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Cheap flights from Chicago Midway Airport to Key West from $118

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Key West departing on 10/19. 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 Chicago Midway Airport to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:45 am - 11:05 amMDW-EYW
24h 20m1 stop
Multiple Airlines Logo
3:23 pm - 8:32 amEYW-MDW
18h 09m1 stop
$219Multiple Airlines
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Mon, Oct 27 - Thu, Oct 30
Multiple Airlines Logo
6:06 pm - 11:05 amMDW-EYW
15h 59m1 stop
Multiple Airlines Logo
5:40 pm - 6:46 pmEYW-MDW
26h 06m1 stop
$243Multiple Airlines
Find Deal
Mon, Nov 17 - Thu, Nov 20
Multiple Airlines Logo
7:50 am - 9:02 amMDW-EYW
24h 12m1 stop
Multiple Airlines Logo
9:57 am - 12:30 amEYW-MDW
15h 33m1 stop
$244Multiple Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
Multiple Airlines Logo
10:12 am - 8:46 pmMDW-EYW
9h 34m1 stop
Multiple Airlines Logo
9:01 am - 2:07 pmEYW-MDW
6h 06m1 stop
$250Multiple Airlines
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Thu, Nov 6 - Fri, Nov 7
Delta Logo
6:00 am - 11:31 amMDW-EYW
4h 31m1 stop
Delta Logo
6:18 pm - 11:40 pmEYW-MDW
6h 22m1 stop
$289Delta
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Tue, Nov 11 - Fri, Nov 21
Allegiant Air Logo
5:35 pm - 9:01 amMDW-EYW
14h 26m2 stops
Allegiant Air Logo
10:41 am - 3:22 pmEYW-MDW
5h 41m1 stop
$301Allegiant Air
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Fri, Nov 7 - Mon, Nov 10
Delta Logo
3:29 pm - 8:53 pmMDW-EYW
4h 24m1 stop
Delta Logo
6:00 pm - 9:46 pmEYW-MDW
4h 46m1 stop
$306Delta
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Wed, Dec 31 - Wed, Jan 7
Delta Logo
12:50 pm - 8:06 pmMDW-EYW
6h 16m1 stop
Delta Logo
6:10 pm - 11:49 pmEYW-MDW
6h 39m1 stop
$320Delta
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Tue, Dec 2 - Sat, Dec 6
Delta Logo
6:48 pm - 2:03 pmMDW-EYW
18h 15m2 stops
Delta Logo
7:40 am - 11:52 amEYW-MDW
5h 12m1 stop
$327Delta
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Mon, Nov 10 - Wed, Nov 19
Allegiant Air Logo
2:11 pm - 12:11 pmMDW-EYW
21h 00m2 stops
Allegiant Air Logo
3:13 pm - 9:32 amEYW-MDW
19h 19m2 stops
$445Allegiant Air
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Fri, Nov 21 - Mon, Nov 24

Allegiant Air flights from Chicago Midway Airport to Key West

Our best Allegiant Air deals on Chicago Midway Airport to Key West flight tickets
Allegiant Air
Nov 7
MDW5:35 pmChicago Midway
14h 26m
2 stops
EYW9:01 amKey West
Nov 10
EYW10:41 amKey West
5h 41m
1 stop
MDW3:22 pmChicago Midway
$301
Find similar
Allegiant Air
Nov 21
MDW2:11 pmChicago Midway
21h 00m
2 stops
EYW12:11 pmKey West
Nov 24
EYW3:13 pmKey West
19h 19m
2 stops
MDW9:32 amChicago Midway
$445
Find similar

Delta flights from Chicago Midway Airport to Key West

Our best Delta deals on Chicago Midway Airport to Key West flight tickets
Delta
Nov 11
MDW6:00 amChicago Midway
4h 31m
1 stop
EYW11:31 amKey West
Nov 21
EYW6:18 pmKey West
6h 22m
1 stop
MDW11:40 pmChicago Midway
$289
Find similar
Delta
Dec 31
MDW3:29 pmChicago Midway
4h 24m
1 stop
EYW8:53 pmKey West
Jan 7
EYW6:00 pmKey West
4h 46m
1 stop
MDW9:46 pmChicago Midway
$306
Find similar
Delta
Dec 2
MDW12:50 pmChicago Midway
6h 16m
1 stop
EYW8:06 pmKey West
Dec 6
EYW6:10 pmKey West
6h 39m
1 stop
MDW11:49 pmChicago Midway
$320
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated October 7, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 10/27

9:45 am-11:05 am

1 stop24h 20m

Key West

Thu 10/30

3:23 pm-8:32 am

1 stop18h 09m

$219

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 11/17

6:06 pm-11:05 am

1 stop15h 59m

Key West

Thu 11/20

5:40 pm-6:46 pm

1 stop26h 06m

$243

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 10/31

7:50 am-9:02 am

1 stop24h 12m

Key West

Mon 11/3

9:57 am-12:30 am

1 stop15h 33m

$244

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 11/6

10:12 am-8:46 pm

1 stop9h 34m

Key West

Fri 11/7

9:01 am-2:07 pm

1 stop6h 06m

$250

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 11/11

6:00 am-11:31 am

1 stop4h 31m

Key West

Fri 11/21

6:18 pm-11:40 pm

1 stop6h 22m

$289

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 11/7

5:35 pm-9:01 am

2 stops14h 26m

Key West

Mon 11/10

10:41 am-3:22 pm

1 stop5h 41m

$301

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Wed 12/31

3:29 pm-8:53 pm

1 stop4h 24m

Key West

Wed 1/7

6:00 pm-9:46 pm

1 stop4h 46m

$306

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Tue 12/2

12:50 pm-8:06 pm

1 stop6h 16m

Key West

Sat 12/6

6:10 pm-11:49 pm

1 stop6h 39m

$320

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Mon 11/10

6:48 pm-2:03 pm

2 stops18h 15m

Key West

Wed 11/19

7:40 am-11:52 am

1 stop5h 12m

$327

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 11/21

2:11 pm-12:11 pm

2 stops21h 00m

Key West

Mon 11/24

3:13 pm-9:32 am

2 stops19h 19m

$445

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Key West from

How to get the cheapest flight ticket from Chicago Midway Airport to Key West

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 month to fly to Key West?

In general, July is the cheapest month to fly from Chicago Midway Airport to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $343. If you are unable to visit Key West during the month of July, then departing from Chicago Midway Airport during the month January is also very affordable. Most momondo users find prices during this month for around $364.

What is the cheapest day to depart on your flight to Key West?

On average, the least expensive day to fly to Key West from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $362. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago Midway Airport to Key West for around $542.

What is the cheapest time of day to depart on your flight to Key West?

According to our data, the cheapest time of day to fly to Key West is in the morning. momondo users have found flights departing from Chicago Midway Airport to Key West in the morning for as low as $471. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly in the evening, with an average ticket price of $822. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from Chicago Midway Airport to Key West

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Key West according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Key West (MDW to EYW) flight deals and tips

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

Direct flights

None
There are no direct flights from Chicago Midway Airport to Key West. There are no popular flight routes from Chicago Midway Airport to Key West.
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  • How far is Chicago Midway to Key West by plane?

    The distance between Chicago Midway and Key West is about 1237.6 mi. Typically, this will take 4h 24m by plane in normal conditions.

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

    Prices for flights from Chicago Midway Airport to Key West Airport refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Key West Airport?

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The required travel and health documents for your Key West Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Key West Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Chicago Midway Airport to Key West?

Best airlines flying from Chicago Midway Airport to Key West

Compare and see reviews for airlines that fly from Chicago Midway Airport to Key West with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $262Free CancellationRating
7.9
7,969 reviews
Search Delta flights

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Key West. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Chicago to Key West with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Chicago to Key West 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 Chicago to Key West right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Key West, momondo offers a useful price alert feature which will track prices for flights to Key West from Chicago and alert you when they change.

An easier way to manage your Key West trip

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