$102 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.
$262 Roundtrip, found 13 hours ago
$262
Roundtrip
found 13 hours ago
RFD
Greater Rockford
MIA
Miami Intl.
$381 Roundtrip, found 13 hours ago
$381
Roundtrip
found 13 hours ago
ORD
O'Hare Intl.
MIA
Miami Intl.
$398 Roundtrip, found 1 hour ago
$398
Roundtrip
found 1 hour ago
ORD
O'Hare Intl.
EYW
Key West Intl.
$450 Roundtrip, found 20 hours ago
$450
Roundtrip
found 20 hours ago
Airfares from $102 One Way, $201 Round Trip from Chicago to Key Colony Beach
Prices starting at $201 for return flights and $102 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
$201 Roundtrip, found 4 days ago
$201
Roundtrip
found 4 days ago
MDW
Chicago
MIA
Miami
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
ORD
Chicago
MIA
Miami
$211 Roundtrip, found 4 days ago
$211
Roundtrip
found 4 days ago
ORD
Chicago
MIA
Miami
$221 Roundtrip, found 4 days ago
$221
Roundtrip
found 4 days ago
MDW
Chicago
MIA
Miami
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
Key Colony Beach economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Southernmost House - Adult Exclusive
9.4/10 Exceptional! (1,000 reviews)
Jul 8 - Jul 13
5 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,279, price is now $1,266 per person
$1,266
per person
found 1 day ago
Staff was professional, courteous, and responsive.
Breakfast was very fresh, well arranged and very delicious!!!
Views of the ocean were amazing. The pool was well kept and picturesque!
Truly a wonderful experience at a first class, historic facility!
Reviewed on Oct 30, 2025
3.0-star property
Casablanca Miami Beach
5.8/10 (324 reviews)
Jul 12 - Jul 18
6 night stay
Chicago (ORD) to Miami (MIA)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,723, price is now $963 per person
$963
per person
found 1 day ago
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
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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.
3.5-star property
Cavalier Hotel South Beach
8.6/10 Excellent! (1,002 reviews)
Jul 11 - Jul 17
6 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,450, price is now $818 per person
$818
per person
found 1 hour ago
Staff was great, elevator is tired, but I loved the proximity to everything
Reviewed on Jan 3, 2026
4.0-star property
Hotel Riu Plaza Miami Beach
8/10 Very Good! (1,150 reviews)
Jul 11 - Jul 17
6 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,077, price is now $1,225 per person
$1,225
per person
found 1 hour ago
The hotel is clean. The staff will greet you but not immediately. The rooms are ok but the beds are small and everything is built for shorter stature people. I am average and the beds and toilet are short! TV's are older. Everything is average and ok.
Reviewed on Jan 19, 2026
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,512 reviews)
Jul 11 - Jul 17
6 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $4,627, price is now $2,808 per person
$2,808
per person
found 1 hour ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 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.
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,512 reviews)
Jul 7 - Jul 10
3 night stay
Chicago (CHI) to Miami (MIA)
United • FirstClass
Miami (MIA) to Chicago (CHI)
Delta • FirstClass
Price was $2,591, price is now $1,848 per person
$1,848
per person
found 17 hours ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 2026
4.5-star property
Fontainebleau Miami Beach
8.4/10 Very Good! (8,242 reviews)
Jul 7 - Jul 10
3 night stay
Chicago (CHI) to Miami (MIA)
United • FirstClass
Miami (MIA) to Chicago (CHI)
Delta • FirstClass
Price was $1,829, price is now $1,439 per person
$1,439
per person
found 17 hours ago
The hotel itself is very elegant. However, there were many things you weren't notified of before the visit including a security deposit which ranged between $500 and $1000 depending on the length of stay and upon check in the front desk clerk failed to tell of us of including our credit card for the deposit and we were locked out of our room on the third day and actually checked out of the hotel, the pool area and poolside bars close at sundown and nobody is allowed to congregate near the pools after that time, the availability of poolside or beach side chairs is very limited and not ample enough for the amount of guests, you are not allowed to carry beach towels back into the hotel, the car valet service is average at best and we waited over 30 minutes on several occasions for our vehicle which altered our schedules, the room key was not validated for late departure and we had to return to the front desk to do so after being locked out of the room, and last but certainly not least the fees for everything from a bottle of water and food to the price for valet parking ($80 per night) is inconceivable for a family to visit Miami Beach. There are plenty of other nice hotels in the area that offer better services and I doubt we will ever return to Fontainebleau based on our experience. Otherwise, the beach and weather were excellent.
Reviewed on May 31, 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.