$183 Cheap Delta flights Key West (EYW) to Chicago (ORD)

View $183 flight on Tue, Oct 21, 2025Opens in a new window

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$183 Cheap Delta flights Key West (EYW) to Chicago (ORD)

Prices were available within the past 7 days and start at $183 for one-way flights and $269 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Aug 27 - Tue, Sep 9
EYW
Key West
ORD
Chicago
$269 Roundtrip, found 6 hours ago
$269
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Aug 27 from Key West to Chicago, returning Tue, Sep 9, priced at $269 found 6 hours ago
Delta
Sat, Sep 13 - Tue, Sep 30
EYW
Key West
ORD
Chicago
$311 Roundtrip, found 6 hours ago
$311
Roundtrip
found 6 hours ago
Select Delta flight, departing Sat, Sep 13 from Key West to Chicago, returning Tue, Sep 30, priced at $311 found 6 hours ago
Delta
Sat, Sep 6 - Sat, Sep 13
EYW
Key West
ORD
Chicago
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 6 from Key West to Chicago, returning Sat, Sep 13, priced at $314 found 1 day ago
Delta
Sat, Aug 23 - Tue, Sep 9
EYW
Key West
ORD
Chicago
$320 Roundtrip, found 6 hours ago
$320
Roundtrip
found 6 hours ago
Select Delta flight, departing Sat, Aug 23 from Key West to Chicago, returning Tue, Sep 9, priced at $320 found 6 hours ago
Delta
Fri, Aug 29 - Mon, Sep 15
EYW
Key West
ORD
Chicago
$324 Roundtrip, found 6 hours ago
$324
Roundtrip
found 6 hours ago
Select Delta flight, departing Fri, Aug 29 from Key West to Chicago, returning Mon, Sep 15, priced at $324 found 6 hours ago
Delta
Fri, Sep 19 - Tue, Sep 23
EYW
Key West
ORD
Chicago
$331 Roundtrip, found 4 days ago
$331
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Sep 19 from Key West to Chicago, returning Tue, Sep 23, priced at $331 found 4 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, Spirit Airlines, United
Popular airline
United
Distance
1254 mi

Frequently asked questions

How much is a Delta Air Lines flight from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
Landing cheap one-way Delta Air Lines flights from EYW to ORD from $183 on Expedia is simple — just filter by "Price (lowest to highest)." Alternatively, check out our budget-friendly return fares from $269 for your next adventure.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from EYW to ORD with Delta Air Lines?
Delta Air Lines flights to Chicago tend to be more affordable in the quieter months of January and February. Whether you need a one-way or a return ticket, you could score a better deal then.
What is the cheapest time to book flights from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD) with Delta Air Lines?
Search for cheap Delta Air Lines flights from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD) one to three months prior to your departure date. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare class and journey, the best day to book a domestic flight is generally Sunday and the most expensive is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does Delta Air Lines fly nonstop from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
Click on our "Nonstop" filter when searching for direct Delta Air Lines flights from EYW to ORD. You can also compare other airlines servicing the same nonstop journey.
What is the earliest Delta Air Lines flight from EYW to ORD?
Filter your results by "Early Morning" and "Morning" to see the earliest flights from EYW to ORD. Setting off early means you're 20% less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does Delta Air Lines fly into in Chicago?
O'Hare Intl. Airport (ORD) is the primary Chicago gateway for Delta Air Lines flights from Key West Intl. Airport (EYW).
Why fly with Delta Air Lines from EYW to ORD?
Offering a rewarding loyalty program and an excellent in-flight experience, Delta Air Lines is a favorite for many travelers heading from EYW to ORD. Also, if you're a Delta SkyMiles and One Key™ member booking with Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles, which can go toward future travel.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Delta Air Lines flight from Key West Intl. Airport (EYW) to O'Hare Intl. Airport (ORD)?
Typically, you can modify or cancel your flight, although additional fees may apply if your booking was made over 24 hours ago. Need flexible options? Make use of our "No cancel fee" or "Changes included" filter to find flights that won't charge extra if you need to adjust your plans. To modify your booking, head to "Trips," select your flight and click on "Manage Booking" for more information.

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