$26 Cheap flight deals from Chicago (CHI) to Key Biscayne (MIA)

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This Weekend's Flight Deals from Chicago to Key Biscayne

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, Dec 27 - Tue, Jan 13
ORD
O'Hare Intl.
MIA
Miami Intl.
$338 Roundtrip, just found
$338
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Dec 27 from O'Hare Intl. to Miami Intl., returning Tue, Jan 13, priced at $338 just found
Sun, Dec 28 - Wed, Dec 31
MDW
Midway Intl.
MIA
Miami Intl.
$348 Roundtrip, found 5 hours ago
$348
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sun, Dec 28 from Midway Intl. to Miami Intl., returning Wed, Dec 31, priced at $348 found 5 hours ago
Sat, Dec 27 - Mon, Dec 29
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$486 Roundtrip, just found
$486
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Dec 27 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Dec 29, priced at $486 just found
Sat, Dec 27 - Wed, Dec 31
RFD
Greater Rockford
FLL
Fort Lauderdale - Hollywood Intl.
$506 Roundtrip, found 1 day ago
$506
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Dec 27 from Greater Rockford to Fort Lauderdale - Hollywood Intl., returning Wed, Dec 31, priced at $506 found 1 day ago

Airfares from $26 One Way, $51 Round Trip from Chicago to Key Biscayne

Prices starting at $51 for return flights and $26 for one-way flights to Key Biscayne were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Jan 28 - Wed, Feb 11
ORD
Chicago
FLL
Fort Lauderdale
$51 Roundtrip, just found
$51
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jan 28 from Chicago to Fort Lauderdale, returning Wed, Feb 11, priced at $51 just found
Sun, Feb 22 - Thu, Feb 26
MDW
Chicago
MIA
Miami
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Feb 22 from Chicago to Miami, returning Thu, Feb 26, priced at $58 found 1 day ago
Mon, Feb 23 - Fri, Feb 27
ORD
Chicago
MIA
Miami
$58 Roundtrip, found 18 hours ago
$58
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Chicago to Miami, returning Fri, Feb 27, priced at $58 found 18 hours ago
Wed, Feb 11 - Wed, Feb 18
MDW
Chicago
FLL
Fort Lauderdale
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Feb 11 from Chicago to Fort Lauderdale, returning Wed, Feb 18, priced at $128 found 2 days ago
Sun, Jan 18 - Wed, Jan 28
ORD
Chicago
FLL
Fort Lauderdale
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select United flight, departing Sun, Jan 18 from Chicago to Fort Lauderdale, returning Wed, Jan 28, priced at $144 found 1 day ago

Key Biscayne economy flight packages

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 19 - Feb 22

3 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $948, price is now $426 per person
$426
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

Hawks Cay Resort
4.0-star property

Hawks Cay Resort

8/10 Very Good! (1,003 reviews)

Feb 19 - Feb 22

3 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $1,323, price is now $660 per person
$660
per person
found 1 day ago
Front desk service was exceptional!! Thank you Ashley & Kim for assisting us on this last minute reservation.

Reviewed on Mar 21, 2025

Flow Miami Hotel
3.5-star property

Flow Miami Hotel

9.2/10 Wonderful! (172 reviews)

Feb 14 - Feb 22

8 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $2,920, price is now $1,549 per person
$1,549
per person
found 1 day ago
INCREDIBLE! The front desk girls are amazing. They were so friendly and held our luggage while we went and explored. They even let us hang out by the pool until our room was ready. Our room was on the 43rd floor and it was so clean and perfect. We loved everything about this hotel. We can’t wait to be back for Ultra Miami 2026. It’s in super close proximity to anything you would want. Only a 7 min walk to the Ultra festival. This hotel is perfect!

Reviewed on Apr 6, 2025

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Key Biscayne first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sugarloaf Key Hotel at KOA Resort
3.0-star property

Sugarloaf Key Hotel at KOA Resort

9.8/10 Exceptional! (456 reviews)

Jan 28 - Jan 31

3 night stay

Chicago (ORD) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $1,527, price is now $1,316 per person
$1,316
per person
found 20 hours ago
Great campground with vacation rental access. Water sport activities for rent and a short drive to key west. Camp store and pub on site as well!

Reviewed on Mar 27, 2025

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,365 reviews)

Feb 6 - Feb 10

4 night stay

Chicago (CHI) to Miami (MIA)

Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,455, price is now $2,723 per person
$2,723
per person
found 1 day ago
This property is amazing. Food was great, staff was friendly and welcoming. We enjoyed our stay.

Reviewed on Jun 10, 2025

Barnacle Resort
3.0-star property

Barnacle Resort

8.2/10 Very Good! (40 reviews)

Jan 28 - Jan 31

3 night stay

Chicago (ORD) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $1,547, price is now $1,353 per person
$1,353
per person
found 20 hours ago
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More About Flying To Key Biscayne from Chicago

Route Information for Flights from Chicago to Key Biscayne

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

Chicago to Key Biscayne

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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.