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

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Cheap Flights from ORD to EYW starting at $105 One Way, $246 Round Trip

Prices starting at $246 for return flights and $105 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.

Thu, Apr 9 - Fri, Apr 17
ORD
Chicago
EYW
Key West
$246 Roundtrip, found 5 hours ago
$246
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Thu, Apr 9 from Chicago to Key West, returning Fri, Apr 17, priced at $246 found 5 hours ago
Thu, Apr 9 - Fri, Apr 17
ORD
Chicago
EYW
Key West
$250 Roundtrip, found 17 hours ago
$250
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Thu, Apr 9 from Chicago to Key West, returning Fri, Apr 17, priced at $250 found 17 hours ago
Fri, Apr 10 - Tue, Apr 14
ORD
Chicago
EYW
Key West
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Apr 10 from Chicago to Key West, returning Tue, Apr 14, priced at $264 found 1 day ago
Fri, Apr 10 - Fri, Apr 17
ORD
Chicago
EYW
Key West
$269 Roundtrip, found 5 days ago
$269
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Fri, Apr 10 from Chicago to Key West, returning Fri, Apr 17, priced at $269 found 5 days ago
Mon, Apr 13 - Mon, Apr 20
ORD
Chicago
EYW
Key West
$280 Roundtrip, found 1 day ago
$280
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Apr 13 from Chicago to Key West, returning Mon, Apr 20, priced at $280 found 1 day ago

Hotel Ideas near Key West Intl.

Airport Hotels near Key West Intl.

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
$510 nightly
The price is $574 total per night from Mar 24 to Mar 25
$574 total
Mar 24 - Mar 25
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,008 reviews)
Great place to stay.

Reviewed on Mar 18, 2026

Hyatt Vacation Club at Windward Pointe, Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$377 nightly
The price is $424 total per night from Apr 12 to Apr 13
$424 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,324 reviews)
Spacious rooms with friendly staff. Most staff don’t speak English well but are friendly. Property is well kept. Paid parking through an app was kind of spendy. Pool was nice but needs more lounge chairs. Airport is very close and can be quite loud but flights stop fairly early. Not close to downtown ...

Reviewed on Mar 18, 2026

Hampton Inn Key West FL
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$325 nightly
The price is $366 total per night from Mar 29 to Mar 30
$366 total
Mar 29 - Mar 30
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,004 reviews)
Enjoyed myself here, the pool and hot tub were great. The onsite restaurant was delicious. Our room was clean and odor free. It was a great pick for our stay!

Reviewed on Mar 17, 2026

DoubleTree Resort by Hilton Grand Key - Key West
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
$399 nightly
The price is $449 total per night from Apr 13 to Apr 14
$449 total
Apr 13 - Apr 14
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,795 reviews)
We love margaritaville. The pool, restaurant and bar are all excellent. The rooms were clean and well updated.

Reviewed on Mar 18, 2026

Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$337 nightly
The price is $379 total per night from Apr 13 to Apr 14
$379 total
Apr 13 - Apr 14
Total with taxes and fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.2/10 Very Good! (1,983 reviews)
Very good customer

Reviewed on Mar 18, 2026

Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
$374 nightly
The price is $420 total per night from Apr 13 to Apr 14
$420 total
Apr 13 - Apr 14
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,074 reviews)
Wonderfull staff, shuttle service was a huge help getting around. The food at the pool was excellent.

Reviewed on Mar 17, 2026

Beachside Resort & Residences
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

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$325 nightly
The price is $366 total per night from Mar 29 to Mar 30
$366 total
Mar 29 - Mar 30
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,004 reviews)
Enjoyed myself here, the pool and hot tub were great. The onsite restaurant was delicious. Our room was clean and odor free. It was a great pick for our stay!

Reviewed on Mar 17, 2026

DoubleTree Resort by Hilton Grand Key - Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$377 nightly
The price is $424 total per night from Apr 12 to Apr 13
$424 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,324 reviews)
Spacious rooms with friendly staff. Most staff don’t speak English well but are friendly. Property is well kept. Paid parking through an app was kind of spendy. Pool was nice but needs more lounge chairs. Airport is very close and can be quite loud but flights stop fairly early. Not close to downtown ...

Reviewed on Mar 18, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$484 nightly
The price is $544 total per night from Apr 12 to Apr 13
$544 total
Apr 12 - Apr 13
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,000 reviews)
Charming hotel with a great pool and a very friendly and accommodating staff. Our bedroom was well appointed and very quiet, except for a noisy air-conditioning window unit.i would recoomend it very highly.

Reviewed on Mar 8, 2026

Eden House
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

Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$339 nightly
The price is $382 total per night from Apr 5 to Apr 6
$382 total
Apr 5 - Apr 6
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
8.8/10 Excellent! (1,294 reviews)
We absolutely loved our stay! Our room was so quaint and very clean. The pools were lovely and it was nice to have one heated. Location is excellent. We parked our car and walked everywhere.

Reviewed on Mar 17, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$296 nightly
The price is $333 total per night from Mar 29 to Mar 30
$333 total
Mar 29 - Mar 30
Total with taxes and fees
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 ...
8/10 Very Good! (1,001 reviews)
Good location

Reviewed on Mar 14, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$321 nightly
The price is $358 total per night from Mar 24 to Mar 25
$358 total
Mar 24 - Mar 25
Total with taxes and fees
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.4/10 Exceptional! (1,010 reviews)
no kitchen ....shops nearby good, morning breakfast spotty except for waffle. Attendant was too attentive, sort of in the way.

Reviewed on Mar 17, 2026

Duval House
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Popular attractions Duval Street and Smathers Beach ...
8.4/10 Very Good! (999 reviews)

Families like: Outdoor pool, babysitting, close to beach, bicycle rentals

Travelers say...
Great visit

Reviewed on Feb 27, 2026

Get rates
Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$337 nightly
The price is $379 total per night from Apr 13 to Apr 14
$379 total
Apr 13 - Apr 14
Total with taxes and fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.2/10 Very Good! (1,983 reviews)

Families like: Outdoor pools, miniature golf, game room, bicycle rentals

Travelers say...
Very good customer

Reviewed on Mar 18, 2026

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$358 nightly
The price is $402 total per night from Apr 14 to Apr 15
$402 total
Apr 14 - Apr 15
Total with taxes and fees
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,825 reviews)
Beautiful place Our patio door wouldn’t close , stayed on the first floor so it was a little uncomfortable. Room service forgot to leave fresh towels, never refills Kcup coffee, when asked receptionist they gave us tea. Nice and comfortable room without even a spoon, so why have a kitchen? They had ...

Reviewed on Mar 16, 2026

Oceans Edge Key West Resort, Hotel & Marina
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.

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

Frequently asked questions

Are there non-stop flights from O'Hare Intl. Airport (ORD) to Key West Intl. Airport?
With several companies operating direct flights from O'Hare Airport to EYW, you won't have to worry about switching planes or amusing yourself on a layover. For a stress-free journey, we'd recommend taking to the skies with American Airlines or United Airlines.
What is the shortest flight from ORD to Key West Intl. Airport?
From Chicago, the unique sights and sounds of Key West are around 5 hours and 16 minutes away. Lock in your favorite seat, or maybe even upgrade to one with more legroom, and jet to your destination in comfort.
How many hours flight from O'Hare Intl. Airport (ORD) to EYW?
The journey from ORD to EYW takes an average of 5 hours and 21 minutes. A few TV shows, some podcasts and a decent snooze will make the time fly by.
What airlines have the most flights from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW)?
Outstanding service, punctuality and terrific in-flight entertainment are just a few things that make for a pleasant journey with an airline. If you need to get from O'Hare Intl. Airport (ORD) to Key West Intl. Airport (EYW), why not fly with the best? American Airlines (AA) operates 78 flights on this route each month. If you don't find quite what you need there, have a look at the airfares from United Airlines (UA). This carrier is another reputable choice and operates 30 flights from Chicago to Key West every month.

Map To Nearby Hotels

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.

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