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| Package Name | Price (Round Trip) | Flight Duration | Baggage Allowance | In-Flight Amenities | Flexibility |
|---|---|---|---|---|---|
| Key West Express | $399 | Approx. 3.5 hours | 1 Carry-on, 1 Personal Item | Complimentary Wi-Fi, Refreshments | Standard |
| Chicago Explorer | $479 | Approx. 3.5 hours | 1 Carry-on, 1 Personal Item, 1 Checked Bag (up to 50 lbs) | Premium Wi-Fi, Expanded Beverage Menu, In-Flight Entertainment | Standard |
| Windy City Voyager (Best Value) | $549 | Approx. 3.5 hours | 1 Carry-on, 1 Personal Item, 2 Checked Bags (up to 50 lbs each) | Priority Boarding, Premium Wi-Fi, Full Meal Service, In-Flight Entertainment, Dedicated Service Line | Flexible Date Changes (fee may apply) |
| Chicago Premium Plus | $799 | Approx. 3.5 hours | 1 Carry-on, 1 Personal Item, 2 Checked Bags (up to 70 lbs each), Priority Baggage Handling | First Class Seating, Priority Boarding, Premium Wi-Fi, Full Meal Service, On-Demand Entertainment, Dedicated Concierge Service | Fully Flexible (no change fees) |
Early Bird Discount: Book your Key West to Chicago flights at least 30 days in advance and receive a 10% discount on any package. This offer is perfect for planning your trip ahead and saving significantly.
Weekend Getaway Special: Traveling to Chicago for a weekend escape? Book a Friday departure and Sunday return flight and enjoy complimentary in-flight meal upgrades on both legs of your journey. Valid for bookings made within 14 days of departure.
Business Class Upgrade: For a limited time, upgrade to our Chicago Premium Plus package for the price of the Windy City Voyager. Experience unparalleled comfort and service on your business trip. Offer valid for bookings made this month.
Group Travel Discount: Traveling with friends or family? Groups of 5 or more can receive a special discounted rate. Contact our dedicated group booking team to get a personalized quote and arrange your collective travel with ease.
1 Choose Your Package: Browse our detailed flight packages above. Consider your travel needs, budget, and desired amenities to select the perfect option for your trip from Key West to Chicago.
2 Book Online or Call: Visit our website to complete your booking securely online, or simply call our dedicated flight booking line at +1 (833) 902-2090. Our agents are ready to assist you.
3 Receive Confirmation: Once your booking is complete, you will receive an immediate email confirmation with all your flight details, itinerary, and important travel information.
4 Prepare for Departure: Arrive at Key West International Airport (EYW) with ample time before your scheduled departure. Our friendly staff will guide you through check-in and security for a smooth boarding process.
5 Enjoy Your Flight: Relax and enjoy your journey to Chicago. Our cabin crew is dedicated to making your flight comfortable and pleasant, offering excellent service throughout.
Don't miss out on our incredible offer for flights from Key West to Chicago! For a limited period, all bookings made for travel within the next 60 days will receive a complimentary upgrade to our premium in-flight entertainment system, allowing you to enjoy a wider selection of movies, music, and games during your flight. This is the perfect opportunity to experience the Rapido AIR difference at an even greater value. Secure your seat today and make your journey to Chicago an unforgettable one!
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Real feedback from customers who booked flights to
“Booked a last-minute flight to and was surprised by the price and service. Highly recommended!”
— Sarah M., Los Angeles
“I compared deals and RapidoAir beat them all. Easy booking and no hidden fees.”
— James R., Chicago
“Smooth checkout, helpful support, and flight updates right to my email. Perfect trip!”
— Anita S., New York
