
$44 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.
Airfares from $44 One Way, $87 Round Trip from Chicago to Big Pine Key
Prices starting at $87 for return flights and $44 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.
Big Pine Key economy flight packages

The Savoy Hotel & Beach Club
Nov 6 - Nov 10
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Sep 23, 2024

Cheeca Lodge & Spa
Nov 24 - Nov 29
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Sep 6, 2025

Hotel Riu Plaza Miami Beach
Nov 22 - Nov 27
Chicago (CHI) to Miami (MIA)
Miami (MIA) to Chicago (CHI)
Reviewed on Jun 23, 2025
Big Pine Key packages with premium economy flights

Lighthouse Hotel - Key West Historic Inns
Nov 27 - Nov 30
Chicago (CHI) to Key West (EYW)
Reviewed on Sep 22, 2024

Winslow's Bungalows - Key West Historic Inns
Nov 27 - Nov 30
Chicago (CHI) to Key West (EYW)
Reviewed on Jul 15, 2025

Pier House Resort & Spa
Nov 27 - Nov 30
Chicago (CHI) to Key West (EYW)
Reviewed on Jun 24, 2025
Big Pine Key first class flight packages

Eden Roc Miami Beach
Nov 23 - Nov 27
Chicago (ORD) to Miami (MIA)
Reviewed on Jul 1, 2025

1 Hotel South Beach
Nov 23 - Nov 27
Chicago (ORD) to Miami (MIA)
Reviewed on Jun 10, 2025

Nobu Hotel Miami Beach
Nov 23 - Nov 27
Chicago (ORD) to Miami (MIA)
Reviewed on Jul 17, 2025
More 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 | 1199 mi |
Direct Flight Airlines | American Airlines, Qatar Airways, Air Canada, JAL, Aer Lingus, Copa Airlines, Air New Zealand, United Airlines, Gol, Alaska Airlines, Avianca, Royal Jordanian, Spirit Airlines, British Airways |
Earliest Flight Arrival | 1:05PM UTC |
Latest Flight Arrival | 3:24AM UTC |
Chicago to Big Pine Key
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Miles Better
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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.