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Cheap flights from Chicago Midway Airport to Key West from $122

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 9/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
6:15 am - 9:24 amMDW  Chicago Midway-EYW Key West
26h 09m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
10:14 am - 3:40 pmEYW  Key West-MDW Chicago Midway
6h 26m1 stop Knoxville McGhee Tyson
$289Multiple Airlines
Tue, Oct 13 - Fri, Oct 16
Multiple Airlines Logo
6:15 am - 9:24 amMDW  Chicago Midway-EYW Key West
26h 09m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
10:14 am - 3:40 pmEYW  Key West-MDW Chicago Midway
6h 26m1 stop Knoxville McGhee Tyson
$289Multiple Airlines
Tue, Oct 13 - Fri, Oct 16
Delta Logo
10:48 am - 5:23 pmMDW  Chicago Midway-EYW Key West
5h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:10 pm - 10:33 pmEYW  Key West-MDW Chicago Midway
5h 23m1 stop Atlanta Hartsfield-Jackson
$323Delta
Wed, Sep 30 - Wed, Oct 7
Delta Logo
10:48 am - 5:23 pmMDW  Chicago Midway-EYW Key West
5h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:40 am - 11:54 amEYW  Key West-MDW Chicago Midway
5h 14m1 stop Atlanta Hartsfield-Jackson
$323Delta
Tue, Sep 29 - Tue, Oct 6
Delta Logo
1:00 pm - 8:00 pmMDW  Chicago Midway-EYW Key West
6h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:19 pm - 10:44 pmEYW  Key West-MDW Chicago Midway
5h 25m1 stop Atlanta Hartsfield-Jackson
$323Delta
Wed, Sep 16 - Wed, Sep 23
Delta Logo
1:00 pm - 8:00 pmMDW  Chicago Midway-EYW Key West
6h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:19 pm - 10:44 pmEYW  Key West-MDW Chicago Midway
5h 25m1 stop Atlanta Hartsfield-Jackson
$323Delta
Wed, Sep 16 - Tue, Sep 22
Multiple Airlines Logo
1:29 pm - 10:19 amMDW  Chicago Midway-EYW Key West
19h 50m1 stop Orlando
Multiple Airlines Logo
1:16 pm - 12:59 pmEYW  Key West-MDW Chicago Midway
24h 43m2 stops Tampa Atlanta Hartsfield-Jackson
$421Multiple Airlines
Tue, Nov 24 - Tue, Dec 1
Multiple Airlines Logo
8:07 pm - 10:19 amMDW  Chicago Midway-EYW Key West
13h 12m1 stop Orlando
Multiple Airlines Logo
10:59 am - 7:02 pmEYW  Key West-MDW Chicago Midway
9h 03m1 stop Orlando
$429Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
2:04 pm - 10:19 amMDW  Chicago Midway-EYW Key West
19h 15m2 stops Atlanta Hartsfield-Jackson Orlando
Multiple Airlines Logo
10:59 am - 7:02 pmEYW  Key West-MDW Chicago Midway
9h 03m1 stop Orlando
$444Multiple Airlines
Thu, Dec 3 - Mon, Dec 7
Multiple Airlines Logo
2:04 pm - 10:04 amMDW  Chicago Midway-EYW Key West
19h 00m2 stops Atlanta Hartsfield-Jackson Tampa
Multiple Airlines Logo
10:59 am - 7:02 pmEYW  Key West-MDW Chicago Midway
9h 03m1 stop Orlando
$460Multiple Airlines
Tue, Dec 15 - Mon, Dec 21

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Delta flights from Chicago Midway Airport to Key West

Our best Delta deals on Chicago Midway Airport to Key West flight tickets
Delta
Sep 16
MDW1:00 pmChicago Midway
6h 00m
1 stop
EYW8:00 pmKey West
Sep 22
EYW6:19 pmKey West
5h 25m
1 stop
MDW10:44 pmChicago Midway
$323
Delta
Sep 9
MDW11:35 amChicago Midway
7h 25m
1 stop
EYW8:00 pmKey West
Sep 15
EYW6:19 pmKey West
5h 25m
1 stop
MDW10:44 pmChicago Midway
$331
Delta
Sep 28
MDW10:48 amChicago Midway
5h 35m
1 stop
EYW5:23 pmKey West
Oct 5
EYW6:19 pmKey West
5h 25m
1 stop
MDW10:44 pmChicago Midway
$339

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 August 17, 2026.
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

Cheapest round-trip

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Tue 10/13

6:15 am-9:24 am

2 stops26h 09m

Key West

Fri 10/16

10:14 am-3:40 pm

1 stop6h 26m

$289

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Tue 10/13

6:15 am-9:24 am

2 stops26h 09m

Key West

Fri 10/16

10:14 am-3:40 pm

1 stop6h 26m

$289

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Wed 9/30

10:48 am-5:23 pm

1 stop5h 35m

Key West

Wed 10/7

6:10 pm-10:33 pm

1 stop5h 23m

$323
Quickest round-trip

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Tue 9/29

10:48 am-5:23 pm

1 stop5h 35m

Key West

Tue 10/6

7:40 am-11:54 am

1 stop5h 14m

$323

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Wed 9/16

1:00 pm-8:00 pm

1 stop6h 00m

Key West

Wed 9/23

6:19 pm-10:44 pm

1 stop5h 25m

$323

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Wed 9/16

1:00 pm-8:00 pm

1 stop6h 00m

Key West

Tue 9/22

6:19 pm-10:44 pm

1 stop5h 25m

$323

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Tue 11/24

1:29 pm-10:19 am

1 stop19h 50m

Key West

Tue 12/1

1:16 pm-12:59 pm

2 stops24h 43m

$421

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Thu 12/3

8:07 pm-10:19 am

1 stop13h 12m

Key West

Mon 12/7

10:59 am-7:02 pm

1 stop9h 03m

$429

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Thu 12/3

2:04 pm-10:19 am

2 stops19h 15m

Key West

Mon 12/7

10:59 am-7:02 pm

1 stop9h 03m

$444

ChicagoKey West

MDW Chicago Midway - EYW Key West

MDWEYW

Chicago Midway

Tue 12/15

2:04 pm-10:04 am

2 stops19h 00m

Key West

Mon 12/21

10:59 am-7:02 pm

1 stop9h 03m

$460

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, June 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 $0. If you are unable to visit Key West during the month of June, then departing from Chicago Midway Airport during the month March is also very affordable. Most momondo users find prices during this month for around $0.

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 $372. 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 $503.

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 at noon. momondo users have found flights departing from Chicago Midway Airport to Key West at noon for as low as $448. 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 morning, with an average ticket price of $451. Departure times in the morning 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

Fastest flight time

4h 39m

Direct flights

None
The fastest flight from Chicago Midway Airport to Key West takes 4h 39m
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.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Key West

  • 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 39m 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 $294Free CancellationRating
7.8
8,503 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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