$108 Cheap Flights from Key West (EYW) to Chicago (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 $108 for one-way flights and $202 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Jul 4 - Tue, Jul 16
EYW
Key West
ORD
Chicago
$202 Roundtrip, found 3 days ago
$202
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Jul 4 from Key West to Chicago, returning Tue, Jul 16, priced at $202 found 3 days ago
American Airlines
Tue, Jul 2 - Tue, Jul 16
EYW
Key West
ORD
Chicago
$205 Roundtrip, found 11 hours ago
$205
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Jul 2 from Key West to Chicago, returning Tue, Jul 16, priced at $205 found 11 hours ago
American Airlines
Tue, Jul 2 - Tue, Jul 16
EYW
Key West
ORD
Chicago
$206 Roundtrip, found 11 hours ago
$206
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Jul 2 from Key West to Chicago, returning Tue, Jul 16, priced at $206 found 11 hours ago
American Airlines
Tue, Jul 2 - Tue, Jul 16
EYW
Key West
ORD
Chicago
$208 Roundtrip, found 11 hours ago
$208
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Jul 2 from Key West to Chicago, returning Tue, Jul 16, priced at $208 found 11 hours ago
American Airlines
Tue, Jul 2 - Tue, Jul 16
EYW
Key West
ORD
Chicago
$213 Roundtrip, found 11 hours ago
$213
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Jul 2 from Key West to Chicago, returning Tue, Jul 16, priced at $213 found 11 hours ago
American Airlines
Tue, Jul 2 - Tue, Jul 16
EYW
Key West
ORD
Chicago
$215 Roundtrip, found 11 hours ago
$215
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Jul 2 from Key West to Chicago, returning Tue, Jul 16, priced at $215 found 11 hours ago
Delta
Thu, Jul 4 - Tue, Jul 9
EYW
Key West
ORD
Chicago
$216 Roundtrip, found 1 hour ago
$216
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Jul 4 from Key West to Chicago, returning Tue, Jul 9, priced at $216 found 1 hour ago
American Airlines
Tue, Jul 2 - Tue, Jul 16
EYW
Key West
ORD
Chicago
$225 Roundtrip, found 11 hours ago
$225
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Jul 2 from Key West to Chicago, returning Tue, Jul 16, priced at $225 found 11 hours ago
American Airlines
Tue, Jul 2 - Tue, Jul 16
EYW
Key West
ORD
Chicago
$226 Roundtrip, found 11 hours ago
$226
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Jul 2 from Key West to Chicago, returning Tue, Jul 16, priced at $226 found 11 hours ago
Delta
Tue, Jul 23 - Tue, Aug 13
EYW
Key West
ORD
Chicago
$228 Roundtrip, found 5 days ago
$228
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jul 23 from Key West to Chicago, returning Tue, Aug 13, priced at $228 found 5 days ago
Flights from Key West (EYW) to Chicago (ORD)
Origin airport
Key West Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, United
Roundtrip price
$201
Distance
1254 mi
Average flight time
2 hours 26 mins

Key West to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Key West to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Key West to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from EYW to ORD today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is $108 now!

Frequently asked questions

How much is a one-way flight from EYW to ORD?
You can find one-way Key West flights to Chicago starting from $103. This information is based on the best price located on Expedia for this journey departing across the next three months and was last updated on April 21 2024 and has not changed since. This airfare is for an American Airlines flight, departing from Key West Intl. Airport on July 17 2024 and touching down at O’Hare Intl. Airport (ORD).
Is it cheaper to buy a plane ticket from EYW to O'Hare Intl. Airport (ORD) last minute?
Booking your journey from Key West Intl. Airport (EYW) to ORD last minute could save you a tidy sum if you stumble on an awesome deal. However, airfares usually don’t come down in price as the departure date nears. If you take a wait-and-see approach, flights could also be booked up or the best seats taken. If you’d rather play it safe, book well in advance of when you want to leave. Keep in mind that some of the best deals can be found up to 12 months in advance. If your favorite airline hasn’t released its fares yet, check back regularly as offers are constantly updated on Expedia.
What is the cheapest airline flying from Key West Intl. Airport to O'Hare Airport in the next 90 days?
With plane tickets from $103 for a flight from Key West to Chicago, American Airlines is the cheapest airline found on Expedia. This deal is based on airfares found on Expedia with a departure date within the next 90 days and was updated on April 21 2024 and has not changed since. The flight leaves Key West Intl. Airport (EYW) on July 17 2024 and touches down at O’Hare Intl. Airport (ORD).
What's the cheapest price for a flight from EYW to O'Hare Airport next month?
With a one-way flight from Key West to Chicago on sale for just $107, you’ll have more dough to splash on cool stuff like sightseeing. This fare was found after looking at all available flights on Expedia within the next 30 days. This particular service takes off from Key West Intl. Airport (EYW) on May 14 2024, arrives at O’Hare Airport and is operated by American Airlines. Pricing information was last updated on April 21 2024 and has not changed since.
Can I find cheap nonstop flights from Key West Intl. Airport to ORD in the next three months?
The best price we’ve found for a roundtrip nonstop flight from Key West to Chicago in the next 90 days is $359. This price is based on available flights on Expedia with a departure date in the next three months. This fare is for a flight via American Airlines leaving from Key West Intl. Airport on April 24 2024 and landing at O’Hare Airport, with a return journey on April 28 2024. This price was updated on April 21 2024.To find nonstop cheap flights heading out from Key West Intl. Airport to O’Hare Airport, use our filters once you’ve hit search. Just click on “Nonstop” under “Filter by” on the left-hand side of the page to browse the options. Your results will be organized from the lowest price, so you can see the cheapest nonstop tickets first. You can also check out ticket prices for nearby days by clicking “Flexible dates” located near the top of the page.
What airports do you fly into for Chicago from Key West?
With O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT) to pick from, getting from Key West to Chicago is easy. The city’s key hub, O’Hare Intl. Airport (ORD), is approximately 16 mi northwest of the center. Apart from the price of fares, consider things like bus or train options from the airport and the distance to your hotel when choosing where to fly into. Get your Chicago trip off to a fun start by visiting Wrigley Field and Millennium Park.
Can I change the date of my flight from Key West Intl. Airport to ORD?
You can quickly and easily make changes to your EYW to ORD journey by logging in to the Expedia Trips portal. Before you make any amendments, review the rules in your itinerary to learn what you can do and if charges apply. Some airlines have a change fee per person, in addition to any difference in fares. However, if you booked in the last 24 hours, you may be able to cancel for free and book new flights. You can also stop by our Customer Service portal for more advice and to chat with our Virtual Agent.
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