$34 Cheap flight deals from Chicago (CHI) to Grassy Key (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 Grassy Key

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.

Sat, Jan 31 - Thu, Feb 5
ORD
O'Hare Intl.
MIA
Miami Intl.
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jan 31 from O'Hare Intl. to Miami Intl., returning Thu, Feb 5, priced at $108 just found
Sat, Jan 31 - Tue, Feb 3
RFD
Greater Rockford
MIA
Miami Intl.
$284 Roundtrip, found 5 days ago
$284
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Jan 31 from Greater Rockford to Miami Intl., returning Tue, Feb 3, priced at $284 found 5 days ago
Sun, Feb 1 - Wed, Feb 4
MDW
Midway Intl.
MIA
Miami Intl.
$315 Roundtrip, found 1 day ago
$315
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Feb 1 from Midway Intl. to Miami Intl., returning Wed, Feb 4, priced at $315 found 1 day ago
Sun, Feb 1 - Thu, Feb 5
ORD
O'Hare Intl.
EYW
Key West Intl.
$320 Roundtrip, found 1 day ago
$320
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Feb 1 from O'Hare Intl. to Key West Intl., returning Thu, Feb 5, priced at $320 found 1 day ago

Airfares from $34 One Way, $68 Round Trip from Chicago to Grassy Key

Prices starting at $68 for return flights and $34 for one-way flights to Grassy Key were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 25 - Sat, Feb 28
ORD
Chicago
MIA
Miami
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Feb 25 from Chicago to Miami, returning Sat, Feb 28, priced at $68 just found
Mon, Feb 23 - Sat, Feb 28
ORD
Chicago
MIA
Miami
$71 Roundtrip, found 13 hours ago
$71
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Mon, Feb 23 from Chicago to Miami, returning Sat, Feb 28, priced at $71 found 13 hours ago
Sun, Mar 1 - Sat, Mar 7
MDW
Chicago
MIA
Miami
$71 Roundtrip, just found
$71
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Mar 1 from Chicago to Miami, returning Sat, Mar 7, priced at $71 just found
Wed, Feb 25 - Wed, Mar 4
RFD
Rockford
MIA
Miami
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Feb 25 from Rockford to Miami, returning Wed, Mar 4, priced at $157 found 1 day ago
Sun, Feb 15 - Thu, Feb 19
ORD
Chicago
EYW
Key West
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sun, Feb 15 from Chicago to Key West, returning Thu, Feb 19, priced at $164 found 3 days ago

Grassy Key economy flight packages

Price found within the past 48 hours. Click for updated prices.
Creekside Inn
2.5-star property

Creekside Inn

8/10 Very Good! (1,004 reviews)

Mar 5 - Mar 8

3 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $976, price is now $478 per person
$478
per person
found 1 day ago
I only stayed one night but overall, Creekside was better than I was expecting. For an old keys motel type inn, it was very clean and well kept.

Reviewed on Aug 2, 2025

Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.4/10 Very Good! (1,001 reviews)

Feb 25 - Feb 28

3 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $993, price is now $532 per person
$532
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything

Reviewed on Jan 3, 2026

The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

8/10 Very Good! (1 review)

Feb 25 - Feb 28

3 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $13,468, price is now $7,402 per person
$7,402
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Chicago to Grassy Key
View all trips

Grassy Key first class flight packages

Price found within the past 48 hours. Click for updated prices.
Costa Hollywood Beach Resort
4.0-star property

Costa Hollywood Beach Resort

9/10 Wonderful! (3,848 reviews)

Feb 28 - Mar 5

5 night stay

Chicago (CHI) to Miami (MIA)

Delta • Non-stop roundtrip • FirstClass
Price was $1,864, price is now $1,360 per person
$1,360
per person
found 1 hour ago
Friendly and professional staff. Room was very clean.. The suite I stayed in had beautiful Ugg decor, and it had everything you'll need for a comfortable stay; micro, cook top & oven, kerig & regular coffee maker, even washer and drier, etc. There's plenty of places to eat, drink & party at walking distance on the boardwalk.. Valet parking is a must, hard to find regular parking, valet service was elite.

Reviewed on Aug 6, 2025

Isla Bella Beach Resort & Spa
5.0-star property

Isla Bella Beach Resort & Spa

9.2/10 Wonderful! (1,055 reviews)

Mar 11 - Mar 18

7 night stay

Chicago (ORD) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $7,097, price is now $4,871 per person
$4,871
per person
found 16 hours ago
Mattress encased in plastic. First place I’ve seen that. Really helped my dust mite allergy. Fantastic place in all aspects. We will be back as now one of our favorite places to stay.

Reviewed on Dec 18, 2025

Oceans Edge Key West Resort, Hotel & Marina
4.0-star property

Oceans Edge Key West Resort, Hotel & Marina

9/10 Wonderful! (1,736 reviews)

Feb 26 - Mar 2

4 night stay

Chicago (CHI) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,094, price is now $2,289 per person
$2,289
per person
found 1 day ago
We LOVED the setting and the surrounding area! Absolutely beautiful! Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy. Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you. The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was. Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor! Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am. Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side. Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.

Reviewed on Dec 28, 2025

Don't see what you're looking for?
See all available trips from Chicago to Grassy Key
View all trips

More About Flying To Grassy Key from Chicago

Route Information for Flights from Chicago to Grassy Key

Origin Airport IATA Code
CHI
Destination Airport IATA Code
MIA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Grassy Key

Getting a spectacularly low fare on Chicago to Grassy Key flights is always possible when you use Orbitz as your personal travel planner. Orbitz is your essential travel resource for low cost flights from Chicago to Grassy Key, discount hotel accommodations, cheap car rentals, and more.

Research and Book Chicago to Grassy Key Flights on the Go

Our free cutting-edge mobile apps for iPad, Android, and iPhone make it easy to find the best fares when researching and booking flights from Chicago to Grassy Key. You can also use the apps to check your flight status, find baggage claims details, and get exclusive mobile discount rates on car rentals and hotels.

Earn Miles and Points for Your Frequent Flyer Program

Build up points or miles for your frequent flyer plan with qualifying Chicago to Grassy Key flights. Simply add your frequent flyer number when booking your domestic or international flights or enter the numbers in your Orbitz account profile to automatically add them to your bookings.

Flight Alerts Take the Hassle out of Travel

You can get email, SMS text, or voicemail updates regarding any major changes to your flights from Chicago to Grassy Key. These free alerts can also be sent to as many as six additional contacts, ensuring that your friends, colleagues, or family are aware of changes to your arrival time.

Stay in Your Budget and Still Get Great Accommodations

Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Chicago to Grassy Keyare always found on Orbitz.

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.