Cheap flights from Key West (EYW) to Chicago (CHI) from $104
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 7/23. 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 29 — May 61
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 24, 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 Delta flights from Key West to Chicago
Explore cheap flight options specifically provided by Delta 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 3,073,952 searches. Data last updated April 24, 2024.
Find some of the cheapest Delta flights traveling from Key West to Chicago. Make sure to double check the flight details before booking.
Thu 6/66:10 pmEYW - ORD
1 stop6h 44mDelta
Tue 6/116:05 amORD - EYW
1 stop6h 15mDelta
Deal found 4/23$232
Wed 5/86:10 pmEYW - MDW
1 stop4h 51mDelta
Sat 5/1111:01 amMDW - EYW
1 stop5h 11mDelta
Deal found 4/22$313
Fri 5/311:42 amEYW - ORD
1 stop6h 06mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$333
Fri 5/37:45 amEYW - ORD
1 stop7h 30mDelta
Wed 5/89:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$358
Fri 5/37:45 amEYW - ORD
1 stop7h 30mDelta
Sun 5/59:35 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$378
Fri 5/311:42 amEYW - ORD
1 stop6h 06mDelta
Wed 5/86:00 amORD - EYW
2 stops12h 40mDelta
Deal found 4/23$421
Fri 5/31:55 pmEYW - ORD
1 stop6h 24mDelta
Mon 5/66:00 amORD - EYW
2 stops12h 49mDelta
Deal found 4/23$461
Sat 5/116:10 pmEYW - MDW
1 stop4h 51mDelta
Tue 5/148:45 amMDW - EYW
1 stop7h 27mDelta
Deal found 4/23$463
Tue 4/307:45 amEYW - MDW
1 stop5h 10mDelta
Sat 5/46:00 amMDW - EYW
1 stop6h 00mDelta
Deal found 4/24$478
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 3,073,952 searches. Data last updated April 24, 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 5/1111:25 amEYW - ORD
2 stops13h 05mUnited Airlines
Tue 5/147:00 amORD - EYW
1 stop9h 24mUnited Airlines
Deal found 4/22$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 5/310:35 amEYW - ORD
2 stops12h 17mUnited Airlines
Tue 5/79:12 amORD - EYW
1 stop7h 12mUnited Airlines
Deal found 4/23$468
Sat 5/1111:25 amEYW - ORD
1 stop23h 04mUnited Airlines
Tue 5/147:00 amORD - EYW
1 stop9h 24mUnited Airlines
Deal found 4/22$478
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
Fri 5/31:51 pmEYW - ORD
1 stop9h 01mUnited Airlines
Sat 5/46:00 amORD - EYW
2 stops11h 45mUnited Airlines
Deal found 4/23$513
Thu 6/64:05 pmEYW - ORD
2 stops9h 08mUnited Airlines
Tue 6/119:15 pmORD - EYW
2 stops15h 54mUnited Airlines
Deal found 4/23$561
Fri 5/34:05 pmEYW - ORD
2 stops8h 25mUnited Airlines
Sat 5/48:45 amORD - EYW
2 stops9h 00mUnited Airlines
Deal found 4/23$568
Sun 5/1911:45 amEYW - ORD
1 stop22h 44mUnited Airlines
Thu 5/304:00 pmORD - EYW
2 stops26h 35mUnited Airlines
Deal found 4/23$574
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 3,073,952 searches. Prices were last updated on April 24, 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 5/86:10 pmEYW - MDW
1 stop4h 51mDelta
Sat 5/1111:01 amMDW - EYW
1 stop5h 11mDelta
Deal found 4/22$313
Fri 5/311:42 amEYW - ORD
1 stop6h 06mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$333
Fri 5/37:45 amEYW - ORD
1 stop7h 30mDelta
Wed 5/89:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$358
Fri 5/31:09 pmEYW - ORD
Nonstop3h 25mAmerican Airlines
Mon 5/67:30 amORD - EYW
1 stop5h 06mAmerican Airlines
Deal found 4/23$367
Fri 5/31:03 pmEYW - ORD
1 stop7h 37mAmerican Airlines
Mon 5/67:30 amORD - EYW
1 stop7h 38mAmerican Airlines
Deal found 4/23$375
Fri 5/37:45 amEYW - ORD
1 stop7h 30mDelta
Sun 5/59:35 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$378
Fri 5/36:10 pmEYW - MDW
1 stop5h 40mDelta
Mon 5/66:00 amMDW - EYW
1 stop6h 00mDelta
Deal found 4/23$378
Wed 4/244:04 pmEYW - ORD
Nonstop3h 28mUnited Airlines
Wed 5/110:58 amORD - EYW
Nonstop3h 05mUnited Airlines
Deal found 4/23$409
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 3,073,952 searches. Data last updated April 24, 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 6/62:25 pmEYW - ORD
1 stop8h 03mAmerican Airlines
Tue 6/115:00 amORD - EYW
1 stop7h 01mAmerican Airlines
Deal found 4/23$228
Thu 6/66:10 pmEYW - ORD
1 stop6h 44mDelta
Tue 6/116:05 amORD - EYW
1 stop6h 15mDelta
Deal found 4/23$232
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
Tue 6/256:00 pmEYW - ORD
1 stop6h 56mDelta
Thu 7/116:00 amORD - EYW
1 stop4h 44mDelta
Deal found 4/24$248
Tue 12/248:13 amEYW - ORD
1 stop7h 11mAmerican Airlines
Sat 1/1112:20 pmORD - EYW
1 stop6h 52mAmerican Airlines
Deal found 4/23$265
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 1/1112:20 pmORD - EYW
1 stop6h 52mAmerican Airlines
Deal found 4/23$302
Wed 5/86:10 pmEYW - MDW
1 stop4h 51mDelta
Sat 5/1111:01 amMDW - EYW
1 stop5h 11mDelta
Deal found 4/22$313
Fri 5/311:42 amEYW - ORD
1 stop6h 06mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$333
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 3,073,952 searches. Data last updated April 24, 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.
Fri 5/311:42 amEYW - ORD
1 stop6h 06mDelta
Tue 5/79:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$333
Fri 5/37:45 amEYW - ORD
1 stop7h 30mDelta
Wed 5/89:32 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$358
Fri 5/31:09 pmEYW - ORD
Nonstop3h 25mAmerican Airlines
Mon 5/67:30 amORD - EYW
1 stop5h 06mAmerican Airlines
Deal found 4/23$367
Fri 5/31:03 pmEYW - ORD
1 stop7h 37mAmerican Airlines
Mon 5/67:30 amORD - EYW
1 stop7h 38mAmerican Airlines
Deal found 4/23$375
Fri 5/37:45 amEYW - ORD
1 stop7h 30mDelta
Sun 5/59:35 amORD - EYW
1 stop6h 40mDelta
Deal found 4/23$378
Fri 5/36:10 pmEYW - MDW
1 stop5h 40mDelta
Mon 5/66:00 amMDW - EYW
1 stop6h 00mDelta
Deal found 4/23$378
Fri 5/311:42 amEYW - ORD
1 stop6h 06mDelta
Wed 5/86:00 amORD - EYW
2 stops12h 40mDelta
Deal found 4/23$421
Fri 5/31:55 pmEYW - ORD
1 stop6h 24mDelta
Mon 5/66:00 amORD - EYW
2 stops12h 49mDelta
Deal found 4/23$461
Fri 5/310:35 amEYW - ORD
2 stops12h 17mUnited Airlines
Tue 5/79:12 amORD - EYW
1 stop7h 12mUnited Airlines
Deal found 4/23$468
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 3,073,952 searches. Data last updated April 24, 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 7/231:44 pmEYW - ORD
1 stop8h 31mAmerican Airlines
Deal found 4/23$104
Tue 7/232:44 pmEYW - MDW
1 stop7h 57mDelta
Deal found 4/23$108
Wed 5/1511:30 amEYW - ORD
1 stop12h 59mMultiple Airlines
Deal found 4/22$129
Wed 5/1511:30 amEYW - ORD
3 stops27h 36mMultiple Airlines
Deal found 4/22$161
Wed 5/1511:30 amEYW - ORD
2 stops21h 43mMultiple Airlines
Deal found 4/22$174
Tue 7/238:10 pmEYW - ORD
2 stops21h 03mUnited Airlines
Deal found 4/23$241
Sun 5/262:29 pmEYW - ORD
1 stop6h 25mAmerican Airlines
Deal found 4/23$254
Tue 5/216:10 pmEYW - MDW
1 stop4h 51mDelta
Deal found 4/24$254
Mon 5/2711:42 amEYW - ORD
1 stop5h 04mAmerican Airlines
Deal found 4/23$287
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 3,073,952 searches. Data last updated April 24, 2024.
Fly from
Any airport
Fly to
Any airport
Budget
$228 - $463
Route
Depart
Return
Price
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 6/6
1 stop8h 03m
Chicago O'Hare Intl
Tue 6/11
1 stop7h 01m
$228
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 6/6
1 stop6h 44m
Chicago O'Hare Intl
Tue 6/11
1 stop6h 15m
$232
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 6/19
1 stop9h 16m
Chicago O'Hare Intl
Sun 6/23
1 stop5h 36m
$281
Key WestChicago Midway
EYW - MDW
EYWMDW
Key West
Wed 5/8
1 stop4h 51m
Chicago Midway
Sat 5/11
1 stop5h 11m
$313
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 6/6
2 stops8h 12m
Chicago O'Hare Intl
Tue 6/11
1 stop7h 01m
$397
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
Key WestChicago Midway
EYW - MDW
EYWMDW
Key West
Sat 5/11
1 stop4h 51m
Chicago Midway
Tue 5/14
1 stop7h 27m
$463
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 $190 while a round-trip flight costs $338. 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 24, 2024.
Read reviews from past customers who have flown Delta, United Airlines and American Airlines 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.
11,004 reviews
Comfort
7.9
Food
7.5
Entertainment
8.0
Crew
8.6
Boarding
8.2
Overall
8.1
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
11,004 reviews
11,004 reviews
Comfort
7.9
Food
7.5
Entertainment
8.0
Crew
8.6
Boarding
8.2
Overall
8.1
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
11,255 reviews
11,004 reviews
Comfort
7.9
Food
7.5
Entertainment
8.0
Crew
8.6
Boarding
8.2
Overall
8.1
Reviews
1 / 10
Terrible flight crew that skipped our row for service multiple times.
14,898 reviews
11,004 reviews
Comfort
7.9
Food
7.5
Entertainment
8.0
Crew
8.6
Boarding
8.2
Overall
8.1
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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 3,073,952 searches. Data last updated April 24, 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 24, 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 24, 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
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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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