$109 Cheap flight deals from Chicago (CHI) to Duck Key (MIA)
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This Weekend's Flight Deals from Chicago to Duck Key
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
O'Hare Intl.
MIA
Miami Intl.
$284 Roundtrip, just found
$284
Roundtrip
just found
MDW
Midway Intl.
MIA
Miami Intl.
$290 Roundtrip, found 4 days ago
$290
Roundtrip
found 4 days ago
ORD
O'Hare Intl.
EYW
Key West Intl.
$416 Roundtrip, found 6 days ago
$416
Roundtrip
found 6 days ago
RFD
Greater Rockford
MIA
Miami Intl.
$455 Roundtrip, found 3 days ago
$455
Roundtrip
found 3 days ago
Airfares from $109 One Way, $209 Round Trip from Chicago to Duck Key
Prices starting at $209 for return flights and $109 for one-way flights to Duck Key were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
MIA
Miami
$209 Roundtrip, found 2 hours ago
$209
Roundtrip
found 2 hours ago
MDW
Chicago
MIA
Miami
$237 Roundtrip, found 14 hours ago
$237
Roundtrip
found 14 hours ago
ORD
Chicago
EYW
Key West
$339 Roundtrip, found 3 hours ago
$339
Roundtrip
found 3 hours ago
ORD
Chicago
EYW
Key West
$352 Roundtrip, found 1 day ago
$352
Roundtrip
found 1 day ago
MDW
Chicago
EYW
Key West
$359 Roundtrip, found 1 day ago
$359
Roundtrip
found 1 day ago
Duck Key economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Solé Miami, A Noble House Resort
8.6/10 Excellent! (2,148 reviews)
Oct 15 - Oct 20
5 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $783, price is now $425 per person
$425
per person
found 2 days ago
It was our second time at Solé and we loved it again. Staff is kind and helpful. Good food and drinks. Will keep coming!
Reviewed on Sep 2, 2026
2.5-star property
Park Royal Miami Beach managed by Accor
8.8/10 Excellent! (191 reviews)
Oct 26 - Oct 31
5 night stay
Chicago (CHI) to Miami (MIA)
United • Roundtrip • Coach
Price was $1,132, price is now $529 per person
$529
per person
found 1 day ago
Had been to Ft. Lauderdale and wanted to check for a decent none night stay in Miami and found this hotel Thro Expedia . Expedia rated this high and happy that we chose this place . Nice location. 5 mins off the beach . The beach is just walkable from this hotel. Very good service . The guy in lobby was very helpful . There was a donminos pizza next door , which was very useful for kids.
Amenities were decent . They had an outdoor swimming pool . Slightly smaller .. there were 2-3 families swimming and it was almost full :) washer dryer worked but it was good .. elevator was small and sometimes slow . We didn’t find a gym. No complimentary breakfast.. parking was a bit wierd and cramped ! They charged per night which was slightly expensive .
The rooms were awesome ! It was good sized for the price . Also had a kitchen.. though we didn’t use the kitchen , it is very good to have , just incase . Bed was comfortable .. bathrooms were neat . Price wise I think this room was very good and value for money . Wanted to give 3 , but just for the room and pricing , I’m giving it a 4 . Good experience overall .
Reviewed on Sep 1, 2026
3.5-star property
Sea View Hotel, Bal Harbour, On The Ocean
8.4/10 Very Good! (1,005 reviews)
Oct 15 - Oct 20
5 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $858, price is now $462 per person
$462
per person
found 2 days ago
Great location... But property in serious need of refreshing... Got that old vibe and smell
Reviewed on Aug 31, 2026
Duck Key business class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Miami Beach
8.2/10 Very Good! (1,180 reviews)
Oct 18 - Oct 21
3 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,268, price is now $912 per person
$912
per person
found 1 day ago
I love the fact that was really close to the beach, the property is well maintained clean and all the amenities works. The property looks a little old but well kept. When we stayed there we heard a lot of noises even after quiet hours. Public transportation is right at the front door to go any places, we would stay there again.
Reviewed on Sep 3, 2026
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,625 reviews)
Oct 18 - Oct 21
3 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,491, price is now $2,320 per person
$2,320
per person
found 1 day ago
Amazing and I would stay again. The staff was wonderful from curb to end of stay. The room was spectacular and clean. Room service and bar areas were great. I don't know if I've ever felt so catered to.
Reviewed on Sep 2, 2026
Duck Key first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Ella's Cottages - Key West Historic Inns
9.4/10 Exceptional! (494 reviews)
Oct 22 - Oct 26
4 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,773, price is now $2,227 per person
$2,227
per person
found 1 day ago
It is located in the heart of he old district snd everything was so accessible without having to use our car. The property is only 1 block off Duval so,we had the advantage of,accessibility without the noise. The property is protected by foliage which makes it feel private and protected. The complimentary breakfast is lovely, and there is wine by the pool daily. Dwight welcomes guests upon arrival,and made us feel,at home. The beds are so comfy, and each cottage has its own flavor. I hope to return and stay at Ella’s Cottages again, Expedia does a great job helping us narrow down our priorities, amenities, location, etc. That enabled us to find Ella’s Cottages, which was perfect for us.
Reviewed on Sep 1, 2026
3.0-star property
The Key West Hotel
9.2/10 Wonderful! (562 reviews)
Oct 22 - Oct 26
4 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $6,335, price is now $4,373 per person
$4,373
per person
found 1 day ago
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026
More About Flying To Duck Key from Chicago
Route Information for Flights from Chicago to Duck Key
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Duck Key
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Orbitz Flights Fit Around Your Lifestyle
Orbitz understands that you don’t necessarily want to fly at 5:00 a.m—and that sometimes you do. This is why we allow you to find the best Chicago to Duck Key flights at the times you want with ease.
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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.