Cheap flights from Key West (EYW) to Chicago (CHI) from $207
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/25. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
EYW — CHI
May 21 — May 281
From?
To?
1 adult, Economy
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Cheap flight deals from Key West to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 16, 2024.
Popular in | November |
|---|---|
Cheapest in | October |
Average price | $437 |
Round-trip from | $223 |
What is the cheapest day to fly round-trip from Key West to Chicago?
Monday is generally a great day to depart. Flying on this day could help you save up to 43%.
What is the cheapest month to fly from Key West to Chicago?
October can be a great time to fly to Chicago from Key West with a flight ticket averaging about $373. Cheapflights users have found deals in the month of October for as cheap as $227. The most expensive prices can be found in the month of November.
When is the cheapest time to fly from Key West to Chicago (EYW - CHI)?
A simple way to save on the total cost of your ticket is to fly from Key West to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the afternoon.
Cheap American Airlines flights from Key West to Chicago
Explore cheap flight options specifically provided by American Airlines for the route between Key West and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Find some of the cheapest American Airlines flights traveling from Key West to Chicago. Make sure to double check the flight details before booking.
Thu 6/202:40 pmEYW - ORD
1 stop7h 57mAmerican Airlines
Mon 6/248:30 amORD - EYW
1 stop6h 59mAmerican Airlines
Deal found 5/15$345
Thu 6/202:40 pmEYW - ORD
1 stop7h 57mAmerican Airlines
Mon 6/246:45 amORD - EYW
1 stop6h 10mAmerican Airlines
Deal found 5/15$347
Fri 6/212:40 pmEYW - ORD
1 stop7h 57mAmerican Airlines
Wed 7/248:30 amORD - EYW
1 stop6h 24mAmerican Airlines
Deal found 5/15$415
Sat 7/612:44 pmEYW - ORD
1 stop6h 05mAmerican Airlines
Sun 7/148:30 amORD - EYW
1 stop6h 24mAmerican Airlines
Deal found 5/15$464
Sun 7/73:44 pmEYW - ORD
1 stop9h 02mAmerican Airlines
Sat 7/138:30 amORD - EYW
1 stop6h 24mAmerican Airlines
Deal found 5/15$466
Thu 6/202:25 pmEYW - ORD
2 stops8h 12mAmerican Airlines
Mon 6/248:30 amORD - EYW
1 stop6h 59mAmerican Airlines
Deal found 5/15$471
Sun 7/73:44 pmEYW - ORD
1 stop9h 02mAmerican Airlines
Sat 7/135:00 amORD - EYW
2 stops7h 24mAmerican Airlines
Deal found 5/15$541
Sun 7/73:44 pmEYW - ORD
1 stop9h 02mAmerican Airlines
Fri 7/125:28 amORD - EYW
1 stop5h 36mAmerican Airlines
Deal found 5/15$551
Mon 6/2412:46 pmEYW - ORD
1 stop5h 46mAmerican Airlines
Mon 6/247:45 pmORD - EYW
2 stops15h 21mAmerican Airlines
Deal found 5/15$605
Cheap United Airlines flights from Key West to Chicago
Explore cheap flight options specifically provided by United Airlines for the route between Key West and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Browse through some of the cheapest United Airlines flights traveling from Key West to Chicago. Check back soon if you're not seeing flights that suit your needs.
Sat 11/94:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Mon 11/1110:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Deal found 5/15$374
Sat 11/911:25 amEYW - ORD
1 stop23h 22mUnited Airlines
Mon 11/1110:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Deal found 5/15$404
Fri 8/1611:20 amEYW - ORD
2 stops27h 50mUnited Airlines
Sun 8/186:00 amORD - EYW
1 stop7h 09mUnited Airlines
Deal found 5/16$412
Sun 8/1811:20 amEYW - ORD
1 stop23h 31mUnited Airlines
Sun 8/257:35 amORD - EYW
1 stop25h 20mUnited Airlines
Deal found 5/14$445
Sun 8/1811:20 amEYW - ORD
1 stop23h 31mUnited Airlines
Sun 8/259:15 pmORD - EYW
2 stops15h 54mUnited Airlines
Deal found 5/14$495
Wed 5/223:05 pmEYW - ORD
1 stop8h 49mUnited Airlines
Sun 5/267:10 amORD - EYW
2 stops11h 25mUnited Airlines
Deal found 5/15$505
Sat 11/92:40 pmEYW - ORD
2 stops9h 00mUnited Airlines
Mon 11/115:55 pmORD - EYW
1 stop19h 30mUnited Airlines
Deal found 5/15$527
Fri 8/163:20 pmEYW - ORD
2 stops9h 48mUnited Airlines
Sun 8/189:28 pmORD - EYW
2 stops15h 41mUnited Airlines
Deal found 5/16$568
Sat 7/611:20 amEYW - ORD
2 stops22h 55mUnited Airlines
Sun 7/146:00 amORD - EYW
1 stop7h 09mUnited Airlines
Deal found 5/15$569
Cheap Key West to Chicago flights in May & June 2024
Find cheap flight options from Key West to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Prices were last updated on May 16, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Thu 6/611:43 amEYW - MDW
1 stop7h 15mDelta
Thu 6/1312:45 pmMDW - EYW
1 stop5h 55mDelta
Deal found 5/14$323
Thu 6/65:09 pmEYW - ORD
2 stops25h 31mMultiple Airlines
Thu 6/138:04 pmORD - EYW
1 stop11h 58mMultiple Airlines
Deal found 5/14$339
Thu 6/202:40 pmEYW - ORD
1 stop7h 57mAmerican Airlines
Mon 6/248:30 amORD - EYW
1 stop6h 59mAmerican Airlines
Deal found 5/15$345
Thu 6/202:40 pmEYW - ORD
1 stop7h 57mAmerican Airlines
Mon 6/246:45 amORD - EYW
1 stop6h 10mAmerican Airlines
Deal found 5/15$347
Thu 6/66:10 pmEYW - ORD
1 stop6h 44mDelta
Thu 6/1312:22 pmORD - EYW
1 stop6h 18mDelta
Deal found 5/14$363
Thu 6/610:04 amEYW - ORD
3 stops15h 51mMultiple Airlines
Thu 6/138:04 pmORD - EYW
1 stop11h 58mMultiple Airlines
Deal found 5/14$371
Wed 5/226:10 pmEYW - ORD
1 stop6h 45mDelta
Sun 5/2612:31 pmORD - EYW
1 stop6h 09mDelta
Deal found 5/15$378
Thu 6/65:09 pmEYW - ORD
2 stops25h 31mMultiple Airlines
Thu 6/135:34 pmORD - EYW
3 stops21h 34mMultiple Airlines
Deal found 5/14$401
Fri 6/212:40 pmEYW - ORD
1 stop7h 57mAmerican Airlines
Wed 7/248:30 amORD - EYW
1 stop6h 24mAmerican Airlines
Deal found 5/15$415
Key West to Chicago 2024 flight deals
Discover exclusive flight deals for travel between Key West and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Fri 9/276:05 pmEYW - MDW
1 stop4h 39mDelta
Tue 10/11:05 pmMDW - EYW
1 stop5h 28mDelta
Deal found 5/14$232
Fri 9/276:05 pmEYW - MDW
1 stop4h 39mDelta
Tue 10/110:11 amMDW - EYW
1 stop5h 58mDelta
Deal found 5/15$252
Sat 11/97:00 amEYW - ORD
1 stop8h 12mDelta
Mon 11/116:00 amORD - EYW
1 stop6h 07mDelta
Deal found 5/15$288
Tue 12/241:44 pmEYW - ORD
Nonstop3h 31mAmerican Airlines
Sat 1/115:20 amORD - EYW
1 stop6h 54mAmerican Airlines
Deal found 5/15$292
Tue 12/242:35 pmEYW - ORD
1 stop7h 23mDelta
Sat 1/115:50 amORD - EYW
1 stop6h 22mDelta
Deal found 5/15$303
Thu 6/611:43 amEYW - MDW
1 stop7h 15mDelta
Thu 6/1312:45 pmMDW - EYW
1 stop5h 55mDelta
Deal found 5/14$323
Thu 6/65:09 pmEYW - ORD
2 stops25h 31mMultiple Airlines
Thu 6/138:04 pmORD - EYW
1 stop11h 58mMultiple Airlines
Deal found 5/14$339
Thu 6/202:40 pmEYW - ORD
1 stop7h 57mAmerican Airlines
Mon 6/248:30 amORD - EYW
1 stop6h 59mAmerican Airlines
Deal found 5/15$345
Thu 6/202:40 pmEYW - ORD
1 stop7h 57mAmerican Airlines
Mon 6/246:45 amORD - EYW
1 stop6h 10mAmerican Airlines
Deal found 5/15$347
Non-stop flights to Chicago from Key West
Discover non-stop flight options from Key West to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
For a quicker trip, book one of these direct flights from Key West to Chicago. Users seeking other options on flights from Key West to Chicago should update the search form at the top of the page.
Sat 11/94:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
Mon 11/1110:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Deal found 5/15$374
Key West to Chicago flights leaving soon
Find last-minute flight options from Key West to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Book one of these great deals on flights from Key West to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
Wed 5/226:10 pmEYW - ORD
1 stop6h 45mDelta
Sun 5/2612:31 pmORD - EYW
1 stop6h 09mDelta
Deal found 5/15$378
Wed 5/223:05 pmEYW - ORD
1 stop8h 49mUnited Airlines
Sun 5/267:10 amORD - EYW
2 stops11h 25mUnited Airlines
Deal found 5/15$505
Wed 5/2210:35 amEYW - ORD
2 stops9h 14mUnited Airlines
Sun 5/267:00 amORD - EYW
1 stop6h 40mUnited Airlines
Deal found 5/14$703
One-way flights to Chicago from Key West
Search for one-way flight options from Key West to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Take a look at some of the best available options we've come across on one-way flights from Key West to Chicago. For those needing a return trip from Key West, there is a search form available above.
Tue 6/2511:20 amEYW - ORD
1 stop28h 32mUnited Airlines
Deal found 5/14$207
Tue 5/2811:30 amEYW - ORD
1 stop28h 22mUnited Airlines
Deal found 5/16$214
Sun 8/1811:20 amEYW - ORD
1 stop23h 31mUnited Airlines
Deal found 5/15$217
Sun 7/2811:20 amEYW - ORD
2 stops29h 53mUnited Airlines
Deal found 5/16$222
Wed 6/1211:20 amEYW - ORD
1 stop23h 01mUnited Airlines
Deal found 5/15$227
Tue 6/111:05 pmEYW - ORD
2 stops11h 15mUnited Airlines
Deal found 5/15$234
Sun 7/212:43 pmEYW - ORD
2 stops19h 40mMultiple Airlines
Deal found 5/15$245
Sun 11/1011:45 amEYW - ORD
1 stop23h 02mUnited Airlines
Deal found 5/16$248
Fri 10/2511:45 amEYW - ORD
2 stops27h 17mUnited Airlines
Deal found 5/15$253
Find flights from Key West to Chicago within your budget
Customize your flight search to find flights from Key West 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, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Fly from
Any airport
Fly to
Any airport
Budget
$232 - $374
Route
Depart
Return
Price
Key WestChicago Midway
EYW - MDW
EYWMDW
Key West
Fri 9/27
1 stop4h 39m
Chicago Midway
Tue 10/1
1 stop5h 28m
$232
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Fri 8/16
1 stop5h 26m
Chicago O'Hare Intl
Sun 8/18
1 stop6h 05m
$248
Key WestChicago Midway
EYW - MDW
EYWMDW
Key West
Fri 9/27
1 stop4h 39m
Chicago Midway
Tue 10/1
1 stop5h 58m
$252
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Sat 11/9
1 stop8h 12m
Chicago O'Hare Intl
Mon 11/11
1 stop6h 07m
$288
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 6/6
2 stops25h 31m
Chicago O'Hare Intl
Thu 6/13
1 stop11h 58m
$339
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 6/20
1 stop7h 57m
Chicago O'Hare Intl
Mon 6/24
1 stop6h 59m
$345
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 6/20
1 stop7h 57m
Chicago O'Hare Intl
Mon 6/24
1 stop6h 10m
$347
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 6/6
3 stops15h 51m
Chicago O'Hare Intl
Thu 6/13
1 stop11h 58m
$371
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Sat 11/9
Nonstop3h 24m
Chicago O'Hare Intl
Mon 11/11
Nonstop3h 10m
$374
When is the cheapest time to fly from Key West to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Key West to Chicago. Price data was last updated on May 12, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Key West to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Average price of flights to Chicago by month
Plan your trip from Key West to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Key West to Chicago is currently $230 while a round-trip flight costs $311. Price data was last updated on May 12, 2024.
Currently, February is the cheapest month in which you can book a flight from Key West to Chicago (average of $244). Flying from Key West to Chicago in June is currently the most expensive (average of $342). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$248
February
$244
March
$280
April
$258
May
$278
June
$342
July
$327
August
$274
September
$258
October
$248
November
$270
December
$248
Temperature and rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.
CHI Temperature | 23 - 73.4 °F |
|---|
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 16, 2024.
Read reviews from past customers who have flown American Airlines, United Airlines and Delta from Key West to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
9,157 reviews
Food
7.3
Crew
8.6
Entertainment
7.3
Overall
8.1
Comfort
7.9
Boarding
8.2
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
9,157 reviews
9,157 reviews
Food
7.3
Crew
8.6
Entertainment
7.3
Overall
8.1
Comfort
7.9
Boarding
8.2
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
10,673 reviews
9,157 reviews
Food
7.3
Crew
8.6
Entertainment
7.3
Overall
8.1
Comfort
7.9
Boarding
8.2
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
10,924 reviews
9,157 reviews
Food
7.3
Crew
8.6
Entertainment
7.3
Overall
8.1
Comfort
7.9
Boarding
8.2
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
14,514 reviews
9,157 reviews
Food
7.3
Crew
8.6
Entertainment
7.3
Overall
8.1
Comfort
7.9
Boarding
8.2
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
Related info for your journey
Find useful and relevant information for your journey from Key West to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Key West to ChicagoSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Key West to Chicago
Discover the top 3 airlines that operate flights from Key West to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Search flights from Key West to Chicago by cabin class
Find flights from Key West to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Weekly flight availability from Key West to Chicago
Explore weekly flight availability from Key West to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 16, 2024.
| Sunday | 3daily flights |
|---|---|
| Monday | 3daily flights |
| Tuesday | 3daily flights |
| Wednesday | 3daily flights |
| Thursday | 3daily flights |
| Friday | 3daily flights |
| Saturday | 3daily flights |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
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