$29 Cheap flight deals from Chicago (CHI) to Big Pine Key (MIA)
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This Weekend's Flight Deals from Chicago to Big Pine 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.
ORD
O'Hare Intl.
MIA
Miami Intl.
$150 Roundtrip, just found
$150
Roundtrip
just found
MDW
Midway Intl.
MIA
Miami Intl.
$271 Roundtrip, just found
$271
Roundtrip
just found
RFD
Greater Rockford
MIA
Miami Intl.
$315 Roundtrip, found 5 days ago
$315
Roundtrip
found 5 days ago
MDW
Midway Intl.
EYW
Key West Intl.
$344 Roundtrip, found 5 days ago
$344
Roundtrip
found 5 days ago
Airfares from $29 One Way, $59 Round Trip from Chicago to Big Pine Key
Prices starting at $59 for return flights and $29 for one-way flights to Big Pine 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.
ORD
Chicago
MIA
Miami
$59 Roundtrip, just found
$59
Roundtrip
just found
MDW
Chicago
MIA
Miami
$59 Roundtrip, found 1 day ago
$59
Roundtrip
found 1 day ago
ORD
Chicago
MIA
Miami
$63 Roundtrip, found 3 days ago
$63
Roundtrip
found 3 days ago
RFD
Rockford
MIA
Miami
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
ORD
Chicago
MIA
Miami
$159 Roundtrip, found 9 hours ago
$159
Roundtrip
found 9 hours ago
Big Pine Key economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Casablanca Miami Beach
5.8/10 (311 reviews)
Feb 22 - Mar 1
7 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Price was $1,409, price is now $737 per person
$737
per person
found 8 hours ago
Very good for the price, Right on the beach, has a kitchen, Ocean view. Very easy check-in check-out. 1 -1/2 Block from Publix supermarket. 30 minutes from Miami International Airport. Will come again.
Reviewed on Apr 8, 2025
3.5-star property
Cavalier Hotel South Beach
8.4/10 Very Good! (1,001 reviews)
Feb 13 - Feb 17
4 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Coach
Miami (MIA) to Chicago (CHI)
Spirit Airlines • Coach
Save 100% on your flight
Price was $1,598, price is now $864 per person
$864
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything
Reviewed on Jan 3, 2026
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View all tripsBig Pine Key packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Cavalier Hotel South Beach
8.4/10 Very Good! (1,001 reviews)
Feb 13 - Feb 15
2 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • PremiumEconomy
Miami (MIA) to Chicago (ORD)
Spirit Airlines • PremiumEconomy
Price was $1,256, price is now $868 per person
$868
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything
Reviewed on Jan 3, 2026
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,365 reviews)
Feb 26 - Mar 1
3 night stay
Chicago (CHI) to Miami (MIA)
Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,285, price is now $2,056 per person
$2,056
per person
found 1 day ago
This property is amazing. Food was great, staff was friendly and welcoming. We enjoyed our stay.
Reviewed on Jun 10, 2025
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See all available trips from Chicago to Big Pine Key
View all tripsBig Pine Key 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)
Mar 5 - Mar 8
3 night stay
Chicago (ORD) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,480, price is now $1,997 per person
$1,997
per person
found 14 hours 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)
Mar 5 - Mar 8
3 night stay
Chicago (ORD) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $3,480, price is now $2,433 per person
$2,433
per person
found 14 hours 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)
Mar 5 - Mar 8
3 night stay
Chicago (ORD) to Key West (EYW)
American Airlines • Non-stop roundtrip • FirstClass
Price was $2,656, price is now $2,027 per person
$2,027
per person
found 14 hours 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
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See all available trips from Chicago to Big Pine Key
View all tripsMore About Flying To Big Pine Key from Chicago
Route Information for Flights from Chicago to Big Pine Key
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Big Pine Key
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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.