Flights from Chicago to Sugarloaf 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, Oct 15 - Wed, Oct 22

ORD

O'Hare Intl.

MIA

Miami Intl.

$108 Roundtrip, found 2 hours ago

$108

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Miami Intl., returning Wed, Oct 22, priced at $108 found 2 hours ago

Fri, Jun 20 - Sat, Jun 21

ORD

O'Hare Intl.

MIA

Miami Intl.

$118 Roundtrip, found 19 hours ago

$118

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Miami Intl., returning Sat, Jun 21, priced at $118 found 19 hours ago

Wed, Oct 15 - Thu, Oct 23

ORD

O'Hare Intl.

MIA

Miami Intl.

$128 Roundtrip, found 2 hours ago

$128

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Miami Intl., returning Thu, Oct 23, priced at $128 found 2 hours ago

Thu, Jun 19 - Sat, Jun 21

ORD

O'Hare Intl.

MIA

Miami Intl.

$138 Roundtrip, found 19 hours ago

$138

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to Miami Intl., returning Sat, Jun 21, priced at $138 found 19 hours ago

Tue, Jun 10 - Tue, Jun 17

ORD

O'Hare Intl.

MIA

Miami Intl.

$146 Roundtrip, found 1 day ago

$146

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to Miami Intl., returning Tue, Jun 17, priced at $146 found 1 day ago

Wed, Oct 15 - Mon, Oct 27

ORD

O'Hare Intl.

MIA

Miami Intl.

$148 Roundtrip, found 2 hours ago

$148

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Miami Intl., returning Mon, Oct 27, priced at $148 found 2 hours ago

Fri, Oct 17 - Wed, Oct 22

ORD

O'Hare Intl.

MIA

Miami Intl.

$166 Roundtrip, found 2 hours ago

$166

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Fri, Oct 17 from O'Hare Intl. to Miami Intl., returning Wed, Oct 22, priced at $166 found 2 hours ago

Wed, Oct 15 - Fri, Oct 24

ORD

O'Hare Intl.

MIA

Miami Intl.

$168 Roundtrip, found 2 hours ago

$168

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Miami Intl., returning Fri, Oct 24, priced at $168 found 2 hours ago

Sat, Jun 14 - Tue, Jun 17

ORD

O'Hare Intl.

MIA

Miami Intl.

$184 Roundtrip, found 1 day ago

$184

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Miami Intl., returning Tue, Jun 17, priced at $184 found 1 day ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

MIA

Miami Intl.

$186 Roundtrip, found 19 hours ago

$186

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Miami Intl., returning Tue, Jun 24, priced at $186 found 19 hours ago

Thu, Oct 16 - Mon, Oct 27

ORD

O'Hare Intl.

MIA

Miami Intl.

$188 Roundtrip, found 2 hours ago

$188

Roundtrip

found 2 hours ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Miami Intl., returning Mon, Oct 27, priced at $188 found 2 hours ago

Thu, Jun 19 - Sat, Jun 21

ORD

O'Hare Intl.

MIA

Miami Intl.

$191 Roundtrip, found 19 hours ago

$191

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to Miami Intl., returning Sat, Jun 21, priced at $191 found 19 hours ago

Thu, Jun 19 - Sat, Jun 21

ORD

O'Hare Intl.

MIA

Miami Intl.

$194 Roundtrip, found 19 hours ago

$194

Roundtrip

found 19 hours ago

Select American Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to Miami Intl., returning Sat, Jun 21, priced at $194 found 19 hours ago

Fri, Jun 20 - Sat, Jun 21

ORD

O'Hare Intl.

MIA

Miami Intl.

$194 Roundtrip, found 19 hours ago

$194

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Miami Intl., returning Sat, Jun 21, priced at $194 found 19 hours ago

Sat, Aug 23 - Sun, Aug 31

ORD

O'Hare Intl.

MIA

Miami Intl.

$199 Roundtrip, found 2 days ago

$199

Roundtrip

found 2 days ago

Select American Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Miami Intl., returning Sun, Aug 31, priced at $199 found 2 days ago

Sat, Aug 23 - Mon, Sep 1

ORD

O'Hare Intl.

MIA

Miami Intl.

$210 Roundtrip, found 2 days ago

$210

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Miami Intl., returning Mon, Sep 1, priced at $210 found 2 days ago

Tue, Jun 17 - Tue, Jun 17

ORD

O'Hare Intl.

MIA

Miami Intl.

$211 Roundtrip, found 19 hours ago

$211

Roundtrip

found 19 hours ago

Select Delta flight, departing Tue, Jun 17 from O'Hare Intl. to Miami Intl., returning Tue, Jun 17, priced at $211 found 19 hours ago

Tue, Jun 17 - Wed, Jun 25

MDW

Midway Intl.

MIA

Miami Intl.

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Jun 17 from Midway Intl. to Miami Intl., returning Wed, Jun 25, priced at $217 found 5 days ago

Sat, Jun 7 - Wed, Jun 11

ORD

O'Hare Intl.

EYW

Key West Intl.

$323 Roundtrip, found 1 day ago

$323

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Jun 7 from O'Hare Intl. to Key West Intl., returning Wed, Jun 11, priced at $323 found 1 day ago

Fri, Jun 20 - Sat, Jun 21

ORD

O'Hare Intl.

MIA

Miami Intl.

$353 Roundtrip, found 19 hours ago

$353

Roundtrip

found 19 hours ago

Select United flight, departing Fri, Jun 20 from O'Hare Intl. to Miami Intl., returning Sat, Jun 21, priced at $353 found 19 hours ago