$89 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.
ORD
O'Hare Intl.
MIA
Miami Intl.
$388 Roundtrip, found 1 hour ago
$388
Roundtrip
found 1 hour ago
MDW
Midway Intl.
MIA
Miami Intl.
$438 Roundtrip, found 5 days ago
$438
Roundtrip
found 5 days ago
ORD
O'Hare Intl.
EYW
Key West Intl.
$554 Roundtrip, found 1 day ago
$554
Roundtrip
found 1 day ago
Airfares from $89 One Way, $177 Round Trip from Chicago to Key Colony Beach
Prices starting at $177 for return flights and $89 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.
ORD
Chicago
MIA
Miami
$177 Roundtrip, just found
$177
Roundtrip
just found
MDW
Chicago
MIA
Miami
$182 Roundtrip, found 6 days ago
$182
Roundtrip
found 6 days ago
ORD
Chicago
EYW
Key West
$293 Roundtrip, found 11 hours ago
$293
Roundtrip
found 11 hours ago
ORD
Chicago
AVT
Aventura
$301 Roundtrip, found 6 days ago
$301
Roundtrip
found 6 days ago
ORD
Chicago
EKW
Miami
$301 Roundtrip, found 6 days ago
$301
Roundtrip
found 6 days ago
Key Colony Beach economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Avi Lux Stay
7.6/10 Good! (10 reviews)
Nov 25 - Nov 29
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • Coach
Miami (MIA) to Chicago (CHI)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,594, price is now $753 per person
$753
per person
found 4 hours ago
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.
Reviewed on Aug 28, 2025
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
8/10 Very Good! (1 review)
Nov 15 - Nov 18
3 night stay
Chicago (CHI) to Miami (MIA)
United • Roundtrip • Coach
Price was $9,387, price is now $4,471 per person
$4,471
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
4.0-star property
Arlo Wynwood Miami
9/10 Wonderful! (1,864 reviews)
Dec 7 - Dec 14
7 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,291, price is now $764 per person
$764
per person
found 1 day ago
Everything was spotless, everyone was very kind and I enjoyed my stayed a lot.
Reviewed on Oct 15, 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
Cavalier Hotel South Beach
8.6/10 Excellent! (1,008 reviews)
Dec 4 - Dec 7
3 night stay
Chicago (MDW) to Miami (MIA)
Delta • Non-stop • FirstClass
Miami (MIA) to Chicago (MDW)
Frontier Airlines • Non-stop • FirstClass
Price was $1,588, price is now $1,081 per person
$1,081
per person
found 1 day ago
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
8/10 Very Good! (1 review)
Dec 4 - Dec 7
3 night stay
Chicago (MDW) to Miami (MIA)
Delta • Non-stop • FirstClass
Miami (MIA) to Chicago (MDW)
Frontier Airlines • Non-stop • FirstClass
Price was $16,322, price is now $8,959 per person
$8,959
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
3.0-star property
The Key West Hotel
9.2/10 Wonderful! (563 reviews)
Nov 15 - Nov 21
6 night stay
Chicago (ORD) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $5,332, price is now $3,397 per person
$3,397
per person
found 1 day ago
Property was everything as described, clean, in the heart of the excitement that is Key West
Pool was refreshing and close to tiki bar and local entertainment.
The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w
May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine
Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity
Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator
We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer
Reviewed on Oct 6, 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
When you’re searching for Chicago to Key Colony Beach flights for your family vacation, check out the guaranteed low prices at Orbitz. If you are looking for the best prices on hotels too, you’ll be sure to find great deals to suit your budget. You’ll also benefit from the following features:
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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.