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Cheap flights from Chicago to Florida Keys from $45

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 2/7. 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

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Find the cheapest flights from Chicago to Florida Keys

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:41 pm - 12:42 am
ORD
-
MIA
7h 01m1 stop
Multiple Airlines Logo
5:54 am - 8:18 am
MIA
-
ORD
3h 24mnonstop
$93Multiple Airlines
Sat, Jan 17 - Thu, Jan 22
Spirit Airlines Logo
6:05 pm - 10:21 pm
ORD
-
MIA
3h 16mnonstop
Spirit Airlines Logo
5:54 am - 8:18 am
MIA
-
ORD
3h 24mnonstop
$95Spirit Airlines
Mon, Jan 5 - Thu, Jan 15
Spirit Airlines Logo
6:57 pm - 11:14 pm
ORD
-
MIA
3h 17mnonstop
Spirit Airlines Logo
5:54 am - 8:18 am
MIA
-
ORD
3h 24mnonstop
$96Spirit Airlines
Fri, Jan 9 - Fri, Jan 16
Spirit Airlines Logo
6:57 pm - 11:14 pm
ORD
-
MIA
3h 17mnonstop
Spirit Airlines Logo
2:33 pm - 12:40 am
MIA
-
ORD
11h 07m1 stop
$97Spirit Airlines
Sun, Feb 1 - Thu, Feb 12
Frontier Logo
6:15 am - 10:32 am
MDW
-
MIA
3h 17mnonstop
Frontier Logo
11:43 am - 2:06 pm
MIA
-
MDW
3h 23mnonstop
$99Frontier
Mon, Jan 5 - Wed, Jan 7
Frontier Logo
6:15 am - 10:32 am
MDW
-
MIA
3h 17mnonstop
Frontier Logo
11:43 am - 2:06 pm
MIA
-
MDW
3h 23mnonstop
$100Frontier
Mon, Jan 5 - Fri, Jan 9
American Airlines Logo
6:00 am - 1:49 pm
ORD
-
EYW
6h 49m1 stop
American Airlines Logo
6:44 pm - 9:29 pm
EYW
-
ORD
3h 45mnonstop
$286American Airlines
Tue, Feb 24 - Thu, Mar 5
United Airlines Logo
7:10 am - 11:26 am
ORD
-
EYW
3h 16mnonstop
United Airlines Logo
2:05 pm - 8:14 pm
EYW
-
ORD
7h 09m1 stop
$289United Airlines
Sat, Jan 10 - Sat, Jan 17
Delta Logo
11:06 am - 7:42 pm
MDW
-
EYW
7h 36m1 stop
Delta Logo
5:56 pm - 10:31 pm
EYW
-
MDW
5h 35m1 stop
$294Delta
Sat, Feb 21 - Wed, Feb 25
Delta Logo
11:25 am - 7:41 pm
ORD
-
EYW
7h 16m1 stop
Delta Logo
2:40 pm - 9:30 pm
EYW
-
ORD
7h 50m1 stop
$294Delta
Sat, Apr 11 - Wed, Apr 15

Frontier flights from Chicago to Florida Keys

Our best Frontier deals on Chicago to Florida Keys flight tickets
Frontier
Jan 5
MDW6:15 amChicago Midway
3h 17m
MIA10:32 amMiami
Jan 7
MIA11:43 amMiami
3h 23m
MDW2:06 pmChicago Midway
$99
Find similar
Frontier
Jan 5
MDW6:15 amChicago Midway
3h 17m
MIA10:32 amMiami
Jan 9
MIA11:43 amMiami
3h 23m
MDW2:06 pmChicago Midway
$100
Find similar
Frontier
Jan 12
MDW9:15 amChicago Midway
14h 58m
1 stop
MIA1:13 amMiami
Jan 15
MIA4:44 pmMiami
3h 25m
MDW7:09 pmChicago Midway
$103
Find similar

Spirit Airlines flights from Chicago to Florida Keys

Our best Spirit Airlines deals on Chicago to Florida Keys flight tickets
Spirit Airlines
Jan 5
ORD6:05 pmChicago O'Hare Intl
3h 16m
MIA10:21 pmMiami
Jan 15
MIA5:54 amMiami
3h 24m
ORD8:18 amChicago O'Hare Intl
$95
Find similar
Spirit Airlines
Jan 9
ORD6:57 pmChicago O'Hare Intl
3h 17m
MIA11:14 pmMiami
Jan 16
MIA5:54 amMiami
3h 24m
ORD8:18 amChicago O'Hare Intl
$96
Find similar
Spirit Airlines
Feb 1
ORD6:57 pmChicago O'Hare Intl
3h 17m
MIA11:14 pmMiami
Feb 12
MIA2:33 pmMiami
11h 07m
1 stop
ORD12:40 amChicago O'Hare Intl
$97
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Florida Keys 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 December 23, 2025.
Use the filters below to find and compare flights from Chicago to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 1/17

4:41 pm-12:42 am

1 stop7h 01m

Miami

Thu 1/22

5:54 am-8:18 am

Nonstop3h 24m

$93

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 1/5

6:05 pm-10:21 pm

Nonstop3h 16m

Miami

Thu 1/15

5:54 am-8:18 am

Nonstop3h 24m

$95

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 1/9

6:57 pm-11:14 pm

Nonstop3h 17m

Miami

Fri 1/16

5:54 am-8:18 am

Nonstop3h 24m

$96

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 2/1

6:57 pm-11:14 pm

Nonstop3h 17m

Miami

Thu 2/12

2:33 pm-12:40 am

1 stop11h 07m

$97

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 1/5

6:15 am-10:32 am

Nonstop3h 17m

Miami

Wed 1/7

11:43 am-2:06 pm

Nonstop3h 23m

$99

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 1/5

6:15 am-10:32 am

Nonstop3h 17m

Miami

Fri 1/9

11:43 am-2:06 pm

Nonstop3h 23m

$100

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 2/24

6:00 am-1:49 pm

1 stop6h 49m

Key West

Thu 3/5

6:44 pm-9:29 pm

Nonstop3h 45m

$286

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 1/10

7:10 am-11:26 am

Nonstop3h 16m

Key West

Sat 1/17

2:05 pm-8:14 pm

1 stop7h 09m

$289

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sat 2/21

11:06 am-7:42 pm

1 stop7h 36m

Key West

Wed 2/25

5:56 pm-10:31 pm

1 stop5h 35m

$294

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 4/11

11:25 am-7:41 pm

1 stop7h 16m

Key West

Wed 4/15

2:40 pm-9:30 pm

1 stop7h 50m

$294

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 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 January is another great option to travel to Florida Keys, with average flight prices from Chicago averaging around $231.

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 Monday when prices can be found for as low as $390. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $440.

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 at noon. momondo users have found flights departing from Chicago to Florida Keys at noon for as low as $319. 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 $434.

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 weeks ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $267 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida Keys from Chicago for as low as $220 on momondo.

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?

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

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

Fastest flight time

2h 55m

Direct flights

Every day

Airports in Florida Keys

3 airports
The fastest flight from Chicago to Florida Keys takes 2h 55m
Direct flights go from Chicago to Florida Keys every day.
There are 3 airports in Florida Keys. From Chicago there are direct flights to Miami (MIA).
Search flight deals

  • 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
Spirit AirlinesPriceFrom $169Free CancellationRating
6.3
8,196 reviews
Search Spirit Airlines flights
DeltaPriceFrom $248Free CancellationRating
7.9
8,014 reviews
Search Delta flights
United AirlinesPriceFrom $250Free CancellationRating
7.4
9,106 reviews
Search United Airlines flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
11,054 reviews
Search American 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.
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Find better results for your trip to Florida Keys

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