How many flights depart from Florida Keys to Chicago on average per day?

As of February 2026, there are 57 flights per day flying from Florida Keys to Chicago. The most common time of day flights depart is 3:00PM, with 62% of flights taking off in the afternoon.

What is the cheapest airline that flies from Florida Keys to Chicago?

Spirit Airlines, Frontier, and United Airlines are the most popular carriers operating from Florida Keys to Chicago

How many flights depart from Florida Keys to Chicago on average per week?

400 flights are operational weekly from Florida Keys to Chicago as of February 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.

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?

There are 5 operators available for flights from Florida Keys to Chicago as of February 2026.

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.

$50 Cheap Flights from Florida Keys to Chicago in 2026

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Find the cheapest flights from Florida Keys to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

9:21 pm - 11:59 pm

MIA

ORD

3h 38mnonstop

4:58 pm - 9:17 pm

ORD

MIA

3h 19mnonstop

$74Frontier

Thu, Apr 16 - Mon, Apr 20

7:15 am - 9:53 am

MIA

ORD

3h 38mnonstop

9:50 am - 2:05 pm

ORD

MIA

3h 15mnonstop

$75Frontier

Sat, Mar 14 - Mon, Mar 16

9:21 pm - 11:59 pm

MIA

ORD

3h 38mnonstop

3:52 pm - 8:11 pm

ORD

MIA

3h 19mnonstop

$76Frontier

Thu, Apr 16 - Sun, Apr 19

12:04 pm - 2:42 pm

MIA

ORD

3h 38mnonstop

7:25 am - 11:44 am

ORD

MIA

3h 19mnonstop

$79Frontier

Thu, Apr 9 - Sun, Apr 12

3:47 pm - 6:11 pm

MIA

ORD

3h 24mnonstop

6:34 pm - 10:42 pm

ORD

MIA

3h 08mnonstop

$80Spirit Airlines

Thu, May 14 - Mon, May 18

6:00 am - 8:25 am

MIA

ORD

3h 25mnonstop

9:50 am - 2:05 pm

ORD

MIA

3h 15mnonstop

$81Multiple Airlines

Sat, Mar 14 - Mon, Mar 16

6:00 am - 8:25 am

MIA

ORD

3h 25mnonstop

9:50 am - 2:05 pm

ORD

MIA

3h 15mnonstop

$85Multiple Airlines

Fri, Mar 13 - Mon, Mar 16

6:46 pm - 9:35 pm

EYW

ORD

3h 49mnonstop

8:10 am - 12:38 pm

ORD

EYW

3h 28mnonstop

$249American Airlines

Thu, Apr 9 - Mon, Apr 13

6:49 pm - 9:36 pm

EYW

ORD

3h 47mnonstop

1:53 pm - 6:19 pm

ORD

EYW

3h 26mnonstop

$279American Airlines

Wed, Mar 18 - Tue, Mar 24

4:38 pm - 12:45 am

EYW

ORD

9h 07m

1 stop

7:30 am - 3:57 pm

ORD

EYW

7h 27m

1 stop

$349United Airlines

Thu, Apr 9 - Mon, Apr 13

Spirit Airlines flights from Florida Keys to Chicago

Our best Spirit Airlines deals on Florida Keys to Chicago flight tickets

Spirit Airlines

May 14

MIA3:47 pmMiami

3h 24m

ORD6:11 pmChicago O'Hare Intl

May 18

ORD6:34 pmChicago O'Hare Intl

3h 08m

MIA10:42 pmMiami

$80

Spirit Airlines

Mar 6

MIA7:12 amMiami

3h 27m

ORD9:39 amChicago O'Hare Intl

Mar 16

ORD10:55 amChicago O'Hare Intl

3h 05m

MIA3:00 pmMiami

$84

Spirit Airlines

Mar 6

MIA7:12 amMiami

3h 27m

ORD9:39 amChicago O'Hare Intl

Mar 8

ORD7:23 pmChicago O'Hare Intl

3h 16m

MIA11:39 pmMiami

$87

Delta flights from Florida Keys to Chicago

Our best Delta deals on Florida Keys to Chicago flight tickets

Delta

Apr 30

EYW6:23 pmKey West

6h 36m

1 stop

ORD11:59 pmChicago O'Hare Intl

May 3

ORD5:15 amChicago O'Hare Intl

5h 10m

1 stop

EYW11:25 amKey West

$238

Delta

Apr 30

EYW6:23 pmKey West

6h 36m

1 stop

ORD11:59 pmChicago O'Hare Intl

May 3

ORD5:15 amChicago O'Hare Intl

7h 29m

1 stop

EYW1:44 pmKey West

$248

Delta

Feb 26

EYW5:56 pmKey West

5h 35m

1 stop

MDW10:31 pmChicago Midway

Feb 28

MDW6:00 amChicago Midway

6h 48m

1 stop

EYW1:48 pmKey West

$609

Fly from

Fly to

Route

Depart

Return

Price

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 4/16

9:21 pm-11:59 pm

Nonstop3h 38m

Chicago O'Hare Intl

Mon 4/20

4:58 pm-9:17 pm

Nonstop3h 19m

$74

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 3/14

7:15 am-9:53 am

Nonstop3h 38m

Chicago O'Hare Intl

Mon 3/16

9:50 am-2:05 pm

Nonstop3h 15m

$75

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 4/16

9:21 pm-11:59 pm

Nonstop3h 38m

Chicago O'Hare Intl

Sun 4/19

3:52 pm-8:11 pm

Nonstop3h 19m

$76

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 4/9

12:04 pm-2:42 pm

Nonstop3h 38m

Chicago O'Hare Intl

Sun 4/12

7:25 am-11:44 am

Nonstop3h 19m

$79

MiamiChicago

MIA - ORD

MIAORD

Miami

Thu 5/14

3:47 pm-6:11 pm

Nonstop3h 24m

Chicago O'Hare Intl

Mon 5/18

6:34 pm-10:42 pm

Nonstop3h 08m

$80

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 3/14

6:00 am-8:25 am

Nonstop3h 25m

Chicago O'Hare Intl

Mon 3/16

9:50 am-2:05 pm

Nonstop3h 15m

$81

MiamiChicago

MIA - ORD

MIAORD

Miami

Fri 3/13

6:00 am-8:25 am

Nonstop3h 25m

Chicago O'Hare Intl

Mon 3/16

9:50 am-2:05 pm

Nonstop3h 15m

$85

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

6:46 pm-9:35 pm

Nonstop3h 49m

Chicago O'Hare Intl

Mon 4/13

8:10 am-12:38 pm

Nonstop3h 28m

$249

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 3/18

6:49 pm-9:36 pm

Nonstop3h 47m

Chicago O'Hare Intl

Tue 3/24

1:53 pm-6:19 pm

Nonstop3h 26m

$279

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 4/9

4:38 pm-12:45 am

1 stop9h 07m

Chicago O'Hare Intl

Mon 4/13

7:30 am-3:57 pm

1 stop7h 27m

$349

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Florida Keys, with most prices found around $157. If you’re not able to fly to Chicago in January, 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 $291. 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 $490.

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 $293. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $386.

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 $244 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 05m
Direct flights	Every day
Airports in Chicago	3 airports

The fastest flight from Florida Keys to Chicago takes 3h 05m

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?
There are 5 operators available for flights from Florida Keys to Chicago as of February 2026.
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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Florida Keys to Chicago is Boeing 737-800 (17.64% of total bookings). The next most popular plane models are Airbus A321neo (12.41%), Boeing 737 MAX 8 (8.03%), and Boeing 737-900 (7.67%).

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 Airlines	PriceFrom $249	Free Cancellation	Rating 7.4 9,342 reviews		Search United Airlines flights
American Airlines	PriceFrom $309	Free Cancellation	Rating 7.2 11,339 reviews		Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

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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Cheap flights from Florida Keys to Chicago from $51

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 3/10. 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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Spirit Airlines flights from Florida Keys to Chicago

Our best Spirit Airlines deals on Florida Keys to Chicago flight tickets

Delta flights from Florida Keys to Chicago

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See travel insights to Chicago from

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

What is the cheapest month to fly to Chicago?

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

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

What is the cheapest Florida Keys to Chicago flight route?

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

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

Can stopping save me money on Florida Keys to Chicago flights?

What is the cheapest airline that flies from Florida Keys to Chicago?

How many flights depart from Florida Keys to Chicago on average per day?

How many flights depart from Florida Keys to Chicago on average per week?

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

Direct flights

Airports in Chicago

Best airlines flying from Florida Keys to Chicago

Compare and see reviews for airlines that fly from Florida Keys to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

How can momondo help me find flights 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?

An easier way to manage your Chicago 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.

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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