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 $195 One Way, $319 Round Trip

Prices starting at $319 for return flights and $195 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.

Sat, Aug 22 - Sat, Sep 5
ORD
Chicago
EYW
Key West
$319 Roundtrip, found 1 day ago
$319
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 22 from Chicago to Key West, returning Sat, Sep 5, priced at $319 found 1 day ago
Tue, Dec 1 - Sat, Dec 5
ORD
Chicago
EYW
Key West
$321 Roundtrip, found 12 hours ago
$321
Roundtrip
found 12 hours ago
Select United flight, departing Tue, Dec 1 from Chicago to Key West, returning Sat, Dec 5, priced at $321 found 12 hours ago
Sat, Jul 25 - Thu, Jul 30
ORD
Chicago
EYW
Key West
$326 Roundtrip, found 10 hours ago
$326
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Jul 25 from Chicago to Key West, returning Thu, Jul 30, priced at $326 found 10 hours ago
Thu, Oct 15 - Mon, Oct 19
ORD
Chicago
EYW
Key West
$329 Roundtrip, found 9 hours ago
$329
Roundtrip
found 9 hours ago
Select Delta flight, departing Thu, Oct 15 from Chicago to Key West, returning Mon, Oct 19, priced at $329 found 9 hours ago
Thu, Jul 30 - Mon, Aug 3
ORD
Chicago
EYW
Key West
$336 Roundtrip, found 7 hours ago
$336
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Thu, Jul 30 from Chicago to Key West, returning Mon, Aug 3, priced at $336 found 7 hours 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
$399 nightly
The price is $449 total per night from Jul 8 to Jul 9
$449 total
Jul 8 - Jul 9
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! (1,149 reviews)
"Nice place ,clean, free parking very spacious"

Reviewed on Jun 21, 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
$199 nightly
The price is $224 total per night from Jul 7 to Jul 8
$224 total
Jul 7 - Jul 8
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! (1,404 reviews)
"Room and facility was clean. Enjoyed using the pool, pool bar and free buffet breakfast."

Reviewed on Jun 22, 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
$169 nightly
The price is $190 total per night from Jul 6 to Jul 7
$190 total
Jul 6 - Jul 7
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 ...
8.4/10 Very Good! (1,045 reviews)
"I’m extremely disappointed with my stay this weekend. The room was not clean and the condition of the bedding was unacceptable. The sheets and covers were visibly dirty, which made me question whether the room had been properly cleaned before we arrived. On top of the cleanliness issues, the way ..."

Reviewed on Jun 21, 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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$175 nightly
The price is $197 total per night from Jul 1 to Jul 2
$197 total
Jul 1 - Jul 2
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 ...
8.4/10 Very Good! (2,434 reviews)
"Room was really nice and the water bottles are awesome, brought them home and using everyday. Pool was very nice too. Location to Key West was ideal. Property is well maintained and lawn toys are so fun for the family…appreciated it all."

Reviewed on Jun 23, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$266 nightly
The price is $299 total per night from Jun 29 to Jun 30
$299 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (3,398 reviews)
"Clean room Pools Staff very friendly"

Reviewed on Jun 23, 2026

Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
$132 nightly
The price is $149 total per night from Jun 29 to Jun 30
$149 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
8/10 Very Good! (1,246 reviews)
"it was nice"

Reviewed on Jun 21, 2026

Hilton Garden Inn Key West / The Keys Collection
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
$169 nightly
The price is $190 total per night from Jul 6 to Jul 7
$190 total
Jul 6 - Jul 7
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 ...
8.4/10 Very Good! (1,045 reviews)
"I’m extremely disappointed with my stay this weekend. The room was not clean and the condition of the bedding was unacceptable. The sheets and covers were visibly dirty, which made me question whether the room had been properly cleaned before we arrived. On top of the cleanliness issues, the way ..."

Reviewed on Jun 21, 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
$199 nightly
The price is $224 total per night from Jul 7 to Jul 8
$224 total
Jul 7 - Jul 8
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! (1,404 reviews)
"Room and facility was clean. Enjoyed using the pool, pool bar and free buffet breakfast."

Reviewed on Jun 22, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$159 nightly
The price is $179 total per night from Jun 24 to Jun 25
$179 total
Jun 24 - Jun 25
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! (1,006 reviews)
"Our stay at Eden House was very enjoyable. The hotel was accessible to Duval Street, Mallory Square, and the harbor area. Very easy walks to everything we wanted to do. The hotel is located in a quiet neighborhood and was a welcome respite after a day of exploring. We recommend this property whole-heartedly ..."

Reviewed on Jun 21, 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
$175 nightly
The price is $196 total per night from Jun 24 to Jun 25
$196 total
Jun 24 - Jun 25
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. ...
8.6/10 Excellent! (1,343 reviews)
"Todo limpio."

Reviewed on Jun 22, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$131 nightly
The price is $147 total per night from Jun 25 to Jun 26
$147 total
Jun 25 - Jun 26
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! (1,000 reviews)
"Loved the close proximity to walk to the popular Duvall street for shopping and dining. The bathroom was huge!! Upgraded bathroom fixtures and tile. Great water pressure. Adjustable temperature A/C unit which was cold that I chose to turn up. Comfortable plush mattress, though the bed squeaked a ..."

Reviewed on Jun 8, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$125 nightly
The price is $138 total per night from Jul 6 to Jul 7
$138 total
Jul 6 - Jul 7
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! (1,040 reviews)
"Clean room, friendly staff"

Reviewed on Jun 22, 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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$266 nightly
The price is $299 total per night from Jun 29 to Jun 30
$299 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.8/10 Excellent! (3,398 reviews)
"Clean room Pools Staff very friendly"

Reviewed on Jun 23, 2026

Southernmost Beach Resort and Guesthouses
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 Southernmost Point and Duval Street ...
8.4/10 Very Good! (999 reviews)

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

Travelers say...
"This is a beautiful resort full of amenities! Margaritas when you arrive, smoothies at the pool each day around noon, free airport and old town shuttles so we didn’t need to Uber anywhere, also coffee/water/cookies in the lobby daily. The beach is an easy walk across the street. The hotel is super ..."

Reviewed on Apr 19, 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
$175 nightly
The price is $197 total per night from Jul 1 to Jul 2
$197 total
Jul 1 - Jul 2
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 ...
8.4/10 Very Good! (2,434 reviews)

Families like: Outdoor pools, playground, miniature golf, game room

Travelers say...
"Room was really nice and the water bottles are awesome, brought them home and using everyday. Pool was very nice too. Location to Key West was ideal. Property is well maintained and lawn toys are so fun for the family…appreciated it all."

Reviewed on Jun 23, 2026

Blue Flamingo Resort 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.

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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