Cheap flights from Chicago to Sugarloaf Key

View AU$104 flight on Fri, 3 Oct. 2025Opens in a new window

Popular airlines from Chicago to Sugarloaf Key

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Cheap Flights from Chicago (CHI) to Sugarloaf Key (MIA)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, 10 Sep. - Wed, 17 Sep.
ORD
Chicago
MIA
Miami
AU$208 Return, found 4 days ago
AU$208
Return
found 4 days ago
Select American Airlines flight, departing Wed, 10 Sep. from Chicago to Miami, returning Wed, 17 Sep., priced at AU$208 found 4 days ago
American Airlines
Sat, 6 Sep. - Mon, 8 Sep.
ORD
Chicago
MIA
Miami
AU$211 Return, found 15 hours ago
AU$211
Return
found 15 hours ago
Select American Airlines flight, departing Sat, 6 Sep. from Chicago to Miami, returning Mon, 8 Sep., priced at AU$211 found 15 hours ago
American Airlines
Wed, 10 Sep. - Wed, 17 Sep.
ORD
Chicago
MIA
Miami
AU$270 Return, found 4 days ago
AU$270
Return
found 4 days ago
Select American Airlines flight, departing Wed, 10 Sep. from Chicago to Miami, returning Wed, 17 Sep., priced at AU$270 found 4 days ago
American Airlines
Sat, 6 Sep. - Mon, 8 Sep.
ORD
Chicago
MIA
Miami
AU$282 Return, found 15 hours ago
AU$282
Return
found 15 hours ago
Select American Airlines flight, departing Sat, 6 Sep. from Chicago to Miami, returning Mon, 8 Sep., priced at AU$282 found 15 hours ago
Delta
Wed, 10 Sep. - Wed, 17 Sep.
MDW
Chicago
MIA
Miami
AU$329 Return, found 4 days ago
AU$329
Return
found 4 days ago
Select Delta flight, departing Wed, 10 Sep. from Chicago to Miami, returning Wed, 17 Sep., priced at AU$329 found 4 days ago
United
Sat, 6 Sep. - Mon, 8 Sep.
ORD
Chicago
MIA
Miami
AU$335 Return, found 15 hours ago
AU$335
Return
found 15 hours ago
Select United flight, departing Sat, 6 Sep. from Chicago to Miami, returning Mon, 8 Sep., priced at AU$335 found 15 hours ago

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

September is typically the cheapest month to fly

From AU$112 - AU$210 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.