$26 Cheap flight deals from Chicago (CHI) to Islamorada (MIA)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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.
$168 Roundtrip, just found
$168
Roundtrip
just found
ORD
O'Hare Intl.
MIA
Miami Intl.
$202 Roundtrip, just found
$202
Roundtrip
just found
RFD
Greater Rockford
MIA
Miami Intl.
$326 Roundtrip, found 5 days ago
$326
Roundtrip
found 5 days ago
MDW
Midway Intl.
EYW
Key West Intl.
$406 Roundtrip, found 2 days ago
$406
Roundtrip
found 2 days ago
Airfares from $26 One Way, $57 Round Trip from Chicago to Islamorada
Prices starting at $57 for return flights and $26 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
$57 Roundtrip, found 5 days ago
$57
Roundtrip
found 5 days ago
ORD
Chicago
MIA
Miami
$84 Roundtrip, just found
$84
Roundtrip
just found
RFD
Rockford
MIA
Miami
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
MDW
Chicago
MIA
Miami
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
ORD
Chicago
MIA
Miami
$157 Roundtrip, found 7 hours ago
$157
Roundtrip
found 7 hours ago
Islamorada economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
President Villa
8.2/10 Very Good! (1,000 reviews)
Dec 9 - Dec 13
4 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Coach
Miami (MIA) to Chicago (CHI)
Frontier Airlines • Coach
Price was $495, price is now $272 per person
$272
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
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
8/10 Very Good! (1 review)
Dec 11 - Dec 16
5 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Coach
Miami (MIA) to Chicago (CHI)
Spirit Airlines • Coach
Price was $18,408, price is now $8,596 per person
$8,596
per person
found 20 hours ago
Islamorada packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Diplomat Beach Resort Hollywood, Curio Collection by Hilton
8.4/10 Very Good! (3,151 reviews)
Dec 19 - Dec 22
3 night stay
Chicago (ORD) to Miami (MIA)
United • PremiumEconomy
Miami (MIA) to Chicago (ORD)
Delta • PremiumEconomy
Price was $1,132, price is now $870 per person
$870
per person
found 1 hour ago
Do not have food options or room service, no water for coffee on rooms. Staff not friendly
Reviewed on Oct 18, 2025
4.0-star property
Pelican Grand Beach Resort - A Noble House Resort
8.6/10 Excellent! (1,273 reviews)
Dec 19 - Dec 22
3 night stay
Chicago (ORD) to Miami (MIA)
United • PremiumEconomy
Miami (MIA) to Chicago (ORD)
Delta • PremiumEconomy
Price was $1,493, price is now $1,103 per person
$1,103
per person
found 1 hour ago
Getting chairs at the pool was a mess. They valve the day pool resort pass guest over those staying over nights. Added our name to the pool chair wait list and had to wait hours for a chair around the pool.
Reviewed on May 12, 2025
4.0-star property
Beach House Fort Lauderdale, a Hilton Resort
8.8/10 Excellent! (2,051 reviews)
Dec 19 - Dec 22
3 night stay
Chicago (ORD) to Miami (MIA)
United • PremiumEconomy
Miami (MIA) to Chicago (ORD)
Delta • PremiumEconomy
Price was $1,114, price is now $930 per person
$930
per person
found 1 hour ago
The star of this property is the employees. Welcoming, friendly, responsive and eager to help. The room was immaculately clean and well appointed. Nice views from the ocean view rooms. I can only imagine how great the oceanfront views are. My only complaint is that the towels at the pool area are flimsy and where they looked liked they tried to save some money. However, that didn't diminish my experience. This hotel is beautiful and has such a vibe and Instagram worthy photo opportunities. Stay here!
Reviewed on Oct 27, 2025
Islamorada first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
8.8/10 Excellent! (1,732 reviews)
Dec 6 - Dec 13
7 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,042, price is now $1,494 per person
$1,494
per person
just found
great property, transportation to key west great, missing an additional dining option. Everything else was fantastic
Reviewed on Sep 21, 2025
2.5-star property
The Key West Hotel
9.2/10 Wonderful! (498 reviews)
Dec 6 - Dec 13
7 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,131, price is now $2,834 per person
$2,834
per person
just found
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
Southernmost Beach Resort and Guesthouses
8.6/10 Excellent! (2,787 reviews)
Dec 6 - Dec 13
7 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,505, price is now $1,832 per person
$1,832
per person
just found
We visited in July and were able to upgrade to an oceanfront room with a balcony. If you get the chance, it’s worth it! Pools are beautiful and food and drinks are offered poolside. The view was incredible! The staff were all incredibly accommodating and friendly!! We can’t wait to come back!!
Reviewed on Aug 1, 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
If it is not enough that we have guaranteed low prices for Chicago to Islamorada flights, Orbitz can also integrate your hotel and car rental needs into the package. This ensures your trip goes smoothly and you get the best possible bargain.
Save Big On Hotels With Our Summer Hotel Sale When Booking Chicago to Islamorada Flights
We will get you bargain air tickets for Chicago to Islamorada flights and can save you even more with our Summer Hotel sale. You can get a discount of up to 40% when you book a hotel along with your bargain flight from Orbitz.
If You Are Going To The Beach We Can Save You Even More
When you are arranging budget flights from Chicago to Islamorada, you can save even more by staying near a beach. Orbitz Beach Hotel Deals will allow you to get as much as half off the price of an already cheap hotel. Saving money has never been this fun.
Plan A Spontaneous Trip Using Our Top Hotel and Flight Destinations
Want to know where other people are staying after flights from Chicago to Islamorada? We not only recommend top destinations, but will tell you the most popular places to stay after {origin.name} to Islamorada flights.
Use Orbitz.com For Up To The Minute Hot Deals
Budget deals on flights from Chicago to Islamorada are constantly changing. You can get up-to-the-minute updates on the hottest deals on discount tickets and hotels on our website.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to London
- Chicago to New Orleans
- Chicago to Washington
- Chicago to Rome
- Chicago to Paris
- Chicago to Toronto
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
More Destinations
- Flights from Chicago to Tavernier
- Flights from Houston to Tavernier
- Flights from Kansas City to Tavernier
- Flights from New Orleans to Tavernier
- Flights from New York to Tavernier
- Flights from Washington to Tavernier
- Flights from San José to Tavernier
- Flights from Quito to Tavernier
- Flights from Boston to Duck Key
- Flights from Chicago to Duck Key
- Flights from Denver to Duck Key
- Flights from Detroit to Duck Key
- Flights from Minneapolis - St. Paul to Duck Key
- Flights from Hartford to Duck Key
- Flights from New York to Miami
- Flights from Allentown (ABE) to Marathon (MTH)
- Flights from Albuquerque (ABQ) to Marathon (MTH)
- Flights from Alpena (APN) to Marathon (MTH)
- Flights from Atlanta (ATL) to Marathon (MTH)
- Flights from Asheville (AVL) to Marathon (MTH)
- Flights from Mesa (AZA) to Marathon (MTH)
- Flights from Kalamazoo (AZO) to Marathon (MTH)
- Flights from Hartford (BDL) to Marathon (MTH)
- Flights from Billings (BIL) to Marathon (MTH)
- Flights from Brainerd (BRD) to Marathon (MTH)
- Flights from Columbia (CAE) to Marathon (MTH)
- Flights from Charlotte (CLT) to Marathon (MTH)
- Flights from Champaign (CMI) to Marathon (MTH)
- Flights from Mosinee (CWA) to Marathon (MTH)
- Flights from Dodge City (DDC) to Marathon (MTH)
- Flights from Denver (DEN) to Marathon (MTH)
- Flights from Dallas (DFW) to Marathon (MTH)
- Flights from Des Moines (DSM) to Marathon (MTH)
- Flights from Detroit (DTW) to Marathon (MTH)
- Flights from Fargo (FAR) to Marathon (MTH)
- Flights from Flint (FNT) to Marathon (MTH)
- Flights from Fort Wayne (FWA) to Marathon (MTH)
- Flights from Spokane (GEG) to Marathon (MTH)
- Flights from Green Bay (GRB) to Marathon (MTH)
- Flights from Greenville (GSP) to Marathon (MTH)
- Flights from Huntsville (HSV) to Marathon (MTH)
- Flights from Indiana (IDI) to Marathon (MTH)
- Flights from Jacksonville (JAX) to Marathon (MTH)
- Flights from Los Alamos (LAM) to Marathon (MTH)
- Flights from Las Vegas (LAS) to Marathon (MTH)
- Flights from Lake Charles (LCH) to Marathon (MTH)
- Flights from Leesburg (LEE) to Marathon (MTH)
- Flights from Lexington (LEX) to Marathon (MTH)
- Flights from La Crosse (LSE) to Marathon (MTH)
- Flights from Majuro (MAJ) to Marathon (MTH)
- Flights from Morristown (MMU) to Marathon (MTH)
- Flights from Madison (MSN) to Marathon (MTH)
- Flights from Minneapolis (MSP) to Marathon (MTH)
- Flights from New Orleans (MSY) to Marathon (MTH)
- Flights from Oklahoma City (OKC) to Marathon (MTH)
- Flights from Miami (OPF) to Marathon (MTH)
- Flights from St. Petersburg (PIE) to Marathon (MTH)
- Flights from Pittsburgh (PIT) to Marathon (MTH)
- Flights from Pensacola (PNS) to Marathon (MTH)
- Flights from Chicago (PWK) to Marathon (MTH)
- Flights from Richmond (RIC) to Marathon (MTH)
- Flights from San Diego (SAN) to Marathon (MTH)
- Flights from Savannah (SAV) to Marathon (MTH)
- Flights from Salisbury (SBY) to Marathon (MTH)
- Flights from Seattle (SEA) to Marathon (MTH)
- Flights from Orlando (SFB) to Marathon (MTH)
- Flights from Shreveport (SHV) to Marathon (MTH)
- Flights from Sacramento (SMF) to Marathon (MTH)
- Flights from Shannon (SNN) to Marathon (MTH)
- Flights from Sarasota (SRQ) to Marathon (MTH)
- Flights from Sun Valley (SUN) to Marathon (MTH)
- Flights from Newburgh (SWF) to Marathon (MTH)
- Flights from Tbilisi (TBS) to Marathon (MTH)
- Flights from Tallahassee (TLH) to Marathon (MTH)
- Flights from Tampa (TPA) to Marathon (MTH)
- Flights from Tri-Cities (TRI) to Marathon (MTH)
- Flights from Tucson (TUS) to Marathon (MTH)
- Flights from Cockburn Harbour (XSC) to Marathon (MTH)
- Flights from Atlanta to Key Largo
- Flights from Baltimore to Key Largo
- Flights from Boston to Key Largo
- Flights from Charlotte to Key Largo
- Flights from Chicago to Key Largo
- Flights from Cleveland to Key Largo
- Flights from Columbus to Key Largo
- Flights from Dallas to Key Largo
- Flights from Denver to Key Largo
- Flights from Detroit to Key Largo
- Flights from Houston to Key Largo
- Flights from Indianapolis to Key Largo
- Flights from Los Angeles to Key Largo
- Flights from Minneapolis - St. Paul to Key Largo
- Flights from Nashville to Key Largo
- Flights from New York to Key Largo
- Flights from Philadelphia to Key Largo
- Flights from Raleigh to Key Largo
- Flights from Providence to Key Largo
- Flights from Asuncion to Key Largo
- Flights from Newark to Key Largo
- Flights from Halifax to Key Largo
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.