$30 Cheap flight deals from Chicago (CHI) to Islamorada (MIA)
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This Weekend's Flight Deals from Chicago to Islamorada
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.
$254 Roundtrip, found 5 hours ago
$254
Roundtrip
found 5 hours ago
RFD
Greater Rockford
MIA
Miami Intl.
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
ORD
O'Hare Intl.
EYW
Key West Intl.
$383 Roundtrip, found 2 days ago
$383
Roundtrip
found 2 days ago
MDW
Midway Intl.
MIA
Miami Intl.
$441 Roundtrip, found 9 hours ago
$441
Roundtrip
found 9 hours ago
Airfares from $30 One Way, $58 Round Trip from Chicago to Islamorada
Prices starting at $58 for return flights and $30 for one-way flights to Islamorada were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
MDW
Chicago
MIA
Miami
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
ORD
Chicago
MIA
Miami
$58 Roundtrip, found 5 hours ago
$58
Roundtrip
found 5 hours ago
ORD
Chicago
MIA
Miami
$82 Roundtrip, just found
$82
Roundtrip
just found
ORD
Chicago
MIA
Miami
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
ORD
Chicago
MIA
Miami
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Islamorada economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
President Hotel Villa
8.2/10 Very Good! (997 reviews)
Jan 28 - Jan 31
3 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Price was $816, price is now $399 per person
$399
per person
found 1 day ago
Although we didn't take advantage of it enough the hotel served breakfast every morning. Front desk staff awesome and very accommodating. A few times we had minor issues in our room and front desk staff would have maintenance up to our room in a matter of minutes. Minor drawback. A lot of hotel staff seemed not to know how to speak english well but front desk would let maintenance know the exact problem we were having and when they would arrive to our room we didnt need to talk that much because front desk already gave them the run down. I think hotel is in the best section of south beach. Beach 1 block away and walgreens across the street.
Reviewed on Apr 11, 2025
4.0-star property
Hawks Cay Resort
8/10 Very Good! (1,003 reviews)
Feb 5 - Feb 9
4 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop • Coach
Miami (MIA) to Chicago (CHI)
Spirit Airlines • Non-stop • Coach
Price was $1,365, price is now $663 per person
$663
per person
found 13 hours ago
Front desk service was exceptional!! Thank you Ashley & Kim for assisting us on this last minute reservation.
Reviewed on Mar 21, 2025
3.5-star property
Cavalier Hotel South Beach
8.4/10 Very Good! (1,001 reviews)
Jan 28 - Jan 31
3 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $936, price is now $489 per person
$489
per person
found 1 day ago
The property was decent, and maintenance and cleanliness were fine, but it's not been updated much, and they were short staffed. The room night price seemed high relative to value. Would recommend, as the staff they have is enthusiastic, and the location is in the midst of everything South Beach.
Reviewed on Apr 28, 2025
Islamorada packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Southernmost Beach Resort and Guesthouses
8.6/10 Excellent! (2,844 reviews)
Jan 28 - Feb 1
4 night stay
Rockford (RFD) to Key West (EYW)
American Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,166, price is now $1,457 per person
$1,457
per person
found 1 day ago
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.
Reviewed on Nov 1, 2025
2.5-star property
The Key West Hotel
9.2/10 Wonderful! (505 reviews)
Jan 28 - Feb 1
4 night stay
Rockford (RFD) to Key West (EYW)
American Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,273, price is now $1,953 per person
$1,953
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025
3.5-star property
Lighthouse Hotel - Key West Historic Inns
9/10 Wonderful! (831 reviews)
Jan 28 - Feb 1
4 night stay
Rockford (RFD) to Key West (EYW)
American Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,330, price is now $1,573 per person
$1,573
per person
found 1 day ago
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval
Reviewed on Sep 22, 2024
Islamorada first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Southernmost Beach Resort and Guesthouses
8.6/10 Excellent! (2,844 reviews)
Feb 5 - Feb 11
6 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,311, price is now $2,296 per person
$2,296
per person
found 1 day ago
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.
Reviewed on Nov 1, 2025
2.5-star property
The Key West Hotel
9.2/10 Wonderful! (505 reviews)
Feb 5 - Feb 11
6 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $4,952, price is now $2,985 per person
$2,985
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025
4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
9/10 Wonderful! (1,736 reviews)
Feb 5 - Feb 11
6 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $4,935, price is now $3,000 per person
$3,000
per person
found 1 day ago
great property, transportation to key west great, missing an additional dining option. Everything else was fantastic
Reviewed on Sep 21, 2025
More About Flying To Islamorada from Chicago
Route Information for Flights from Chicago to Islamorada
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Islamorada
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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.