$25 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.
$91 Roundtrip, just found
$91
Roundtrip
just found
MDW
Midway Intl.
MIA
Miami Intl.
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
ORD
O'Hare Intl.
EYW
Key West Intl.
$281 Roundtrip, found 19 hours ago
$281
Roundtrip
found 19 hours ago
RFD
Greater Rockford
MIA
Miami Intl.
$309 Roundtrip, found 1 day ago
$309
Roundtrip
found 1 day ago
Airfares from $25 One Way, $50 Round Trip from Chicago to Duck Key
Prices starting at $50 for return flights and $25 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
$50 Roundtrip, found 5 hours ago
$50
Roundtrip
found 5 hours ago
ORD
Chicago
MIA
Miami
$56 Roundtrip, just found
$56
Roundtrip
just found
MDW
Chicago
MIA
Miami
$63 Roundtrip, found 6 hours ago
$63
Roundtrip
found 6 hours ago
ORD
Chicago
EYW
Key West
$106 Roundtrip, just found
$106
Roundtrip
just found
ORD
Chicago
MIA
Miami
$131 Roundtrip, found 17 hours ago
$131
Roundtrip
found 17 hours ago
Duck Key economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Casablanca Miami Beach
5.8/10 (311 reviews)
Mar 8 - Mar 13
5 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Price was $1,161, price is now $624 per person
$624
per person
found 1 day ago
Very good for the price, Right on the beach, has a kitchen, Ocean view. Very easy check-in check-out. 1 -1/2 Block from Publix supermarket. 30 minutes from Miami International Airport. Will come again.
Reviewed on Apr 8, 2025
2.5-star property
Creekside Inn
8/10 Very Good! (1,004 reviews)
Mar 26 - Mar 30
4 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,333, price is now $698 per person
$698
per person
found 16 hours ago
I only stayed one night but overall, Creekside was better than I was expecting. For an old keys motel type inn, it was very clean and well kept.
Reviewed on Aug 2, 2025
3.5-star property
Cavalier Hotel South Beach
8.4/10 Very Good! (1,001 reviews)
Mar 11 - Mar 15
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • Coach
Miami (MIA) to Chicago (CHI)
Spirit Airlines • Coach
Save 100% on your flight
Price was $1,241, price is now $698 per person
$698
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything
Reviewed on Jan 3, 2026
Duck Key packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Crowne Plaza Hotel Fort Lauderdale Airport/Cruiseport by IHG
8.6/10 Excellent! (3,106 reviews)
Mar 11 - Mar 15
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • PremiumEconomy
Miami (MIA) to Chicago (CHI)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $851, price is now $568 per person
$568
per person
found 1 day ago
Girl at front desk was outstanding!
Reviewed on Jan 4, 2026
3.5-star property
Flow Fort Lauderdale Hotel
9/10 Wonderful! (560 reviews)
Mar 11 - Mar 15
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • PremiumEconomy
Miami (MIA) to Chicago (CHI)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,235, price is now $846 per person
$846
per person
found 1 day ago
We lived everything about this property from the amenities to the food and entertainment options within walking distance.
Reviewed on Jan 13, 2025
4.0-star property
Beachcomber Resort & Club
9/10 Wonderful! (2,028 reviews)
Mar 11 - Mar 15
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • PremiumEconomy
Miami (MIA) to Chicago (CHI)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,096, price is now $778 per person
$778
per person
found 1 day ago
Fabulous location, smartly appointed, great amenities (nice bar and restaurant), very reasonably priced. Would come back in a heartbeat.
Reviewed on Jan 9, 2026
Duck Key first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Hyatt Place Miami Airport-East
8.2/10 Very Good! (2,247 reviews)
Mar 23 - Mar 26
3 night stay
Chicago (ORD) to Miami (MIA)
Delta • Non-stop • FirstClass
Miami (MIA) to Chicago (ORD)
United • Non-stop • FirstClass
Price was $1,205, price is now $886 per person
$886
per person
found 2 hours ago
Breakfast and room carpets
Reviewed on Feb 1, 2026
2.5-star property
The Key West Hotel
9.2/10 Wonderful! (505 reviews)
Mar 27 - Mar 30
3 night stay
Chicago (ORD) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,847, price is now $2,208 per person
$2,208
per person
found 24 hours ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025
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
It has never been easier to find cheap Chicago to Duck Key flights. Orbitz has some of the best deals around to save you more money on your flight, hotel, and vacation package for the trip you have been waiting for.
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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.