Flights from Highwood

Cheapest flights from Highwood

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, Dec 2 - Mon, Dec 7

ORD

O'Hare Intl.

MCO

Orlando Intl.

$128 Roundtrip, found 2 days ago

$128

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Wed, Dec 2 from O'Hare Intl. to Orlando Intl., returning Mon, Dec 7, priced at $128 found 2 days ago

Wed, Nov 25 - Thu, Nov 26

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$140 Roundtrip, found 6 days ago

$140

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Wed, Nov 25 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Thu, Nov 26, priced at $140 found 6 days ago

Fri, Dec 4 - Sun, Dec 13

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$148 Roundtrip, found 2 days ago

$148

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, Dec 4 from O'Hare Intl. to Southwest Florida Intl., returning Sun, Dec 13, priced at $148 found 2 days ago

Tue, Nov 24 - Thu, Nov 26

ORD

O'Hare Intl.

TPA

Tampa Intl.

$165 Roundtrip, found 5 days ago

$165

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Tue, Nov 24 from O'Hare Intl. to Tampa Intl., returning Thu, Nov 26, priced at $165 found 5 days ago

Tue, Nov 3 - Tue, Nov 17

MDW

Midway Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$174 Roundtrip, found 5 days ago

$174

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Tue, Nov 3 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Nov 17, priced at $174 found 5 days ago

Sat, Nov 14 - Mon, Nov 23

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$176 Roundtrip, found 4 hours ago

$176

Roundtrip

found 4 hours ago

Select United flight, departing Sat, Nov 14 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Nov 23, priced at $176 found 4 hours ago

Sun, Nov 22 - Sun, Nov 22

ORD

O'Hare Intl.

LAX

Los Angeles Intl.

$181 Roundtrip, found 3 days ago

$181

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sun, Nov 22 from O'Hare Intl. to Los Angeles Intl., returning Sun, Nov 22, priced at $181 found 3 days ago

Tue, Jan 5 - Sat, Jan 16

MDW

Midway Intl.

MCO

Orlando Intl.

$186 Roundtrip, found 6 days ago

$186

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Tue, Jan 5 from Midway Intl. to Orlando Intl., returning Sat, Jan 16, priced at $186 found 6 days ago

Fri, Dec 4 - Mon, Dec 14

ORD

O'Hare Intl.

PHX

Sky Harbor Intl.

$196 Roundtrip, found 5 days ago

$196

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Fri, Dec 4 from O'Hare Intl. to Sky Harbor Intl., returning Mon, Dec 14, priced at $196 found 5 days ago

Thu, Jan 21 - Sat, Jan 30

MDW

Midway Intl.

TPA

Tampa Intl.

$200 Roundtrip, found 6 days ago

$200

Roundtrip

found 6 days ago

Select Delta flight, departing Thu, Jan 21 from Midway Intl. to Tampa Intl., returning Sat, Jan 30, priced at $200 found 6 days ago

Mon, Nov 16 - Thu, Nov 19

ORD

O'Hare Intl.

LAS

Harry Reid Intl.

$218 Roundtrip, found 12 hours ago

$218

Roundtrip

found 12 hours ago

Select Frontier Airlines flight, departing Mon, Nov 16 from O'Hare Intl. to Harry Reid Intl., returning Thu, Nov 19, priced at $218 found 12 hours ago

Thu, Nov 26 - Wed, Dec 2

MDW

Midway Intl.

MIA

Miami Intl.

$235 Roundtrip, found 2 days ago

$235

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Nov 26 from Midway Intl. to Miami Intl., returning Wed, Dec 2, priced at $235 found 2 days ago

Mon, Dec 7 - Thu, Dec 17

ORD

O'Hare Intl.

MIA

Miami Intl.

$235 Roundtrip, found 2 days ago

$235

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Mon, Dec 7 from O'Hare Intl. to Miami Intl., returning Thu, Dec 17, priced at $235 found 2 days ago

Tue, Nov 10 - Wed, Nov 11

MDW

Midway Intl.

LAS

Harry Reid Intl.

$248 Roundtrip, found 1 day ago

$248

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Tue, Nov 10 from Midway Intl. to Harry Reid Intl., returning Wed, Nov 11, priced at $248 found 1 day ago

Sat, Nov 14 - Mon, Nov 23

ORD

O'Hare Intl.

SFO

San Francisco Intl.

$280 Roundtrip, found 12 hours ago

$280

Roundtrip

found 12 hours ago

Select Frontier Airlines flight, departing Sat, Nov 14 from O'Hare Intl. to San Francisco Intl., returning Mon, Nov 23, priced at $280 found 12 hours ago

Thu, Nov 26 - Wed, Dec 2

MDW

Midway Intl.

PHX

Sky Harbor Intl.

$283 Roundtrip, found 7 hours ago

$283

Roundtrip

found 7 hours ago

Select Southwest Airlines flight, departing Thu, Nov 26 from Midway Intl. to Sky Harbor Intl., returning Wed, Dec 2, priced at $283 found 7 hours ago

Mon, Nov 9 - Wed, Nov 18

ORD

O'Hare Intl.

MEX

Mexico City Intl.

$358 Roundtrip, found 5 days ago

$358

Roundtrip

found 5 days ago

Select Viva flight, departing Mon, Nov 9 from O'Hare Intl. to Mexico City Intl., returning Wed, Nov 18, priced at $358 found 5 days ago

Tue, Oct 20 - Sat, Oct 31

MDW

Midway Intl.

RSW

Southwest Florida Intl.

$424 Roundtrip, found 5 days ago

$424

Roundtrip

found 5 days ago

Select Delta flight, departing Tue, Oct 20 from Midway Intl. to Southwest Florida Intl., returning Sat, Oct 31, priced at $424 found 5 days ago

Tue, Oct 20 - Sat, Oct 24

ORD

O'Hare Intl.

NLU

Felipe Ángeles Intl.

$501 Roundtrip, found 5 days ago

$501

Roundtrip

found 5 days ago

Select Volaris flight, departing Tue, Oct 20 from O'Hare Intl. to Felipe Ángeles Intl., returning Sat, Oct 24, priced at $501 found 5 days ago

Sat, Dec 19 - Sat, Jan 2

ORD

O'Hare Intl.

TLC

Toluca Intl.

$1,220 Roundtrip, found 5 days ago

$1,220

Roundtrip

found 5 days ago

Select Volaris flight, departing Sat, Dec 19 from O'Hare Intl. to Toluca Intl., returning Sat, Jan 2, priced at $1,220 found 5 days ago