$30 Cheap flight deals from Chicago (CHI) to Duck Key (MIA)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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.
MDW
Midway Intl.
MIA
Miami Intl.
$384 Roundtrip, found 16 hours ago
$384
Roundtrip
found 16 hours ago
RFD
Greater Rockford
MIA
Miami Intl.
$477 Roundtrip, found 4 days ago
$477
Roundtrip
found 4 days ago
ORD
O'Hare Intl.
MIA
Miami Intl.
$502 Roundtrip, just found
$502
Roundtrip
just found
ORD
O'Hare Intl.
EYW
Key West Intl.
$740 Roundtrip, found 2 hours ago
$740
Roundtrip
found 2 hours ago
Airfares from $30 One Way, $59 Round Trip from Chicago to Duck Key
Prices starting at $59 for return flights and $30 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.
MDW
Chicago
MIA
Miami
$59 Roundtrip, found 6 hours ago
$59
Roundtrip
found 6 hours ago
ORD
Chicago
MIA
Miami
$61 Roundtrip, just found
$61
Roundtrip
just found
ORD
Chicago
MIA
Miami
$157 Roundtrip, found 5 hours ago
$157
Roundtrip
found 5 hours ago
ORD
Chicago
MIA
Miami
$157 Roundtrip, found 5 hours ago
$157
Roundtrip
found 5 hours ago
RFD
Rockford
MIA
Miami
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Duck Key economy flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Creekside Inn
8/10 Very Good! (1,004 reviews)
Feb 12 - Feb 15
3 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • Coach
Price was $948, price is now $432 per person
$432
per person
found 1 day 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
4.0-star property
Pelican Hotel
9.2/10 Wonderful! (394 reviews)
Feb 5 - Feb 9
4 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Price was $1,189, price is now $509 per person
$509
per person
found 1 day ago
My recent stay at the Pelican Hotel was nothing short of delightful. The location is truly exceptional — perfectly situated to enjoy the very best of the area. From the moment I arrived, the warm and friendly atmosphere made me feel completely at ease.
The service was impeccable. Both room service and management were consistently professional and courteous, with special appreciation to Oscar, whose attentiveness and genuine hospitality made a lasting impression.
The dining experience was outstanding. Every meal was a pleasure, but the fried octopus deserves special mention — perfectly prepared and absolutely unforgettable.
The rooms themselves were a highlight: comfortable, thoughtfully appointed, and each with its own unique design that adds charm and character to the stay. The complimentary cocktails were another memorable touch — expertly made and thoroughly enjoyable.
Overall, my time at the Pelican Hotel was a wonderful experience from start to finish. I look forward to returning and will gladly book again without hesitation.
Reviewed on Aug 11, 2025
Duck Key first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Lighthouse Hotel - Key West Historic Inns
9/10 Wonderful! (831 reviews)
Feb 13 - Feb 16
3 night stay
Chicago (ORD) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,520, price is now $1,888 per person
$1,888
per person
found 1 day ago
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval
Reviewed on Sep 22, 2024
2.5-star property
The Key West Hotel
9.2/10 Wonderful! (505 reviews)
Feb 13 - Feb 16
3 night stay
Chicago (ORD) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $3,124, price is now $2,195 per person
$2,195
per person
found 1 day 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
3.5-star property
Ella's Cottages - Key West Historic Inns
9.4/10 Exceptional! (390 reviews)
Feb 13 - Feb 16
3 night stay
Chicago (ORD) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,746, price is now $2,016 per person
$2,016
per person
found 1 day ago
We chose this historic inn based on central location to everything we wanted in less than 15 min. Front desk staff (Dwight and others) are fantastic and always willing to listen and provide assistance. Fort Zachary Taylor Beach Park is walkable - 25 min (beach water shoes recommended due to rocks). We didn't need to rent any transportation as it was easier for us to walk it out, so I can't comment on parking since I didn't use it (it is limited at most places). We felt very safe walking around, even at night. We used a taxi to and from Key West airport (both drivers familiar with this inn). Room is clean. Both night stands have power and USB charging outlets. Excellent daily room service and Sunshine Breakfast basket hand delivered to your room. Duval Loop bus stop 14 (free) in front of inn (bus route loop is an hour long and two buses running to ensure next bus in 30 min), so this is another convenient option if walking isn't your thing.
Reviewed on Dec 17, 2024
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 can be tedious to sift through pages of Internet search results to find those bargain fares on flights from Chicago to Duck Key and hotels, but at Orbitz, everything you need is in one place. Our guaranteed low prices on Chicago to Duck Key flights mean we are a leader when it comes to giving you great online deals on air fare and hotels.
Huge savings with little effort
Whether you are traveling for pleasure or business, you can use Orbitz to find cheap Chicago to Duck Key flights, together with low-cost accommodations. We pride ourselves on offering you excellent deals that fit your schedule and budget needs.
Unbeatable low fare flights from Chicago to Duck Key
Domestic or international travel presents no obstacles to us. We give you unbeatable bargains on flights from Chicago to Duck Key. Enjoy huge savings on your flight, which can be better used elsewhere on your trip.
Grab that cheap deal on the move
Our innovative and cutting-edge mobile tools make it easy to search or booking cheap flights from Chicago to Duck Key while on the move, via our app for the iPhone, iPad, or Android-based devices. We can also send you instant alerts through email or text messaging if there any delays to your flight.
Orbitz means low-cost trip-planning made easy
Low-cost Chicago to Duck Key flights can be booked with total confidence through Orbitz every time. We also make it very easy to cancel flights or other travel arrangements online should you need to. You can also add activities and car rentals to your flight or hotel reservation for a hassle-free trip.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to London
- Chicago to New Orleans
- Chicago to Washington
- Chicago to Rome
- Chicago to Paris
- Chicago to Toronto
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
More Destinations
- Flights from Chicago to Key Colony Beach
- Flights from Memphis to Key Colony Beach
- Flights from Minneapolis - St. Paul to Key Colony Beach
- Flights from New York to Key Colony Beach
- Flights from Quito to Key Colony Beach
- Flights from Allentown (ABE) to Marathon (MTH)
- Flights from Albuquerque (ABQ) to Marathon (MTH)
- Flights from Izmir (ADB) to Marathon (MTH)
- Flights from Pittsburgh (AGC) to Marathon (MTH)
- Flights from Alpena (APN) to Marathon (MTH)
- Flights from Atlanta (ATL) to Marathon (MTH)
- Flights from Austin (AUS) to Marathon (MTH)
- Flights from Asheville (AVL) to Marathon (MTH)
- Flights from Mesa (AZA) to Marathon (MTH)
- Flights from Kalamazoo (AZO) to Marathon (MTH)
- Flights from Hartford (BDL) to Marathon (MTH)
- Flights from Billings (BIL) to Marathon (MTH)
- Flights from Nashville (BNA) to Marathon (MTH)
- Flights from Brainerd (BRD) to Marathon (MTH)
- Flights from Baltimore (BWI) to Marathon (MTH)
- Flights from Columbia (CAE) to Marathon (MTH)
- Flights from Chattanooga (CHA) to Marathon (MTH)
- Flights from Charleston (CHS) to Marathon (MTH)
- Flights from Cleveland (CLE) to Marathon (MTH)
- Flights from Charlotte (CLT) to Marathon (MTH)
- Flights from Columbus (CMH) to Marathon (MTH)
- Flights from Champaign (CMI) to Marathon (MTH)
- Flights from Mosinee (CWA) to Marathon (MTH)
- Flights from Washington (DCA) to Marathon (MTH)
- Flights from Dodge City (DDC) to Marathon (MTH)
- Flights from Denver (DEN) to Marathon (MTH)
- Flights from Dallas (DFW) to Marathon (MTH)
- Flights from Des Moines (DSM) to Marathon (MTH)
- Flights from Detroit (DTW) to Marathon (MTH)
- Flights from Newark Liberty Intl. Airport (EWR) to Marathon (MTH)
- Flights from Key West (EYW) to Marathon (MTH)
- Flights from Fargo (FAR) to Marathon (MTH)
- Flights from Flint (FNT) to Marathon (MTH)
- Flights from Fort Wayne (FWA) to Marathon (MTH)
- Flights from Spokane (GEG) to Marathon (MTH)
- Flights from Gainesville (GNV) to Marathon (MTH)
- Flights from Gulfport (GPT) to Marathon (MTH)
- Flights from Green Bay (GRB) to Marathon (MTH)
- Flights from Grand Rapids (GRR) to Marathon (MTH)
- Flights from Greenville (GSP) to Marathon (MTH)
- Flights from Huntsville (HSV) to Marathon (MTH)
- Flights from Washington (IAD) to Marathon (MTH)
- Flights from Indianapolis (IND) to Marathon (MTH)
- Flights from Jacksonville (JAX) to Marathon (MTH)
- Flights from New York (JFK) to Marathon (MTH)
- Flights from Los Alamos (LAM) to Marathon (MTH)
- Flights from Las Vegas (LAS) to Marathon (MTH)
- Flights from Lake Charles (LCH) to Marathon (MTH)
- Flights from Leesburg (LEE) to Marathon (MTH)
- Flights from Lexington (LEX) to Marathon (MTH)
- Flights from La Crosse (LSE) to Marathon (MTH)
- Flights from Majuro (MAJ) to Marathon (MTH)
- Flights from Kansas City (MCI) to Marathon (MTH)
- Flights from Orlando (MCO) to Marathon (MTH)
- Flights from Melbourne (MLB) to Marathon (MTH)
- Flights from Monroe (MLU) to Marathon (MTH)
- Flights from Morristown (MMU) to Marathon (MTH)
- Flights from Mobile (MOB) to Marathon (MTH)
- Flights from Madison (MSN) to Marathon (MTH)
- Flights from Minneapolis (MSP) to Marathon (MTH)
- Flights from New Orleans (MSY) to Marathon (MTH)
- Flights from Oklahoma City (OKC) to Marathon (MTH)
- Flights from Miami (OPF) to Marathon (MTH)
- Flights from Chicago (ORD) to Marathon (MTH)
- Flights from West Palm Beach (PBI) to Marathon (MTH)
- Flights from Philadelphia (PHL) to Marathon (MTH)
- Flights from Phoenix (PHX) to Marathon (MTH)
- Flights from St. Petersburg (PIE) to Marathon (MTH)
- Flights from Pittsburgh (PIT) to Marathon (MTH)
- Flights from Pensacola (PNS) to Marathon (MTH)
- Flights from Chicago (PWK) to Marathon (MTH)
- Flights from Portland (PWM) to Marathon (MTH)
- Flights from Richmond (RIC) to Marathon (MTH)
- Flights from San Diego (SAN) to Marathon (MTH)
- Flights from San Antonio (SAT) to Marathon (MTH)
- Flights from Savannah (SAV) to Marathon (MTH)
- Flights from Salisbury (SBY) to Marathon (MTH)
- Flights from Seattle (SEA) to Marathon (MTH)
- Flights from Sebring (SEF) to Marathon (MTH)
- Flights from Orlando (SFB) to Marathon (MTH)
- Flights from Weyers Cave (SHD) to Marathon (MTH)
- Flights from Shreveport (SHV) to Marathon (MTH)
- Flights from Sacramento (SMF) to Marathon (MTH)
- Flights from Shannon (SNN) to Marathon (MTH)
- Flights from Sarasota (SRQ) to Marathon (MTH)
- Flights from Sun Valley (SUN) to Marathon (MTH)
- Flights from Newburgh (SWF) to Marathon (MTH)
- Flights from Syracuse (SYR) to Marathon (MTH)
- Flights from Tallahassee (TLH) to Marathon (MTH)
- Flights from Tampa (TPA) to Marathon (MTH)
- Flights from Tri-Cities (TRI) to Marathon (MTH)
- Flights from Tucson (TUS) to Marathon (MTH)
- Flights from St. Augustine (UST) to Marathon (MTH)
- Flights from Fayetteville (XNA) to Marathon (MTH)
- Flights from Cockburn Harbour (XSC) to Marathon (MTH)
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.