Cheap flights from Key West (EYW) to Chicago (CHI) from $220
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 5/21. 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
Apr 30 — May 71
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 April 25, 2024.
Popular in | March |
|---|---|
Cheapest in | October |
Average price | $372 |
Round-trip from | $222 |
What is the cheapest day to fly round-trip from Key West to Chicago?
Tuesday is generally a great day to depart. Flying on this day could help you save up to 39%.
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 $376. 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 March.
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 35% on your trip compared to booking a flight in the afternoon.
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 3,068,701 searches. Data last updated April 25, 2024.
Find some of the cheapest United Airlines flights traveling from Key West to Chicago. Make sure to double check the flight details before booking.
Sat 5/1111:25 amEYW - ORD
2 stops13h 05mUnited Airlines
Tue 5/147:00 amORD - EYW
1 stop9h 24mUnited Airlines
Deal found 4/23$443
Wed 5/2212:30 pmEYW - ORD
2 stops12h 00mUnited Airlines
Wed 5/296:00 amORD - EYW
1 stop7h 09mUnited Airlines
Deal found 4/24$444
Sat 5/1111:25 amEYW - ORD
1 stop23h 04mUnited Airlines
Tue 5/147:00 amORD - EYW
1 stop9h 24mUnited Airlines
Deal found 4/23$478
Tue 8/133:10 pmEYW - ORD
2 stops16h 20mUnited Airlines
Tue 8/279:19 pmORD - EYW
2 stops15h 50mUnited Airlines
Deal found 4/24$492
Tue 4/304:04 pmEYW - ORD
Nonstop3h 28mUnited Airlines
Sat 5/49:12 amORD - EYW
1 stop7h 12mUnited Airlines
Deal found 4/24$498
Wed 5/2212:30 pmEYW - ORD
2 stops12h 00mUnited Airlines
Wed 5/291:10 pmORD - EYW
2 stops19h 45mUnited Airlines
Deal found 4/24$512
Tue 4/3010:35 amEYW - ORD
2 stops8h 56mUnited Airlines
Sat 5/47:00 amORD - EYW
1 stop9h 24mUnited Airlines
Deal found 4/24$513
Tue 4/304:05 pmEYW - ORD
2 stops8h 25mUnited Airlines
Sat 5/48:45 amORD - EYW
2 stops9h 00mUnited Airlines
Deal found 4/24$568
Sat 5/113:30 pmEYW - ORD
2 stops9h 00mUnited Airlines
Tue 5/148:48 amORD - EYW
2 stops9h 47mUnited Airlines
Deal found 4/24$618
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 3,068,701 searches. Data last updated April 25, 2024.
Browse through some of the cheapest American Airlines flights traveling from Key West to Chicago. Check back soon if you're not seeing flights that suit your needs.
Wed 5/225:09 pmEYW - ORD
1 stop7h 50mAmerican Airlines
Wed 5/298:30 amORD - EYW
1 stop7h 55mAmerican Airlines
Deal found 4/24$245
Wed 6/55:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Wed 6/266:02 amORD - EYW
1 stop5h 59mAmerican Airlines
Deal found 4/25$248
Tue 8/1311:43 amEYW - ORD
1 stop4h 53mAmerican Airlines
Tue 8/275:30 amORD - EYW
2 stops6h 35mAmerican Airlines
Deal found 4/24$250
Wed 6/193:25 pmEYW - ORD
1 stop9h 16mAmerican Airlines
Sun 6/235:30 amORD - EYW
1 stop5h 36mAmerican Airlines
Deal found 4/24$281
Thu 6/205:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Sat 6/225:07 amORD - EYW
2 stops7h 13mAmerican Airlines
Deal found 4/25$366
Wed 6/55:47 pmEYW - ORD
2 stops7h 11mAmerican Airlines
Wed 6/266:02 amORD - EYW
1 stop9h 22mAmerican Airlines
Deal found 4/25$368
Wed 6/195:47 pmEYW - ORD
2 stops7h 11mAmerican Airlines
Sun 6/235:30 amORD - EYW
1 stop5h 34mAmerican Airlines
Deal found 4/24$414
Tue 6/253:10 pmEYW - ORD
2 stops7h 27mAmerican Airlines
Thu 7/118:40 amORD - EYW
1 stop6h 42mAmerican Airlines
Deal found 4/24$416
Thu 6/202:25 pmEYW - ORD
2 stops8h 12mAmerican Airlines
Sat 6/225:07 amORD - EYW
2 stops7h 13mAmerican Airlines
Deal found 4/25$535
Cheap Key West to Chicago flights in April & May 2024
Find cheap flight options from Key West to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,068,701 searches. Prices were last updated on April 25, 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.
Wed 5/225:09 pmEYW - ORD
1 stop7h 50mAmerican Airlines
Wed 5/298:30 amORD - EYW
1 stop7h 55mAmerican Airlines
Deal found 4/24$245
Fri 5/246:10 pmEYW - MDW
1 stop4h 51mDelta
Fri 5/3112:42 pmMDW - EYW
1 stop5h 58mDelta
Deal found 4/24$367
Tue 4/301:55 pmEYW - ORD
1 stop6h 23mDelta
Sat 5/412:35 pmORD - EYW
1 stop6h 10mDelta
Deal found 4/24$428
Sat 5/1111:25 amEYW - ORD
2 stops13h 05mUnited Airlines
Tue 5/147:00 amORD - EYW
1 stop9h 24mUnited Airlines
Deal found 4/23$443
Wed 5/2212:30 pmEYW - ORD
2 stops12h 00mUnited Airlines
Wed 5/296:00 amORD - EYW
1 stop7h 09mUnited Airlines
Deal found 4/24$444
Fri 4/261:09 pmEYW - ORD
Nonstop3h 25mAmerican Airlines
Tue 4/308:25 amORD - EYW
Nonstop3h 14mAmerican Airlines
Deal found 4/24$459
Sat 5/116:10 pmEYW - MDW
1 stop4h 51mDelta
Tue 5/148:45 amMDW - EYW
1 stop7h 27mDelta
Deal found 4/23$463
Fri 4/264:47 pmEYW - ORD
1 stop6h 11mAmerican Airlines
Tue 4/308:25 amORD - EYW
Nonstop3h 14mAmerican Airlines
Deal found 4/24$467
Fri 4/264:47 pmEYW - ORD
1 stop6h 11mAmerican Airlines
Tue 4/309:55 amORD - EYW
1 stop5h 10mAmerican Airlines
Deal found 4/24$475
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 3,068,701 searches. Data last updated April 25, 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.
Wed 5/225:09 pmEYW - ORD
1 stop7h 50mAmerican Airlines
Wed 5/298:30 amORD - EYW
1 stop7h 55mAmerican Airlines
Deal found 4/24$245
Wed 6/55:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Wed 6/266:02 amORD - EYW
1 stop5h 59mAmerican Airlines
Deal found 4/25$248
Tue 8/1311:43 amEYW - ORD
1 stop4h 53mAmerican Airlines
Tue 8/275:30 amORD - EYW
2 stops6h 35mAmerican Airlines
Deal found 4/24$250
Tue 12/248:13 amEYW - ORD
1 stop7h 11mAmerican Airlines
Sat 1/118:17 amORD - EYW
1 stop5h 52mAmerican Airlines
Deal found 4/24$265
Fri 7/196:00 pmEYW - ORD
1 stop6h 59mDelta
Mon 7/226:00 amORD - EYW
1 stop4h 44mDelta
Deal found 4/25$268
Wed 6/193:25 pmEYW - ORD
1 stop9h 16mAmerican Airlines
Sun 6/235:30 amORD - EYW
1 stop5h 36mAmerican Airlines
Deal found 4/24$281
Tue 12/241:44 pmEYW - ORD
Nonstop3h 31mAmerican Airlines
Sat 1/118:17 amORD - EYW
1 stop5h 52mAmerican Airlines
Deal found 4/24$302
Thu 6/205:04 pmEYW - ORD
1 stop6h 30mAmerican Airlines
Sat 6/225:07 amORD - EYW
2 stops7h 13mAmerican Airlines
Deal found 4/25$366
Fri 5/246:10 pmEYW - MDW
1 stop4h 51mDelta
Fri 5/3112:42 pmMDW - EYW
1 stop5h 58mDelta
Deal found 4/24$367
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 3,068,701 searches. Data last updated April 25, 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.
Tue 4/301:55 pmEYW - ORD
1 stop6h 23mDelta
Sat 5/412:35 pmORD - EYW
1 stop6h 10mDelta
Deal found 4/24$428
Tue 4/307:45 amEYW - MDW
1 stop5h 10mDelta
Sat 5/46:00 amMDW - EYW
1 stop6h 00mDelta
Deal found 4/24$478
Tue 4/304:04 pmEYW - ORD
Nonstop3h 28mUnited Airlines
Sat 5/49:12 amORD - EYW
1 stop7h 12mUnited Airlines
Deal found 4/24$498
Tue 4/3010:35 amEYW - ORD
2 stops8h 56mUnited Airlines
Sat 5/47:00 amORD - EYW
1 stop9h 24mUnited Airlines
Deal found 4/24$513
Tue 4/304:05 pmEYW - ORD
2 stops8h 25mUnited Airlines
Sat 5/48:45 amORD - EYW
2 stops9h 00mUnited Airlines
Deal found 4/24$568
Tue 4/307:45 amEYW - MDW
1 stop5h 10mDelta
Sat 5/49:30 amMDW - EYW
2 stops6h 45mDelta
Deal found 4/24$913
Tue 4/307:45 amEYW - MDW
2 stops9h 39mDelta
Sat 5/49:30 amMDW - EYW
2 stops9h 15mDelta
Deal found 4/24$2,400
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 3,068,701 searches. Data last updated April 25, 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 5/2111:30 amEYW - ORD
1 stop22h 59mUnited Airlines
Deal found 4/24$220
Wed 5/1511:30 amEYW - ORD
2 stops13h 00mUnited Airlines
Deal found 4/24$225
Wed 5/152:11 pmEYW - ORD
1 stop8h 18mAmerican Airlines
Deal found 4/24$253
Sun 5/2612:49 pmEYW - ORD
1 stop8h 56mAmerican Airlines
Deal found 4/23$254
Tue 5/216:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/24$254
Tue 6/48:10 pmEYW - ORD
2 stops28h 10mUnited Airlines
Deal found 4/24$283
Mon 6/103:25 pmEYW - ORD
1 stop7h 00mAmerican Airlines
Deal found 4/24$288
Sat 5/186:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/25$369
Mon 6/1011:45 amEYW - ORD
2 stops27h 30mUnited Airlines
Deal found 4/24$375
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 3,068,701 searches. Data last updated April 25, 2024.
Fly from
Any airport
Fly to
Any airport
Budget
$245 - $444
Route
Depart
Return
Price
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Wed 5/22
1 stop7h 50m
Chicago O'Hare Intl
Wed 5/29
1 stop7h 55m
$245
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Wed 6/5
1 stop6h 30m
Chicago O'Hare Intl
Wed 6/26
1 stop5h 59m
$248
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Tue 8/13
1 stop4h 53m
Chicago O'Hare Intl
Tue 8/27
2 stops6h 35m
$250
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Fri 7/19
1 stop6h 59m
Chicago O'Hare Intl
Mon 7/22
1 stop4h 44m
$268
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Wed 6/19
1 stop9h 16m
Chicago O'Hare Intl
Sun 6/23
1 stop5h 36m
$281
Key WestChicago Midway
EYW - MDW
EYWMDW
Key West
Fri 5/24
1 stop4h 51m
Chicago Midway
Fri 5/31
1 stop5h 58m
$367
Key WestChicago Midway
EYW - MDW
EYWMDW
Key West
Wed 6/5
1 stop4h 51m
Chicago Midway
Wed 6/26
1 stop4h 44m
$438
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Sat 5/11
2 stops13h 05m
Chicago O'Hare Intl
Tue 5/14
1 stop9h 24m
$443
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Wed 5/22
2 stops12h 00m
Chicago O'Hare Intl
Wed 5/29
1 stop7h 09m
$444
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 April 21, 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 $280 while a round-trip flight costs $332. Price data was last updated on April 21, 2024.
Currently, February is the cheapest month in which you can book a flight from Key West to Chicago (average of $245). Flying from Key West to Chicago in June is currently the most expensive (average of $356). 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
$245
March
$280
April
$273
May
$282
June
$356
July
$336
August
$276
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 April 25, 2024.
Read reviews from past customers who have flown United Airlines, American 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.
10,975 reviews
Boarding
8.2
Crew
8.6
Comfort
7.9
Overall
8.1
Entertainment
8.0
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
10,975 reviews
10,975 reviews
Boarding
8.2
Crew
8.6
Comfort
7.9
Overall
8.1
Entertainment
8.0
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
11,234 reviews
10,975 reviews
Boarding
8.2
Crew
8.6
Comfort
7.9
Overall
8.1
Entertainment
8.0
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
14,898 reviews
10,975 reviews
Boarding
8.2
Crew
8.6
Comfort
7.9
Overall
8.1
Entertainment
8.0
Food
7.4
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
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 3,068,701 searches. Data last updated April 25, 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.
Hourly flight availability from Key West to Chicago
Find hourly flight availability from Key West to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 25, 2024.
| 0%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 0%of flight departures | Morning6 am to noon |
| 100%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Midnight
6 AM
Noon
6 PM
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 April 25, 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
Fly with Cheapflights
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Key West to Chicago?
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Why should you use Cheapflights to find cheap flight tickets from Key West to Chicago?
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Key West to Chicago.
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Users can book flights with no change fees policies with our dedicated filters. Book flights from Key West to Chicago flexibly with Cheapflights today.
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