￥38,760 Cheap Flights from Key West (EYW) to Chicago (ORD)

View ￥38,760 flight on Wed, May 6, 2026Opens in a new window

Popular airlines from Key West Intl. Airport (EYW) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Key West to Chicago (EYW-ORD)

Prices were available within the past 7 days and start at ￥38,760 for one-way flights and ￥47,320 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥47,320 Roundtrip, found 2 days ago
￥47,320
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥47,320 found 2 days ago
American Airlines
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥49,060 Roundtrip, found 2 days ago
￥49,060
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥49,060 found 2 days ago
American Airlines
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥50,440 Roundtrip, found 2 days ago
￥50,440
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥50,440 found 2 days ago
American Airlines
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥53,650 Roundtrip, found 2 days ago
￥53,650
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥53,650 found 2 days ago
American Airlines
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥53,770 Roundtrip, found 2 days ago
￥53,770
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥53,770 found 2 days ago
American Airlines
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥55,170 Roundtrip, found 2 days ago
￥55,170
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥55,170 found 2 days ago
American Airlines
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥55,820 Roundtrip, found 2 days ago
￥55,820
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥55,820 found 2 days ago
American Airlines
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥56,350 Roundtrip, found 2 days ago
￥56,350
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥56,350 found 2 days ago
United
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥74,950 Roundtrip, found 2 days ago
￥74,950
Roundtrip
found 2 days ago
Select United flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥74,950 found 2 days ago
Delta
Mon, Sep 15 - Sat, Sep 20
EYW
Key West
ORD
Chicago
￥87,510 Roundtrip, found 2 days ago
￥87,510
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Sep 15 from Key West to Chicago, returning Sat, Sep 20, priced at ￥87,510 found 2 days ago

Find the cheapest month to fly from Key West (EYW) to Chicago (ORD)

November is typically the cheapest month to fly

From ￥27,926 - ￥127,275 per traveler.

Graph displaying average flight prices per month

Flights from Key West (EYW) to Chicago (ORD)
Origin airport
Key West Intl.
Destination airport
O'Hare Intl.
Roundtrip price
￥47,320
Distance
2006 km

Key West to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Key West to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with EYW to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Key West for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
The lowest price advertised for a round-trip flight from EYW to O'Hare Airport is ￥47,320. But you better get moving. This figure is taken from fares quoted within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from EYW to O'Hare Airport?
The majority of flights can be conveniently canceled online, but whether or not you incur a fee varies between airlines. If you do have to cancel your getaway, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from Key West Intl. Airport to O'Hare Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Key West Intl. Airport (EYW) to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from EYW to O'Hare Airport?
Lasting around 4 hours and 52 minutes, the flight between EYW and O'Hare Airport is a great opportunity to do some last-minute trip planning. How about using the time to work on your itinerary for Chicago?
How far is the flight from Key West Intl. Airport to O'Hare Airport?
The flying distance between Key West Intl. Airport (EYW) (EYW) and O'Hare Airport (ORD) is 2,000 kilometers. Listen to some music or finish that novel and the trip will zip on by.
Which airlines fly direct from EYW to O'Hare Intl. Airport (ORD)?
If you want to travel straight from EYW to O'Hare Intl. Airport (ORD), you'll need to book a flight with one or more stops. Unfortunately, there are no airlines that fly directly on this route.
Are Key West Intl. Airport (EYW) to ORD flight tickets cheaper when they're purchased at the last minute?
It is possible to find a fantastic last-minute deal from Key West Intl. Airport to O'Hare Airport, but there's no guarantee. As many airlines advertise prices up to a year in advance, it's worth keeping an eye on fares early and being ready to book when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can feel confident knowing you're always seeing the latest offers.

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