$42 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, Jun 27 - Tue, Jun 30
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$277 Roundtrip, found 2 hours ago
$277
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Jun 27 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Jun 30, priced at $277 found 2 hours ago
Sat, Jun 27 - Tue, Jun 30
MDW
Midway Intl.
MIA
Miami Intl.
$312 Roundtrip, found 4 hours ago
$312
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Jun 27 from Midway Intl. to Miami Intl., returning Tue, Jun 30, priced at $312 found 4 hours ago
Sat, Jun 27 - Tue, Jun 30
RFD
Greater Rockford
MIA
Miami Intl.
$392 Roundtrip, found 1 day ago
$392
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jun 27 from Greater Rockford to Miami Intl., returning Tue, Jun 30, priced at $392 found 1 day ago
Sat, Jun 27 - Mon, Jun 29
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$397 Roundtrip, found 1 hour ago
$397
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jun 27 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Jun 29, priced at $397 found 1 hour ago

Airfares from $42 One Way, $82 Round Trip from Chicago to Key Biscayne

Prices starting at $82 for return flights and $42 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.

Tue, Sep 1 - Sat, Sep 5
ORD
Chicago
FLL
Fort Lauderdale
$82 Roundtrip, found 1 hour ago
$82
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Sep 1 from Chicago to Fort Lauderdale, returning Sat, Sep 5, priced at $82 found 1 hour ago
Sat, Aug 1 - Sat, Aug 8
RFD
Rockford
MIA
Miami
$171 Roundtrip, found 12 hours ago
$171
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sat, Aug 1 from Rockford to Miami, returning Sat, Aug 8, priced at $171 found 12 hours ago
Sat, Sep 12 - Sat, Sep 19
MDW
Chicago
FLL
Fort Lauderdale
$171 Roundtrip, found 15 hours ago
$171
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sat, Sep 12 from Chicago to Fort Lauderdale, returning Sat, Sep 19, priced at $171 found 15 hours ago
Wed, Aug 5 - Tue, Aug 11
ORD
Chicago
MIA
Miami
$171 Roundtrip, found 1 hour ago
$171
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Aug 5 from Chicago to Miami, returning Tue, Aug 11, priced at $171 found 1 hour ago
Wed, Aug 5 - Tue, Aug 11
ORD
Chicago
MIA
Miami
$171 Roundtrip, found 1 hour ago
$171
Roundtrip
found 1 hour ago
Select United flight, departing Wed, Aug 5 from Chicago to Miami, returning Tue, Aug 11, priced at $171 found 1 hour ago

Key Biscayne economy flight packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.6/10 Excellent! (1,002 reviews)

Aug 11 - Aug 16

5 night stay

Chicago (CHI) to Miami (MIA)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,131, price is now $560 per person
$560
per person
found 2 days ago
Staff was great, elevator is tired, but I loved the proximity to everything

Reviewed on Jan 3, 2026

The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

8/10 Very Good! (1 review)

Aug 15 - Aug 20

5 night stay

Chicago (CHI) to Miami (MIA)

Southwest Airlines • Coach

Miami (MIA) to Chicago (CHI)

American Airlines • Coach
Price was $16,234, price is now $7,534 per person
$7,534
per person
found 1 day ago
Andaz Miami Beach Resort & Spa
5.0-star property

Andaz Miami Beach Resort & Spa

9/10 Wonderful! (312 reviews)

Aug 11 - Aug 16

5 night stay

Chicago (CHI) to Miami (MIA)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,098, price is now $584 per person
$584
per person
found 2 days ago
Clean, soothing, upscale, excellent amenities

Reviewed on Mar 26, 2026

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Key Biscayne business class flight packages

Price found within the past 48 hours. Click for updated prices.
The Sunny
4.0-star property

The Sunny

8.8/10 Excellent! (387 reviews)

Jul 30 - Aug 3

4 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,108, price is now $860 per person
$860
per person
found 1 day ago
This was our first time staying at The Sunny, but are very familiar with the area. My father lives a few blocks away and over the years we have sampled several of the loca properties. The transformation from the Newport to the Sunny is remarkable. The rooms are beautiful. The lobby is incredible. The real key is the pool deck. Most of the competition close by have very small pools, which are largely in the shade of the building. Not here. This is wonderful. The staff is top notch. Very well trained and they really go out of their way to make everything just right. I would say the hotel is 90% done. Still waiting for the restaurant to open. That will also enhance the poolside dining options as well. Go, you won’t regret it.

Reviewed on Apr 8, 2026

Fontainebleau Miami Beach
4.5-star property

Fontainebleau Miami Beach

8.4/10 Very Good! (8,366 reviews)

Jul 30 - Aug 3

4 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,428, price is now $1,047 per person
$1,047
per person
found 1 day ago
Overall experience was great! However, they need to fire the current house keeping. They’re lazy and you walk into a dirty room with stains and hair everywhere . Thank God they upgraded me to a one bedroom suite which made me give them a 5 star. There were dozens of people complaining of dirty rooms. Fire management if they cannot hire quality housekeepers.

Reviewed on Jun 2, 2026

Eden Roc Miami Beach
4.5-star property

Eden Roc Miami Beach

8.6/10 Excellent! (3,291 reviews)

Jul 30 - Aug 3

4 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,357, price is now $1,049 per person
$1,049
per person
found 1 day ago
Very communicative hotel. Super friendly and professional

Reviewed on Mar 8, 2026

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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.