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.

Mon, Sep 28 - Thu, Oct 1

ORD

O'Hare Intl.

MCO

Orlando Intl.

$78 Roundtrip, found 4 hours ago

$78

Roundtrip

found 4 hours ago

Select Frontier Airlines flight, departing Mon, Sep 28 from O'Hare Intl. to Orlando Intl., returning Thu, Oct 1, priced at $78 found 4 hours ago

Tue, Sep 22 - Wed, Oct 7

ORD

O'Hare Intl.

DEN

Denver Intl.

$94 Roundtrip, found 2 days ago

$94

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Tue, Sep 22 from O'Hare Intl. to Denver Intl., returning Wed, Oct 7, priced at $94 found 2 days ago

Sun, Jul 26 - Thu, Jul 30

ORD

O'Hare Intl.

LAS

Harry Reid Intl.

$128 Roundtrip, found 5 days ago

$128

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Sun, Jul 26 from O'Hare Intl. to Harry Reid Intl., returning Thu, Jul 30, priced at $128 found 5 days ago

Thu, Oct 15 - Mon, Oct 19

ORD

O'Hare Intl.

PHX

Sky Harbor Intl.

$150 Roundtrip, found 10 hours ago

$150

Roundtrip

found 10 hours ago

Select Frontier Airlines flight, departing Thu, Oct 15 from O'Hare Intl. to Sky Harbor Intl., returning Mon, Oct 19, priced at $150 found 10 hours ago

Wed, Jun 10 - Tue, Jun 16

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$158 Roundtrip, found 8 hours ago

$158

Roundtrip

found 8 hours ago

Select Frontier Airlines flight, departing Wed, Jun 10 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Tue, Jun 16, priced at $158 found 8 hours ago

Tue, Jul 7 - Wed, Jul 15

ORD

O'Hare Intl.

LAX

Los Angeles Intl.

$164 Roundtrip, found 3 days ago

$164

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Jul 7 from O'Hare Intl. to Los Angeles Intl., returning Wed, Jul 15, priced at $164 found 3 days ago

Fri, Jun 19 - Sat, Jun 27

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$167 Roundtrip, found 6 days ago

$167

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Fri, Jun 19 from Midway Intl. to Dallas-Fort Worth Intl., returning Sat, Jun 27, priced at $167 found 6 days ago

Tue, Jul 21 - Wed, Jul 22

ORD

O'Hare Intl.

TPA

Tampa Intl.

$189 Roundtrip, found 1 day ago

$189

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Jul 21 from O'Hare Intl. to Tampa Intl., returning Wed, Jul 22, priced at $189 found 1 day ago

Wed, Oct 21 - Wed, Nov 4

MDW

Midway Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$189 Roundtrip, found 1 day ago

$189

Roundtrip

found 1 day ago

Select Southwest Airlines flight, departing Wed, Oct 21 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Nov 4, priced at $189 found 1 day ago

Wed, Jul 29 - Wed, Aug 5

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$189 Roundtrip, found 1 day ago

$189

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 29 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Aug 5, priced at $189 found 1 day ago

Tue, Jun 9 - Wed, Jun 10

MDW

Midway Intl.

DEN

Denver Intl.

$200 Roundtrip, found 3 days ago

$200

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Jun 9 from Midway Intl. to Denver Intl., returning Wed, Jun 10, priced at $200 found 3 days ago

Tue, Oct 27 - Tue, Nov 3

MDW

Midway Intl.

MCO

Orlando Intl.

$200 Roundtrip, found 1 day ago

$200

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Tue, Oct 27 from Midway Intl. to Orlando Intl., returning Tue, Nov 3, priced at $200 found 1 day ago

Tue, Jun 9 - Tue, Jun 16

MDW

Midway Intl.

TPA

Tampa Intl.

$200 Roundtrip, found 3 days ago

$200

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Jun 9 from Midway Intl. to Tampa Intl., returning Tue, Jun 16, priced at $200 found 3 days ago

Wed, Jun 24 - Wed, Jul 1

MDW

Midway Intl.

MIA

Miami Intl.

$200 Roundtrip, found 6 days ago

$200

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Wed, Jun 24 from Midway Intl. to Miami Intl., returning Wed, Jul 1, priced at $200 found 6 days ago

Tue, Sep 1 - Wed, Sep 9

ORD

O'Hare Intl.

MIA

Miami Intl.

$200 Roundtrip, found 2 days ago

$200

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Tue, Sep 1 from O'Hare Intl. to Miami Intl., returning Wed, Sep 9, priced at $200 found 2 days ago

Tue, Jul 14 - Wed, Jul 22

MDW

Midway Intl.

LAX

Los Angeles Intl.

$239 Roundtrip, found 3 days ago

$239

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Jul 14 from Midway Intl. to Los Angeles Intl., returning Wed, Jul 22, priced at $239 found 3 days ago

Wed, Oct 7 - Tue, Oct 13

MDW

Midway Intl.

LAS

Harry Reid Intl.

$250 Roundtrip, found 1 hour ago

$250

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Wed, Oct 7 from Midway Intl. to Harry Reid Intl., returning Tue, Oct 13, priced at $250 found 1 hour ago

Wed, Jul 29 - Sat, Aug 8

MDW

Midway Intl.

PHX

Sky Harbor Intl.

$254 Roundtrip, found 3 days ago

$254

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Wed, Jul 29 from Midway Intl. to Sky Harbor Intl., returning Sat, Aug 8, priced at $254 found 3 days ago

Tue, Jun 16 - Tue, Jun 30

MDW

Midway Intl.

DAL

Love Field

$291 Roundtrip, found 6 days ago

$291

Roundtrip

found 6 days ago

Select Southwest Airlines flight, departing Tue, Jun 16 from Midway Intl. to Love Field, returning Tue, Jun 30, priced at $291 found 6 days ago

Tue, Sep 22 - Wed, Sep 30

ORD

O'Hare Intl.

DAL

Love Field

$301 Roundtrip, found 3 hours ago

$301

Roundtrip

found 3 hours ago

Select Delta flight, departing Tue, Sep 22 from O'Hare Intl. to Love Field, returning Wed, Sep 30, priced at $301 found 3 hours ago