Latest deals
Insights
FAQs
Reviews
Price Alerts

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 12/17. 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
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

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.
8:02 pm - 12:20 amORD-MIA
3h 18mnonstop
4:38 pm - 7:07 pmMIA-ORD
3h 29mnonstop
$96Spirit Airlines
Find Deal
Wed, Dec 11 - Tue, Dec 17
7:35 am - 11:48 amMDW-MIA
3h 13mnonstop
11:08 am - 1:36 pmMIA-MDW
3h 28mnonstop
$96Frontier
Find Deal
Tue, Dec 17 - Sun, Dec 22
4:28 pm - 11:46 pmORD-MIA
6h 18m1 stop
7:00 am - 11:47 amMIA-ORD
5h 47m1 stop
$98Frontier
Find Deal
Mon, Jan 6 - Wed, Jan 8
8:02 pm - 12:20 amORD-MIA
3h 18mnonstop
4:38 pm - 7:07 pmMIA-ORD
3h 29mnonstop
$103Spirit Airlines
Find Deal
Tue, Dec 10 - Tue, Dec 17
5:15 pm - 12:51 amORD-MIA
6h 36m1 stop
8:10 am - 1:42 pmMIA-ORD
6h 32m1 stop
$216Delta
Find Deal
Sat, Jan 18 - Sat, Jan 25
10:57 am - 5:25 pmMDW-EYW
5h 28m1 stop
6:20 pm - 10:20 pmEYW-MDW
5h 00m1 stop
$218Delta
Find Deal
Tue, Jan 28 - Tue, Feb 4
8:10 am - 12:35 pmORD-EYW
3h 25mnonstop
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
$224American Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
7:35 am - 4:01 pmORD-EYW
7h 26m1 stop
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
$234United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 18
7:35 am - 4:01 pmORD-EYW
7h 26m1 stop
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
$237United Airlines
Find Deal
Sat, Feb 8 - Wed, Feb 12
12:25 pm - 6:54 pmORD-EYW
5h 29m1 stop
1:05 pm - 3:42 pmEYW-ORD
3h 37mnonstop
$254American Airlines
Find Deal
Sat, Dec 14 - Wed, Dec 18
7:35 am - 11:48 amMDW-MIA
3h 13mnonstop
$38Frontier
Find Deal
Tue, Dec 17
1:34 pm - 5:48 pmORD-MIA
3h 14mnonstop
$42Spirit Airlines
Find Deal
Wed, Jan 15
5:07 pm - 9:25 pmORD-MIA
3h 18mnonstop
$47Spirit Airlines
Find Deal
Tue, Jan 7
9:57 pm - 2:05 amMDW-MIA
3h 08mnonstop
$48Frontier
Find Deal
Mon, Dec 16
2:06 pm - 6:26 pmORD-MIA
3h 20mnonstop
$99United Airlines
Find Deal
Sun, Feb 16
8:14 am - 12:32 pmORD-EYW
3h 18mnonstop
$100American Airlines
Find Deal
Fri, Nov 29
12:44 pm - 9:27 pmMDW-MIA
7h 43m1 stop
$108Delta
Find Deal
Tue, Jan 21
11:17 am - 8:11 pmORD-EYW
7h 54m1 stop
$109Delta
Find Deal
Wed, Feb 19
7:00 am - 11:16 amORD-MIA
3h 16mnonstop
$130United Airlines
Find Deal
Wed, Dec 11
8:19 am - 3:20 pmORD-EYW
6h 01m1 stop
$159American Airlines
Find Deal
Fri, Nov 29
6:30 pm - 10:49 pmMDW-MIA
3h 19mnonstop
11:08 am - 1:36 pmMIA-MDW
3h 28mnonstop
$166Frontier
Find Deal
Tue, Nov 26 - Sun, Dec 29
7:59 pm - 12:17 amORD-MIA
3h 18mnonstop
4:38 pm - 7:07 pmMIA-ORD
3h 29mnonstop
$188Spirit Airlines
Find Deal
Mon, Nov 25 - Sat, Dec 7
5:24 pm - 9:43 pmMDW-MIA
3h 19mnonstop
8:00 am - 12:13 amMIA-MDW
17h 13m1 stop
$193Frontier
Find Deal
Mon, Nov 25 - Wed, Dec 4
7:59 pm - 12:17 amORD-MIA
3h 18mnonstop
9:28 pm - 9:43 amMIA-ORD
13h 15m1 stop
$236Spirit Airlines
Find Deal
Mon, Nov 25 - Sat, Dec 7
12:15 pm - 6:48 pmORD-EYW
5h 33m1 stop
12:55 pm - 3:26 pmEYW-ORD
3h 31mnonstop
$359American Airlines
Find Deal
Fri, Nov 22 - Tue, Nov 26
8:04 am - 12:20 pmORD-EYW
3h 16mnonstop
1:07 pm - 3:38 pmEYW-ORD
3h 31mnonstop
$374American Airlines
Find Deal
Sun, Nov 24 - Thu, Dec 26
9:25 am - 5:18 pmORD-EYW
6h 53m1 stop
7:25 am - 12:21 pmEYW-ORD
5h 56m1 stop
$377Delta
Find Deal
Fri, Nov 22 - Tue, Nov 26
6:00 am - 11:38 amMDW-EYW
4h 38m1 stop
7:25 am - 11:58 amEYW-MDW
5h 33m1 stop
$458Delta
Find Deal
Fri, Nov 22 - Wed, Nov 27
10:55 am - 3:01 pmORD-EYW
3h 06mnonstop
10:55 am - 2:19 pmEYW-ORD
28h 24m2 stops
$579United Airlines
Find Deal
Mon, Nov 25 - Wed, Nov 27
6:00 am - 5:15 pmORD-EYW
10h 15m2 stops
7:40 pm - 9:33 amEYW-ORD
14h 53m1 stop
$607United Airlines
Find Deal
Mon, Nov 25 - Wed, Nov 27
5:07 pm - 9:25 pmORD-MIA
3h 18mnonstop
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
$96Spirit Airlines
Find Deal
Wed, Jan 8 - Tue, Jan 14
7:35 am - 11:48 amMDW-MIA
3h 13mnonstop
6:00 am - 8:21 amMIA-MDW
3h 21mnonstop
$96Frontier
Find Deal
Tue, Dec 17 - Mon, Dec 23
9:57 pm - 2:05 amMDW-MIA
3h 08mnonstop
11:08 am - 1:36 pmMIA-MDW
3h 28mnonstop
$97Frontier
Find Deal
Mon, Dec 16 - Thu, Dec 19
1:34 pm - 5:48 pmORD-MIA
3h 14mnonstop
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
$98Spirit Airlines
Find Deal
Wed, Jan 22 - Wed, Jan 29
7:09 pm - 11:18 pmORD-MIA
3h 09mnonstop
5:00 pm - 7:28 pmMIA-ORD
3h 28mnonstop
$157American Airlines
Find Deal
Sat, Mar 1 - Wed, Mar 5
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
8:10 am - 10:20 amMIA-MDW
3h 10mnonstop
$158Southwest
Find Deal
Wed, Jan 8 - Sat, Jan 11
4:55 pm - 9:00 pmORD-MIA
3h 05mnonstop
8:30 pm - 11:18 pmMIA-ORD
3h 48mnonstop
$177American Airlines
Find Deal
Sat, Feb 22 - Mon, Mar 3
10:35 am - 2:55 pmORD-MIA
3h 20mnonstop
7:00 am - 9:34 amMIA-ORD
3h 34mnonstop
$192United Airlines
Find Deal
Sun, Feb 16 - Tue, Feb 18
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
8:10 am - 10:20 amMIA-MDW
3h 10mnonstop
$194Southwest
Find Deal
Tue, Jan 14 - Sat, Jan 18
10:35 am - 2:49 pmORD-EYW
3h 14mnonstop
3:50 pm - 6:21 pmEYW-ORD
3h 31mnonstop
$199United Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15

Frontier flights from Chicago to Florida Keys

Our best Frontier deals on Chicago to Florida Keys flight tickets
Frontier
Dec 17
MDW7:35 amChicago Midway
3h 13m
MIA11:48 amMiami
Dec 22
MIA11:08 amMiami
3h 28m
MDW1:36 pmChicago Midway
Frontier
Jan 6
ORD4:28 pmChicago O'Hare Intl
6h 18m
1 stop
MIA11:46 pmMiami
Jan 8
MIA7:00 amMiami
5h 47m
1 stop
ORD11:47 amChicago O'Hare Intl
Frontier
Dec 16
MDW9:57 pmChicago Midway
3h 08m
MIA2:05 amMiami
Dec 19
MIA11:08 amMiami
3h 28m
MDW1:36 pmChicago Midway

Spirit Airlines flights from Chicago to Florida Keys

Our best Spirit Airlines deals on Chicago to Florida Keys flight tickets
Spirit Airlines
Dec 11
ORD8:02 pmChicago O'Hare Intl
3h 18m
MIA12:20 amMiami
Dec 17
MIA4:38 pmMiami
3h 29m
ORD7:07 pmChicago O'Hare Intl
Spirit Airlines
Dec 10
ORD8:02 pmChicago O'Hare Intl
3h 18m
MIA12:20 amMiami
Dec 17
MIA4:38 pmMiami
3h 29m
ORD7:07 pmChicago O'Hare Intl
Spirit Airlines
Dec 10
ORD8:02 pmChicago O'Hare Intl
3h 18m
MIA12:20 amMiami
Dec 12
MIA4:38 pmMiami
3h 29m
ORD7:07 pmChicago 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 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 $218. The most expensive day to fly to Florida Keys is Friday, with ticket prices averaging around $298.

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

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

There are 3 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 40% 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

3h 00m

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 $96.
The fastest flight from Chicago to Florida Keys takes 3h 00m
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
8,755 reviews
Search Delta flights
American AirlinesPriceFrom $246Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $263Free CancellationRating
7.4
9,172 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.


An easier way to manage your Florida Keys trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 11/26
Tue 12/3
Email me momondo's favorite deals

Find better results for your trip to Florida Keys

Popular cities in Florida Keys

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