Flights from Chicago to Summerland 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, Jun 26 - Tue, Jul 1

ORD

O'Hare Intl.

MIA

Miami Intl.

$138 Roundtrip, found 1 day ago

$138

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, Jun 26 from O'Hare Intl. to Miami Intl., returning Tue, Jul 1, priced at $138 found 1 day ago

Sat, Nov 1 - Tue, Nov 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$143 Roundtrip, found 6 days ago

$143

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sat, Nov 1 from O'Hare Intl. to Miami Intl., returning Tue, Nov 4, priced at $143 found 6 days ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

MIA

Miami Intl.

$148 Roundtrip, found 21 hours ago

$148

Roundtrip

found 21 hours ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Miami Intl., returning Thu, Aug 14, priced at $148 found 21 hours ago

Wed, Jul 30 - Thu, Jul 31

ORD

O'Hare Intl.

MIA

Miami Intl.

$153 Roundtrip, found 4 days ago

$153

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Miami Intl., returning Thu, Jul 31, priced at $153 found 4 days ago

Wed, Jul 30 - Mon, Aug 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$157 Roundtrip, found 22 hours ago

$157

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Miami Intl., returning Mon, Aug 4, priced at $157 found 22 hours ago

Mon, Aug 11 - Thu, Aug 14

ORD

O'Hare Intl.

MIA

Miami Intl.

$158 Roundtrip, found 21 hours ago

$158

Roundtrip

found 21 hours ago

Select Spirit Airlines flight, departing Mon, Aug 11 from O'Hare Intl. to Miami Intl., returning Thu, Aug 14, priced at $158 found 21 hours ago

Wed, Jul 30 - Mon, Aug 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$163 Roundtrip, found 22 hours ago

$163

Roundtrip

found 22 hours ago

Select United flight, departing Wed, Jul 30 from O'Hare Intl. to Miami Intl., returning Mon, Aug 4, priced at $163 found 22 hours ago

Sat, Nov 1 - Tue, Nov 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$166 Roundtrip, found 6 days ago

$166

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sat, Nov 1 from O'Hare Intl. to Miami Intl., returning Tue, Nov 4, priced at $166 found 6 days ago

Wed, Jul 30 - Thu, Jul 31

ORD

O'Hare Intl.

MIA

Miami Intl.

$167 Roundtrip, found 4 days ago

$167

Roundtrip

found 4 days ago

Select United flight, departing Wed, Jul 30 from O'Hare Intl. to Miami Intl., returning Thu, Jul 31, priced at $167 found 4 days ago

Wed, Jul 30 - Thu, Jul 31

ORD

O'Hare Intl.

MIA

Miami Intl.

$167 Roundtrip, found 4 days ago

$167

Roundtrip

found 4 days ago

Select United flight, departing Wed, Jul 30 from O'Hare Intl. to Miami Intl., returning Thu, Jul 31, priced at $167 found 4 days ago

Wed, Jul 30 - Thu, Jul 31

ORD

O'Hare Intl.

MIA

Miami Intl.

$167 Roundtrip, found 4 days ago

$167

Roundtrip

found 4 days ago

Select American Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Miami Intl., returning Thu, Jul 31, priced at $167 found 4 days ago

Wed, Jul 30 - Mon, Aug 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$176 Roundtrip, found 22 hours ago

$176

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Miami Intl., returning Mon, Aug 4, priced at $176 found 22 hours ago

Sat, Nov 1 - Tue, Nov 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$177 Roundtrip, found 6 days ago

$177

Roundtrip

found 6 days ago

Select United flight, departing Sat, Nov 1 from O'Hare Intl. to Miami Intl., returning Tue, Nov 4, priced at $177 found 6 days ago

Sat, Aug 2 - Tue, Aug 5

ORD

O'Hare Intl.

MIA

Miami Intl.

$181 Roundtrip, found 4 days ago

$181

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Miami Intl., returning Tue, Aug 5, priced at $181 found 4 days ago

Wed, Jul 30 - Mon, Aug 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$183 Roundtrip, found 22 hours ago

$183

Roundtrip

found 22 hours ago

Select Delta flight, departing Wed, Jul 30 from O'Hare Intl. to Miami Intl., returning Mon, Aug 4, priced at $183 found 22 hours ago

Mon, Nov 3 - Sat, Nov 8

MDW

Midway Intl.

MIA

Miami Intl.

$201 Roundtrip, found 6 days ago

$201

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Mon, Nov 3 from Midway Intl. to Miami Intl., returning Sat, Nov 8, priced at $201 found 6 days ago

Fri, Aug 8 - Tue, Aug 19

ORD

O'Hare Intl.

MIA

Miami Intl.

$217 Roundtrip, found 21 hours ago

$217

Roundtrip

found 21 hours ago

Select Delta flight, departing Fri, Aug 8 from O'Hare Intl. to Miami Intl., returning Tue, Aug 19, priced at $217 found 21 hours ago

Thu, Oct 30 - Tue, Nov 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$245 Roundtrip, found 6 days ago

$245

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Oct 30 from O'Hare Intl. to Miami Intl., returning Tue, Nov 4, priced at $245 found 6 days ago

Tue, Nov 4 - Sat, Nov 8

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, Nov 4 from O'Hare Intl. to Key West Intl., returning Sat, Nov 8, priced at $269 found 1 day ago

Thu, Nov 6 - Wed, Nov 12

MDW

Midway Intl.

EYW

Key West Intl.

$361 Roundtrip, found 1 day ago

$361

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Nov 6 from Midway Intl. to Key West Intl., returning Wed, Nov 12, priced at $361 found 1 day ago