$76 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.
MDW
Midway Intl.
MIA
Miami Intl.
$272 Roundtrip, found 9 hours ago
$272
Roundtrip
found 9 hours ago
ORD
O'Hare Intl.
MIA
Miami Intl.
$276 Roundtrip, found 1 hour ago
$276
Roundtrip
found 1 hour ago
RFD
Greater Rockford
MIA
Miami Intl.
$353 Roundtrip, found 5 days ago
$353
Roundtrip
found 5 days ago
ORD
O'Hare Intl.
EYW
Key West Intl.
$506 Roundtrip, found 6 days ago
$506
Roundtrip
found 6 days ago
Airfares from $76 One Way, $144 Round Trip from Chicago to Islamorada
Prices starting at $144 for return flights and $76 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.
ORD
Chicago
MIA
Miami
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
MDW
Chicago
MIA
Miami
$164 Roundtrip, found 4 days ago
$164
Roundtrip
found 4 days ago
RFD
Rockford
MIA
Miami
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
ORD
Chicago
MIA
Miami
$204 Roundtrip, just found
$204
Roundtrip
just found
MDW
Chicago
MIA
Miami
$212 Roundtrip, found 5 days ago
$212
Roundtrip
found 5 days ago
Islamorada economy flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Creekside Inn
7.8/10 Good! (1,007 reviews)
May 28 - Jun 1
4 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Coach
Miami (MIA) to Chicago (CHI)
Southwest Airlines • Coach
Price was $1,319, price is now $663 per person
$663
per person
found 21 hours ago
Leaving a review to let Travellers know that this place deserves a better rating and reviews than what some Travellers have left. We had a great stay! The property is older and could use some upgrades but it was exactly suited for our stay. Property is right on a canal where you can see Tarpon, Manatees and other fish, if you have a boat you can dock right there. Our stay was quiet and peaceful and housekeeping took care of any needs we had. Its within walking distance of a few restaurants, dive shop, bait shop, snorkel tour. I would recommend Lido73, Mar Bar and Old Tavernier restaurants all within walking distance. Just know it not the 4 seasons just and older property that will suit your needs. I would definitely come stay again.
Reviewed on Mar 22, 2026
Islamorada packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
President Hotel
8.4/10 Very Good! (2,251 reviews)
Jun 4 - Jun 8
4 night stay
Chicago (MDW) to Miami (MIA)
Spirit Airlines • Roundtrip • PremiumEconomy
Price was $1,275, price is now $892 per person
$892
per person
found 1 day ago
the location and breakfast and some of the staff are clearly a great value. However the bathroom in general are not at par with a 2* star hotel. The closet door was broken. The shower only had a curtain and floor corners had signs of aging and sticky. On second day while I was on a work call, the house keeping lady comes in and even if I told her to come later as I’m in a call, she didn’t bother she kept coming in and dumped towels on my luggage and was checking the closet door. I told her to go and come back. She have a look and left and that day they didn’t clean the room. The bathroom soap gel was not refilled on day 2 as the lady decided not to come. And you are given only 1 travel size gel. The 3rd day was pleasant. But overall for what I paid I was tad upset.
In short I will have marked it as very good if the housekeeping didn’t mess up and bathroom has more soap and was not sticky.
Reviewed on Apr 17, 2026
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,483 reviews)
Jun 4 - Jun 8
4 night stay
Chicago (MDW) to Miami (MIA)
Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,647, price is now $1,847 per person
$1,847
per person
found 1 day ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 2026
4.0-star property
The Shelborne By Proper, a Member of Design Hotels
9.4/10 Exceptional! (165 reviews)
Jun 4 - Jun 8
4 night stay
Chicago (MDW) to Miami (MIA)
Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,964, price is now $1,448 per person
$1,448
per person
found 1 day ago
Islamorada first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Fort Lauderdale Marriott Pompano Beach Resort
8.2/10 Very Good! (142 reviews)
Jun 9 - Jun 16
7 night stay
Chicago (ORD) to Miami (MIA)
United • FirstClass
Miami (MIA) to Chicago (ORD)
Delta • FirstClass
Price was $1,647, price is now $1,222 per person
$1,222
per person
found 1 day ago
Pool was overly crowded. Drinks were outrageously expensive. Lobby had no TVs or places to hang out.
Reviewed on Apr 1, 2026
3.5-star property
Flow Hotel Fort Lauderdale
9/10 Wonderful! (848 reviews)
Jun 9 - Jun 16
7 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • FirstClass
Miami (MIA) to Chicago (CHI)
Delta • FirstClass
Price was $2,114, price is now $1,507 per person
$1,507
per person
found 24 hours ago
Clean and roomy! Balcony view is a plus. Be aware of the Brightline train behind the building. Great location with food and shopping nearby.
Reviewed on Mar 16, 2026
3.5-star property
Riverside Hotel
9/10 Wonderful! (2,899 reviews)
Jun 9 - Jun 16
7 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • FirstClass
Miami (MIA) to Chicago (CHI)
Delta • FirstClass
Price was $1,921, price is now $1,373 per person
$1,373
per person
found 24 hours ago
Beautiful view, large room, great venue, wonderful staff!
Reviewed on Apr 15, 2026
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.