Flights from Chicago

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.

Sat, May 10 - Sat, May 17

ORD

O'Hare Intl.

MCO

Orlando Intl.

$89 Roundtrip, found 5 days ago

$89

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sat, May 10 from O'Hare Intl. to Orlando Intl., returning Sat, May 17, priced at $89 found 5 days ago

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

Wed, Sep 3 - Sat, Sep 6

ORD

O'Hare Intl.

MIA

Miami Intl.

$98 Roundtrip, found 3 days ago

$98

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Miami Intl., returning Sat, Sep 6, priced at $98 found 3 days ago

Wed, Jun 25 - Mon, Jun 30

ORD

O'Hare Intl.

DEN

Denver Intl.

$116 Roundtrip, found 9 hours ago

$116

Roundtrip

found 9 hours ago

Select Frontier Airlines flight, departing Wed, Jun 25 from O'Hare Intl. to Denver Intl., returning Mon, Jun 30, priced at $116 found 9 hours ago

Sat, Oct 25 - Sat, Nov 1

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$128 Roundtrip, found 3 hours ago

$128

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Sat, Oct 25 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Nov 1, priced at $128 found 3 hours ago

Mon, May 26 - Fri, May 30

ORD

O'Hare Intl.

LAS

Harry Reid Intl.

$129 Roundtrip, found 1 day ago

$129

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, May 26 from O'Hare Intl. to Harry Reid Intl., returning Fri, May 30, priced at $129 found 1 day ago

Tue, May 13 - Sat, May 24

ORD

O'Hare Intl.

LAX

Los Angeles Intl.

$130 Roundtrip, found 1 day ago

$130

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, May 13 from O'Hare Intl. to Los Angeles Intl., returning Sat, May 24, priced at $130 found 1 day ago

Sun, Jun 1 - Mon, Jun 2

MDW

Midway Intl.

MCO

Orlando Intl.

$138 Roundtrip, found 1 day ago

$138

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sun, Jun 1 from Midway Intl. to Orlando Intl., returning Mon, Jun 2, priced at $138 found 1 day 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

Sun, May 18 - Mon, May 19

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$156 Roundtrip, found 3 days ago

$156

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sun, May 18 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Mon, May 19, priced at $156 found 3 days ago

Sun, May 18 - Sun, May 25

MDW

Midway Intl.

LAS

Harry Reid Intl.

$174 Roundtrip, found 4 days ago

$174

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sun, May 18 from Midway Intl. to Harry Reid Intl., returning Sun, May 25, priced at $174 found 4 days ago

Mon, May 5 - Mon, May 5

MDW

Midway Intl.

LAX

Los Angeles Intl.

$188 Roundtrip, found 17 hours ago

$188

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Mon, May 5 from Midway Intl. to Los Angeles Intl., returning Mon, May 5, priced at $188 found 17 hours ago

Thu, May 8 - Sun, May 11

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$193 Roundtrip, found 5 days ago

$193

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Thu, May 8 from Midway Intl. to Dallas-Fort Worth Intl., returning Sun, May 11, priced at $193 found 5 days ago

Thu, May 8 - Mon, May 12

ORD

O'Hare Intl.

PHX

Sky Harbor Intl.

$194 Roundtrip, found 6 days ago

$194

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, May 8 from O'Hare Intl. to Sky Harbor Intl., returning Mon, May 12, priced at $194 found 6 days ago

Thu, Jul 24 - Sun, Jul 27

MDW

Midway Intl.

PHX

Sky Harbor Intl.

$208 Roundtrip, found 11 hours ago

$208

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Thu, Jul 24 from Midway Intl. to Sky Harbor Intl., returning Sun, Jul 27, priced at $208 found 11 hours ago

Wed, Jun 11 - Wed, Jun 11

MDW

Midway Intl.

MIA

Miami Intl.

$211 Roundtrip, found 1 day ago

$211

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jun 11 from Midway Intl. to Miami Intl., returning Wed, Jun 11, priced at $211 found 1 day ago

Fri, Jun 13 - Mon, Jun 16

MDW

Midway Intl.

DEN

Denver Intl.

$216 Roundtrip, found 2 days ago

$216

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, Jun 13 from Midway Intl. to Denver Intl., returning Mon, Jun 16, priced at $216 found 2 days ago

Wed, Jun 4 - Wed, Jun 11

MDW

Midway Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Jun 4 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Jun 11, priced at $217 found 5 days ago

Sat, May 3 - Sat, May 10

MDW

Midway Intl.

DAL

Love Field

$307 Roundtrip, found 5 days ago

$307

Roundtrip

found 5 days ago

Select Delta flight, departing Sat, May 3 from Midway Intl. to Love Field, returning Sat, May 10, priced at $307 found 5 days ago

Sat, May 3 - Sat, May 10

ORD

O'Hare Intl.

DAL

Love Field

$307 Roundtrip, found 5 days ago

$307

Roundtrip

found 5 days ago

Select Delta flight, departing Sat, May 3 from O'Hare Intl. to Love Field, returning Sat, May 10, priced at $307 found 5 days ago