Find Chicago - Key West Flights (CHI - EYW)

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Chicago to Key West Flight Information
Origin airport IATA code
CHI
Destination airport IATA code
EYW
Number of flight options
1
Average flight time
4 hours 25 mins

Key West Flight Information

Traveling From
Chicago
Origin Airport IATA Code
CHI
Traveling To
Key West
Destination Airport IATA Code
EYW
Number of Airlines Serving
Available Airlines
Distance
Direct Flight Time
Flight Price

Car Hire offers in Key West

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
Stay at this family-friendly hotel in Key West. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their ...
8.2/10 Very Good! (2,037 reviews)
The hotel is really awesome. There are a lot of activities on the property. We stayed with kids ages 10-18 and they loved it. The hotel staff were wonderful.

Reviewed on 4 Apr 2026

Opens in a new windowBlue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Stay at this beach hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (3,169 reviews)
Ocean view from our room was amazing.

Reviewed on 4 Apr 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service and a 24-hour fitness centre. Our guests praise the pool and the restaurant in ...
8.8/10 Excellent! (1,799 reviews)
Ideal for families with smaller children, and the pool was smaller than was indicated in the pictures overall good experience

Reviewed on 2 Apr 2026

Opens in a new windowMargaritaville Beach House Key West
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Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Stay at this beach hotel in Key West. Enjoy free Wi-Fi, 2 restaurants and a private beach. Our guests praise the pool and the helpful staff in their reviews. ...
8.6/10 Excellent! (2,110 reviews)
Great place

Reviewed on 4 Apr 2026

Opens in a new windowBeachside Resort & Residences
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Stay at this beach hotel in Key West. Enjoy free breakfast, free Wi-Fi and a private beach. Our guests praise the breakfast and the pool in their reviews. Popular ...
8/10 Very Good! (2,179 reviews)
Staff was great. Liked the pool and restaurant. The floor in the room needed to be replaced, it was peeling and buckling. The shower in the bathroom was the smallest shower I have ever seen.

Reviewed on 4 Apr 2026

Opens in a new windowIbis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Stay at this business-friendly hotel in Key West. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,723 reviews)
Pool perfect. Hot tub private. Drinks and breakfast very good. Through Expedia they offered free breakfast for everyday we stayed. Came around with free Jell-O shots, smoothies and snacks. Flama Cabana bar was nice with good music, dinner was ok. Espresso Martinis on point! Beautiful sunset from ...

Reviewed on 4 Apr 2026

Opens in a new windowHavana Cabana at Key West
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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.

*Terms & Conditions: Etihad 4x BONUS+

Eligible to all ebookers BONUS+ members with stand-alone flight bookings made on ebookers’ website from 00:01 UTC 30 October 2015 through 23:59 UTC 1 November 2015 where the validating carrier is Etihad. Etihad multiplier (“Etihad Multiplier”) applies to the base of 1% BONUS+ earned on eligible flight bookings. Members will be issued an additional amount of BONUS+, equal to 4% (“Promotional Earn”) of the amount paid for each of the aforementioned bookings if the members were logged in to their BONUS+ account at the time of booking. If such a member has already earned the annual air cap in BONUS+, the member will not earn the Base Earn but will still earn the promotional BONUS+. In all of the above-mentioned cases, customers booking when logged in on the ebookers mobile application will earn triple the 2% Mobile Earn on the purchase price, totalling 8% earn. The earned promotional BONUS+ will expire if not redeemed within 60 calendar days from the date of issuance. Offer is non-transferrable and not redeemable for cash. The earned promotional BONUS+ will be deposited in your BONUS+ account at the time of booking. ebookers reserves the right to change, limit, or cancel the promotion in its sole discretion. See ebookers Terms and Conditions for additional applicable terms and conditions on: http://www.ebookers.ie/info/win?id=LoyaltyTerms

Fare, taxes & fees: Fares were found on ebookers.com and are updated daily. They include all taxes and fees, except baggage fees.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a £25.00 / 45.00 Euro service fee charged by ebookers, plus any airline fare and tax increase that may be applicable.

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. 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.