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.

Thu, Oct 29 - Tue, Nov 17

ORD

O'Hare Intl.

DEN

Denver Intl.

$101 Roundtrip, found 4 days ago

$101

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Oct 29 from O'Hare Intl. to Denver Intl., returning Tue, Nov 17, priced at $101 found 4 days ago

Mon, Aug 17 - Tue, Aug 18

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$106 Roundtrip, found 4 days ago

$106

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Mon, Aug 17 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Aug 18, priced at $106 found 4 days ago

Mon, Nov 16 - Tue, Dec 1

ORD

O'Hare Intl.

MCO

Orlando Intl.

$149 Roundtrip, found 4 days ago

$149

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Mon, Nov 16 from O'Hare Intl. to Orlando Intl., returning Tue, Dec 1, priced at $149 found 4 days ago

Sat, Nov 14 - Sat, Nov 28

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$174 Roundtrip, found 4 days ago

$174

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Nov 14 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Sat, Nov 28, priced at $174 found 4 days ago

Tue, Oct 13 - Mon, Nov 2

ORD

O'Hare Intl.

TPA

Tampa Intl.

$186 Roundtrip, found 11 hours ago

$186

Roundtrip

found 11 hours ago

Select American Airlines flight, departing Tue, Oct 13 from O'Hare Intl. to Tampa Intl., returning Mon, Nov 2, priced at $186 found 11 hours ago

Tue, Aug 18 - Mon, Aug 24

ORD

O'Hare Intl.

LAX

Los Angeles Intl.

$188 Roundtrip, found 5 days ago

$188

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Tue, Aug 18 from O'Hare Intl. to Los Angeles Intl., returning Mon, Aug 24, priced at $188 found 5 days ago

Mon, Nov 9 - Thu, Nov 12

ORD

O'Hare Intl.

PHX

Sky Harbor Intl.

$190 Roundtrip, found 12 hours ago

$190

Roundtrip

found 12 hours ago

Select Frontier Airlines flight, departing Mon, Nov 9 from O'Hare Intl. to Sky Harbor Intl., returning Thu, Nov 12, priced at $190 found 12 hours ago

Sat, Oct 24 - Tue, Oct 27

ORD

O'Hare Intl.

LAS

Harry Reid Intl.

$202 Roundtrip, found 1 hour ago

$202

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Sat, Oct 24 from O'Hare Intl. to Harry Reid Intl., returning Tue, Oct 27, priced at $202 found 1 hour ago

Sat, Aug 22 - Tue, Aug 25

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$203 Roundtrip, found 3 hours ago

$203

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Sat, Aug 22 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Aug 25, priced at $203 found 3 hours ago

Mon, Aug 17 - Tue, Sep 1

ORD

O'Hare Intl.

MIA

Miami Intl.

$203 Roundtrip, just found

$203

Roundtrip

just found

Select United flight, departing Mon, Aug 17 from O'Hare Intl. to Miami Intl., returning Tue, Sep 1, priced at $203 just found

Tue, Sep 15 - Tue, Sep 22

MDW

Midway Intl.

MIA

Miami Intl.

$203 Roundtrip, found 2 hours ago

$203

Roundtrip

found 2 hours ago

Select Southwest Airlines flight, departing Tue, Sep 15 from Midway Intl. to Miami Intl., returning Tue, Sep 22, priced at $203 found 2 hours ago

Mon, Aug 17 - Tue, Sep 1

ORD

O'Hare Intl.

MIA

Miami Intl.

$203 Roundtrip, just found

$203

Roundtrip

just found

Select American Airlines flight, departing Mon, Aug 17 from O'Hare Intl. to Miami Intl., returning Tue, Sep 1, priced at $203 just found

Wed, Oct 14 - Wed, Oct 21

MDW

Midway Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$203 Roundtrip, found 12 hours ago

$203

Roundtrip

found 12 hours ago

Select Southwest Airlines flight, departing Wed, Oct 14 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Oct 21, priced at $203 found 12 hours ago

Tue, Aug 25 - Tue, Sep 1

MDW

Midway Intl.

TPA

Tampa Intl.

$220 Roundtrip, found 6 days ago

$220

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Tue, Aug 25 from Midway Intl. to Tampa Intl., returning Tue, Sep 1, priced at $220 found 6 days ago

Wed, Jul 22 - Wed, Aug 5

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$228 Roundtrip, found 4 days ago

$228

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Wed, Jul 22 from Midway Intl. to Dallas-Fort Worth Intl., returning Wed, Aug 5, priced at $228 found 4 days ago

Fri, Sep 11 - Tue, Sep 29

MDW

Midway Intl.

DEN

Denver Intl.

$236 Roundtrip, found 8 hours ago

$236

Roundtrip

found 8 hours ago

Select Delta flight, departing Fri, Sep 11 from Midway Intl. to Denver Intl., returning Tue, Sep 29, priced at $236 found 8 hours ago

Sat, Oct 3 - Wed, Oct 14

MDW

Midway Intl.

LAX

Los Angeles Intl.

$237 Roundtrip, found 13 hours ago

$237

Roundtrip

found 13 hours ago

Select Southwest Airlines flight, departing Sat, Oct 3 from Midway Intl. to Los Angeles Intl., returning Wed, Oct 14, priced at $237 found 13 hours ago

Wed, Sep 16 - Mon, Sep 21

MDW

Midway Intl.

MCO

Orlando Intl.

$237 Roundtrip, found 5 days ago

$237

Roundtrip

found 5 days ago

Select Southwest Airlines flight, departing Wed, Sep 16 from Midway Intl. to Orlando Intl., returning Mon, Sep 21, priced at $237 found 5 days ago

Wed, Dec 9 - Mon, Dec 14

MDW

Midway Intl.

PHX

Sky Harbor Intl.

$245 Roundtrip, found 3 days ago

$245

Roundtrip

found 3 days ago

Select Southwest Airlines flight, departing Wed, Dec 9 from Midway Intl. to Sky Harbor Intl., returning Mon, Dec 14, priced at $245 found 3 days ago

Sat, Aug 22 - Tue, Aug 25

MDW

Midway Intl.

LAS

Harry Reid Intl.

$254 Roundtrip, found 1 day ago

$254

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Aug 22 from Midway Intl. to Harry Reid Intl., returning Tue, Aug 25, priced at $254 found 1 day ago