Flights from Chicago to Florida

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.

Mon, Oct 6 - Thu, Oct 9

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$258 Roundtrip, found 22 hours ago

$258

Roundtrip

found 22 hours ago

Select Frontier Airlines flight, departing Mon, Oct 6 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, Oct 9, priced at $258 found 22 hours ago

Wed, Oct 8 - Wed, Oct 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$264 Roundtrip, found 22 hours ago

$264

Roundtrip

found 22 hours ago

Select Frontier Airlines flight, departing Wed, Oct 8 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Oct 15, priced at $264 found 22 hours ago

Thu, Oct 9 - Thu, Oct 9

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$266 Roundtrip, found 22 hours ago

$266

Roundtrip

found 22 hours ago

Select Frontier Airlines flight, departing Thu, Oct 9 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, Oct 9, priced at $266 found 22 hours ago

Sun, Oct 12 - Sun, Oct 12

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$267 Roundtrip, found 22 hours ago

$267

Roundtrip

found 22 hours ago

Select Frontier Airlines flight, departing Sun, Oct 12 from Midway Intl. to Luis Munoz Marin Intl., returning Sun, Oct 12, priced at $267 found 22 hours ago

Fri, Sep 19 - Thu, Sep 25

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$279 Roundtrip, found 2 days ago

$279

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Sep 25, priced at $279 found 2 days ago

Sun, Sep 21 - Mon, Sep 22

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$281 Roundtrip, found 2 days ago

$281

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sun, Sep 21 from O'Hare Intl. to Luis Munoz Marin Intl., returning Mon, Sep 22, priced at $281 found 2 days ago

Mon, Sep 22 - Thu, Sep 25

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$282 Roundtrip, found 2 days ago

$282

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Sep 22 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Sep 25, priced at $282 found 2 days ago

Sat, May 24 - Fri, May 30

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$289 Roundtrip, found 2 days ago

$289

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sat, May 24 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, May 30, priced at $289 found 2 days ago

Mon, Sep 22 - Tue, Sep 23

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$295 Roundtrip, found 2 days ago

$295

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Sep 22 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Sep 23, priced at $295 found 2 days ago

Wed, Sep 17 - Mon, Sep 22

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$300 Roundtrip, found 2 days ago

$300

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Sep 17 from O'Hare Intl. to Luis Munoz Marin Intl., returning Mon, Sep 22, priced at $300 found 2 days ago

Fri, Sep 19 - Thu, Sep 25

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$300 Roundtrip, found 2 days ago

$300

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Sep 25, priced at $300 found 2 days ago

Sat, May 24 - Sun, May 25

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$303 Roundtrip, found 6 days ago

$303

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, May 24 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, May 25, priced at $303 found 6 days ago

Mon, Aug 25 - Wed, Sep 3

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$305 Roundtrip, found 6 days ago

$305

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Mon, Aug 25 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Sep 3, priced at $305 found 6 days ago

Fri, Sep 19 - Thu, Sep 25

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$307 Roundtrip, found 2 days ago

$307

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Sep 25, priced at $307 found 2 days ago

Sat, May 24 - Thu, May 29

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$308 Roundtrip, found 6 days ago

$308

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, May 24 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, May 29, priced at $308 found 6 days ago

Mon, Sep 22 - Mon, Sep 22

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$309 Roundtrip, found 2 days ago

$309

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Sep 22 from O'Hare Intl. to Luis Munoz Marin Intl., returning Mon, Sep 22, priced at $309 found 2 days ago

Tue, Oct 7 - Sat, Oct 11

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$321 Roundtrip, found 22 hours ago

$321

Roundtrip

found 22 hours ago

Select Delta flight, departing Tue, Oct 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Oct 11, priced at $321 found 22 hours ago

Fri, Sep 19 - Thu, Sep 25

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$382 Roundtrip, found 2 days ago

$382

Roundtrip

found 2 days ago

Select United flight, departing Fri, Sep 19 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Sep 25, priced at $382 found 2 days ago

Fri, Sep 19 - Thu, Sep 25

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$391 Roundtrip, found 2 days ago

$391

Roundtrip

found 2 days ago

Select American Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Sep 25, priced at $391 found 2 days ago

Sun, Jan 4 - Mon, Jan 12

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$468 Roundtrip, found 12 hours ago

$468

Roundtrip

found 12 hours ago

Select JetBlue Airways flight, departing Sun, Jan 4 from O'Hare Intl. to Luis Munoz Marin Intl., returning Mon, Jan 12, priced at $468 found 12 hours ago