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, Oct 27 - Sat, Nov 1

MDW

Midway Intl.

MCO

Orlando Intl.

$92 Roundtrip, found 11 hours ago

$92

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Mon, Oct 27 from Midway Intl. to Orlando Intl., returning Sat, Nov 1, priced at $92 found 11 hours ago

Sun, Oct 12 - Thu, Oct 16

ORD

O'Hare Intl.

TPA

Tampa Intl.

$92 Roundtrip, found 3 days ago

$92

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sun, Oct 12 from O'Hare Intl. to Tampa Intl., returning Thu, Oct 16, priced at $92 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

MCO

Orlando Intl.

$94 Roundtrip, found 17 hours ago

$94

Roundtrip

found 17 hours ago

Select Spirit Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Orlando Intl., returning Thu, Oct 23, priced at $94 found 17 hours ago

Sat, Oct 11 - Thu, Oct 16

ORD

O'Hare Intl.

TPA

Tampa Intl.

$94 Roundtrip, found 6 days ago

$94

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Sat, Oct 11 from O'Hare Intl. to Tampa Intl., returning Thu, Oct 16, priced at $94 found 6 days ago

Tue, Oct 7 - Sat, Oct 11

MDW

Midway Intl.

DFW

Dallas-Fort Worth Intl.

$96 Roundtrip, found 1 day ago

$96

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Tue, Oct 7 from Midway Intl. to Dallas-Fort Worth Intl., returning Sat, Oct 11, priced at $96 found 1 day ago

Mon, Nov 3 - Fri, Nov 7

ORD

O'Hare Intl.

MIA

Miami Intl.

$98 Roundtrip, found 2 days ago

$98

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Nov 3 from O'Hare Intl. to Miami Intl., returning Fri, Nov 7, priced at $98 found 2 days ago

Fri, Oct 3 - Fri, Oct 10

ORD

O'Hare Intl.

DEN

Denver Intl.

$99 Roundtrip, found 4 days ago

$99

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Fri, Oct 3 from O'Hare Intl. to Denver Intl., returning Fri, Oct 10, priced at $99 found 4 days ago

Thu, Oct 30 - Wed, Nov 5

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$100 Roundtrip, found 1 day ago

$100

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, Oct 30 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Wed, Nov 5, priced at $100 found 1 day ago

Tue, Jan 13 - Thu, Jan 22

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$108 Roundtrip, found 4 days ago

$108

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jan 13 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Thu, Jan 22, priced at $108 found 4 days ago

Sat, Nov 15 - Sat, Nov 22

MDW

Midway Intl.

MIA

Miami Intl.

$112 Roundtrip, found 6 days ago

$112

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Nov 15 from Midway Intl. to Miami Intl., returning Sat, Nov 22, priced at $112 found 6 days ago

Mon, Nov 3 - Thu, Nov 6

ORD

O'Hare Intl.

LAS

Harry Reid Intl.

$115 Roundtrip, found 6 days ago

$115

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Mon, Nov 3 from O'Hare Intl. to Harry Reid Intl., returning Thu, Nov 6, priced at $115 found 6 days ago

Mon, Dec 8 - Fri, Dec 12

MDW

Midway Intl.

TPA

Tampa Intl.

$120 Roundtrip, found 2 days ago

$120

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Mon, Dec 8 from Midway Intl. to Tampa Intl., returning Fri, Dec 12, priced at $120 found 2 days ago

Sat, Oct 4 - Wed, Oct 8

ORD

O'Hare Intl.

MIA

Miami Intl.

$133 Roundtrip, found 4 days ago

$133

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Oct 4 from O'Hare Intl. to Miami Intl., returning Wed, Oct 8, priced at $133 found 4 days ago

Wed, Oct 29 - Tue, Nov 4

ORD

O'Hare Intl.

MCO

Orlando Intl.

$133 Roundtrip, found 6 days ago

$133

Roundtrip

found 6 days ago

Select United flight, departing Wed, Oct 29 from O'Hare Intl. to Orlando Intl., returning Tue, Nov 4, priced at $133 found 6 days ago

Sun, Oct 26 - Sat, Nov 1

MDW

Midway Intl.

PHX

Sky Harbor Intl.

$137 Roundtrip, found 2 days ago

$137

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sun, Oct 26 from Midway Intl. to Sky Harbor Intl., returning Sat, Nov 1, priced at $137 found 2 days ago

Sat, Sep 20 - Sat, Sep 27

ORD

O'Hare Intl.

LAX

Los Angeles Intl.

$150 Roundtrip, found 6 days ago

$150

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sat, Sep 20 from O'Hare Intl. to Los Angeles Intl., returning Sat, Sep 27, priced at $150 found 6 days ago

Mon, Sep 29 - Thu, Oct 2

MDW

Midway Intl.

LAS

Harry Reid Intl.

$162 Roundtrip, found 12 hours ago

$162

Roundtrip

found 12 hours ago

Select Frontier Airlines flight, departing Mon, Sep 29 from Midway Intl. to Harry Reid Intl., returning Thu, Oct 2, priced at $162 found 12 hours ago

Fri, Oct 3 - Sun, Oct 12

MDW

Midway Intl.

DEN

Denver Intl.

$163 Roundtrip, found 2 days ago

$163

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, Oct 3 from Midway Intl. to Denver Intl., returning Sun, Oct 12, priced at $163 found 2 days ago

Tue, Nov 4 - Thu, Nov 6

ORD

O'Hare Intl.

LAS

Harry Reid Intl.

$178 Roundtrip, found 6 days ago

$178

Roundtrip

found 6 days ago

Select Alaska Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Harry Reid Intl., returning Thu, Nov 6, priced at $178 found 6 days ago

Tue, Nov 4 - Fri, Nov 21

ORD

O'Hare Intl.

LAS

Harry Reid Intl.

$178 Roundtrip, found 3 days ago

$178

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Harry Reid Intl., returning Fri, Nov 21, priced at $178 found 3 days ago