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Cheap flights from Chicago O'Hare Intl Airport to Florida Keys from $66

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 O'Hare Intl Airport to Florida Keys departing on 9/2. 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 O'Hare Intl Airport to Florida Keys

Cheap round-trip flights

Spirit Airlines Logo
10:27 am - 2:29 pmORD-MIA
3h 02mnonstop
Spirit Airlines Logo
7:01 pm - 10:46 pmMIA-ORD
4h 45m1 stop
$130Spirit Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Spirit Airlines Logo
10:27 am - 2:49 pmORD-MIA
3h 22mnonstop
Spirit Airlines Logo
7:00 am - 9:18 amMIA-ORD
3h 18mnonstop
$131Spirit Airlines
Find Deal
Wed, Sep 3 - Mon, Sep 8
Logo
5:50 am - 9:13 pmORD-MIA
14h 23m1 stop
Logo
7:00 am - 9:22 amMIA-ORD
3h 22mnonstop
$132
Find Deal
Fri, Oct 10 - Tue, Oct 14
American Airlines Logo
4:40 pm - 8:52 pmORD-MIA
3h 12mnonstop
American Airlines Logo
9:26 pm - 11:49 pmMIA-ORD
3h 23mnonstop
$137American Airlines
Find Deal
Sat, Sep 20 - Mon, Sep 22
Frontier Logo
11:50 am - 12:54 amORD-MIA
12h 04m1 stop
Frontier Logo
7:07 pm - 12:11 amMIA-ORD
6h 04m1 stop
$143Frontier
Find Deal
Thu, Oct 30 - Mon, Nov 3
Frontier Logo
2:41 pm - 4:03 pmORD-MIA
24h 22m1 stop
Frontier Logo
4:16 pm - 11:18 amMIA-ORD
20h 02m1 stop
$144Frontier
Find Deal
Thu, Oct 9 - Sun, Oct 12
American Airlines Logo
6:09 am - 10:14 amORD-MIA
3h 05mnonstop
American Airlines Logo
9:10 am - 11:32 amMIA-ORD
3h 22mnonstop
$147American Airlines
Find Deal
Sun, Sep 14 - Tue, Sep 16
Southwest Logo
1:30 pm - 11:05 pmORD-MIA
8h 35m1 stop
Southwest Logo
7:00 am - 1:05 pmMIA-ORD
7h 05m1 stop
$157Southwest
Find Deal
Fri, Sep 26 - Sun, Sep 28
Delta Logo
5:30 am - 10:55 amORD-EYW
4h 25m1 stop
Delta Logo
6:00 pm - 10:14 pmEYW-ORD
5h 14m1 stop
$269Delta
Find Deal
Mon, Sep 22 - Wed, Oct 1
Delta Logo
11:19 am - 7:44 pmORD-EYW
7h 25m1 stop
Delta Logo
6:00 pm - 11:53 pmEYW-ORD
6h 53m1 stop
$289Delta
Find Deal
Tue, Dec 2 - Sat, Dec 6

Spirit Airlines flights from Chicago O'Hare Intl Airport to Florida Keys

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Florida Keys flight tickets
Spirit Airlines
Oct 30
ORD10:27 amChicago O'Hare Intl
3h 02m
MIA2:29 pmMiami
Nov 2
MIA7:01 pmMiami
4h 45m
1 stop
ORD10:46 pmChicago O'Hare Intl
$130
Find similar
Spirit Airlines
Sep 3
ORD10:27 amChicago O'Hare Intl
3h 22m
MIA2:49 pmMiami
Sep 8
MIA7:00 amMiami
3h 18m
ORD9:18 amChicago O'Hare Intl
$131
Find similar
Spirit Airlines
Nov 1
ORD9:27 amChicago O'Hare Intl
3h 03m
MIA1:30 pmMiami
Nov 8
MIA11:32 amMiami
8h 44m
1 stop
ORD7:16 pmChicago O'Hare Intl
$134
Find similar

American Airlines flights from Chicago O'Hare Intl Airport to Florida Keys

Our best American Airlines deals on Chicago O'Hare Intl Airport to Florida Keys flight tickets
American Airlines
Sep 20
ORD4:40 pmChicago O'Hare Intl
3h 12m
MIA8:52 pmMiami
Sep 22
MIA9:26 pmMiami
3h 23m
ORD11:49 pmChicago O'Hare Intl
$137
Find similar
American Airlines
Sep 14
ORD6:09 amChicago O'Hare Intl
3h 05m
MIA10:14 amMiami
Sep 16
MIA9:10 amMiami
3h 22m
ORD11:32 amChicago O'Hare Intl
$147
Find similar
American Airlines
Oct 30
ORD5:00 amChicago O'Hare Intl
3h 05m
MIA9:05 amMiami
Nov 3
MIA9:57 pmMiami
3h 24m
ORD12:21 amChicago O'Hare Intl
$177
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 August 18, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 10/30

10:27 am-2:29 pm

Nonstop3h 02m

Miami

Sun 11/2

7:01 pm-10:46 pm

1 stop4h 45m

$130

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 9/3

10:27 am-2:49 pm

Nonstop3h 22m

Miami

Mon 9/8

7:00 am-9:18 am

Nonstop3h 18m

$131

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 10/10

5:50 am-9:13 pm

1 stop14h 23m

Miami

Tue 10/14

7:00 am-9:22 am

Nonstop3h 22m

$132

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/20

4:40 pm-8:52 pm

Nonstop3h 12m

Miami

Mon 9/22

9:26 pm-11:49 pm

Nonstop3h 23m

$137

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 10/30

11:50 am-12:54 am

1 stop12h 04m

Miami

Mon 11/3

7:07 pm-12:11 am

1 stop6h 04m

$143

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 10/9

2:41 pm-4:03 pm

1 stop24h 22m

Miami

Sun 10/12

4:16 pm-11:18 am

1 stop20h 02m

$144

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 9/14

6:09 am-10:14 am

Nonstop3h 05m

Miami

Tue 9/16

9:10 am-11:32 am

Nonstop3h 22m

$147

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 9/26

1:30 pm-11:05 pm

1 stop8h 35m

Miami

Sun 9/28

7:00 am-1:05 pm

1 stop7h 05m

$157

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 9/22

5:30 am-10:55 am

1 stop4h 25m

Key West

Wed 10/1

6:00 pm-10:14 pm

1 stop5h 14m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 12/2

11:19 am-7:44 pm

1 stop7h 25m

Key West

Sat 12/6

6:00 pm-11:53 pm

1 stop6h 53m

$289

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 O'Hare Intl 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 August is another great option to travel to Florida Keys, with average flight prices from Chicago O'Hare Intl Airport averaging around $234.

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

The cheapest day to depart from Chicago O'Hare Intl Airport to Florida Keys is on a Thursday when prices can be found for as low as $432. The most expensive day to fly to Florida Keys is Sunday, with ticket prices averaging around $452.

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 O'Hare Intl Airport to Florida Keys in the evening for as low as $242. 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 $472.

What is the cheapest Chicago O'Hare Intl to Florida Keys flight route?

Fly from Chicago O'Hare Intl to Key West for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $270 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 O'Hare Intl Airport for as low as $214 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Florida Keys flights?

There are 3 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to Florida Keys.

Cheap Chicago O'Hare Intl Airport to Florida Keys flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Florida Keys

Best Price Found

$66

Fastest flight time

3h 02m

Direct flights

Every day

Airports in Florida Keys

2 airports
The best one-way flight to Florida Keys from Chicago O'Hare Intl Airport in the past 72 hours is $66. The best round-trip flight deal from Chicago O'Hare Intl Airport to Florida Keys found on momondo in the last 72 hours is $130.
The fastest flight from Chicago O'Hare Intl Airport to Florida Keys takes 3h 02m
Direct flights go from Chicago O'Hare Intl Airport to Florida Keys every day.
There are 2 airports near Florida Keys: Key West (EYW), Miami (MIA)
Search flight deals

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Florida Keys?

    Prices for flights from Chicago O'Hare Intl Airport to Florida Keys are updated daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Florida Keys?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Florida Keys?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Florida Keys.

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

    The required travel and health documents for your Florida Keys trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Florida Keys. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Florida Keys?

Best airlines flying from Chicago O'Hare Intl Airport to Florida Keys

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Florida Keys with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $216Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $261Free CancellationRating
7.4
8,925 reviews
Search United Airlines flights
American AirlinesPriceFrom $295Free CancellationRating
7.2
10,000 reviews
Search American Airlines 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. All flights to Florida Keys from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search for Chicago to Florida Keys flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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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