Flights from Chicago to Key Colony Beach

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, Jun 18 - Sat, Jul 5

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 18 from O'Hare Intl. to Miami Intl., returning Sat, Jul 5, priced at $128 found 5 days ago

Wed, Jun 18 - Thu, Jul 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 Wed, Jun 18 from O'Hare Intl. to Miami Intl., returning Thu, Jul 10, priced at $143 found 5 days ago

Mon, Jun 23 - Thu, Jul 10

ORD

O'Hare Intl.

MIA

Miami Intl.

$158 Roundtrip, found 5 days ago

$158

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Mon, Jun 23 from O'Hare Intl. to Miami Intl., returning Thu, Jul 10, priced at $158 found 5 days ago

Wed, Jun 18 - Tue, Jul 8

ORD

O'Hare Intl.

MIA

Miami Intl.

$171 Roundtrip, found 5 days ago

$171

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Miami Intl., returning Tue, Jul 8, priced at $171 found 5 days ago

Fri, Jun 20 - Sat, Jul 5

ORD

O'Hare Intl.

MIA

Miami Intl.

$173 Roundtrip, found 5 days ago

$173

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Miami Intl., returning Sat, Jul 5, priced at $173 found 5 days ago

Mon, Jun 23 - Tue, Jul 8

ORD

O'Hare Intl.

MIA

Miami Intl.

$186 Roundtrip, found 5 days ago

$186

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Mon, Jun 23 from O'Hare Intl. to Miami Intl., returning Tue, Jul 8, priced at $186 found 5 days ago

Fri, Jun 20 - Thu, Jul 10

ORD

O'Hare Intl.

MIA

Miami Intl.

$188 Roundtrip, found 5 days ago

$188

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Miami Intl., returning Thu, Jul 10, priced at $188 found 5 days ago

Sun, Jun 22 - Mon, Jul 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$207 Roundtrip, found 5 days ago

$207

Roundtrip

found 5 days ago

Select United flight, departing Sun, Jun 22 from O'Hare Intl. to Miami Intl., returning Mon, Jul 7, priced at $207 found 5 days ago

Wed, Jun 18 - Mon, Jul 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$213 Roundtrip, found 5 days ago

$213

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Miami Intl., returning Mon, Jul 7, priced at $213 found 5 days ago

Fri, Jun 20 - Tue, Jul 8

ORD

O'Hare Intl.

MIA

Miami Intl.

$216 Roundtrip, found 5 days ago

$216

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Miami Intl., returning Tue, Jul 8, priced at $216 found 5 days ago

Tue, Jul 1 - Tue, Jul 8

MDW

Midway Intl.

MIA

Miami Intl.

$217 Roundtrip, found 4 days ago

$217

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Jul 1 from Midway Intl. to Miami Intl., returning Tue, Jul 8, priced at $217 found 4 days ago

Tue, Jun 24 - Fri, Jul 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Jun 24 from O'Hare Intl. to Miami Intl., returning Fri, Jul 4, priced at $217 found 5 days ago

Wed, Jun 18 - Fri, Jul 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$220 Roundtrip, found 5 days ago

$220

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Miami Intl., returning Fri, Jul 4, priced at $220 found 5 days ago

Sat, Jun 21 - Mon, Jul 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$223 Roundtrip, found 5 days ago

$223

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Miami Intl., returning Mon, Jul 7, priced at $223 found 5 days ago

Sun, Jun 22 - Mon, Jul 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$225 Roundtrip, found 5 days ago

$225

Roundtrip

found 5 days ago

Select United flight, departing Sun, Jun 22 from O'Hare Intl. to Miami Intl., returning Mon, Jul 7, priced at $225 found 5 days ago

Sat, Jun 21 - Fri, Jul 4

ORD

O'Hare Intl.

MIA

Miami Intl.

$227 Roundtrip, found 5 days ago

$227

Roundtrip

found 5 days ago

Select Delta flight, departing Sat, Jun 21 from O'Hare Intl. to Miami Intl., returning Fri, Jul 4, priced at $227 found 5 days ago

Sat, Jun 21 - Mon, Jul 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$227 Roundtrip, found 5 days ago

$227

Roundtrip

found 5 days ago

Select United flight, departing Sat, Jun 21 from O'Hare Intl. to Miami Intl., returning Mon, Jul 7, priced at $227 found 5 days ago

Sat, Jun 21 - Mon, Jul 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$264 Roundtrip, found 5 days ago

$264

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Miami Intl., returning Mon, Jul 7, priced at $264 found 5 days ago

Mon, Aug 25 - Wed, Sep 3

ORD

O'Hare Intl.

EYW

Key West Intl.

$269 Roundtrip, found 2 days ago

$269

Roundtrip

found 2 days ago

Select Delta flight, departing Mon, Aug 25 from O'Hare Intl. to Key West Intl., returning Wed, Sep 3, priced at $269 found 2 days ago

Tue, Nov 18 - Tue, Dec 2

ORD

O'Hare Intl.

MIA

Miami Intl.

$273 Roundtrip, found 1 day ago

$273

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Nov 18 from O'Hare Intl. to Miami Intl., returning Tue, Dec 2, priced at $273 found 1 day ago