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Cheap flights from Chicago to Key West from $92

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 to Key West departing on 1/8. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 1:48 pmMDW-EYW
6h 48m1 stop
Delta Logo
6:07 pm - 10:44 pmEYW-MDW
5h 37m1 stop
$294Delta
Find Deal
mar., feb. 24 - mié., mar. 4
Multiple Airlines Logo
1:52 pm - 8:15 amORD-EYW
17h 23m2 stops
Multiple Airlines Logo
8:55 am - 2:21 pmEYW-ORD
6h 26m1 stop
$298Multiple Airlines
Find Deal
jue., dic. 11 - lun., dic. 15
Multiple Airlines Logo
8:00 am - 8:15 amORD-EYW
23h 15m1 stop
Multiple Airlines Logo
11:45 am - 4:15 pmEYW-ORD
29h 30m2 stops
$299Multiple Airlines
Find Deal
sáb., nov. 15 - mar., nov. 18
United Airlines Logo
11:00 am - 3:19 pmORD-EYW
3h 19mnonstop
United Airlines Logo
4:00 pm - 6:46 pmEYW-ORD
3h 46mnonstop
$300United Airlines
Find Deal
mar., nov. 18 - lun., nov. 24
Multiple Airlines Logo
5:18 pm - 2:46 pmORD-EYW
20h 28m1 stop
Multiple Airlines Logo
1:10 pm - 7:02 pmEYW-ORD
6h 52m1 stop
$301Multiple Airlines
Find Deal
vie., dic. 19 - lun., dic. 22
United Airlines Logo
6:02 am - 2:04 pmORD-EYW
7h 02m1 stop
United Airlines Logo
4:00 pm - 6:46 pmEYW-ORD
3h 46mnonstop
$310United Airlines
Find Deal
mar., nov. 18 - lun., nov. 24
American Airlines Logo
8:50 am - 1:20 pmORD-EYW
3h 30mnonstop
American Airlines Logo
3:18 pm - 8:34 pmEYW-ORD
6h 16m1 stop
$313American Airlines
Find Deal
mar., dic. 9 - sáb., dic. 13
Spirit Airlines Logo
8:20 am - 1:29 pmORD-EYW
28h 09m3 stops
Spirit Airlines Logo
12:20 pm - 9:48 pmEYW-ORD
10h 28m2 stops
$318Spirit Airlines
Find Deal
vie., nov. 28 - jue., dic. 4
Spirit Airlines Logo
5:00 am - 1:29 pmORD-EYW
7h 29m1 stop
Spirit Airlines Logo
12:20 pm - 10:11 pmEYW-ORD
34h 51m3 stops
$319Spirit Airlines
Find Deal
sáb., nov. 29 - jue., dic. 4
American Airlines Logo
6:00 am - 4:05 pmORD-EYW
9h 05m1 stop
American Airlines Logo
5:24 pm - 12:13 amEYW-ORD
7h 49m1 stop
$323American Airlines
Find Deal
mié., mar. 25 - mar., mar. 31

United Airlines flights from Chicago to Key West

Our best United Airlines deals on Chicago to Key West flight tickets
United Airlines
Nov 18
ORD11:00 amChicago O'Hare Intl
3h 19m
EYW3:19 pmKey West
Nov 24
EYW4:00 pmKey West
3h 46m
ORD6:46 pmChicago O'Hare Intl
$300
Find similar
United Airlines
Nov 18
ORD6:02 amChicago O'Hare Intl
7h 02m
1 stop
EYW2:04 pmKey West
Nov 24
EYW4:00 pmKey West
3h 46m
ORD6:46 pmChicago O'Hare Intl
$310
Find similar
United Airlines
Dec 16
ORD11:05 amChicago O'Hare Intl
3h 19m
EYW3:24 pmKey West
Dec 21
EYW12:22 pmKey West
3h 45m
ORD3:07 pmChicago O'Hare Intl
$315
Find similar

American Airlines flights from Chicago to Key West

Our best American Airlines deals on Chicago to Key West flight tickets
American Airlines
Dec 9
ORD8:50 amChicago O'Hare Intl
3h 30m
EYW1:20 pmKey West
Dec 13
EYW3:18 pmKey West
6h 16m
1 stop
ORD8:34 pmChicago O'Hare Intl
$313
Find similar
American Airlines
Mar 25
ORD6:00 amChicago O'Hare Intl
9h 05m
1 stop
EYW4:05 pmKey West
Mar 31
EYW5:24 pmKey West
7h 49m
1 stop
ORD12:13 amChicago O'Hare Intl
$323
Find similar
American Airlines
Mar 25
ORD8:00 amChicago O'Hare Intl
3h 16m
EYW12:16 pmKey West
Apr 1
EYW1:33 pmKey West
3h 37m
ORD4:10 pmChicago O'Hare Intl
$342
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 noviembre 4, 2025.
Use the filters below to find and compare flights from Chicago to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

mar. 2/24

6:00 am-1:48 pm

1 stop6h 48m

Key West

mié. 3/4

6:07 pm-10:44 pm

1 stop5h 37m

$294

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

jue. 12/11

1:52 pm-8:15 am

2 stops17h 23m

Key West

lun. 12/15

8:55 am-2:21 pm

1 stop6h 26m

$298

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

sáb. 11/15

8:00 am-8:15 am

1 stop23h 15m

Key West

mar. 11/18

11:45 am-4:15 pm

2 stops29h 30m

$299

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 11/18

11:00 am-3:19 pm

Nonstop3h 19m

Key West

lun. 11/24

4:00 pm-6:46 pm

Nonstop3h 46m

$300

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 12/19

5:18 pm-2:46 pm

1 stop20h 28m

Key West

lun. 12/22

1:10 pm-7:02 pm

1 stop6h 52m

$301

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 11/18

6:02 am-2:04 pm

1 stop7h 02m

Key West

lun. 11/24

4:00 pm-6:46 pm

Nonstop3h 46m

$310

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mar. 12/9

8:50 am-1:20 pm

Nonstop3h 30m

Key West

sáb. 12/13

3:18 pm-8:34 pm

1 stop6h 16m

$313

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 11/28

8:20 am-1:29 pm

3 stops28h 09m

Key West

jue. 12/4

12:20 pm-9:48 pm

2 stops10h 28m

$318

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

sáb. 11/29

5:00 am-1:29 pm

1 stop7h 29m

Key West

jue. 12/4

12:20 pm-10:11 pm

3 stops34h 51m

$319

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

mié. 3/25

6:00 am-4:05 pm

1 stop9h 05m

Key West

mar. 3/31

5:24 pm-12:13 am

1 stop7h 49m

$323

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 Chicago 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 typical price of a round-trip flight between Chicago and Key West?

What is the cheapest month to fly to Key West?

In general, August is the cheapest month to fly from Chicago 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 Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $407.

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 Chicago 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 Chicago to Key West for around $543.

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 Chicago to Key West in the morning for as low as $477. 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 Chicago to Key West flight route?

Fly from Chicago O'Hare Intl to Key West for the best Chicago - 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 Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $442 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Chicago for as low as $370 on momondo.

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

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

You could potentially save up to 22% on your flight if you consider stops on a Chicago to Key West flight.

How have Chicago to Key West flight prices changed over time?

As of November 2025, prices for Chicago to Key West flights are approximately 5% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Key West

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Key West according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Key West (CHI to EYW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago 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 Chicago in the past 72 hours is $253. The best round-trip flight deal from Chicago to Key West found on momondo in the last 72 hours is $357.
The fastest flight from Chicago to Key West takes 3h 11m
Direct flights go from Chicago to Key West every day.
There is 1 airport near Key West: Key West (EYW)
Search flight deals

  • How far is Chicago to Key West by plane?

    The distance between Chicago and Key West is about 1241.6 mi. 3h 16m is a normal flight duration for this route.

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

    Prices for flights from Chicago to Key West Airport refresh daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago 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 Chicago to Key West?

  • What is the most popular airline from Chicago to Key West?

Best airlines flying from Chicago to Key West

Compare and see reviews for airlines that fly from Chicago to Key West with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $218Free CancellationRating
7.9
8,003 reviews
Search Delta flights
United AirlinesPriceFrom $255Free CancellationRating
7.4
9,002 reviews
Search United Airlines flights
American AirlinesPriceFrom $314Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago to Key West

    United Airlines flight deals from Chicago to Key West start from $255 round-trip. Over the 7 United Airlines flights for this route in a normal week, average airfare is usually $490 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago to Key West

    Across 11,040 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Chicago to Key West about 5 times each week, with ticket deals ranging from $314 to $452. Price data is based on momondo searches in the last 72 hours.

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 Chicago to Key West?

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

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

momondo does allow users to show only those flights to Key West from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to Key West from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Key West from Chicago 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

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.
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