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Lowest round trip fares by airline from Chicago and Key West

Cheapest prices ($107 One Way, $230 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Key West

Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street, Key West, FL
The price is $242 per night from Mar 31 to Apr 1
$242
per night
Mar 31 - Apr 1
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! (1,000 reviews)
"for a 2 star motel this is as nice as it gets. it is an old motel that is obviously well maintained and staff is great. rooms are small but clean. location is great. they gave us passes to access beach club with pools and bar that was nice."

Reviewed on Mar 25, 2024

Southwinds Motel
Seashell Motel & Key West Hostel

Seashell Motel & Key West Hostel

1.5 out of 5
718 South Street, Key West, FL
The price is $131 per night from Apr 1 to Apr 2
$131
per night
Apr 1 - Apr 2
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 ...
7.4/10 Good! (1,000 reviews)
"The use of the barbecue and the common dining aria is interesting."

Reviewed on Mar 25, 2024

Seashell Motel & Key West Hostel
Duval House

Duval House

3 out of 5
815 Duval St, Key West, FL
The price is $209 per night from Mar 31 to Apr 1
$209
per night
Mar 31 - Apr 1
Stay at this 3-star B&B in Key West. Enjoy a terrace, daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.2/10 Wonderful! (1,008 reviews)
"It was such a relaxing and welcoming place to stay. I was very impressed with how well taken care of it is. I love the 2 resident cats!"

Reviewed on Mar 26, 2024

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.

Fly From Chicago to Key West

Origin
Chicago
Destination
Key West
Number of Daily Flights
2
Earliest Flight Departure Date
Apr 4
Latest Flight Departure Date
Apr 4
Popular Airlines
American Airlines

Cheap flights from Chicago to Key West

Are you ready to book your flight, but feeling nervous about paying too much if prices drop in a few days? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus $50 more in CheapCash, which you can use to save on your hotel reservation.

If you have a frequent flier account, add it to your reservation to earn miles. And don't worry about getting stuck in a middle seat. Choose your seats when you book, so you'll be right where you want to be on departure day.

Save Even More Time and Money With a Key West Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Key West vacation that you can't get when you book flights and hotel separately.

Relax in Key West With Confidence and Convenience

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.