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Cheap flights from Chicago Midway Airport to Florida Keys from $37

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 2/2. 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 - 11:37 amMDW-MIA
3h 12mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$76Frontier
Find Deal
Thu, Feb 6 - Wed, Feb 12
7:45 am - 11:57 amMDW-MIA
3h 12mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$77Frontier
Find Deal
Mon, Feb 3 - Wed, Feb 12
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$78Frontier
Find Deal
Thu, Feb 6 - Thu, Feb 13
7:45 am - 11:57 amMDW-MIA
3h 12mnonstop
11:50 am - 2:19 pmMIA-MDW
3h 29mnonstop
$79Frontier
Find Deal
Mon, Feb 3 - Fri, Feb 7
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
4:40 pm - 6:55 pmMIA-MDW
3h 15mnonstop
$157Southwest
Find Deal
Wed, Feb 5 - Wed, Feb 12
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
5:55 pm - 8:15 pmMIA-MDW
3h 20mnonstop
$177Southwest
Find Deal
Tue, Feb 4 - Thu, Feb 6
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
4:40 pm - 6:55 pmMIA-MDW
3h 15mnonstop
$197Southwest
Find Deal
Tue, Jan 21 - Wed, Feb 5
12:44 pm - 7:03 pmMDW-MIA
5h 19m1 stop
7:00 am - 11:59 amMIA-MDW
5h 59m1 stop
$217Delta
Find Deal
Wed, Feb 5 - Tue, Feb 11
10:57 am - 5:21 pmMDW-EYW
5h 24m1 stop
7:00 am - 11:59 amEYW-MDW
5h 59m1 stop
$249Delta
Find Deal
Tue, Jan 28 - Tue, Feb 4
12:51 pm - 8:30 pmMDW-EYW
6h 39m1 stop
7:00 am - 12:06 pmEYW-MDW
6h 06m1 stop
$269Delta
Find Deal
Tue, Mar 18 - Wed, Mar 26
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
$37Frontier
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Sun, Feb 2
7:45 am - 11:57 amMDW-MIA
3h 12mnonstop
$39Frontier
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Mon, Feb 10
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
$40Frontier
Find Deal
Sun, Feb 9
8:30 am - 3:50 pmMDW-MIA
6h 20m1 stop
$89Southwest
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Tue, Feb 11
5:05 pm - 12:51 amMDW-MIA
6h 46m1 stop
$109Delta
Find Deal
Wed, Feb 19
5:10 pm - 9:05 pmMDW-MIA
2h 55mnonstop
$111Southwest
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Wed, Apr 9
10:57 am - 5:00 pmMDW-MIA
5h 03m1 stop
$129Delta
Find Deal
Tue, Jan 21
8:04 pm - 3:02 pmMDW-EYW
17h 58m2 stops
$208Allegiant Air
Find Deal
Fri, May 30
6:26 pm - 11:56 pmMDW-MIA
28h 30m3 stops
Sun, Mar 9
11:38 am - 10:23 amMDW-EYW
21h 45m2 stops
$318Allegiant Air
Find Deal
Thu, Feb 20
7:45 am - 11:58 amMDW-MIA
3h 13mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$200Frontier
Find Deal
Mon, Jan 13 - Thu, Jan 23
7:45 am - 11:58 amMDW-MIA
3h 13mnonstop
11:50 am - 2:19 pmMIA-MDW
3h 29mnonstop
$203Frontier
Find Deal
Mon, Jan 13 - Fri, Jan 24
7:45 am - 11:58 amMDW-MIA
3h 13mnonstop
1:36 pm - 6:26 pmMIA-MDW
5h 50m1 stop
$205Frontier
Find Deal
Mon, Jan 13 - Thu, Jan 23
3:57 pm - 12:15 amMDW-MIA
7h 18m1 stop
11:50 am - 2:19 pmMIA-MDW
3h 29mnonstop
$206Frontier
Find Deal
Mon, Jan 13 - Fri, Jan 24
7:45 am - 11:58 amMDW-MIA
3h 13mnonstop
11:50 am - 2:19 pmMIA-MDW
3h 29mnonstop
$208Frontier
Find Deal
Sun, Jan 12 - Fri, Jan 17
9:05 am - 1:10 pmMDW-MIA
3h 05mnonstop
4:40 pm - 6:55 pmMIA-MDW
3h 15mnonstop
$510Southwest
Find Deal
Sun, Jan 12 - Wed, Jan 15
6:00 am - 2:08 pmMDW-EYW
7h 08m1 stop
6:16 pm - 10:20 pmEYW-MDW
5h 04m1 stop
$519Delta
Find Deal
Sat, Jan 11 - Tue, Jan 14
1:25 pm - 10:30 pmMDW-MIA
8h 05m2 stops
4:40 pm - 6:55 pmMIA-MDW
3h 15mnonstop
$524Southwest
Find Deal
Sun, Jan 12 - Wed, Jan 15
10:57 am - 7:03 pmMDW-MIA
7h 06m1 stop
11:30 am - 6:14 pmMIA-MDW
7h 44m1 stop
$647Delta
Find Deal
Sat, Jan 11 - Fri, Jan 17
5:40 am - 1:15 pmMDW-EYW
6h 35m1 stop
10:00 am - 3:16 pmEYW-MDW
6h 16m1 stop
Fri, Jan 10 - Sun, Jan 12
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$76Frontier
Find Deal
Thu, Feb 6 - Wed, Feb 12
7:45 am - 11:57 amMDW-MIA
3h 12mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$77Frontier
Find Deal
Mon, Feb 3 - Wed, Feb 12
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$78Frontier
Find Deal
Thu, Feb 6 - Thu, Feb 13
7:45 am - 11:57 amMDW-MIA
3h 12mnonstop
11:50 am - 2:19 pmMIA-MDW
3h 29mnonstop
$79Frontier
Find Deal
Mon, Feb 3 - Fri, Feb 7
7:45 am - 11:57 amMDW-MIA
3h 12mnonstop
3:47 pm - 6:15 pmMIA-MDW
3h 28mnonstop
$82Frontier
Find Deal
Mon, Feb 3 - Sat, Feb 15
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
7:25 am - 9:48 amMIA-MDW
3h 23mnonstop
$85Frontier
Find Deal
Thu, Feb 6 - Sat, Feb 15
10:43 am - 2:52 pmMDW-MIA
3h 09mnonstop
7:25 am - 9:48 amMIA-MDW
3h 23mnonstop
$86Frontier
Find Deal
Sat, Feb 15 - Sat, Feb 22
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
11:50 am - 2:19 pmMIA-MDW
3h 29mnonstop
$87Frontier
Find Deal
Sun, Jan 26 - Fri, Jan 31
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
4:40 pm - 6:55 pmMIA-MDW
3h 15mnonstop
$157Southwest
Find Deal
Wed, Feb 5 - Wed, Feb 12
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
5:55 pm - 8:15 pmMIA-MDW
3h 20mnonstop
$177Southwest
Find Deal
Tue, Feb 4 - Thu, Feb 6

Frontier flights from Chicago Midway Airport to Florida Keys

Our best Frontier deals on Chicago Midway Airport to Florida Keys flight tickets
Frontier
Feb 6
MDW7:25 amChicago Midway
3h 12m
MIA11:37 amMiami
Feb 12
MIA12:42 pmMiami
3h 31m
MDW3:13 pmChicago Midway
Frontier
Feb 3
MDW7:45 amChicago Midway
3h 12m
MIA11:57 amMiami
Feb 12
MIA12:42 pmMiami
3h 31m
MDW3:13 pmChicago Midway
Frontier
Feb 6
MDW7:25 amChicago Midway
3h 12m
MIA11:37 amMiami
Feb 13
MIA12:42 pmMiami
3h 31m
MDW3:13 pmChicago Midway

Delta flights from Chicago Midway Airport to Florida Keys

Our best Delta deals on Chicago Midway Airport to Florida Keys flight tickets
Delta
Feb 5
MDW12:44 pmChicago Midway
5h 19m
1 stop
MIA7:03 pmMiami
Feb 11
MIA7:00 amMiami
5h 59m
1 stop
MDW11:59 amChicago Midway
Delta
Jan 22
MDW12:44 pmChicago Midway
5h 19m
1 stop
MIA7:03 pmMiami
Feb 8
MIA6:00 amMiami
5h 12m
1 stop
MDW10:12 amChicago Midway
Delta
Jan 28
MDW10:57 amChicago Midway
5h 24m
1 stop
EYW5:21 pmKey West
Feb 4
EYW7:00 amKey West
5h 59m
1 stop
MDW11:59 amChicago Midway

See travel insights to Florida Keys from

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 month to fly to Florida Keys?

The month of April is another great option to travel to Florida Keys, with average flight prices from Chicago Midway Airport averaging around $146.

What is the cheapest day to depart on your flight to Florida Keys?

The cheapest day to depart from Chicago Midway Airport to Florida Keys is on a Tuesday when prices can be found for as low as $89. The most expensive day to fly to Florida Keys is Saturday, with ticket prices averaging around $264.

What is the cheapest time of day to depart on your flight to Florida Keys?

According to our data, the cheapest time of day to fly to Florida Keys is in the evening. momondo users have found flights departing from Chicago Midway Airport to Florida Keys in the evening for as low as $131. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the morning are often more expensive with an average ticket price of $227.

How far in advance should I book a flight to Florida Keys?

You are more likely to see cheaper flights to Florida Keys from Chicago Midway Airport when booking 56 days ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $204 when searching 56 days out. However, in the past 72 hours, people saw flights from Chicago Midway Airport for as low as $38.

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

$37

Fastest flight time

2h 55m

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 $37. The best round-trip flight deal from Chicago Midway Airport to Florida Keys found on momondo in the last 72 hours is $76.
The fastest flight from Chicago Midway Airport to Florida Keys takes 2h 55m
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
8,499 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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Popular flights according to clicks in the last 7 days on momondo