MDW - EYW

$104 Find Cheap Flights from Chicago Midway Airport to Key West

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Key West departing on 5/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Key West

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Key West, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$299
Overall average: $383
Delta
Wed 3/18Wed 3/25
MDW - EYW • 1 stop
Cheapest one-way
$104
Delta
Wed 5/6
MDW - EYW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Midway and Key West. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Miami (MIA)
Cheapest • Avg $313 (round-trip)
Miami (MIA)
Shortest trip • 4h 57m (one-way)
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 37% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 Key West!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Key West that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Key West

Wed, Mar 18 - Wed, Mar 25
Delta Logo
12:47 pm - 7:41 pm
MDW
-
EYW
5h 54m
1 stop
Delta Logo
6:25 pm - 10:31 pm
EYW
-
MDW
5h 06m
1 stop
$299Delta
Sun, Mar 8 - Thu, Mar 12
Multiple Airlines Logo
6:05 am - 9:09 am
MDW
-
EYW
26h 04m
2 stops
Multiple Airlines Logo
9:46 am - 3:52 pm
EYW
-
MDW
7h 06m
1 stop
$307Multiple Airlines
Mon, Mar 9 - Thu, Mar 12
Multiple Airlines Logo
2:41 pm - 12:21 pm
MDW
-
EYW
20h 40m
2 stops
Multiple Airlines Logo
9:46 am - 3:52 pm
EYW
-
MDW
7h 06m
1 stop
$312Multiple Airlines
Tue, May 12 - Tue, May 19
Delta Logo
12:51 pm - 7:49 pm
MDW
-
EYW
5h 58m
1 stop
Delta Logo
11:48 am - 4:12 pm
EYW
-
MDW
5h 24m
1 stop
$314Delta
Sat, Mar 14 - Mon, Mar 23
Multiple Airlines Logo
2:56 pm - 9:06 am
MDW
-
EYW
17h 10m
1 stop
Multiple Airlines Logo
9:49 am - 8:54 pm
EYW
-
MDW
36h 05m
2 stops
$316Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
2:41 pm - 8:06 am
MDW
-
EYW
40h 25m
2 stops
Multiple Airlines Logo
1:06 pm - 8:53 pm
EYW
-
MDW
8h 47m
1 stop
$321Multiple Airlines
Sat, Apr 18 - Wed, Apr 22
Delta Logo
10:41 am - 5:23 pm
MDW
-
EYW
5h 42m
1 stop
Delta Logo
6:23 pm - 10:28 pm
EYW
-
MDW
5h 05m
1 stop
$324Delta
Wed, Mar 25 - Sun, Mar 29
Multiple Airlines Logo
11:19 am - 9:06 am
MDW
-
EYW
20h 47m
1 stop
Multiple Airlines Logo
4:36 pm - 10:19 pm
EYW
-
MDW
30h 43m
2 stops
$328Multiple Airlines
Wed, Mar 4 - Sat, Mar 7
Delta Logo
10:49 am - 5:01 pm
MDW
-
EYW
5h 12m
1 stop
Delta Logo
5:56 pm - 10:31 pm
EYW
-
MDW
5h 35m
1 stop
$329Delta
Fri, Apr 17 - Wed, Apr 22
Delta Logo
12:52 pm - 7:40 pm
MDW
-
EYW
5h 48m
1 stop
Delta Logo
6:23 pm - 10:28 pm
EYW
-
MDW
5h 05m
1 stop
$333Delta
Booking Insights

KAYAK's insights & trends for Midway to Key West flights

Get data-powered insights and trends into flights from Midway to Key West to help you find the cheapest flights, the best time to fly and much more.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Key West, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Key West is May, where tickets cost $342 (return) on average. On the other hand, the most expensive months are November and April, where the average cost of round-trip tickets is $1,356 and $588 respectively.

Good to know

Low seasonAugust
Cheapest flight$104
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 8% increase in price.
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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Key West flights

  • What is the cheapest flight from Chicago Midway Airport to Key West?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Key West was $104 for a one-way ticket and $299 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Key West?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Key West?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Key West.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Key West?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Key West.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Key West?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Key West from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Key West?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Key West with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and EYW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Key West?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Key West from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Key West

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Key West. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Key West? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8236 reviews
7.9Comfort
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

4.0 OkayJahmes, Feb 2026
LAX - MCO
Read more Delta reviews

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

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

Information on your arrival and departure airports