March

Cheap flights from Key West to Midway in May, June 2022

The best prices found for EYW to MDW flights for May, June
27 May - 29 May
$394pp
EYW
Key West
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
EYW
Key West
26 May - 29 May
$420pp
EYW
Key West
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
EYW
Key West
26 May - 29 May
$460pp
EYW
Key West
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
EYW
Key West

Key West to Midway 2022 flight deals

Cheap flights to Midway from Key West found for this year
27 May - 29 May
$394pp
EYW
Key West
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
EYW
Key West
26 May - 29 May
$420pp
EYW
Key West
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
EYW
Key West
27 Jul - 3 Aug
$428pp
EYW
Key West
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
EYW
Key West

One-way flights to Midway from Key West

The cheapest one-way flights from Key West to Midway
11:45 am - 10:55 am
Allegiant Air
1 Stop
24h 10m
EYW - MDW
Allegiant Air
$358
Kiwi.com
3:00 am - 12:45 pm
Delta
2 Stops
10h 45m
EYW - MDW
Delta
$383
Delta
7:45 am - 11:07 am
Multiple Airlines
2 Stops
28h 22m
EYW - MDW
Multiple Airlines
$389
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Key West</span> to <span class="emphasized">Midway</span> flights.

Flight FAQs

From Key West to Midway

What airport do you fly from for flights from Key West to Chicago Midway?

If you book a flight to Chicago Midway from Key West, you will be flying from Key West, which is the city’s only airport. Key West (EYW) is located 2.6 mi from the center of Key West. There are 0 flights from Key West to Chicago Midway per day from 1 airline.

Which airlines flying from Key West to Chicago Midway have flexible changes due to COVID-19?

Some of our airline partners flying from Key West to Chicago Midway have new flexible policies in place due to COVID-19. Delta is one of the carriers where you may find flexible change policies. You can use our site to filter for airlines like Delta with this kind of flexibility.

Can I find flights from Key West to Chicago Midway Airport for under $500 on Cheapflights?

Yes, there are multiple flights from Key West to Chicago Midway Airport for under $500. The cheapest flight booked recently is on Delta for just $428, but on average you can expect to pay $718.

COVID Restrictions

View COVID Travel Restrictions for Midway (MDW)

Do I need a COVID test to fly to Midway from Key West?

Information is based on travel restrictions for travel to Chicago Midway within the United States

Most visitors from Key West need to provide a negative COVID-19 test result and/or quarantine to enter Chicago Midway.

COVID-19 testing requirements
Visitors from Key West must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Chicago Midway.

Quarantine requirements
Visitors from Key West are not required to quarantine after entering Chicago Midway.

Do I need a test to fly back to Key West from Midway?

Returning to Key West from Chicago Midway

COVID-19 testing requirements
Visitors from Chicago Midway must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Key West.

Quarantine requirements
Visitors from Chicago Midway are not required to quarantine after entering Key West.

Hide COVID Travel Restrictions for Midway (MDW)

Alternative routes for Key West to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Midway

Things to know before you go - useful duration and weather info for your trip from Key West to Midway.
Average temperature for May in Midway
71.6 °F
Avg rainfall for May in Midway
4.3 ″

Airports servicing Key West

Airports servicing Chicago