$86 Cheap flight deals from Chicago (CHI) to Florida Keys (MIA)

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This Weekend's Flight Deals from Chicago to Florida Keys

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.

Fri, Jul 17 - Wed, Jul 22
MDW
Midway Intl.
MIA
Miami Intl.
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jul 17 from Midway Intl. to Miami Intl., returning Wed, Jul 22, priced at $317 found 2 days ago
Fri, Jul 17 - Wed, Jul 22
ORD
O'Hare Intl.
MIA
Miami Intl.
$317 Roundtrip, found 4 hours ago
$317
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Jul 17 from O'Hare Intl. to Miami Intl., returning Wed, Jul 22, priced at $317 found 4 hours ago
Fri, Jul 17 - Mon, Jul 20
ORD
O'Hare Intl.
EYW
Key West Intl.
$523 Roundtrip, found 9 hours ago
$523
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Fri, Jul 17 from O'Hare Intl. to Key West Intl., returning Mon, Jul 20, priced at $523 found 9 hours ago
Sun, Jul 19 - Fri, Jul 24
RFD
Greater Rockford
MIA
Miami Intl.
$646 Roundtrip, found 3 days ago
$646
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Jul 19 from Greater Rockford to Miami Intl., returning Fri, Jul 24, priced at $646 found 3 days ago

Airfares from $86 One Way, $171 Round Trip from Chicago to Florida Keys

Prices starting at $171 for return flights and $86 for one-way flights to Florida Keys 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, Oct 14 - Sat, Oct 17
ORD
Chicago
MIA
Miami
$171 Roundtrip, found 7 hours ago
$171
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, Oct 14 from Chicago to Miami, returning Sat, Oct 17, priced at $171 found 7 hours ago
Mon, Sep 14 - Thu, Sep 17
MDW
Chicago
MIA
Miami
$171 Roundtrip, found 2 hours ago
$171
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, Sep 14 from Chicago to Miami, returning Thu, Sep 17, priced at $171 found 2 hours ago
Thu, Aug 27 - Mon, Aug 31
ORD
Chicago
MIA
Miami
$175 Roundtrip, found 15 hours ago
$175
Roundtrip
found 15 hours ago
Select United flight, departing Thu, Aug 27 from Chicago to Miami, returning Mon, Aug 31, priced at $175 found 15 hours ago
Thu, Aug 6 - Mon, Aug 10
RFD
Rockford
MIA
Miami
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Aug 6 from Rockford to Miami, returning Mon, Aug 10, priced at $207 found 2 days ago
Wed, Aug 5 - Wed, Aug 12
ORD
Chicago
MIA
Miami
$210 Roundtrip, found 12 hours ago
$210
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, Aug 5 from Chicago to Miami, returning Wed, Aug 12, priced at $210 found 12 hours ago

Florida Keys economy flight packages

Price found within the past 48 hours. Click for updated prices.
Andaz Miami Beach Resort & Spa
5.0-star property

Andaz Miami Beach Resort & Spa

9/10 Wonderful! (320 reviews)

Aug 27 - Sep 2

6 night stay

Chicago (CHI) to Miami (MIA)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,118, price is now $605 per person
$605
per person
found 1 day ago
Smaller boutique property, which we loved. More personal than larger chain property. Would certainly return.

Reviewed on Jul 11, 2026

Nobu Hotel Miami Beach
5.0-star property

Nobu Hotel Miami Beach

8.6/10 Excellent! (1,415 reviews)

Aug 27 - Sep 2

6 night stay

Chicago (CHI) to Miami (MIA)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,468, price is now $806 per person
$806
per person
found 1 day ago
Our room was not ready when we arrived due to water issues at the hotel. We were relocated to a room at the hotel next door, which was in poor condition. The room was dirty, and the sink was clogged with standing water. We had to stay there for approximately four days, which was a very disappointing experience. We received only $200 in compensation, which did not come close to covering the difference in value or the inconvenience we experienced. We paid significantly more for our stay at Nobu than what we received in return, and the hotel was unwilling to adjust the rate to reflect the accommodations at the neighboring hotel. Overall, we were very disappointed with how the situation was handled and with the level of customer service. Unfortunately, we will not be returning.

Reviewed on Jul 8, 2026

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,577 reviews)

Aug 27 - Sep 2

6 night stay

Chicago (CHI) to Miami (MIA)

United • Roundtrip • Coach
Save 100% on your flight
Price was $2,686, price is now $1,506 per person
$1,506
per person
found 1 day ago
I expected a true five-star experience, but unfortunately my stay fell well below that standard. The room was consistently too warm at night. It felt as though the air conditioning was intentionally limited and never reached a comfortable sleeping temperature, giving the impression that energy savings were prioritized over guest comfort. The service at both the rooftop and third-floor pools was disappointing. Staff were inattentive and not customer-focused. Our second round of drinks took over an hour to arrive with no communication or follow-up from the server. On another occasion, an employee dropped an entire tray, and a full can of Coke struck me while I was in the pool, staining my cap. While accidents happen, the overall attitude of the staff lacked professionalism and genuine hospitality. It often felt like they were simply doing a job rather than caring about the guest experience. Is this really what is considered a five-star hotel? Based on my experience, the level of service, attention to detail, and accountability fell far short of what guests should expect from a property of this caliber.

Reviewed on Jul 11, 2026

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Florida Keys first class flight packages

Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Miami Beach
5.0-star property

Nobu Hotel Miami Beach

8.6/10 Excellent! (1,415 reviews)

Aug 16 - Aug 19

3 night stay

Chicago (CHI) to Miami (MIA)

United • FirstClass

Miami (MIA) to Chicago (CHI)

Delta • FirstClass
Price was $1,452, price is now $1,193 per person
$1,193
per person
found 9 hours ago
Our room was not ready when we arrived due to water issues at the hotel. We were relocated to a room at the hotel next door, which was in poor condition. The room was dirty, and the sink was clogged with standing water. We had to stay there for approximately four days, which was a very disappointing experience. We received only $200 in compensation, which did not come close to covering the difference in value or the inconvenience we experienced. We paid significantly more for our stay at Nobu than what we received in return, and the hotel was unwilling to adjust the rate to reflect the accommodations at the neighboring hotel. Overall, we were very disappointed with how the situation was handled and with the level of customer service. Unfortunately, we will not be returning.

Reviewed on Jul 8, 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 16 - Aug 19

3 night stay

Chicago (CHI) to Miami (MIA)

United • FirstClass

Miami (MIA) to Chicago (CHI)

Delta • FirstClass
Price was $9,277, price is now $5,249 per person
$5,249
per person
found 9 hours ago
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,577 reviews)

Aug 16 - Aug 19

3 night stay

Chicago (CHI) to Miami (MIA)

United • FirstClass

Miami (MIA) to Chicago (CHI)

Delta • FirstClass
Price was $1,935, price is now $1,495 per person
$1,495
per person
found 9 hours ago
I expected a true five-star experience, but unfortunately my stay fell well below that standard. The room was consistently too warm at night. It felt as though the air conditioning was intentionally limited and never reached a comfortable sleeping temperature, giving the impression that energy savings were prioritized over guest comfort. The service at both the rooftop and third-floor pools was disappointing. Staff were inattentive and not customer-focused. Our second round of drinks took over an hour to arrive with no communication or follow-up from the server. On another occasion, an employee dropped an entire tray, and a full can of Coke struck me while I was in the pool, staining my cap. While accidents happen, the overall attitude of the staff lacked professionalism and genuine hospitality. It often felt like they were simply doing a job rather than caring about the guest experience. Is this really what is considered a five-star hotel? Based on my experience, the level of service, attention to detail, and accountability fell far short of what guests should expect from a property of this caliber.

Reviewed on Jul 11, 2026

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More About Flying To Florida Keys from Chicago

Route Information for Flights from Chicago to Florida Keys

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

Chicago to Florida Keys

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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.