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Cheap flights from Illinois to Key West from $102

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Key West departing on 10/11. 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 Illinois to Key West

Cheap round-trip flights

Multiple Airlines Logo
7:43 pm - 2:40 pmORD-EYW
17h 57m1 stop
Multiple Airlines Logo
3:23 pm - 6:46 pmEYW-ORD
28h 23m1 stop
$202Multiple Airlines
Find Deal
Sat, Oct 25 - Thu, Oct 30
Spirit Airlines Logo
5:05 am - 1:30 pmORD-EYW
7h 25m1 stop
Spirit Airlines Logo
2:25 pm - 11:42 pmEYW-ORD
10h 17m1 stop
$213Spirit Airlines
Find Deal
Mon, Nov 17 - Thu, Nov 20
Delta Logo
9:33 am - 5:23 pmSTL-EYW
6h 50m1 stop
Delta Logo
6:18 pm - 9:58 pmEYW-STL
4h 40m1 stop
$223Delta
Find Deal
Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
7:00 am - 5:01 pmSTL-EYW
9h 01m2 stops
American Airlines Logo
4:10 pm - 10:27 pmEYW-STL
7h 17m1 stop
$228American Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
2:11 pm - 11:07 pmSTL-EYW
7h 56m2 stops
American Airlines Logo
7:00 am - 1:18 pmEYW-STL
7h 18m2 stops
$233American Airlines
Find Deal
Wed, Dec 3 - Sat, Dec 6
Delta Logo
7:05 am - 1:02 pmSTL-EYW
4h 57m1 stop
Delta Logo
12:26 pm - 4:07 pmEYW-STL
4h 41m1 stop
$241Delta
Find Deal
Tue, Nov 4 - Fri, Nov 14
Allegiant Air Logo
2:45 pm - 8:55 pmMDW-EYW
5h 10m1 stop
Allegiant Air Logo
2:57 pm - 7:34 pmEYW-MDW
5h 37m1 stop
$292Allegiant Air
Find Deal
Fri, Oct 24 - Mon, Oct 27
Allegiant Air Logo
10:42 am - 4:04 pmPIA-EYW
4h 22m1 stop
Allegiant Air Logo
10:02 am - 10:22 amEYW-PIA
25h 20m1 stop
$305Allegiant Air
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Sun, Oct 26 - Wed, Oct 29
United Airlines Logo
6:45 am - 3:19 pmPIA-EYW
7h 34m1 stop
United Airlines Logo
3:00 pm - 10:16 amEYW-PIA
20h 16m2 stops
$483United Airlines
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Tue, Oct 28 - Tue, Nov 4
United Airlines Logo
6:30 am - 3:17 pmPIA-EYW
7h 47m1 stop
United Airlines Logo
4:15 pm - 9:39 pmEYW-PIA
6h 24m1 stop
$493United Airlines
Find Deal
Tue, Feb 3 - Tue, Feb 10

American Airlines flights from Illinois to Key West

Our best American Airlines deals on Illinois to Key West flight tickets
American Airlines
Nov 11
STL7:00 amLambert-St Louis
9h 01m
2 stops
EYW5:01 pmKey West
Nov 18
EYW4:10 pmKey West
7h 17m
1 stop
STL10:27 pmLambert-St Louis
$228
Find similar
American Airlines
Dec 3
STL2:11 pmLambert-St Louis
7h 56m
2 stops
EYW11:07 pmKey West
Dec 6
EYW7:00 amKey West
7h 18m
2 stops
STL1:18 pmLambert-St Louis
$233
Find similar
American Airlines
Nov 4
STL6:02 amLambert-St Louis
8h 26m
1 stop
EYW3:28 pmKey West
Nov 14
EYW4:18 pmKey West
7h 49m
2 stops
STL11:07 pmLambert-St Louis
$246
Find similar

United Airlines flights from Illinois to Key West

Our best United Airlines deals on Illinois to Key West flight tickets
United Airlines
Oct 28
PIA6:45 amGreater Peoria
7h 34m
1 stop
EYW3:19 pmKey West
Nov 4
EYW3:00 pmKey West
20h 16m
2 stops
PIA10:16 amGreater Peoria
$483
Find similar
United Airlines
Feb 3
PIA6:30 amGreater Peoria
7h 47m
1 stop
EYW3:17 pmKey West
Feb 10
EYW4:15 pmKey West
6h 24m
1 stop
PIA9:39 pmGreater Peoria
$493
Find similar
United Airlines
Oct 3
ORD6:00 amChicago O'Hare Intl
7h 29m
1 stop
EYW2:29 pmKey West
Oct 7
EYW3:12 pmKey West
9h 18m
1 stop
ORD11:30 pmChicago O'Hare Intl
$589
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Key West 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 September 23, 2025.
Use the filters below to find and compare flights from Illinois to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 10/25

7:43 pm-2:40 pm

1 stop17h 57m

Key West

Thu 10/30

3:23 pm-6:46 pm

1 stop28h 23m

$202

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 11/17

5:05 am-1:30 pm

1 stop7h 25m

Key West

Thu 11/20

2:25 pm-11:42 pm

1 stop10h 17m

$213

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 11/11

9:33 am-5:23 pm

1 stop6h 50m

Key West

Tue 11/18

6:18 pm-9:58 pm

1 stop4h 40m

$223

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 11/11

7:00 am-5:01 pm

2 stops9h 01m

Key West

Tue 11/18

4:10 pm-10:27 pm

1 stop7h 17m

$228

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Wed 12/3

2:11 pm-11:07 pm

2 stops7h 56m

Key West

Sat 12/6

7:00 am-1:18 pm

2 stops7h 18m

$233

St. LouisKey West

STL - EYW

STLEYW

Lambert-St Louis

Tue 11/4

7:05 am-1:02 pm

1 stop4h 57m

Key West

Fri 11/14

12:26 pm-4:07 pm

1 stop4h 41m

$241

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 10/24

2:45 pm-8:55 pm

1 stop5h 10m

Key West

Mon 10/27

2:57 pm-7:34 pm

1 stop5h 37m

$292

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

Sun 10/26

10:42 am-4:04 pm

1 stop4h 22m

Key West

Wed 10/29

10:02 am-10:22 am

1 stop25h 20m

$305

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

Tue 10/28

6:45 am-3:19 pm

1 stop7h 34m

Key West

Tue 11/4

3:00 pm-10:16 am

2 stops20h 16m

$483

PeoriaKey West

PIA - EYW

PIAEYW

Greater Peoria

Tue 2/3

6:30 am-3:17 pm

1 stop7h 47m

Key West

Tue 2/10

4:15 pm-9:39 pm

1 stop6h 24m

$493

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 Key West from

How to get the cheapest flight ticket from Illinois to Key West

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 Key West?

In general, August is the cheapest month to fly from Illinois to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $404. If you are unable to visit Key West during the month of August, then departing from Illinois during the month January is also very affordable. Most momondo users find prices during this month for around $408.

What is the cheapest day to depart on your flight to Key West?

On average, the least expensive day to fly to Key West from Illinois is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $361. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Illinois to Key West for around $538.

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

According to our data, the cheapest time of day to fly to Key West is in the morning. momondo users have found flights departing from Illinois to Key West in the morning for as low as $469. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly in the evening, with an average ticket price of $822. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Illinois to Key West flight route?

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

How far in advance should I book a flight to Key West?

You are more likely to see cheaper flights to Key West from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $438 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Illinois for as low as $367 on momondo.

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

There are 3 cabin classes available to choose from on Illinois to Key West 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 Illinois to Key West flights?

No. A direct flight is the cheapest option for a flight between Illinois to Key West.

Cheap Illinois to Key West flight deals and tips

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

Best Price Found

$253

Fastest flight time

3h 11m

Direct flights

Every day

Airports in Key West

1 airport
The best one-way flight to Key West from Illinois in the past 72 hours is $253. The best round-trip flight deal from Illinois to Key West found on momondo in the last 72 hours is $360.
The fastest flight from Illinois to Key West takes 3h 11m
Direct flights go from Illinois to Key West every day.
There is 1 airport near Key West: Key West (EYW)
Search flight deals

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

    Prices for flights from Illinois to Key West Airport were last updated today.

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

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

    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 Illinois to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The travel and health documents you'll need for your trip to Key West Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Key West Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Illinois to Key West?

Best airlines flying from Illinois to Key West

Compare and see reviews for airlines that fly from Illinois to Key West with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $218Free CancellationRating
7.9
7,974 reviews
Search Delta flights
United AirlinesPriceFrom $252Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $268Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Key West from Illinois.

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

Yes. momondo allows you to filter the results for Illinois to Key West flights to just show those with flexible booking policies.

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

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 Key West from Illinois.

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

Price alerts on flights to Key West from Illinois are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Key West trip

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