$76 Cheap flight deals from Chicago (CHI) to Key Colony Beach (MIA)
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This Weekend's Flight Deals from Chicago to Key Colony Beach
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.
$292 Roundtrip, found 2 days ago
$292
Roundtrip
found 2 days ago
ORD
O'Hare Intl.
MIA
Miami Intl.
$360 Roundtrip, found 2 hours ago
$360
Roundtrip
found 2 hours ago
ORD
O'Hare Intl.
EYW
Key West Intl.
$430 Roundtrip, found 1 day ago
$430
Roundtrip
found 1 day ago
MDW
Midway Intl.
EYW
Key West Intl.
$441 Roundtrip, found 5 days ago
$441
Roundtrip
found 5 days ago
Airfares from $76 One Way, $171 Round Trip from Chicago to Key Colony Beach
Prices starting at $171 for return flights and $76 for one-way flights to Key Colony Beach were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
RFD
Rockford
MIA
Miami
$171 Roundtrip, found 3 days ago
$171
Roundtrip
found 3 days ago
MDW
Chicago
MIA
Miami
$172 Roundtrip, just found
$172
Roundtrip
just found
ORD
Chicago
MIA
Miami
$172 Roundtrip, just found
$172
Roundtrip
just found
ORD
Chicago
MIA
Miami
$181 Roundtrip, found 9 hours ago
$181
Roundtrip
found 9 hours ago
ORD
Chicago
MIA
Miami
$181 Roundtrip, found 9 hours ago
$181
Roundtrip
found 9 hours ago
Key Colony Beach economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Luxuri Suites
6.8/10 (57 reviews)
Sep 3 - Sep 11
8 night stay
Chicago (ORD) to Miami (MIA)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,207, price is now $682 per person
$682
per person
found 1 day ago
Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work.
Reviewed on Jul 9, 2026
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
8/10 Very Good! (1 review)
Sep 4 - Sep 7
3 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • Coach
Price was $11,428, price is now $6,504 per person
$6,504
per person
found 1 day 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
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View all tripsKey Colony Beach packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Loews Miami Beach Hotel – South Beach
9.4/10 Exceptional! (1,044 reviews)
Sep 3 - Sep 6
3 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,058, price is now $724 per person
$724
per person
found 1 day ago
Amazing stay. Like a 5 star experience. Staff was friendly EVERYWHERE! Room was beautiful. Great view, pool and beach. Newly refurbished which elevates the experience. Location was fantastic. Beautiful hotel and amazing people.
Reviewed on Aug 2, 2026
4.0-star property
Bentley Hotel South Beach
9.4/10 Exceptional! (991 reviews)
Sep 3 - Sep 6
3 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,068, price is now $807 per person
$807
per person
found 1 day ago
Great hotel and staff. Brilliant location.
Reviewed on Aug 2, 2026
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View all tripsKey Colony Beach first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Riverside Hotel
9.2/10 Wonderful! (3,150 reviews)
Sep 8 - Sep 12
4 night stay
Chicago (CHI) to Miami (MIA)
Delta • Non-stop roundtrip • FirstClass
Price was $1,085, price is now $946 per person
$946
per person
found 1 day ago
Do not pay for the breakfast that Expedia offers as an added cost because the hotel does not have breakfast directly and is not notified or aware of this add on through the travel agent. However, there is a restaurant with in the hotel and it is great
Reviewed on Aug 2, 2026
4.5-star property
JW Marriott Turnberry Resort & Spa
8.6/10 Excellent! (1,569 reviews)
Sep 8 - Sep 12
4 night stay
Chicago (CHI) to Miami (MIA)
Delta • Non-stop roundtrip • FirstClass
Price was $1,517, price is now $1,269 per person
$1,269
per person
found 1 day ago
We stayed at the JW Marriott Turnberry Resort & Spa from August 1–2. Our stay began with an extremely frustrating check-in. The lobby was overwhelmed with what appeared to be over 100 families waiting, and the process was completely disorganized.
The associate assisting us, Mrs. Hyatt, was condescending and unaccommodating. We were traveling as four families with young children and were told one of our rooms would not be ready until approximately 9:50 PM. It took nearly two hours of discussions before we were able to get a room so our toddlers could shower, change, and settle in. Once we were in our rooms, they were clean, and the housekeeping staff was wonderful.
The following day, as we were leaving the Orchid Building at Elevator #3, we witnessed a housekeeping employee trapped inside the elevator. The outer doors opened, but the inner doors remained jammed shut. She was visibly terrified and called for security. My husband and several others eventually pried the doors open enough to reach the emergency release and free her. We have photos and video of the incident.
Our group included seven children, who were terrified after witnessing this. None of us felt safe using the elevators afterward, so we took the stairs until we reached valet.
The housekeeping staff was excellent, but the chaotic check-in and serious elevator malfunction made this a very disappointing and concerning stay.
Reviewed on Aug 2, 2026
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View all tripsMore About Flying To Key Colony Beach from Chicago
Route Information for Flights from Chicago to Key Colony Beach
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Key Colony Beach
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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.