Flights from Chicago to Clearwater 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.

Sun, Jun 1 - Thu, Jun 5

MDW

Midway Intl.

TPA

Tampa Intl.

$98 Roundtrip, found 3 days ago

$98

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sun, Jun 1 from Midway Intl. to Tampa Intl., returning Thu, Jun 5, priced at $98 found 3 days ago

Thu, May 29 - Thu, Jun 5

MDW

Midway Intl.

TPA

Tampa Intl.

$104 Roundtrip, found 4 hours ago

$104

Roundtrip

found 4 hours ago

Select Frontier Airlines flight, departing Thu, May 29 from Midway Intl. to Tampa Intl., returning Thu, Jun 5, priced at $104 found 4 hours ago

Thu, May 29 - Thu, Jun 5

MDW

Midway Intl.

TPA

Tampa Intl.

$120 Roundtrip, found 4 hours ago

$120

Roundtrip

found 4 hours ago

Select Frontier Airlines flight, departing Thu, May 29 from Midway Intl. to Tampa Intl., returning Thu, Jun 5, priced at $120 found 4 hours ago

Thu, May 22 - Thu, May 29

MDW

Midway Intl.

TPA

Tampa Intl.

$134 Roundtrip, found 3 days ago

$134

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, May 22 from Midway Intl. to Tampa Intl., returning Thu, May 29, priced at $134 found 3 days ago

Thu, May 29 - Tue, Jun 3

MDW

Midway Intl.

TPA

Tampa Intl.

$142 Roundtrip, found 3 hours ago

$142

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Thu, May 29 from Midway Intl. to Tampa Intl., returning Tue, Jun 3, priced at $142 found 3 hours ago

Thu, May 29 - Tue, Jun 3

MDW

Midway Intl.

TPA

Tampa Intl.

$143 Roundtrip, found 3 hours ago

$143

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Thu, May 29 from Midway Intl. to Tampa Intl., returning Tue, Jun 3, priced at $143 found 3 hours ago

Thu, Jun 5 - Fri, Jun 6

ORD

O'Hare Intl.

TPA

Tampa Intl.

$153 Roundtrip, found 4 days ago

$153

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Jun 5 from O'Hare Intl. to Tampa Intl., returning Fri, Jun 6, priced at $153 found 4 days ago

Thu, May 29 - Mon, Jun 2

ORD

O'Hare Intl.

TPA

Tampa Intl.

$156 Roundtrip, found 6 days ago

$156

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, May 29 from O'Hare Intl. to Tampa Intl., returning Mon, Jun 2, priced at $156 found 6 days ago

Thu, May 29 - Thu, Jun 5

ORD

O'Hare Intl.

TPA

Tampa Intl.

$157 Roundtrip, found 6 days ago

$157

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, May 29 from O'Hare Intl. to Tampa Intl., returning Thu, Jun 5, priced at $157 found 6 days ago

Sun, May 25 - Sun, May 25

ORD

O'Hare Intl.

TPA

Tampa Intl.

$159 Roundtrip, found 6 days ago

$159

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sun, May 25 from O'Hare Intl. to Tampa Intl., returning Sun, May 25, priced at $159 found 6 days ago

Sun, May 25 - Wed, Jun 4

ORD

O'Hare Intl.

TPA

Tampa Intl.

$160 Roundtrip, found 6 days ago

$160

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sun, May 25 from O'Hare Intl. to Tampa Intl., returning Wed, Jun 4, priced at $160 found 6 days ago

Thu, May 29 - Sun, Jun 8

MDW

Midway Intl.

TPA

Tampa Intl.

$168 Roundtrip, found 3 days ago

$168

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, May 29 from Midway Intl. to Tampa Intl., returning Sun, Jun 8, priced at $168 found 3 days ago

Thu, May 22 - Sun, Jun 1

MDW

Midway Intl.

TPA

Tampa Intl.

$169 Roundtrip, found 3 days ago

$169

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, May 22 from Midway Intl. to Tampa Intl., returning Sun, Jun 1, priced at $169 found 3 days ago

Tue, Aug 26 - Wed, Sep 3

ORD

O'Hare Intl.

TPA

Tampa Intl.

$170 Roundtrip, found 4 days ago

$170

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Aug 26 from O'Hare Intl. to Tampa Intl., returning Wed, Sep 3, priced at $170 found 4 days ago

Sun, May 25 - Fri, May 30

MDW

Midway Intl.

TPA

Tampa Intl.

$172 Roundtrip, found 3 hours ago

$172

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Sun, May 25 from Midway Intl. to Tampa Intl., returning Fri, May 30, priced at $172 found 3 hours ago

Thu, May 29 - Sat, May 31

ORD

O'Hare Intl.

TPA

Tampa Intl.

$172 Roundtrip, found 6 days ago

$172

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, May 29 from O'Hare Intl. to Tampa Intl., returning Sat, May 31, priced at $172 found 6 days ago

Mon, May 26 - Thu, May 29

ORD

O'Hare Intl.

TPA

Tampa Intl.

$178 Roundtrip, found 6 days ago

$178

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Mon, May 26 from O'Hare Intl. to Tampa Intl., returning Thu, May 29, priced at $178 found 6 days ago

Wed, May 28 - Wed, May 28

ORD

O'Hare Intl.

TPA

Tampa Intl.

$191 Roundtrip, found 6 days ago

$191

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, May 28 from O'Hare Intl. to Tampa Intl., returning Wed, May 28, priced at $191 found 6 days ago

Sat, Aug 30 - Sat, Aug 30

ORD

O'Hare Intl.

TPA

Tampa Intl.

$239 Roundtrip, found 4 days ago

$239

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 30 from O'Hare Intl. to Tampa Intl., returning Sat, Aug 30, priced at $239 found 4 days ago

Sat, Aug 30 - Tue, Sep 2

ORD

O'Hare Intl.

TPA

Tampa Intl.

$247 Roundtrip, found 4 days ago

$247

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Sat, Aug 30 from O'Hare Intl. to Tampa Intl., returning Tue, Sep 2, priced at $247 found 4 days ago