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Cheap flights from Florida Keys to Chicago from $62

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Florida Keys to Chicago departing on 2/12. 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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0 bags

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Find the cheapest flights from Florida Keys to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:54 am - 8:18 am
MIA
-
ORD
3h 24mnonstop
Spirit Airlines Logo
6:57 pm - 11:14 pm
ORD
-
MIA
3h 17mnonstop
$79Spirit Airlines
Thu, Jan 15 - Sat, Jan 24
Spirit Airlines Logo
1:01 pm - 10:38 pm
MIA
-
ORD
10h 37m1 stop
Spirit Airlines Logo
9:23 am - 1:41 pm
ORD
-
MIA
3h 18mnonstop
$80Spirit Airlines
Wed, Jan 21 - Wed, Jan 28
Multiple Airlines Logo
12:40 pm - 3:18 pm
MIA
-
ORD
3h 38mnonstop
Multiple Airlines Logo
7:13 pm - 11:29 pm
ORD
-
MIA
3h 16mnonstop
$83Multiple Airlines
Fri, Feb 20 - Fri, Feb 20
Multiple Airlines Logo
1:21 pm - 6:27 pm
MIA
-
ORD
6h 06m1 stop
Multiple Airlines Logo
9:23 am - 1:41 pm
ORD
-
MIA
3h 18mnonstop
$90Multiple Airlines
Wed, Feb 4 - Wed, Feb 11
Frontier Logo
12:10 pm - 7:07 pm
MIA
-
MDW
7h 57m1 stop
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
$93Frontier
Wed, Feb 25 - Sun, Mar 1
Frontier Logo
12:16 pm - 12:02 am
MIA
-
MDW
12h 46m1 stop
Frontier Logo
8:19 pm - 12:28 am
MDW
-
MIA
3h 09mnonstop
$100Frontier
Thu, Jan 15 - Sun, Jan 18
American Airlines Logo
6:39 pm - 9:20 pm
EYW
-
ORD
3h 41mnonstop
American Airlines Logo
8:00 am - 12:16 pm
ORD
-
EYW
3h 16mnonstop
$249American Airlines
Thu, Apr 9 - Mon, Apr 13
Delta Logo
6:06 pm - 10:22 pm
EYW
-
MDW
5h 16m1 stop
Delta Logo
6:00 am - 1:48 pm
MDW
-
EYW
6h 48m1 stop
$269Delta
Fri, Jan 23 - Sun, Jan 25
American Airlines Logo
6:39 pm - 9:20 pm
EYW
-
ORD
3h 41mnonstop
American Airlines Logo
12:07 pm - 6:23 pm
ORD
-
EYW
5h 16m1 stop
$289American Airlines
Thu, Apr 9 - Mon, Apr 13
Delta Logo
6:06 pm - 10:22 pm
EYW
-
MDW
5h 16m1 stop
Delta Logo
10:48 am - 5:11 pm
MDW
-
EYW
5h 23m1 stop
$354Delta
Wed, Jan 21 - Thu, Jan 29

Spirit Airlines flights from Florida Keys to Chicago

Our best Spirit Airlines deals on Florida Keys to Chicago flight tickets
Spirit Airlines
Jan 21
MIA5:54 amMiami
3h 24m
ORD8:18 amChicago O'Hare Intl
Jan 23
ORD6:57 pmChicago O'Hare Intl
3h 17m
MIA11:14 pmMiami
$79
Find similar
Spirit Airlines
Jan 21
MIA1:01 pmMiami
10h 37m
1 stop
ORD10:38 pmChicago O'Hare Intl
Jan 28
ORD9:23 amChicago O'Hare Intl
3h 18m
MIA1:41 pmMiami
$80
Find similar
Spirit Airlines
Jan 9
MIA5:54 amMiami
3h 24m
ORD8:18 amChicago O'Hare Intl
Jan 12
ORD6:57 pmChicago O'Hare Intl
3h 17m
MIA11:14 pmMiami
$84
Find similar

Frontier flights from Florida Keys to Chicago

Our best Frontier deals on Florida Keys to Chicago flight tickets
Frontier
Feb 25
MIA12:10 pmMiami
7h 57m
1 stop
MDW7:07 pmChicago Midway
Mar 1
MDW6:15 amChicago Midway
3h 13m
MIA10:28 amMiami
$93
Find similar
Frontier
Feb 13
MIA12:40 pmMiami
3h 38m
ORD3:18 pmChicago O'Hare Intl
Feb 16
ORD11:43 amChicago O'Hare Intl
3h 15m
MIA3:58 pmMiami
$97
Find similar
Frontier
Jan 15
MIA12:16 pmMiami
12h 46m
1 stop
MDW12:02 amChicago Midway
Jan 18
MDW8:19 pmChicago Midway
3h 09m
MIA12:28 amMiami
$100
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Florida Keys to Chicago 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 Florida Keys to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 1/15

5:54 am-8:18 am

Nonstop3h 24m

Chicago O'Hare Intl

Sat 1/24

6:57 pm-11:14 pm

Nonstop3h 17m

$79

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 1/21

1:01 pm-10:38 pm

1 stop10h 37m

Chicago O'Hare Intl

Wed 1/28

9:23 am-1:41 pm

Nonstop3h 18m

$80

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 2/20

12:40 pm-3:18 pm

Nonstop3h 38m

Chicago O'Hare Intl

Fri 2/20

7:13 pm-11:29 pm

Nonstop3h 16m

$83

MiamiChicago

MIA - ORD

MIAORD

Miami

Wed 2/4

1:21 pm-6:27 pm

1 stop6h 06m

Chicago O'Hare Intl

Wed 2/11

9:23 am-1:41 pm

Nonstop3h 18m

$90

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 2/25

12:10 pm-7:07 pm

1 stop7h 57m

Chicago Midway

Sun 3/1

6:15 am-10:28 am

Nonstop3h 13m

$93

MiamiChicago

MIA - MDW

MIAMDW

Miami

Thu 1/15

12:16 pm-12:02 am

1 stop12h 46m

Chicago Midway

Sun 1/18

8:19 pm-12:28 am

Nonstop3h 09m

$100

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

6:39 pm-9:20 pm

Nonstop3h 41m

Chicago O'Hare Intl

Mon 4/13

8:00 am-12:16 pm

Nonstop3h 16m

$249

Key WestChicago

EYW - MDW

EYWMDW

Key West

Fri 1/23

6:06 pm-10:22 pm

1 stop5h 16m

Chicago Midway

Sun 1/25

6:00 am-1:48 pm

1 stop6h 48m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

6:39 pm-9:20 pm

Nonstop3h 41m

Chicago O'Hare Intl

Mon 4/13

12:07 pm-6:23 pm

1 stop5h 16m

$289

Key WestChicago

EYW - MDW

EYWMDW

Key West

Wed 1/21

6:06 pm-10:22 pm

1 stop5h 16m

Chicago Midway

Thu 1/29

10:48 am-5:11 pm

1 stop5h 23m

$354

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 Chicago from

How to get the cheapest flight ticket from Florida Keys to Chicago

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 Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Florida Keys, with most prices found around $159. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Florida Keys to Chicago during September average around $177.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $292. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Florida Keys to Chicago for around $462.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Florida Keys to Chicago during this time can be as low as $282. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $406.

What is the cheapest Florida Keys to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Florida Keys when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $248 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Florida Keys for as low as $178 on momondo.

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

There are 4 cabin classes available to choose from on Florida Keys to Chicago 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 Florida Keys to Chicago flights?

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

Cheap Florida Keys to Chicago flight deals and tips

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

Fastest flight time

3h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The fastest flight from Florida Keys to Chicago takes 3h 10m
Direct flights go from Florida Keys to Chicago every day.
There are 3 airports in Chicago. From Florida Keys there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

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

    Prices for flights from Florida Keys to Chicago are updated daily.

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

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

    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 Florida Keys to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Best airlines flying from Florida Keys to Chicago

Compare and see reviews for airlines that fly from Florida Keys to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $249Free CancellationRating
7.4
9,105 reviews
Search United Airlines flights
American AirlinesPriceFrom $289Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

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 Florida Keys to Chicago for you.

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

Yes. All flights to Chicago from Florida Keys on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Florida Keys to Chicago.

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

Of course. momondo tracks the price of Florida Keys to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport