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Cheap flights from Chicago O'Hare Intl Airport to Florida Keys from $105

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 8/18. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago O'Hare Intl Airport to Florida Keys

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:05 am - 1:32 pm
ORD
-
MIA
5h 27m
1 stop
Frontier Logo
9:59 am - 3:59 pm
MIA
-
ORD
7h 00m
1 stop
$232Frontier
Wed, Aug 19 - Sat, Aug 22
Frontier Logo
7:05 am - 4:33 pm
ORD
-
MIA
8h 28m
1 stop
Frontier Logo
6:30 am - 12:33 am
MIA
-
ORD
19h 03m
1 stop
$233Frontier
Thu, Jul 30 - Wed, Aug 5
Frontier Logo
7:05 am - 1:53 pm
ORD
-
MIA
5h 48m
1 stop
Frontier Logo
10:50 am - 7:53 pm
MIA
-
ORD
10h 03m
1 stop
$234Frontier
Wed, Aug 5 - Thu, Aug 13
Frontier Logo
5:46 pm - 1:53 pm
ORD
-
MIA
19h 07m
2 stops
Frontier Logo
6:30 am - 12:49 am
MIA
-
ORD
19h 19m
1 stop
$235Frontier
Tue, Jul 21 - Tue, Jul 28
Frontier Logo
7:05 am - 4:21 pm
ORD
-
MIA
8h 16m
1 stop
Frontier Logo
6:00 am - 1:36 pm
MIA
-
ORD
8h 36m
1 stop
$236Frontier
Fri, Aug 28 - Wed, Sep 2
Frontier Logo
7:05 am - 4:33 pm
ORD
-
MIA
8h 28m
1 stop
Frontier Logo
6:00 am - 1:36 pm
MIA
-
ORD
8h 36m
1 stop
$237Frontier
Mon, Aug 3 - Tue, Aug 25
Frontier Logo
1:50 pm - 11:06 pm
ORD
-
MIA
8h 16m
1 stop
Frontier Logo
10:15 pm - 5:37 am
MIA
-
ORD
32h 22m
1 stop
$238Frontier
Wed, Aug 5 - Sun, Aug 9
Frontier Logo
7:05 am - 4:33 pm
ORD
-
MIA
8h 28m
1 stop
Frontier Logo
6:50 am - 4:08 pm
MIA
-
ORD
10h 18m
1 stop
$239Frontier
Thu, Jul 30 - Tue, Aug 4
Multiple Airlines Logo
7:44 pm - 11:25 am
ORD
-
EYW
14h 41m
1 stop
Multiple Airlines Logo
10:04 am - 3:26 pm
EYW
-
ORD
30h 22m
2 stops
$262Multiple Airlines
Sat, Sep 5 - Wed, Sep 9
Multiple Airlines Logo
5:13 pm - 11:27 am
ORD
-
EYW
17h 14m
1 stop
Multiple Airlines Logo
12:05 pm - 11:08 pm
EYW
-
ORD
12h 03m
1 stop
$266Multiple Airlines
Thu, Aug 13 - Thu, Aug 20

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

Our best United Airlines deals on Chicago O'Hare Intl Airport to Florida Keys flight tickets
United Airlines
Jul 21
ORD6:05 pmChicago O'Hare Intl
3h 22m
MIA10:27 pmMiami
Jul 28
MIA4:53 pmMiami
8h 52m
1 stop
ORD12:45 amChicago O'Hare Intl
$245
United Airlines
Sep 5
ORD7:30 amChicago O'Hare Intl
3h 24m
MIA11:54 amMiami
Sep 12
MIA8:25 amMiami
9h 09m
1 stop
ORD4:34 pmChicago O'Hare Intl
$246
United Airlines
Jul 25
ORD6:05 pmChicago O'Hare Intl
3h 22m
MIA10:27 pmMiami
Aug 1
MIA6:30 amMiami
9h 21m
1 stop
ORD2:51 pmChicago O'Hare Intl
$249

Frontier flights from Chicago O'Hare Intl Airport to Florida Keys

Our best Frontier deals on Chicago O'Hare Intl Airport to Florida Keys flight tickets
Frontier
Aug 19
ORD7:05 amChicago O'Hare Intl
5h 27m
1 stop
MIA1:32 pmMiami
Aug 22
MIA9:59 amMiami
7h 00m
1 stop
ORD3:59 pmChicago O'Hare Intl
$232
Frontier
Jul 30
ORD7:05 amChicago O'Hare Intl
8h 28m
1 stop
MIA4:33 pmMiami
Aug 5
MIA6:30 amMiami
19h 03m
1 stop
ORD12:33 amChicago O'Hare Intl
$233
Frontier
Aug 5
ORD7:05 amChicago O'Hare Intl
5h 48m
1 stop
MIA1:53 pmMiami
Aug 13
MIA10:50 amMiami
10h 03m
1 stop
ORD7:53 pmChicago O'Hare Intl
$234

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 June 30, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 8/19

7:05 am-1:32 pm

1 stop5h 27m

Miami

Sat 8/22

9:59 am-3:59 pm

1 stop7h 00m

$232

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 7/30

7:05 am-4:33 pm

1 stop8h 28m

Miami

Wed 8/5

6:30 am-12:33 am

1 stop19h 03m

$233

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 8/5

7:05 am-1:53 pm

1 stop5h 48m

Miami

Thu 8/13

10:50 am-7:53 pm

1 stop10h 03m

$234

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 7/21

5:46 pm-1:53 pm

2 stops19h 07m

Miami

Tue 7/28

6:30 am-12:49 am

1 stop19h 19m

$235

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 8/28

7:05 am-4:21 pm

1 stop8h 16m

Miami

Wed 9/2

6:00 am-1:36 pm

1 stop8h 36m

$236

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 8/3

7:05 am-4:33 pm

1 stop8h 28m

Miami

Tue 8/25

6:00 am-1:36 pm

1 stop8h 36m

$237

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 8/5

1:50 pm-11:06 pm

1 stop8h 16m

Miami

Sun 8/9

10:15 pm-5:37 am

1 stop32h 22m

$238

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 7/30

7:05 am-4:33 pm

1 stop8h 28m

Miami

Tue 8/4

6:50 am-4:08 pm

1 stop10h 18m

$239

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 9/5

7:44 pm-11:25 am

1 stop14h 41m

Key West

Wed 9/9

10:04 am-3:26 pm

2 stops30h 22m

$262

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Thu 8/13

5:13 pm-11:27 am

1 stop17h 14m

Key West

Thu 8/20

12:05 pm-11:08 pm

1 stop12h 03m

$266

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 January is another great option to travel to Florida Keys, with average flight prices from Chicago O'Hare Intl Airport averaging around $187.

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 Monday when prices can be found for as low as $432. The most expensive day to fly to Florida Keys is Tuesday, with ticket prices averaging around $516.

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 $379. 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 $467.

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 from Chicago O'Hare Intl Airport 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 $284 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 $224 on momondo.

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

There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport 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?

You could potentially save up to 27% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Florida Keys flight.

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

Fastest flight time

2h 08m

Direct flights

Every day

Airports in Florida Keys

3 airports
The fastest flight from Chicago O'Hare Intl Airport to Florida Keys takes 2h 08m
Direct flights go from Chicago O'Hare Intl Airport to Florida Keys every day.
There are 3 airports in Florida Keys. From Chicago O'Hare Intl Airport there are direct flights to Key West (EYW), Miami (MIA).
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Florida Keys

  • 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 $206Free CancellationRating
7.8
8,451 reviews
Search Delta flights
United AirlinesPriceFrom $249Free CancellationRating
7.4
9,901 reviews
Search United Airlines flights
American AirlinesPriceFrom $308Free CancellationRating
7.1
11,762 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.

An easier way to manage your Florida Keys trip

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