What is the cheapest airline that flies from Key West to Illinois?

Delta, United Airlines, and American Airlines are the most popular carriers operating from Key West to Illinois

How many flights depart from Key West to Illinois on average per day?

2 flights are operational daily from Key West to Illinois as of July 2026. The most popular departure time for this route is 4:00PM, with 100% of flights per day taking off in the afternoon.

How many flights depart from Key West to Illinois on average per week?

As of July 2026, 15 flights take off from Key West and land in Illinois each week. The most common flight departure day for this route is Thu, with 20% of weekly flights taking off on this day.

When did momondo last update prices for flights from Key West Airport to Illinois?

Prices for flights from Key West Airport to Illinois are refreshed on a daily basis.

How many operators does momondo search for flights from Key West Airport to Illinois?

There is 1 operator available for flights from Key West Airport to Illinois as of July 2026.

How old do you have to be to fly from Key West Airport to Illinois?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Key West Airport to Illinois.

What documentation or ID do you need to fly to Illinois?

The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$126 Cheap Flights from Key West to Illinois in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Key West to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:36 pm - 7:59 am

EYW

RFD

12h 23m

1 stop

10:08 am - 2:03 pm

RFD

EYW

26h 55m

2 stops

$261Multiple Airlines

Thu, Oct 1 - Sun, Oct 4

12:05 pm - 11:08 pm

EYW

ORD

12h 03m

1 stop

8:05 am - 12:34 pm

ORD

EYW

27h 29m

2 stops

$262Multiple Airlines

Thu, Sep 3 - Mon, Sep 7

12:05 pm - 11:08 pm

EYW

ORD

12h 03m

1 stop

8:05 am - 12:34 pm

ORD

EYW

27h 29m

2 stops

$263Multiple Airlines

Thu, Sep 3 - Mon, Sep 7

10:59 am - 10:20 am

EYW

ORD

24h 21m

1 stop

10:26 am - 12:19 pm

ORD

EYW

24h 53m

2 stops

$274Multiple Airlines

Thu, Sep 10 - Sun, Sep 13

12:07 pm - 11:08 pm

EYW

ORD

12h 01m

1 stop

7:05 am - 12:34 pm

ORD

EYW

52h 29m

2 stops

$285Multiple Airlines

Mon, Aug 24 - Sun, Aug 30

4:56 pm - 7:48 pm

EYW

ORD

3h 52mnonstop

12:08 pm - 4:27 pm

ORD

EYW

3h 19mnonstop

$312American Airlines

Sat, Sep 5 - Sun, Sep 6

12:05 pm - 11:08 pm

EYW

ORD

12h 03m

1 stop

8:05 am - 12:34 pm

ORD

EYW

27h 29m

2 stops

$316Multiple Airlines

Thu, Sep 3 - Mon, Sep 7

4:56 pm - 7:48 pm

EYW

ORD

3h 52mnonstop

11:59 am - 4:18 pm

ORD

EYW

3h 19mnonstop

$319American Airlines

Wed, Aug 26 - Mon, Aug 31

4:56 pm - 7:48 pm

EYW

ORD

3h 52mnonstop

11:59 am - 4:18 pm

ORD

EYW

3h 19mnonstop

$319American Airlines

Thu, Sep 3 - Mon, Sep 7

4:56 pm - 7:48 pm

EYW

ORD

3h 52mnonstop

12:08 pm - 4:27 pm

ORD

EYW

3h 19mnonstop

$319American Airlines

Mon, Aug 24 - Sun, Aug 30

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

American Airlines flights from Key West to Illinois

Our best American Airlines deals on Key West to Illinois flight tickets

American Airlines

Sep 3

EYW4:56 pmKey West

3h 52m

ORD7:48 pmChicago O'Hare Intl

Sep 7

ORD11:59 amChicago O'Hare Intl

3h 19m

EYW4:18 pmKey West

$319

American Airlines

Sep 3

EYW4:56 pmKey West

3h 52m

ORD7:48 pmChicago O'Hare Intl

Sep 7

ORD5:00 amChicago O'Hare Intl

4h 56m

1 stop

EYW10:56 amKey West

$329

American Airlines

Oct 1

EYW1:47 pmKey West

6h 51m

1 stop

ORD7:38 pmChicago O'Hare Intl

Oct 3

ORD11:50 amChicago O'Hare Intl

5h 05m

1 stop

EYW5:55 pmKey West

$331

Delta flights from Key West to Illinois

Our best Delta deals on Key West to Illinois flight tickets

Delta

Oct 1

EYW7:40 amKey West

5h 14m

1 stop

MDW11:54 amChicago Midway

Oct 3

MDW11:35 amChicago Midway

7h 25m

1 stop

EYW8:00 pmKey West

$331

Delta

Sep 5

EYW4:00 pmKey West

7h 36m

1 stop

MDW10:36 pmChicago Midway

Sep 6

MDW6:05 amChicago Midway

5h 21m

1 stop

EYW12:26 pmKey West

$332

Delta

Aug 27

EYW11:48 amKey West

5h 27m

1 stop

MDW4:15 pmChicago Midway

Sep 2

MDW6:05 amChicago Midway

5h 55m

1 stop

EYW1:00 pmKey West

$339

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestChicago

EYW - RFD

EYWRFD

Key West

Thu 10/1

8:36 pm-7:59 am

1 stop12h 23m

Chicago Greater Rockford

Sun 10/4

10:08 am-2:03 pm

2 stops26h 55m

$261

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Mon 9/7

8:05 am-12:34 pm

2 stops27h 29m

$262

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Mon 9/7

8:05 am-12:34 pm

2 stops27h 29m

$263

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/10

10:59 am-10:20 am

1 stop24h 21m

Chicago O'Hare Intl

Sun 9/13

10:26 am-12:19 pm

2 stops24h 53m

$274

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 8/24

12:07 pm-11:08 pm

1 stop12h 01m

Chicago O'Hare Intl

Sun 8/30

7:05 am-12:34 pm

2 stops52h 29m

$285

Quickest round-trip

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 9/5

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Sun 9/6

12:08 pm-4:27 pm

Nonstop3h 19m

$312

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

12:05 pm-11:08 pm

1 stop12h 03m

Chicago O'Hare Intl

Mon 9/7

8:05 am-12:34 pm

2 stops27h 29m

$316

Key WestChicago

EYW - ORD

EYWORD

Key West

Wed 8/26

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Mon 8/31

11:59 am-4:18 pm

Nonstop3h 19m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 9/3

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Mon 9/7

11:59 am-4:18 pm

Nonstop3h 19m

$319

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 8/24

4:56 pm-7:48 pm

Nonstop3h 52m

Chicago O'Hare Intl

Sun 8/30

12:08 pm-4:27 pm

Nonstop3h 19m

$319

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 Key West to Illinois

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 Illinois?

The cheapest month to fly to Illinois from Key West is in March. Flight prices, which tend to average around $0, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of March, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $268.

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

The cheapest day to depart from Key West to Illinois is on a Wednesday when prices can be found for as low as $339. Flights from Key West to Illinois on a Monday will generally be more expensive and average around $484. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the morning. Flights from Key West to Illinois during this time can be as low as $366. Flights in the afternoon are often more expensive with an average ticket price of $438.

What is the cheapest Key West to Illinois flight route?

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

What cabin class options are available on Key West to Illinois flights?

There are 4 cabin classes available to choose from on Key West to Illinois 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 Key West to Illinois flights?

You could potentially save up to 9% on your flight if you consider stops on a Key West to Illinois flight.

Cheap Key West to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Key West to Illinois

Best Price Found	$283
Fastest flight time	3h 48m
Direct flights	Mon, Tue, Wed, Thu, Fri and Sun
Airports in Illinois	98 airports

The best one-way flight to Illinois from Key West in the past 72 hours is $283. The best round-trip flight deal from Key West to Illinois found on momondo in the last 72 hours is $446.

The fastest flight from Key West to Illinois takes 3h 48m

Direct flights go from Key West to Illinois on Monday, Tuesday, Wednesday, Thursday, Friday and Sunday. There are no airlines offering direct flights.

There are 98 airports in Illinois. From Key West there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Key West to Illinois

When did momondo last update prices for flights from Key West Airport to Illinois?
Prices for flights from Key West Airport to Illinois are refreshed on a daily basis.
How many operators does momondo search for flights from Key West Airport to Illinois?
There is 1 operator available for flights from Key West Airport to Illinois as of July 2026.
How old do you have to be to fly from Key West Airport to Illinois?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Key West Airport to Illinois.
What documentation or ID do you need to fly to Illinois?
The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Key West to Illinois?
Based on momondo bookings for flights between Key West and Illinois, the leading plane model is Embraer 170, making up 37.50% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 25.00%, Embraer 175 with 12.50%, and Boeing 737-700 with 6.25%.

Best airlines flying from Key West to Illinois

Compare and see reviews for airlines that fly from Key West to Illinois with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $329	Free Cancellation	Rating 7.1 11,846 reviews		Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Key West to Illinois?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Key West to Illinois. momondo saves you time and could save you money on your trip.

Can I find flights from Key West to Illinois with flexible booking policies on momondo?

Flights from Key West to Illinois with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Key West to Illinois?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Illinois from Key West.

I’m not ready to book a flight from Key West to Illinois right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Illinois from Key West. 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.