Flights from Chicago to Duck Key

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Sep 10 - Thu, Sep 11

ORD

O'Hare Intl.

MIA

Miami Intl.

$98 Roundtrip, found 5 hours ago

$98

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Wed, Sep 10 from O'Hare Intl. to Miami Intl., returning Thu, Sep 11, priced at $98 found 5 hours ago

Wed, Sep 10 - Thu, Sep 11

ORD

O'Hare Intl.

MIA

Miami Intl.

$112 Roundtrip, found 5 hours ago

$112

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Wed, Sep 10 from O'Hare Intl. to Miami Intl., returning Thu, Sep 11, priced at $112 found 5 hours ago

Sat, Aug 23 - Wed, Aug 27

ORD

O'Hare Intl.

MIA

Miami Intl.

$118 Roundtrip, found 2 days ago

$118

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Miami Intl., returning Wed, Aug 27, priced at $118 found 2 days ago

Sun, Sep 14 - Sat, Sep 20

ORD

O'Hare Intl.

MIA

Miami Intl.

$123 Roundtrip, found 6 days ago

$123

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Miami Intl., returning Sat, Sep 20, priced at $123 found 6 days ago

Fri, Aug 22 - Sat, Aug 30

ORD

O'Hare Intl.

MIA

Miami Intl.

$123 Roundtrip, found 2 days ago

$123

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Aug 22 from O'Hare Intl. to Miami Intl., returning Sat, Aug 30, priced at $123 found 2 days ago

Sun, Sep 14 - Sat, Sep 20

ORD

O'Hare Intl.

MIA

Miami Intl.

$128 Roundtrip, found 6 days ago

$128

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Miami Intl., returning Sat, Sep 20, priced at $128 found 6 days ago

Fri, Aug 22 - Wed, Aug 27

ORD

O'Hare Intl.

MIA

Miami Intl.

$133 Roundtrip, found 2 days ago

$133

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Aug 22 from O'Hare Intl. to Miami Intl., returning Wed, Aug 27, priced at $133 found 2 days ago

Wed, Sep 10 - Thu, Sep 11

ORD

O'Hare Intl.

MIA

Miami Intl.

$135 Roundtrip, found 5 hours ago

$135

Roundtrip

found 5 hours ago

Select Spirit Airlines flight, departing Wed, Sep 10 from O'Hare Intl. to Miami Intl., returning Thu, Sep 11, priced at $135 found 5 hours ago

Wed, Sep 10 - Thu, Sep 11

ORD

O'Hare Intl.

MIA

Miami Intl.

$137 Roundtrip, found 5 hours ago

$137

Roundtrip

found 5 hours ago

Select United flight, departing Wed, Sep 10 from O'Hare Intl. to Miami Intl., returning Thu, Sep 11, priced at $137 found 5 hours ago

Wed, Sep 10 - Thu, Sep 11

ORD

O'Hare Intl.

MIA

Miami Intl.

$137 Roundtrip, found 5 hours ago

$137

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Wed, Sep 10 from O'Hare Intl. to Miami Intl., returning Thu, Sep 11, priced at $137 found 5 hours ago

Thu, Nov 13 - Mon, Nov 17

ORD

O'Hare Intl.

MIA

Miami Intl.

$138 Roundtrip, found 3 days ago

$138

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Nov 13 from O'Hare Intl. to Miami Intl., returning Mon, Nov 17, priced at $138 found 3 days ago

Thu, Nov 13 - Mon, Nov 17

ORD

O'Hare Intl.

MIA

Miami Intl.

$140 Roundtrip, found 3 days ago

$140

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Nov 13 from O'Hare Intl. to Miami Intl., returning Mon, Nov 17, priced at $140 found 3 days ago

Fri, Aug 22 - Sat, Aug 30

ORD

O'Hare Intl.

MIA

Miami Intl.

$143 Roundtrip, found 2 days ago

$143

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Aug 22 from O'Hare Intl. to Miami Intl., returning Sat, Aug 30, priced at $143 found 2 days ago

Fri, Aug 22 - Sat, Aug 30

ORD

O'Hare Intl.

MIA

Miami Intl.

$148 Roundtrip, found 2 days ago

$148

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Aug 22 from O'Hare Intl. to Miami Intl., returning Sat, Aug 30, priced at $148 found 2 days ago

Mon, Nov 24 - Wed, Dec 3

ORD

O'Hare Intl.

MIA

Miami Intl.

$148 Roundtrip, found 1 day ago

$148

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Nov 24 from O'Hare Intl. to Miami Intl., returning Wed, Dec 3, priced at $148 found 1 day ago

Fri, Aug 22 - Sat, Aug 30

ORD

O'Hare Intl.

MIA

Miami Intl.

$213 Roundtrip, found 2 days ago

$213

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, Aug 22 from O'Hare Intl. to Miami Intl., returning Sat, Aug 30, priced at $213 found 2 days ago

Wed, Sep 10 - Thu, Sep 11

ORD

O'Hare Intl.

MIA

Miami Intl.

$217 Roundtrip, found 5 hours ago

$217

Roundtrip

found 5 hours ago

Select Delta flight, departing Wed, Sep 10 from O'Hare Intl. to Miami Intl., returning Thu, Sep 11, priced at $217 found 5 hours ago

Tue, Sep 9 - Fri, Sep 19

ORD

O'Hare Intl.

EYW

Key West Intl.

$269 Roundtrip, found 1 day ago

$269

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Sep 9 from O'Hare Intl. to Key West Intl., returning Fri, Sep 19, priced at $269 found 1 day ago

Thu, Sep 11 - Tue, Sep 16

MDW

Midway Intl.

EYW

Key West Intl.

$324 Roundtrip, found 1 day ago

$324

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Sep 11 from Midway Intl. to Key West Intl., returning Tue, Sep 16, priced at $324 found 1 day ago

Mon, Dec 22 - Mon, Dec 29

MDW

Midway Intl.

MIA

Miami Intl.

$452 Roundtrip, found 2 days ago

$452

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Mon, Dec 22 from Midway Intl. to Miami Intl., returning Mon, Dec 29, priced at $452 found 2 days ago