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 $186 One Way, $309 Round Trip

Prices starting at $309 for return flights and $186 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.

Wed, Sep 2 - Sat, Sep 5
ORD
Chicago
EYW
Key West
$309 Roundtrip, found 4 hours ago
$309
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Sep 2 from Chicago to Key West, returning Sat, Sep 5, priced at $309 found 4 hours ago
Tue, Feb 16 - Thu, Feb 25
ORD
Chicago
EYW
Key West
$309 Roundtrip, found 6 days ago
$309
Roundtrip
found 6 days ago
Select United flight, departing Tue, Feb 16 from Chicago to Key West, returning Thu, Feb 25, priced at $309 found 6 days ago
Tue, Feb 16 - Thu, Feb 25
ORD
Chicago
EYW
Key West
$315 Roundtrip, found 6 days ago
$315
Roundtrip
found 6 days ago
Select United flight, departing Tue, Feb 16 from Chicago to Key West, returning Thu, Feb 25, priced at $315 found 6 days ago
Tue, Jun 23 - Tue, Jun 30
ORD
Chicago
EYW
Key West
$316 Roundtrip, found 1 day ago
$316
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 23 from Chicago to Key West, returning Tue, Jun 30, priced at $316 found 1 day ago
Wed, Sep 2 - Sat, Sep 5
ORD
Chicago
EYW
Key West
$319 Roundtrip, found 4 hours ago
$319
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Sep 2 from Chicago to Key West, returning Sat, Sep 5, priced at $319 found 4 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
$417 nightly
The price is $470 total per night from Jun 1 to Jun 2
$470 total
Jun 1 - Jun 2
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! (1,065 reviews)
Everything was as pictured on web site. Loved the pool. Would definitely go back again

Reviewed on May 3, 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
$212 nightly
The price is $238 total per night from Jun 1 to Jun 2
$238 total
Jun 1 - Jun 2
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! (1,351 reviews)
This place was wonderful. Spacious room with great view. The bathroom was large and had everything needed. Bed was very comfortable and no issues with anything in the room. Will definitely go back there again. Pool and outside area was clean and beautiful too.

Reviewed on May 2, 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
$190 nightly
The price is $214 total per night from May 31 to Jun 1
$214 total
May 31 - Jun 1
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! (1,008 reviews)
Breakfast was good and the shuttle service each day was exceptional.

Reviewed on May 4, 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
$202 nightly
The price is $227 total per night from May 26 to May 27
$227 total
May 26 - May 27
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! (2,186 reviews)
We love it. Exceptional staff specially at front desk Flora.

Reviewed on May 4, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
$272 nightly
The price is $306 total per night from May 20 to May 21
$306 total
May 20 - May 21
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! (1,804 reviews)
Breakfast was great. Check in was easy. Pool was refreshing.

Reviewed on May 3, 2026

Margaritaville Beach House Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$312 nightly
The price is $352 total per night from May 25 to May 26
$352 total
May 25 - May 26
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! (3,270 reviews)
My husband and I woke up with bed bug bites and the air conditioner was not functioning properly the last night of our visit. This was not the room that was shown on your website - we did not have a partial island view. The hallway was open to the beach all day and all night. We were surprised when ...

Reviewed on May 3, 2026

Southernmost Beach Resort and Guesthouses
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
$190 nightly
The price is $214 total per night from May 31 to Jun 1
$214 total
May 31 - Jun 1
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! (1,008 reviews)
Breakfast was good and the shuttle service each day was exceptional.

Reviewed on May 4, 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
$212 nightly
The price is $238 total per night from Jun 1 to Jun 2
$238 total
Jun 1 - Jun 2
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! (1,351 reviews)
This place was wonderful. Spacious room with great view. The bathroom was large and had everything needed. Bed was very comfortable and no issues with anything in the room. Will definitely go back there again. Pool and outside area was clean and beautiful too.

Reviewed on May 2, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$227 nightly
The price is $255 total per night from May 18 to May 19
$255 total
May 18 - May 19
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! (1,005 reviews)
It was wonderful! Staff very helpful

Reviewed on May 1, 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
$194 nightly
The price is $218 total per night from Jun 1 to Jun 2
$218 total
Jun 1 - Jun 2
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! (1,325 reviews)
We loved our stay! Location was perfect. Could walk to bars and restaurants. Great onsite bar with live music. Room was set up perfectly with space for our family. Staff was wonderful as well. Will definitely stat again!

Reviewed on May 4, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$164 nightly
The price is $185 total per night from May 5 to May 6
$185 total
May 5 - May 6
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! (1,002 reviews)
The room looked recently remodeled and was very clean. The bed was very comfortable with many pillows and comfy linen. The refrigerator was very cold and the AC kept the room very cold and was a nice reprieve from the heat. The outside is very deceptive because it looks a little run down but the ...

Reviewed on May 3, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$221 nightly
The price is $245 total per night from Jun 3 to Jun 4
$245 total
Jun 3 - Jun 4
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! (1,028 reviews)
Very clean and convenient staff was very nice will stay again

Reviewed on May 4, 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
$312 nightly
The price is $352 total per night from May 25 to May 26
$352 total
May 25 - May 26
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! (3,270 reviews)
My husband and I woke up with bed bug bites and the air conditioner was not functioning properly the last night of our visit. This was not the room that was shown on your website - we did not have a partial island view. The hallway was open to the beach all day and all night. We were surprised when ...

Reviewed on May 3, 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 Duval Street and Smathers Beach ...
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
$202 nightly
The price is $227 total per night from May 26 to May 27
$227 total
May 26 - May 27
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! (2,186 reviews)

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

Travelers say...
We love it. Exceptional staff specially at front desk Flora.

Reviewed on May 4, 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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