Flights from Chicago to Islamorada

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, Jul 22 - Wed, Jul 23

ORD

O'Hare Intl.

MIA

Miami Intl.

$138 Roundtrip, just found

$138

Roundtrip

just found

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to Miami Intl., returning Wed, Jul 23, priced at $138 just found

Fri, Aug 15 - Mon, Aug 18

ORD

O'Hare Intl.

MIA

Miami Intl.

$148 Roundtrip, found 3 days ago

$148

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Fri, Aug 15 from O'Hare Intl. to Miami Intl., returning Mon, Aug 18, priced at $148 found 3 days ago

Wed, Aug 13 - Fri, Aug 15

MDW

Midway Intl.

MIA

Miami Intl.

$154 Roundtrip, found 4 days ago

$154

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Wed, Aug 13 from Midway Intl. to Miami Intl., returning Fri, Aug 15, priced at $154 found 4 days ago

Wed, Jul 30 - Mon, Aug 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$157 Roundtrip, found 6 days ago

$157

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Miami Intl., returning Mon, Aug 4, priced at $157 found 6 days ago

Mon, Jul 28 - Thu, Aug 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$158 Roundtrip, found 3 days ago

$158

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Mon, Jul 28 from O'Hare Intl. to Miami Intl., returning Thu, Aug 7, priced at $158 found 3 days ago

Sun, Jul 20 - Fri, Jul 25

ORD

O'Hare Intl.

MIA

Miami Intl.

$163 Roundtrip, just found

$163

Roundtrip

just found

Select Spirit Airlines flight, departing Sun, Jul 20 from O'Hare Intl. to Miami Intl., returning Fri, Jul 25, priced at $163 just found

Thu, Jul 31 - Tue, Aug 5

ORD

O'Hare Intl.

MIA

Miami Intl.

$173 Roundtrip, found 2 days ago

$173

Roundtrip

found 2 days ago

Select United flight, departing Thu, Jul 31 from O'Hare Intl. to Miami Intl., returning Tue, Aug 5, priced at $173 found 2 days ago

Fri, Aug 1 - Tue, Aug 5

ORD

O'Hare Intl.

MIA

Miami Intl.

$173 Roundtrip, found 3 days ago

$173

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Fri, Aug 1 from O'Hare Intl. to Miami Intl., returning Tue, Aug 5, priced at $173 found 3 days ago

Sun, Jul 20 - Fri, Jul 25

ORD

O'Hare Intl.

MIA

Miami Intl.

$177 Roundtrip, just found

$177

Roundtrip

just found

Select United flight, departing Sun, Jul 20 from O'Hare Intl. to Miami Intl., returning Fri, Jul 25, priced at $177 just found

Sat, Jul 19 - Tue, Jul 22

ORD

O'Hare Intl.

MIA

Miami Intl.

$179 Roundtrip, just found

$179

Roundtrip

just found

Select Spirit Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Miami Intl., returning Tue, Jul 22, priced at $179 just found

Thu, Jul 31 - Tue, Aug 5

ORD

O'Hare Intl.

MIA

Miami Intl.

$183 Roundtrip, found 2 days ago

$183

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Jul 31 from O'Hare Intl. to Miami Intl., returning Tue, Aug 5, priced at $183 found 2 days ago

Sun, Jul 20 - Fri, Jul 25

ORD

O'Hare Intl.

MIA

Miami Intl.

$183 Roundtrip, just found

$183

Roundtrip

just found

Select Spirit Airlines flight, departing Sun, Jul 20 from O'Hare Intl. to Miami Intl., returning Fri, Jul 25, priced at $183 just found

Tue, Aug 12 - Fri, Aug 15

MDW

Midway Intl.

MIA

Miami Intl.

$186 Roundtrip, found 4 days ago

$186

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Aug 12 from Midway Intl. to Miami Intl., returning Fri, Aug 15, priced at $186 found 4 days ago

Sun, Jul 20 - Fri, Jul 25

ORD

O'Hare Intl.

MIA

Miami Intl.

$186 Roundtrip, just found

$186

Roundtrip

just found

Select Spirit Airlines flight, departing Sun, Jul 20 from O'Hare Intl. to Miami Intl., returning Fri, Jul 25, priced at $186 just found

Sun, Jul 20 - Fri, Jul 25

ORD

O'Hare Intl.

MIA

Miami Intl.

$189 Roundtrip, just found

$189

Roundtrip

just found

Select United flight, departing Sun, Jul 20 from O'Hare Intl. to Miami Intl., returning Fri, Jul 25, priced at $189 just found

Tue, Jul 22 - Mon, Jul 28

ORD

O'Hare Intl.

MIA

Miami Intl.

$191 Roundtrip, just found

$191

Roundtrip

just found

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to Miami Intl., returning Mon, Jul 28, priced at $191 just found

Fri, Jul 18 - Tue, Jul 22

ORD

O'Hare Intl.

MIA

Miami Intl.

$193 Roundtrip, just found

$193

Roundtrip

just found

Select Spirit Airlines flight, departing Fri, Jul 18 from O'Hare Intl. to Miami Intl., returning Tue, Jul 22, priced at $193 just found

Wed, Jul 23 - Wed, Jul 23

ORD

O'Hare Intl.

MIA

Miami Intl.

$211 Roundtrip, just found

$211

Roundtrip

just found

Select Delta flight, departing Wed, Jul 23 from O'Hare Intl. to Miami Intl., returning Wed, Jul 23, priced at $211 just found

Sun, Jul 20 - Fri, Jul 25

ORD

O'Hare Intl.

MIA

Miami Intl.

$217 Roundtrip, just found

$217

Roundtrip

just found

Select American Airlines flight, departing Sun, Jul 20 from O'Hare Intl. to Miami Intl., returning Fri, Jul 25, priced at $217 just found

Sun, Jul 20 - Fri, Jul 25

ORD

O'Hare Intl.

MIA

Miami Intl.

$950 Roundtrip, just found

$950

Roundtrip

just found

Select JetBlue Airways flight, departing Sun, Jul 20 from O'Hare Intl. to Miami Intl., returning Fri, Jul 25, priced at $950 just found