Flights from Chicago to Big Pine 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.

Thu, Sep 11 - Thu, Sep 18

ORD

O'Hare Intl.

MIA

Miami Intl.

$118 Roundtrip, found 1 day ago

$118

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, Sep 11 from O'Hare Intl. to Miami Intl., returning Thu, Sep 18, priced at $118 found 1 day ago

Sun, Sep 14 - Sat, Sep 20

ORD

O'Hare Intl.

MIA

Miami Intl.

$123 Roundtrip, found 1 day ago

$123

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Miami Intl., returning Sat, Sep 20, priced at $123 found 1 day ago

Sun, Sep 14 - Sat, Sep 20

ORD

O'Hare Intl.

MIA

Miami Intl.

$128 Roundtrip, found 1 day ago

$128

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Miami Intl., returning Sat, Sep 20, priced at $128 found 1 day ago

Sat, Oct 18 - Fri, Oct 24

ORD

O'Hare Intl.

MIA

Miami Intl.

$137 Roundtrip, found 6 days ago

$137

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Miami Intl., returning Fri, Oct 24, priced at $137 found 6 days ago

Sun, Sep 14 - Sat, Sep 20

ORD

O'Hare Intl.

MIA

Miami Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Miami Intl., returning Sat, Sep 20, priced at $137 found 1 day ago

Fri, Nov 14 - Mon, Nov 17

ORD

O'Hare Intl.

MIA

Miami Intl.

$138 Roundtrip, found 3 hours ago

$138

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Fri, Nov 14 from O'Hare Intl. to Miami Intl., returning Mon, Nov 17, priced at $138 found 3 hours ago

Sun, Sep 14 - Sat, Sep 20

ORD

O'Hare Intl.

MIA

Miami Intl.

$143 Roundtrip, found 1 day ago

$143

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Miami Intl., returning Sat, Sep 20, priced at $143 found 1 day ago

Fri, Nov 14 - Mon, Nov 17

ORD

O'Hare Intl.

MIA

Miami Intl.

$152 Roundtrip, found 3 hours ago

$152

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Fri, Nov 14 from O'Hare Intl. to Miami Intl., returning Mon, Nov 17, priced at $152 found 3 hours ago

Sun, Sep 14 - Sat, Sep 20

ORD

O'Hare Intl.

MIA

Miami Intl.

$153 Roundtrip, found 1 day ago

$153

Roundtrip

found 1 day ago

Select United flight, departing Sun, Sep 14 from O'Hare Intl. to Miami Intl., returning Sat, Sep 20, priced at $153 found 1 day ago

Fri, Sep 12 - Fri, Sep 19

ORD

O'Hare Intl.

MIA

Miami Intl.

$158 Roundtrip, found 1 day ago

$158

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Sep 12 from O'Hare Intl. to Miami Intl., returning Fri, Sep 19, priced at $158 found 1 day ago

Tue, Nov 11 - Fri, Nov 14

ORD

O'Hare Intl.

MIA

Miami Intl.

$159 Roundtrip, found 4 days ago

$159

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Nov 11 from O'Hare Intl. to Miami Intl., returning Fri, Nov 14, priced at $159 found 4 days ago

Thu, Nov 13 - Sat, Nov 15

ORD

O'Hare Intl.

MIA

Miami Intl.

$161 Roundtrip, found 4 days ago

$161

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Nov 13 from O'Hare Intl. to Miami Intl., returning Sat, Nov 15, priced at $161 found 4 days ago

Sun, Sep 14 - Sat, Sep 20

ORD

O'Hare Intl.

MIA

Miami Intl.

$163 Roundtrip, found 1 day ago

$163

Roundtrip

found 1 day ago

Select United flight, departing Sun, Sep 14 from O'Hare Intl. to Miami Intl., returning Sat, Sep 20, priced at $163 found 1 day ago

Tue, Nov 11 - Sat, Nov 15

ORD

O'Hare Intl.

MIA

Miami Intl.

$163 Roundtrip, found 4 days ago

$163

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Nov 11 from O'Hare Intl. to Miami Intl., returning Sat, Nov 15, priced at $163 found 4 days ago

Sun, Sep 14 - Sat, Sep 20

ORD

O'Hare Intl.

MIA

Miami Intl.

$166 Roundtrip, found 1 day ago

$166

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Miami Intl., returning Sat, Sep 20, priced at $166 found 1 day ago

Sat, Aug 2 - Sat, Aug 9

ORD

O'Hare Intl.

MIA

Miami Intl.

$208 Roundtrip, found 2 days ago

$208

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Miami Intl., returning Sat, Aug 9, priced at $208 found 2 days ago

Tue, Nov 11 - Thu, Nov 13

MDW

Midway Intl.

MIA

Miami Intl.

$217 Roundtrip, found 4 days ago

$217

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Nov 11 from Midway Intl. to Miami Intl., returning Thu, Nov 13, priced at $217 found 4 days ago

Wed, Dec 10 - Thu, Dec 18

ORD

O'Hare Intl.

MIA

Miami Intl.

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Dec 10 from O'Hare Intl. to Miami Intl., returning Thu, Dec 18, priced at $217 found 5 days ago

Fri, Nov 14 - Mon, Nov 17

ORD

O'Hare Intl.

MIA

Miami Intl.

$242 Roundtrip, found 3 hours ago

$242

Roundtrip

found 3 hours ago

Select United flight, departing Fri, Nov 14 from O'Hare Intl. to Miami Intl., returning Mon, Nov 17, priced at $242 found 3 hours ago

Tue, Aug 26 - Wed, Sep 3

ORD

O'Hare Intl.

EYW

Key West Intl.

$269 Roundtrip, found 9 hours ago

$269

Roundtrip

found 9 hours ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Key West Intl., returning Wed, Sep 3, priced at $269 found 9 hours ago