$29 Cheap flight deals from Chicago (CHI) to Fleming Key (MIA)

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This Weekend's Flight Deals from Chicago to Fleming 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.

Sat, Jan 3 - Fri, Jan 9
MDW
Midway Intl.
MIA
Miami Intl.
$190 Roundtrip, found 1 hour ago
$190
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jan 3 from Midway Intl. to Miami Intl., returning Fri, Jan 9, priced at $190 found 1 hour ago
Sat, Jan 3 - Fri, Jan 9
ORD
O'Hare Intl.
MIA
Miami Intl.
$204 Roundtrip, found 1 hour ago
$204
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Jan 3 from O'Hare Intl. to Miami Intl., returning Fri, Jan 9, priced at $204 found 1 hour ago
Sun, Jan 4 - Sun, Jan 18
ORD
O'Hare Intl.
EYW
Key West Intl.
$408 Roundtrip, found 1 day ago
$408
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jan 4 from O'Hare Intl. to Key West Intl., returning Sun, Jan 18, priced at $408 found 1 day ago
Sat, Jan 3 - Sat, Jan 17
MDW
Midway Intl.
EYW
Key West Intl.
$428 Roundtrip, found 2 days ago
$428
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jan 3 from Midway Intl. to Key West Intl., returning Sat, Jan 17, priced at $428 found 2 days ago

Airfares from $29 One Way, $58 Round Trip from Chicago to Fleming Key

Prices starting at $58 for return flights and $29 for one-way flights to Fleming 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.

Mon, Feb 16 - Fri, Feb 27
ORD
Chicago
MIA
Miami
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Feb 16 from Chicago to Miami, returning Fri, Feb 27, priced at $58 found 1 hour ago
Sun, Feb 15 - Thu, Feb 19
MDW
Chicago
MIA
Miami
$59 Roundtrip, found 5 hours ago
$59
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Feb 15 from Chicago to Miami, returning Thu, Feb 19, priced at $59 found 5 hours ago
Tue, Jan 20 - Sat, Jan 31
ORD
Chicago
MIA
Miami
$67 Roundtrip, found 1 day ago
$67
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jan 20 from Chicago to Miami, returning Sat, Jan 31, priced at $67 found 1 day ago
Wed, Feb 4 - Sat, Feb 14
RFD
Rockford
MIA
Miami
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Feb 4 from Rockford to Miami, returning Sat, Feb 14, priced at $157 found 2 hours ago
Sun, Feb 1 - Wed, Feb 4
ORD
Chicago
MIA
Miami
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Select United flight, departing Sun, Feb 1 from Chicago to Miami, returning Wed, Feb 4, priced at $157 found 3 hours ago

Fleming Key economy flight packages

Price found within the past 48 hours. Click for updated prices.
President Hotel Villa
3.5-star property

President Hotel Villa

8.2/10 Very Good! (997 reviews)

Feb 23 - Feb 27

4 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Roundtrip • Coach
Price was $772, price is now $373 per person
$373
per person
found 1 day ago
Although we didn't take advantage of it enough the hotel served breakfast every morning. Front desk staff awesome and very accommodating. A few times we had minor issues in our room and front desk staff would have maintenance up to our room in a matter of minutes. Minor drawback. A lot of hotel staff seemed not to know how to speak english well but front desk would let maintenance know the exact problem we were having and when they would arrive to our room we didnt need to talk that much because front desk already gave them the run down. I think hotel is in the best section of south beach. Beach 1 block away and walgreens across the street.

Reviewed on Apr 11, 2025

Creekside Inn
2.5-star property

Creekside Inn

8/10 Very Good! (1,004 reviews)

Feb 7 - Feb 11

4 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $1,201, price is now $479 per person
$479
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

Pelican Hotel
4.0-star property

Pelican Hotel

9.2/10 Wonderful! (394 reviews)

Feb 4 - Feb 8

4 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $1,193, price is now $568 per person
$568
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

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Fleming Key packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Creekside Inn
2.5-star property

Creekside Inn

8/10 Very Good! (1,004 reviews)

Feb 5 - Feb 11

6 night stay

Chicago (ORD) to Miami (MIA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,027, price is now $1,022 per person
$1,022
per person
found 10 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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3.5-star property

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

9/10 Wonderful! (108 reviews)

Feb 5 - Feb 11

6 night stay

Chicago (ORD) to Miami (MIA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,484, price is now $1,645 per person
$1,645
per person
found 10 hours ago
Waterfront House with Boat Dock
5.0-star property

Waterfront House with Boat Dock

6/10 (1 review)

Feb 5 - Feb 11

6 night stay

Chicago (ORD) to Miami (MIA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,272, price is now $1,559 per person
$1,559
per person
found 10 hours ago
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Fleming Key first class flight packages

Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach
3.0-star property

Casablanca Miami Beach

5.8/10 (311 reviews)

Feb 3 - Feb 10

7 night stay

Chicago (CHI) to Miami (MIA)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,036, price is now $1,197 per person
$1,197
per person
just found
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

Solé Miami, A Noble House Resort
4.0-star property

Solé Miami, A Noble House Resort

8.4/10 Very Good! (1,935 reviews)

Feb 3 - Feb 10

7 night stay

Chicago (CHI) to Miami (MIA)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,784, price is now $1,687 per person
$1,687
per person
found 7 hours ago
Everything was just great.

Reviewed on Dec 27, 2025

Park Central South Beach
4.0-star property

Park Central South Beach

8.6/10 Excellent! (385 reviews)

Feb 3 - Feb 10

7 night stay

Chicago (CHI) to Miami (MIA)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,252, price is now $1,374 per person
$1,374
per person
found 5 hours ago
There were quite a few issues — the bathroom door and the safe were broken, the beach chairs on the beach couldn’t be used, and we had to carry folding chairs and towels provided by the hotel down to the beach. There was also only one slow elevator, and even though we booked Park Central, we were actually put in the building next door. Still, the staff were all friendly and helpful, the room was clean, and the breakfast was good.

Reviewed on Dec 23, 2025

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More About Flying To Fleming Key from Chicago

Route Information for Flights from Chicago to Fleming Key

Origin Airport IATA Code
CHI
Destination Airport IATA Code
MIA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Fleming Key

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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.