Cheap flights from Chicago to Cudjoe Key from CA $60

View CA $60 flight on Tue, Jul. 29, 2025Opens in a new window

Popular airlines from Chicago to Cudjoe Key

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Cheap flights from Chicago (CHI) to Cudjoe Key (MIA)

Prices were available within the past 7 days and start at CA $60 for one-way flights and CA $119 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Jul. 29 - Tue, Aug. 5
ORD
Chicago
MIA
Miami
CA $119 Roundtrip, found 4 days ago
CA $119
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Jul. 29 from Chicago to Miami, returning Tue, Aug. 5, priced at CA $119 found 4 days ago
Spirit Airlines
Tue, Jul. 29 - Tue, Aug. 5
ORD
Chicago
MIA
Miami
CA $137 Roundtrip, found 4 days ago
CA $137
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Jul. 29 from Chicago to Miami, returning Tue, Aug. 5, priced at CA $137 found 4 days ago
American Airlines
Wed, Sep. 24 - Tue, Sep. 30
ORD
Chicago
MIA
Miami
CA $156 Roundtrip, found 4 days ago
CA $156
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep. 24 from Chicago to Miami, returning Tue, Sep. 30, priced at CA $156 found 4 days ago
United
Wed, Oct. 29 - Tue, Nov. 18
ORD
Chicago
MIA
Miami
CA $266 Roundtrip, found 4 days ago
CA $266
Roundtrip
found 4 days ago
Select United flight, departing Wed, Oct. 29 from Chicago to Miami, returning Tue, Nov. 18, priced at CA $266 found 4 days ago
Delta
Tue, Jan. 6 - Wed, Jan. 21
MDW
Chicago
MIA
Miami
CA $297 Roundtrip, found 1 hour ago
CA $297
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan. 6 from Chicago to Miami, returning Wed, Jan. 21, priced at CA $297 found 1 hour ago
JetBlue Airways
Sat, Jul. 26 - Mon, Jul. 28
ORD
Chicago
MIA
Miami
CA $636 Roundtrip, found 12 hours ago
CA $636
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Sat, Jul. 26 from Chicago to Miami, returning Mon, Jul. 28, priced at CA $636 found 12 hours ago

Find the cheapest month to fly from Chicago (CHI) to Miami (MIA)

September is typically the cheapest month to fly

From CA $79 - CA $202 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.