Flights from Chicago to Highland Park

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 - Fri, Jun 27

ORD

O'Hare Intl.

TPA

Tampa Intl.

$122 Roundtrip, found 2 days ago

$122

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Jun 26 from O'Hare Intl. to Tampa Intl., returning Fri, Jun 27, priced at $122 found 2 days ago

Sat, Jun 21 - Fri, Jun 27

ORD

O'Hare Intl.

TPA

Tampa Intl.

$124 Roundtrip, found 2 days ago

$124

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Tampa Intl., returning Fri, Jun 27, priced at $124 found 2 days ago

Wed, Jun 4 - Sat, Jun 7

ORD

O'Hare Intl.

TPA

Tampa Intl.

$134 Roundtrip, found 4 days ago

$134

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to Tampa Intl., returning Sat, Jun 7, priced at $134 found 4 days ago

Sat, Jun 7 - Sat, Jun 7

ORD

O'Hare Intl.

TPA

Tampa Intl.

$141 Roundtrip, found 4 days ago

$141

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to Tampa Intl., returning Sat, Jun 7, priced at $141 found 4 days ago

Fri, Jun 20 - Fri, Jun 27

ORD

O'Hare Intl.

TPA

Tampa Intl.

$144 Roundtrip, found 2 days ago

$144

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Tampa Intl., returning Fri, Jun 27, priced at $144 found 2 days ago

Wed, Jun 4 - Fri, Jun 6

ORD

O'Hare Intl.

TPA

Tampa Intl.

$145 Roundtrip, found 4 days ago

$145

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to Tampa Intl., returning Fri, Jun 6, priced at $145 found 4 days ago

Sat, Jun 7 - Mon, Jun 9

ORD

O'Hare Intl.

TPA

Tampa Intl.

$146 Roundtrip, found 4 days ago

$146

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to Tampa Intl., returning Mon, Jun 9, priced at $146 found 4 days ago

Wed, Jun 4 - Mon, Jun 9

ORD

O'Hare Intl.

TPA

Tampa Intl.

$149 Roundtrip, found 4 days ago

$149

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to Tampa Intl., returning Mon, Jun 9, priced at $149 found 4 days ago

Sun, Jun 1 - Sun, Jun 8

MDW

Midway Intl.

TPA

Tampa Intl.

$152 Roundtrip, found 2 days ago

$152

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sun, Jun 1 from Midway Intl. to Tampa Intl., returning Sun, Jun 8, priced at $152 found 2 days ago

Tue, Jun 3 - Fri, Jun 6

ORD

O'Hare Intl.

TPA

Tampa Intl.

$157 Roundtrip, found 4 days ago

$157

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Tue, Jun 3 from O'Hare Intl. to Tampa Intl., returning Fri, Jun 6, priced at $157 found 4 days ago

Tue, Jun 3 - Sat, Jun 7

ORD

O'Hare Intl.

TPA

Tampa Intl.

$158 Roundtrip, found 4 days ago

$158

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Tue, Jun 3 from O'Hare Intl. to Tampa Intl., returning Sat, Jun 7, priced at $158 found 4 days ago

Sat, Jun 21 - Thu, Jun 26

ORD

O'Hare Intl.

TPA

Tampa Intl.

$160 Roundtrip, found 2 days ago

$160

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Tampa Intl., returning Thu, Jun 26, priced at $160 found 2 days ago

Thu, Jun 26 - Mon, Jun 30

ORD

O'Hare Intl.

TPA

Tampa Intl.

$161 Roundtrip, found 2 days ago

$161

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Jun 26 from O'Hare Intl. to Tampa Intl., returning Mon, Jun 30, priced at $161 found 2 days ago

Fri, May 30 - Sat, Jun 7

ORD

O'Hare Intl.

TPA

Tampa Intl.

$163 Roundtrip, found 2 days ago

$163

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, May 30 from O'Hare Intl. to Tampa Intl., returning Sat, Jun 7, priced at $163 found 2 days ago

Thu, Jun 5 - Mon, Jun 9

ORD

O'Hare Intl.

TPA

Tampa Intl.

$166 Roundtrip, found 4 days ago

$166

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Jun 5 from O'Hare Intl. to Tampa Intl., returning Mon, Jun 9, priced at $166 found 4 days ago

Thu, May 29 - Sun, Jun 8

MDW

Midway Intl.

TPA

Tampa Intl.

$167 Roundtrip, found 2 days ago

$167

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, May 29 from Midway Intl. to Tampa Intl., returning Sun, Jun 8, priced at $167 found 2 days ago

Thu, Nov 6 - Fri, Nov 14

ORD

O'Hare Intl.

TPA

Tampa Intl.

$180 Roundtrip, found 1 day ago

$180

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Nov 6 from O'Hare Intl. to Tampa Intl., returning Fri, Nov 14, priced at $180 found 1 day ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

TPA

Tampa Intl.

$197 Roundtrip, found 1 day ago

$197

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Nov 4 from O'Hare Intl. to Tampa Intl., returning Tue, Nov 11, priced at $197 found 1 day ago

Thu, Nov 6 - Fri, Nov 14

ORD

O'Hare Intl.

TPA

Tampa Intl.

$223 Roundtrip, found 1 day ago

$223

Roundtrip

found 1 day ago

Select United flight, departing Thu, Nov 6 from O'Hare Intl. to Tampa Intl., returning Fri, Nov 14, priced at $223 found 1 day ago

Fri, May 30 - Thu, Jun 5

ORD

O'Hare Intl.

TPA

Tampa Intl.

$403 Roundtrip, found 2 days ago

$403

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, May 30 from O'Hare Intl. to Tampa Intl., returning Thu, Jun 5, priced at $403 found 2 days ago