Flights from Chicago to Long 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.

Tue, Aug 26 - Wed, Sep 3

ORD

O'Hare Intl.

MIA

Miami Intl.

$108 Roundtrip, just found

$108

Roundtrip

just found

Select Spirit Airlines flight, departing Tue, Aug 26 from O'Hare Intl. to Miami Intl., returning Wed, Sep 3, priced at $108 just found

Tue, Jun 10 - Fri, Jun 13

ORD

O'Hare Intl.

MIA

Miami Intl.

$118 Roundtrip, found 5 days ago

$118

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Miami Intl., returning Fri, Jun 13, priced at $118 found 5 days ago

Wed, Jun 4 - Sat, Jun 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$120 Roundtrip, found 5 days ago

$120

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to Miami Intl., returning Sat, Jun 7, priced at $120 found 5 days ago

Wed, Jun 4 - Sat, Jun 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$128 Roundtrip, found 5 days ago

$128

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to Miami Intl., returning Sat, Jun 7, priced at $128 found 5 days ago

Mon, Aug 25 - Wed, Sep 3

ORD

O'Hare Intl.

MIA

Miami Intl.

$128 Roundtrip, just found

$128

Roundtrip

just found

Select Spirit Airlines flight, departing Mon, Aug 25 from O'Hare Intl. to Miami Intl., returning Wed, Sep 3, priced at $128 just found

Sat, Aug 23 - Sun, Aug 31

ORD

O'Hare Intl.

MIA

Miami Intl.

$139 Roundtrip, just found

$139

Roundtrip

just found

Select Spirit Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Miami Intl., returning Sun, Aug 31, priced at $139 just found

Mon, May 12 - Tue, May 13

ORD

O'Hare Intl.

MIA

Miami Intl.

$140 Roundtrip, found 5 days ago

$140

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Mon, May 12 from O'Hare Intl. to Miami Intl., returning Tue, May 13, priced at $140 found 5 days ago

Wed, Jun 4 - Sat, Jun 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$143 Roundtrip, found 5 days ago

$143

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to Miami Intl., returning Sat, Jun 7, priced at $143 found 5 days ago

Mon, Jun 9 - Tue, Jun 10

ORD

O'Hare Intl.

MIA

Miami Intl.

$143 Roundtrip, found 5 days ago

$143

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Miami Intl., returning Tue, Jun 10, priced at $143 found 5 days ago

Wed, Aug 20 - Wed, Sep 3

ORD

O'Hare Intl.

MIA

Miami Intl.

$146 Roundtrip, just found

$146

Roundtrip

just found

Select Spirit Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Miami Intl., returning Wed, Sep 3, priced at $146 just found

Thu, Aug 21 - Wed, Sep 3

ORD

O'Hare Intl.

MIA

Miami Intl.

$148 Roundtrip, just found

$148

Roundtrip

just found

Select Spirit Airlines flight, departing Thu, Aug 21 from O'Hare Intl. to Miami Intl., returning Wed, Sep 3, priced at $148 just found

Tue, Jun 10 - Fri, Jun 13

ORD

O'Hare Intl.

MIA

Miami Intl.

$151 Roundtrip, found 5 days ago

$151

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Miami Intl., returning Fri, Jun 13, priced at $151 found 5 days ago

Wed, Jun 4 - Sat, Jun 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$153 Roundtrip, found 5 days ago

$153

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to Miami Intl., returning Sat, Jun 7, priced at $153 found 5 days ago

Sat, Aug 23 - Sun, Aug 31

ORD

O'Hare Intl.

MIA

Miami Intl.

$199 Roundtrip, just found

$199

Roundtrip

just found

Select American Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Miami Intl., returning Sun, Aug 31, priced at $199 just found

Sat, Aug 23 - Mon, Sep 1

ORD

O'Hare Intl.

MIA

Miami Intl.

$210 Roundtrip, just found

$210

Roundtrip

just found

Select Frontier Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Miami Intl., returning Mon, Sep 1, priced at $210 just found

Wed, Jun 11 - Wed, Jun 11

MDW

Midway Intl.

MIA

Miami Intl.

$211 Roundtrip, found 5 days ago

$211

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Jun 11 from Midway Intl. to Miami Intl., returning Wed, Jun 11, priced at $211 found 5 days ago

Tue, Jun 10 - Tue, Jun 10

ORD

O'Hare Intl.

MIA

Miami Intl.

$211 Roundtrip, found 5 days ago

$211

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Jun 10 from O'Hare Intl. to Miami Intl., returning Tue, Jun 10, priced at $211 found 5 days ago

Mon, Oct 27 - Wed, Nov 5

ORD

O'Hare Intl.

MIA

Miami Intl.

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Mon, Oct 27 from O'Hare Intl. to Miami Intl., returning Wed, Nov 5, priced at $217 found 5 days ago

Sun, Jun 8 - Wed, Jun 11

ORD

O'Hare Intl.

MIA

Miami Intl.

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select United flight, departing Sun, Jun 8 from O'Hare Intl. to Miami Intl., returning Wed, Jun 11, priced at $217 found 5 days ago

Tue, Jun 17 - Wed, Jun 25

ORD

O'Hare Intl.

EYW

Key West Intl.

$323 Roundtrip, found 6 days ago

$323

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jun 17 from O'Hare Intl. to Key West Intl., returning Wed, Jun 25, priced at $323 found 6 days ago