$30 Cheap flight deals from Chicago (CHI) to Key Largo (MIA)
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This Weekend's Flight Deals from Chicago to Key Largo
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.
RFD
Greater Rockford
MIA
Miami Intl.
$314 Roundtrip, found 15 hours ago
$314
Roundtrip
found 15 hours ago
MDW
Midway Intl.
MIA
Miami Intl.
$335 Roundtrip, found 12 hours ago
$335
Roundtrip
found 12 hours ago
ORD
O'Hare Intl.
MIA
Miami Intl.
$336 Roundtrip, found 1 hour ago
$336
Roundtrip
found 1 hour ago
MDW
Midway Intl.
EYW
Key West Intl.
$354 Roundtrip, found 6 days ago
$354
Roundtrip
found 6 days ago
Airfares from $30 One Way, $58 Round Trip from Chicago to Key Largo
Prices starting at $58 for return flights and $30 for one-way flights to Key Largo 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
$58 Roundtrip, found 19 hours ago
$58
Roundtrip
found 19 hours ago
ORD
Chicago
MIA
Miami
$58 Roundtrip, found 8 hours ago
$58
Roundtrip
found 8 hours ago
ORD
Chicago
MIA
Miami
$82 Roundtrip, found 4 hours ago
$82
Roundtrip
found 4 hours ago
ORD
Chicago
MIA
Miami
$157 Roundtrip, found 8 hours ago
$157
Roundtrip
found 8 hours ago
ORD
Chicago
MIA
Miami
$157 Roundtrip, found 12 hours ago
$157
Roundtrip
found 12 hours ago
Key Largo economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Pelican Hotel
9.2/10 Wonderful! (394 reviews)
Jan 28 - Jan 31
3 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Price was $816, price is now $380 per person
$380
per person
found 1 day ago
My recent stay at the Pelican Hotel was nothing short of delightful. The location is truly exceptional — perfectly situated to enjoy the very best of the area. From the moment I arrived, the warm and friendly atmosphere made me feel completely at ease.
The service was impeccable. Both room service and management were consistently professional and courteous, with special appreciation to Oscar, whose attentiveness and genuine hospitality made a lasting impression.
The dining experience was outstanding. Every meal was a pleasure, but the fried octopus deserves special mention — perfectly prepared and absolutely unforgettable.
The rooms themselves were a highlight: comfortable, thoughtfully appointed, and each with its own unique design that adds charm and character to the stay. The complimentary cocktails were another memorable touch — expertly made and thoroughly enjoyable.
Overall, my time at the Pelican Hotel was a wonderful experience from start to finish. I look forward to returning and will gladly book again without hesitation.
Reviewed on Aug 11, 2025
4.0-star property
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
8.8/10 Excellent! (1,275 reviews)
Jan 21 - Jan 27
6 night stay
Chicago (ORD) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Price was $1,289, price is now $534 per person
$534
per person
found 1 day ago
Clean attractive property
Reviewed on Dec 14, 2025
Key Largo packages with premium economy flights
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)
Jan 28 - Feb 1
4 night stay
Rockford (RFD) to Key West (EYW)
American Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,166, price is now $1,457 per person
$1,457
per person
found 15 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)
Jan 28 - Feb 1
4 night stay
Rockford (RFD) to Key West (EYW)
American Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,273, price is now $1,953 per person
$1,953
per person
found 15 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
3.5-star property
Lighthouse Hotel - Key West Historic Inns
9/10 Wonderful! (831 reviews)
Jan 28 - Feb 1
4 night stay
Rockford (RFD) to Key West (EYW)
American Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,330, price is now $1,573 per person
$1,573
per person
found 15 hours ago
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval
Reviewed on Sep 22, 2024
Key Largo 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)
Feb 5 - Feb 11
6 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,311, price is now $2,296 per person
$2,296
per person
found 9 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)
Feb 5 - Feb 11
6 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $4,952, price is now $2,985 per person
$2,985
per person
found 9 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)
Feb 5 - Feb 11
6 night stay
Chicago (CHI) to Key West (EYW)
American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $4,935, price is now $3,000 per person
$3,000
per person
found 9 hours ago
great property, transportation to key west great, missing an additional dining option. Everything else was fantastic
Reviewed on Sep 21, 2025
More About Flying To Key Largo from Chicago
Route Information for Flights from Chicago to Key Largo
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Key Largo
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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.