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Cheap flights from Chicago Midway Airport to Florida Keys from $59

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 Florida Keys departing on 12/15. 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 Florida Keys

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Florida Keys that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago Midway Airport to Florida Keys.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Florida Keys? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Florida Keys, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Florida Keys

Find recent round-trip train or bus tickets from Chicago Midway Airport to Florida Keys.

All round-trip flight deals to Florida Keys

The cheapest plane tickets to Florida Keys found on KAYAK recently.
7:25 am - 11:38 amMDW-MIA
3h 13mnonstop
8:06 am - 1:40 pmMIA-MDW
6h 34m1 stop
$120Frontier
Find Deal
Fri, Dec 6 - Mon, Dec 9
8:15 am - 3:28 pmMDW-MIA
6h 13m1 stop
12:43 pm - 3:13 pmMIA-MDW
3h 30mnonstop
$121Frontier
Find Deal
Mon, Dec 16 - Sat, Dec 21
2:20 pm - 11:59 pmMDW-MIA
8h 39m1 stop
12:43 pm - 3:13 pmMIA-MDW
3h 30mnonstop
$122Frontier
Find Deal
Tue, Dec 17 - Tue, Dec 24
7:25 am - 11:38 amMDW-MIA
3h 13mnonstop
8:00 am - 12:13 amMIA-MDW
17h 13m1 stop
$123Frontier
Find Deal
Sun, Dec 8 - Wed, Dec 11
7:25 am - 11:38 amMDW-MIA
3h 13mnonstop
8:06 am - 1:40 pmMIA-MDW
6h 34m1 stop
$124Frontier
Find Deal
Thu, Dec 12 - Mon, Dec 16
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
4:40 pm - 6:55 pmMIA-MDW
3h 15mnonstop
$178Southwest
Find Deal
Tue, Jan 7 - Thu, Jan 9
5:10 pm - 9:10 pmMDW-MIA
3h 00mnonstop
8:10 am - 10:20 amMIA-MDW
3h 10mnonstop
$189Southwest
Find Deal
Sat, Jan 25 - Sat, Feb 1
5:07 pm - 12:51 amMDW-MIA
6h 44m1 stop
6:00 am - 10:12 amMIA-MDW
5h 12m1 stop
$216Delta
Find Deal
Tue, Jan 7 - Thu, Jan 23
10:57 am - 5:25 pmMDW-EYW
5h 28m1 stop
7:00 am - 11:59 amEYW-MDW
5h 59m1 stop
$218Delta
Find Deal
Tue, Jan 28 - Tue, Feb 4
6:07 pm - 12:29 amMDW-MIA
5h 22m1 stop
9:20 pm - 12:13 amMIA-MDW
51h 53m2 stops
Thu, Nov 28 - Mon, Dec 2
7:25 am - 11:38 amMDW-MIA
3h 13mnonstop
$59Frontier
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Sun, Dec 15
2:20 pm - 11:59 pmMDW-MIA
8h 39m1 stop
$60Frontier
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Tue, Dec 17
8:31 pm - 12:48 amMDW-MIA
3h 17mnonstop
$61Frontier
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Mon, Nov 18
4:08 pm - 12:49 pmMDW-MIA
19h 41m1 stop
$62Frontier
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Thu, Jan 9
12:09 pm - 10:47 pmMDW-MIA
9h 38m1 stop
Wed, Nov 20
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
$79Southwest
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Tue, Jan 7
6:48 pm - 10:00 amMDW-MIA
14h 12m1 stop
Sat, Nov 23
5:07 pm - 12:51 amMDW-MIA
6h 44m1 stop
$113Delta
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Tue, Jan 7
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
$139Southwest
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Wed, Jan 15
6:49 pm - 12:53 amMDW-MIA
5h 04m1 stop
$144Delta
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Fri, Nov 22
8:31 pm - 12:48 amMDW-MIA
3h 17mnonstop
8:06 am - 6:12 pmMIA-MDW
11h 06m1 stop
$112Frontier
Find Deal
Mon, Nov 18 - Thu, Dec 5
8:31 pm - 12:48 amMDW-MIA
3h 17mnonstop
11:42 am - 2:01 pmMIA-MDW
3h 19mnonstop
$120Frontier
Find Deal
Mon, Nov 18 - Sat, Nov 23
10:41 am - 5:18 pmMDW-EYW
5h 37m1 stop
2:13 pm - 6:02 pmEYW-MDW
4h 49m1 stop
$368Delta
Find Deal
Tue, Nov 19 - Mon, Nov 25
10:41 am - 5:18 pmMDW-EYW
5h 37m1 stop
7:25 am - 11:58 amEYW-MDW
5h 33m1 stop
$377Delta
Find Deal
Tue, Nov 19 - Mon, Nov 25
11:25 am - 3:30 pmMDW-MIA
3h 05mnonstop
12:10 pm - 11:10 pmMIA-MDW
12h 00m1 stop
$544Southwest
Find Deal
Mon, Nov 18 - Thu, Nov 21
8:15 am - 10:55 pmMDW-MIA
13h 40m2 stops
12:10 pm - 11:10 pmMIA-MDW
12h 00m1 stop
$558Southwest
Find Deal
Mon, Nov 18 - Thu, Nov 21
7:55 pm - 9:48 pmMDW-MIA
24h 53m3 stops
9:17 am - 8:45 amMIA-MDW
24h 28m2 stops
Sat, Nov 16 - Tue, Nov 19
7:55 pm - 11:49 amMDW-MIA
14h 54m1 stop
9:17 am - 8:45 amMIA-MDW
24h 28m2 stops
Sat, Nov 16 - Tue, Nov 19
7:55 pm - 11:49 amMDW-MIA
14h 54m1 stop
4:08 pm - 8:45 amMIA-MDW
17h 37m2 stops
$1,182Volaris
Find Deal
Mon, Nov 18 - Wed, Nov 20
7:50 pm - 2:05 pmMDW-MIA
17h 15m2 stops
4:08 pm - 8:45 amMIA-MDW
17h 37m2 stops
$1,453Volaris
Find Deal
Tue, Nov 19 - Sun, Nov 24
8:31 pm - 12:48 amMDW-MIA
3h 17mnonstop
11:42 am - 2:01 pmMIA-MDW
3h 19mnonstop
$120Frontier
Find Deal
Mon, Nov 18 - Sat, Nov 23
7:45 am - 11:58 amMDW-MIA
3h 13mnonstop
11:50 am - 2:19 pmMIA-MDW
3h 29mnonstop
$122Frontier
Find Deal
Mon, Jan 13 - Fri, Jan 17
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$125Frontier
Find Deal
Thu, Jan 23 - Thu, Jan 30
9:16 am - 1:30 pmMDW-MIA
3h 14mnonstop
6:00 am - 8:21 amMIA-MDW
3h 21mnonstop
$126Frontier
Find Deal
Wed, Dec 18 - Mon, Dec 23
9:57 pm - 2:05 amMDW-MIA
3h 08mnonstop
11:08 am - 1:36 pmMIA-MDW
3h 28mnonstop
$128Frontier
Find Deal
Mon, Dec 16 - Thu, Dec 26
9:16 am - 1:30 pmMDW-MIA
3h 14mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$131Frontier
Find Deal
Mon, Jan 6 - Thu, Jan 16
8:00 am - 12:15 pmMDW-MIA
3h 15mnonstop
12:42 pm - 3:12 pmMIA-MDW
3h 30mnonstop
$136Frontier
Find Deal
Fri, Nov 29 - Thu, Dec 5
7:35 am - 11:48 amMDW-MIA
3h 13mnonstop
11:08 am - 1:36 pmMIA-MDW
3h 28mnonstop
$138Frontier
Find Deal
Tue, Dec 17 - Thu, Dec 26
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
4:40 pm - 6:55 pmMIA-MDW
3h 15mnonstop
$178Southwest
Find Deal
Tue, Jan 7 - Thu, Jan 9
12:00 pm - 4:05 pmMDW-MIA
3h 05mnonstop
6:30 am - 8:40 amMIA-MDW
3h 10mnonstop
$249Southwest
Find Deal
Sat, Dec 7 - Sat, Dec 14

Southwest flights from Chicago Midway Airport to Florida Keys

Our best Southwest deals on Chicago Midway Airport to Florida Keys flight tickets
Southwest
Jan 7
MDW6:10 pmChicago Midway
3h 00m
MIA10:10 pmMiami
Jan 9
MIA4:40 pmMiami
3h 15m
MDW6:55 pmChicago Midway
Southwest
Jan 25
MDW5:10 pmChicago Midway
3h 00m
MIA9:10 pmMiami
Feb 1
MIA8:10 amMiami
3h 10m
MDW10:20 amChicago Midway
Southwest
Dec 15
MDW11:25 amChicago Midway
3h 05m
MIA3:30 pmMiami
Jan 15
MIA4:40 pmMiami
3h 15m
MDW6:55 pmChicago Midway

Frontier flights from Chicago Midway Airport to Florida Keys

Our best Frontier deals on Chicago Midway Airport to Florida Keys flight tickets
Frontier
Dec 6
MDW7:25 amChicago Midway
3h 13m
MIA11:38 amMiami
Dec 9
MIA8:06 amMiami
6h 34m
1 stop
MDW1:40 pmChicago Midway
Frontier
Dec 16
MDW8:15 amChicago Midway
6h 13m
1 stop
MIA3:28 pmMiami
Dec 21
MIA12:43 pmMiami
3h 30m
MDW3:13 pmChicago Midway
Frontier
Dec 17
MDW2:20 pmChicago Midway
8h 39m
1 stop
MIA11:59 pmMiami
Dec 24
MIA12:43 pmMiami
3h 30m
MDW3:13 pmChicago Midway

How to get the cheapest flight ticket from Chicago Midway Airport to Florida Keys

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 airline that flies to Florida Keys from Chicago Midway Airport?

Delta. Delta is the most popular carrier operating from Chicago Midway Airport to Florida Keys

Can stopping save me money on Chicago Midway Airport to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Florida Keys.

Cheap Chicago Midway Airport to Florida Keys flight deals and tips

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

Best Price Found

$59

Fastest flight time

3h 00m

Direct flights

Every day

Airports in Florida Keys

1 airport
The best one-way flight to Florida Keys from Chicago Midway Airport in the past 72 hours is $59. The best round-trip flight deal from Chicago Midway Airport to Florida Keys found on momondo in the last 72 hours is $120.
The fastest flight from Chicago Midway Airport to Florida Keys takes 3h 00m
Direct flights go from Chicago Midway Airport to Florida Keys every day.
There is 1 airport near Florida Keys: Miami (MIA)

  • When did momondo last update prices for flights from Chicago Midway Airport to Florida Keys?

    Prices for flights from Chicago Midway Airport to Florida Keys were last updated today.

  • How many operators does momondo search for flights from Chicago Midway Airport to Florida Keys?

  • How old do you have to be to fly from Chicago Midway Airport to Florida Keys?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Florida Keys.

  • What documentation or ID do you need to fly to Florida Keys?

    The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Florida Keys?


Best airlines flying from Chicago Midway Airport to Florida Keys

Compare and see reviews for airlines that fly from Chicago Midway Airport to Florida Keys with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $247Free CancellationRating
8.0
8,788 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Florida Keys?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Florida Keys for you.

Can I find flights from Chicago to Florida Keys with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Florida Keys flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Florida Keys?

momondo provides multiple filters to help you find the best flight to Florida Keys from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Florida Keys right now. Can momondo alert me if prices change?

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


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