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Cheap flights from Chicago to Florida Keys from $38

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 to Florida Keys departing on 1/29. 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 to Florida Keys

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago 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 to Florida Keys.

Cheap last minute flights

Planning a quick getaway from Chicago 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 to Florida Keys

Find recent round-trip train or bus tickets from Chicago 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
12:52 pm - 3:23 pmMIA-MDW
3h 31mnonstop
$70Frontier
Find Deal
Thu, Jan 23 - Mon, Jan 27
7:45 am - 11:57 amMDW-MIA
3h 12mnonstop
12:42 pm - 3:13 pmMIA-MDW
3h 31mnonstop
$76Frontier
Find Deal
Mon, Feb 3 - Wed, Feb 12
2:02 pm - 6:16 pmORD-MIA
3h 14mnonstop
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
$80Spirit Airlines
Find Deal
Tue, Jan 28 - Tue, Feb 4
2:02 pm - 6:16 pmORD-MIA
3h 14mnonstop
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
$86Spirit Airlines
Find Deal
Tue, Jan 28 - Wed, Feb 5
7:09 pm - 11:31 pmORD-MIA
3h 22mnonstop
8:30 pm - 11:17 pmMIA-ORD
3h 47mnonstop
$157American Airlines
Find Deal
Sun, Feb 16 - Fri, Feb 21
7:09 pm - 11:17 pmORD-MIA
3h 08mnonstop
6:35 am - 9:02 amMIA-ORD
3h 27mnonstop
$168American Airlines
Find Deal
Sat, Feb 22 - Wed, Feb 26
9:35 am - 3:42 pmORD-MIA
5h 07m1 stop
8:00 am - 12:55 pmMIA-ORD
5h 55m1 stop
$216Delta
Find Deal
Wed, Jan 22 - Tue, Jan 28
10:57 am - 5:00 pmMDW-MIA
5h 03m1 stop
8:10 am - 11:59 amMIA-MDW
4h 49m1 stop
$216Delta
Find Deal
Wed, Jan 29 - Wed, Feb 5
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
$249United Airlines
Find Deal
Tue, Jan 28 - Tue, Feb 4
7:35 am - 4:01 pmORD-EYW
7h 26m1 stop
12:12 pm - 6:52 pmEYW-ORD
7h 40m1 stop
$254United Airlines
Find Deal
Mon, Feb 10 - Wed, Feb 19
2:02 pm - 6:16 pmORD-MIA
3h 14mnonstop
$38Spirit Airlines
Find Deal
Wed, Jan 29
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
$39Frontier
Find Deal
Thu, Jan 30
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
$40Frontier
Find Deal
Sun, Feb 9
5:07 pm - 9:25 pmORD-MIA
3h 18mnonstop
$42Spirit Airlines
Find Deal
Tue, Jan 7
10:35 am - 2:55 pmORD-MIA
3h 20mnonstop
$79United Airlines
Find Deal
Tue, Mar 4
7:09 pm - 11:17 pmORD-MIA
3h 08mnonstop
$90American Airlines
Find Deal
Sat, Mar 1
6:58 pm - 11:17 pmORD-MIA
3h 19mnonstop
$99American Airlines
Find Deal
Wed, Mar 19
2:55 pm - 9:21 pmMDW-MIA
5h 26m1 stop
$108Delta
Find Deal
Tue, Mar 25
2:08 pm - 9:42 pmMDW-MIA
6h 34m1 stop
$128Delta
Find Deal
Wed, Jan 15
6:25 pm - 10:45 pmORD-MIA
3h 20mnonstop
$167United Airlines
Find Deal
Mon, Mar 24
6:10 am - 12:13 amORD-MIA
17h 03m1 stop
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
Sun, Jan 5 - Fri, Jan 10
6:10 am - 12:13 amORD-MIA
17h 03m1 stop
6:25 am - 12:39 amMIA-ORD
19h 14m1 stop
$137Frontier
Find Deal
Sun, Jan 5 - Fri, Jan 31
5:07 pm - 9:25 pmORD-MIA
3h 18mnonstop
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
$201Spirit Airlines
Find Deal
Sun, Jan 5 - Tue, Feb 4
5:07 pm - 9:25 pmORD-MIA
3h 18mnonstop
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
$205Spirit Airlines
Find Deal
Sun, Jan 5 - Fri, Jan 10
8:15 am - 12:52 pmORD-EYW
3h 37mnonstop
12:57 pm - 7:26 pmEYW-ORD
7h 29m1 stop
$449American Airlines
Find Deal
Sat, Jan 4 - Wed, Jan 8
10:00 am - 5:18 pmORD-EYW
6h 18m1 stop
7:00 am - 1:45 pmEYW-ORD
7h 45m1 stop
$458Delta
Find Deal
Sat, Jan 4 - Sat, Jan 11
8:00 am - 12:37 pmORD-EYW
3h 37mnonstop
12:27 pm - 8:07 pmEYW-ORD
8h 40m1 stop
$509American Airlines
Find Deal
Thu, Jan 2 - Sun, Jan 5
11:02 am - 3:13 pmORD-EYW
3h 11mnonstop
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
$519United Airlines
Find Deal
Sat, Jan 4 - Wed, Jan 8
7:20 am - 4:09 pmORD-EYW
7h 49m1 stop
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
$529United Airlines
Find Deal
Sat, Jan 4 - Wed, Jan 8
5:03 pm - 10:44 pmMDW-MIA
4h 41m1 stop
6:00 am - 10:12 amMIA-MDW
5h 12m1 stop
$646Delta
Find Deal
Thu, Jan 2 - Fri, Jan 10
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
12:52 pm - 3:23 pmMIA-MDW
3h 31mnonstop
$70Frontier
Find Deal
Thu, Jan 23 - Mon, Jan 27
7:25 am - 11:37 amMDW-MIA
3h 12mnonstop
12:52 pm - 3:23 pmMIA-MDW
3h 31mnonstop
$77Frontier
Find Deal
Thu, Jan 23 - Mon, Jan 27
2:02 pm - 6:16 pmORD-MIA
3h 14mnonstop
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
$80Spirit Airlines
Find Deal
Tue, Jan 28 - Tue, Feb 4
2:02 pm - 6:16 pmORD-MIA
3h 14mnonstop
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
$86Spirit Airlines
Find Deal
Sat, Jan 25 - Wed, Jan 29
7:09 pm - 11:31 pmORD-MIA
3h 22mnonstop
8:30 pm - 11:17 pmMIA-ORD
3h 47mnonstop
$157American Airlines
Find Deal
Sun, Feb 16 - Fri, Feb 21
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
4:40 pm - 6:55 pmMIA-MDW
3h 15mnonstop
$160Southwest
Find Deal
Wed, Jan 29 - Wed, Feb 5
7:09 pm - 11:17 pmORD-MIA
3h 08mnonstop
6:35 am - 9:02 amMIA-ORD
3h 27mnonstop
$168American Airlines
Find Deal
Sat, Feb 22 - Wed, Feb 26
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
4:40 pm - 6:55 pmMIA-MDW
3h 15mnonstop
$178Southwest
Find Deal
Tue, Jan 28 - Tue, Feb 4
5:56 pm - 10:14 pmORD-MIA
3h 18mnonstop
7:00 am - 9:34 amMIA-ORD
3h 34mnonstop
$202United Airlines
Find Deal
Thu, Feb 20 - Tue, Feb 25
5:56 pm - 10:14 pmORD-MIA
3h 18mnonstop
7:34 pm - 10:07 pmMIA-ORD
3h 33mnonstop
$222United Airlines
Find Deal
Thu, Feb 27 - Sun, Mar 2

Spirit Airlines flights from Chicago to Florida Keys

Our best Spirit Airlines deals on Chicago to Florida Keys flight tickets
Spirit Airlines
Jan 28
ORD2:02 pmChicago O'Hare Intl
3h 14m
MIA6:16 pmMiami
Feb 4
MIA10:00 amMiami
3h 29m
ORD12:29 pmChicago O'Hare Intl
Spirit Airlines
Jan 28
ORD2:02 pmChicago O'Hare Intl
3h 14m
MIA6:16 pmMiami
Feb 5
MIA10:00 amMiami
3h 29m
ORD12:29 pmChicago O'Hare Intl
Spirit Airlines
Jan 28
ORD2:02 pmChicago O'Hare Intl
3h 14m
MIA6:16 pmMiami
Feb 1
MIA10:00 amMiami
3h 29m
ORD12:29 pmChicago O'Hare Intl

American Airlines flights from Chicago to Florida Keys

Our best American Airlines deals on Chicago to Florida Keys flight tickets
American Airlines
Feb 16
ORD7:09 pmChicago O'Hare Intl
3h 22m
MIA11:31 pmMiami
Feb 21
MIA8:30 pmMiami
3h 47m
ORD11:17 pmChicago O'Hare Intl
American Airlines
Feb 22
ORD7:09 pmChicago O'Hare Intl
3h 08m
MIA11:17 pmMiami
Feb 26
MIA6:35 amMiami
3h 27m
ORD9:02 amChicago O'Hare Intl
American Airlines
Feb 21
ORD7:09 pmChicago O'Hare Intl
3h 22m
MIA11:31 pmMiami
Feb 26
MIA6:35 amMiami
3h 27m
ORD9:02 amChicago O'Hare Intl

See travel insights to Florida Keys from

How to get the cheapest flight ticket from Chicago 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 September is another great option to travel to Florida Keys, with average flight prices from Chicago averaging around $199.

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

The cheapest day to depart from Chicago to Florida Keys is on a Tuesday when prices can be found for as low as $212. The most expensive day to fly to Florida Keys is Friday, with ticket prices averaging around $299.

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 to Florida Keys in the evening for as low as $181. 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 afternoon are often more expensive with an average ticket price of $277.

What is the cheapest Chicago to Florida Keys flight route?

Fly from Chicago O'Hare Intl to Key West for the best Chicago - Florida Keys flight prices

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 when booking 30 days ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $255 when searching 30 days out. However, in the past 72 hours, people saw flights from Chicago for as low as $156.

What cabin class options are available on Chicago to Florida Keys flights?

There are 4 cabin classes available to choose from on Chicago to Florida Keys flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

You could potentially save up to 34% on your flight if you consider stops on a Chicago to Florida Keys flight.

Cheap Chicago to Florida Keys flight deals and tips

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

Best Price Found

$38

Fastest flight time

2h 55m

Direct flights

Every day

Airports in Florida Keys

2 airports
The best one-way flight to Florida Keys from Chicago in the past 72 hours is $38. The best round-trip flight deal from Chicago to Florida Keys found on momondo in the last 72 hours is $70.
The fastest flight from Chicago to Florida Keys takes 2h 55m
Direct flights go from Chicago to Florida Keys every day.
There are 2 airports near Florida Keys: Key West (EYW), Miami (MIA)

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Florida Keys.

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

    The travel and health documents you'll need for your trip to Florida Keys may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Florida Keys. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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


Best airlines flying from Chicago to Florida Keys

Compare and see reviews for airlines that fly from Chicago to Florida Keys with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $216Free CancellationRating
8.0
8,540 reviews
Search Delta flights
American AirlinesPriceFrom $246Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $257Free CancellationRating
7.4
8,980 reviews
Search United Airlines flights

Why use momondo?

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

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

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

All flight searches from Chicago to Florida Keys on momondo can be filtered to show those which offer flexible booking policies.

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

momondo helps you find the best flight between Chicago and Florida Keys by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Florida Keys from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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Popular cities in Florida Keys

Popular flights according to clicks in the last 7 days on momondo