Cheap flights from ORD to EYW from $108

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Cheap Flights from ORD to EYW starting at $108 One Way, $216 Round Trip

Prices starting at $216 for return flights and $108 for one-way flights to Key West Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jul 2 - Thu, Jul 4

ORD

Chicago

EYW

Key West

$216

Roundtrip

found 2 days ago

Sun, Sep 1 - Fri, Sep 13

ORD

Chicago

EYW

Key West

$232

Roundtrip

found 8 hours ago

Wed, Aug 7 - Tue, Aug 20

ORD

Chicago

EYW

Key West

$248

Roundtrip

found 8 hours ago

Sat, Aug 24 - Fri, Sep 6

ORD

Chicago

EYW

Key West

$252

Roundtrip

found 8 hours ago

Mon, Aug 5 - Tue, Aug 20

ORD

Chicago

EYW

Key West

$268

Roundtrip

found 8 hours ago

Hotel Ideas near Key West Intl.

Airport Hotels near Key West Intl.

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd, Key West, FL

$187

per night

Jun 3 - Jun 4

Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff ...

7.8/10 Good! (1,006 reviews)

"We celebrated our 40th anniversary there the staff was all very nice and welcoming and the atmosphere was just so upbeat and enjoyable"

Reviewed on May 29, 2024

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard, Key West, FL

$229

per night

Jun 4 - Jun 5

Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...

8.4/10 Very Good! (1,771 reviews)

Margaritaville

"Room was nice and large had all amenities need for a family stay. Restaurant on premises was good, staff was friendly and knowledgeable."

Reviewed on May 31, 2024

Hampton Inn Key West FL

3755 S Roosevelt Blvd, Key West, FL

$209

per night

Jun 2 - Jun 3

Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...

8.8/10 Excellent! (1,091 reviews)

"Especially enjoyed the shuttle so we didn't have to search for parking and no one had to be the designated driver ;)"

Reviewed on May 29, 2024

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Key West

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

$161

per night

Jun 9 - Jun 10

Stay at this 4-star golf hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the bar in our reviews. Popular attractions ...

8.8/10 Excellent! (1,518 reviews)

"The hotel was great!!! The staff was great. The property is on stock island and set back away from busy streets yet close to everything. Downtown key west was 5 minutes away. We rented a scooter and drove everywhere on that."

Reviewed on May 31, 2024

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard, Key West, FL

$229

per night

Jun 4 - Jun 5

Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...

8.4/10 Very Good! (1,771 reviews)

Margaritaville

"Room was nice and large had all amenities need for a family stay. Restaurant on premises was good, staff was friendly and knowledgeable."

Reviewed on May 31, 2024

Fairfield Inn and Suites by Marriott Key West

2400 N Roosevelt Blvd, Key West, FL

$175

per night

Jun 3 - Jun 4

Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...

7.8/10 Good! (1,059 reviews)

"Very professional"

Reviewed on May 27, 2024

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Key West Hotels With Airport Transportation

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd, Key West, FL

$187

per night

Jun 3 - Jun 4

Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff ...

7.8/10 Good! (1,006 reviews)

"We celebrated our 40th anniversary there the staff was all very nice and welcoming and the atmosphere was just so upbeat and enjoyable"

Reviewed on May 29, 2024

Hampton Inn Key West FL

3755 S Roosevelt Blvd, Key West, FL

$209

per night

Jun 2 - Jun 3

Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...

8.8/10 Excellent! (1,091 reviews)

"Especially enjoyed the shuttle so we didn't have to search for parking and no one had to be the designated driver ;)"

Reviewed on May 29, 2024

Eden House

1015 Fleming St, Key West, FL

$294

per night

Jun 2 - Jun 3

Stay at this 3.5-star family-friendly hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful ...

9/10 Wonderful! (1,002 reviews)

"Excellent place, walking distance to downtown. Only one thing was very upsetting, gentleman who was on the front desk was very unpleasant to us . Hope he had a bed day and he would not give this beautiful place a bad name."

Reviewed on May 29, 2024

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Key West Hotels

Seashell Motel & Key West Hostel

718 South Street, Key West, FL

$99

per night

Jun 2 - Jun 3

Stay at this hostel in Key West. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...

7.6/10 Good! (1,003 reviews)

"silence and inconspicuous appearance of the facility. The city's attractions and shopping are reachable in 10 to 15 minutes on foot. The beach is only 5 minutes away! :)"

Reviewed on May 29, 2024

Southwinds Motel

1321 Simonton Street, Key West, FL

$164

per night

Jun 2 - Jun 3

Stay at this hotel in Key West. Enjoy 2 outdoor pools, a 24-hour front desk, and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. ...

8.8/10 Excellent! (1,003 reviews)

"Cottage like with plenty of room, 2 inviting pools. Walk to everything or rent a bike or scooter. Extremely helpful staff"

Reviewed on May 30, 2024

Duval House

815 Duval St, Key West, FL

$129

per night

Jun 12 - Jun 13

Stay at this 3-star B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. ...

9.2/10 Wonderful! (1,003 reviews)

"Everything is sparkling clean, and the staff are so warm and welcoming. Great communication and accommodation. Lovely perks and amenities. I feel completely comfortable here; Duval House has made my key west visit exceptional."

Reviewed on May 31, 2024

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Key West

24 North Hotel Key West

3820 North Roosevelt Boulevard, Key West, FL

$159

per night

Jun 2 - Jun 3

Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...

7.2/10 Good! (1,467 reviews)

Families like: Outdoor pools, bicycle rentals, extra beds/cribs, laundry

Service the way it should be!

"Friendly and helpful staff. Very Accommodating! Room was clean and spacious."

Reviewed on May 30, 2024

Southernmost Beach Resort

1319 Duval Street, Key West, FL

$272

per night

Jun 19 - Jun 20

Stay at this 4-star beach hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and a beach locale. Our guests praise the pool and the bar in our reviews. ...

8.2/10 Very Good! (1,896 reviews)

Families like: Outdoor pools, on the beach, bicycle rentals, extra beds/cribs

Travelers say...

"Bad timing on our part, large heavy construction going on repairing their sea wall. I dont hold it against them repairing their sea wall but when I purchased an ocean view room they could have informed me my view would be of cranes and very little ocean. The property & staff were very nice but on ..."

Reviewed on May 31, 2024

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

$161

per night

Jun 9 - Jun 10

Stay at this 4-star golf hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the bar in our reviews. Popular attractions ...

8.8/10 Excellent! (1,518 reviews)

Families like: Outdoor pools, bicycle rentals, laundry

Travelers say...

"The hotel was great!!! The staff was great. The property is on stock island and set back away from busy streets yet close to everything. Downtown key west was 5 minutes away. We rented a scooter and drove everywhere on that."

Reviewed on May 31, 2024

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Map To Nearby Hotels

ORD to EYW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

ORD Address & GPS

Address:

10000 West O'Hare

Chicago IL, 60666

United States

IATA Code:

ORD

Longitude:

-87.904876

Latitude:

41.976912

Time Zone:

America/Chicago

EYW Address & GPS

Address:

3491 South Roosevelt Boulevard

Key West FL, 33040-5260

United States

IATA Code:

EYW

Longitude:

-81.75501

Latitude:

24.553574

Time Zone:

America/New_York

Other Flights from O'Hare Intl. Airport (ORD)

Other Flights to Key West Intl. Airport (EYW)

Frequently asked questions

Am I able to catch a flight from Chicago, IL Airport (ORD-O'Hare Intl.) to Key West, FL Airport (EYW-Key West Intl.) now?

If you’re concerned about quarantine requirements and travel restrictions when catching a flight from Chicago, IL Airport (ORD-O’Hare Intl.) to Key West, FL Airport (EYW-Key West Intl.), go right to our Covid-19 Travel Advisor.

Are there non-stop flights from Chicago, IL Airport (ORD-O'Hare Intl.) to EYW?

You can jet straight from O’Hare Intl. Airport (ORD) to EYW. Direct flights are operated by several airlines, including United Airlines and American Airlines.

What is the shortest flight from O'Hare Airport to Key West Intl. Airport?

Take the opportunity to unwind on your trip from Chicago Museum Campus to Summerland Key. The shortest flight time from ORD to EYW is 4 hours and 44 minutes, which gives you plenty of time to enjoy a beverage or lose yourself in a good book.

How many hours flight from Chicago, IL Airport (ORD-O'Hare Intl.) to Key West, FL Airport (EYW-Key West Intl.)?

It takes an average of 4 hours and 50 minutes to go from ORD to EYW. Breeze through this medium-haul flight by watching a few movies and reading magazines. Alternatively, why not catch up on some sleep?

If I am not able to travel due to COVID-19, can I cancel my flight to Key West, FL Airport (EYW-Key West Intl.)?

We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Key West, FL Airport (EYW-Key West Intl.) have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Key West, FL Airport (EYW-Key West Intl.) with flexible change policies?

In most cases you’ll have the option to reschedule your flight to Key West, FL Airport (EYW-Key West Intl.) without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.

What airlines have the most flights from Chicago, IL Airport (ORD-O'Hare Intl.) to Key West, FL Airport (EYW-Key West Intl.)?

Escaping on vacation is one of life’s biggest pleasures, but how you arrive at your destination should be just as enjoyable. Consider booking your flight from ORD to Key West Intl. Airport (EYW) with American Airlines (AA). One of the most popular carriers, it offers 47 flights on this route every month. United Airlines (UA) will also fly you to your destination in comfort. Offering 36 monthly flights between Chicago Museum Campus and Summerland Key, it’s also highly rated.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

Cheap flights from ORD to EYW (O'Hare Intl. to Key West Intl.)

Cheap Flights from ORD to EYW starting at $108 One Way, $216 Round Trip

Hotel Ideas near Key West Intl.

Airport Hotels near Key West Intl.

Hotels In Key West

Key West Hotels With Airport Transportation

Low Priced Key West Hotels

Family Friendly Hotels in Key West

Map To Nearby Hotels

ORD to EYW Route Info

Other Flights from O'Hare Intl. Airport (ORD)

Other Flights to Key West Intl. Airport (EYW)

Frequently asked questions