Flights from Chicago to Crystal River

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.

Fri, Nov 14 - Wed, Nov 19

ORD

O'Hare Intl.

MCO

Orlando Intl.

$100 Roundtrip, found 2 days ago

$100

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Nov 14 from O'Hare Intl. to Orlando Intl., returning Wed, Nov 19, priced at $100 found 2 days ago

Thu, Aug 28 - Thu, Aug 28

ORD

O'Hare Intl.

MCO

Orlando Intl.

$105 Roundtrip, found 5 days ago

$105

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Aug 28 from O'Hare Intl. to Orlando Intl., returning Thu, Aug 28, priced at $105 found 5 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

TPA

Tampa Intl.

$109 Roundtrip, found 6 days ago

$109

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, Aug 14 from O'Hare Intl. to Tampa Intl., returning Mon, Aug 18, priced at $109 found 6 days ago

Sat, Sep 6 - Thu, Sep 11

ORD

O'Hare Intl.

MCO

Orlando Intl.

$110 Roundtrip, found 3 days ago

$110

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Sep 6 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 11, priced at $110 found 3 days ago

Sun, Sep 14 - Fri, Sep 19

ORD

O'Hare Intl.

MCO

Orlando Intl.

$111 Roundtrip, found 3 days ago

$111

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Orlando Intl., returning Fri, Sep 19, priced at $111 found 3 days ago

Thu, Aug 14 - Mon, Aug 18

ORD

O'Hare Intl.

TPA

Tampa Intl.

$113 Roundtrip, found 6 days ago

$113

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Thu, Aug 14 from O'Hare Intl. to Tampa Intl., returning Mon, Aug 18, priced at $113 found 6 days ago

Sun, Sep 14 - Sun, Sep 21

ORD

O'Hare Intl.

MCO

Orlando Intl.

$120 Roundtrip, found 2 days ago

$120

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Orlando Intl., returning Sun, Sep 21, priced at $120 found 2 days ago

Thu, Aug 14 - Sat, Aug 16

ORD

O'Hare Intl.

TPA

Tampa Intl.

$121 Roundtrip, found 5 days ago

$121

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Thu, Aug 14 from O'Hare Intl. to Tampa Intl., returning Sat, Aug 16, priced at $121 found 5 days ago

Mon, Sep 8 - Mon, Sep 15

MDW

Midway Intl.

TPA

Tampa Intl.

$122 Roundtrip, found 6 days ago

$122

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Mon, Sep 8 from Midway Intl. to Tampa Intl., returning Mon, Sep 15, priced at $122 found 6 days ago

Thu, Sep 4 - Sun, Sep 14

ORD

O'Hare Intl.

MCO

Orlando Intl.

$122 Roundtrip, found 5 days ago

$122

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Orlando Intl., returning Sun, Sep 14, priced at $122 found 5 days ago

Sun, Sep 14 - Fri, Sep 19

ORD

O'Hare Intl.

MCO

Orlando Intl.

$123 Roundtrip, found 3 days ago

$123

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sun, Sep 14 from O'Hare Intl. to Orlando Intl., returning Fri, Sep 19, priced at $123 found 3 days ago

Fri, Sep 5 - Fri, Sep 5

ORD

O'Hare Intl.

MCO

Orlando Intl.

$125 Roundtrip, found 1 day ago

$125

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Orlando Intl., returning Fri, Sep 5, priced at $125 found 1 day ago

Fri, Aug 15 - Sat, Aug 16

ORD

O'Hare Intl.

TPA

Tampa Intl.

$125 Roundtrip, found 6 days ago

$125

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Fri, Aug 15 from O'Hare Intl. to Tampa Intl., returning Sat, Aug 16, priced at $125 found 6 days ago

Fri, Sep 12 - Sat, Sep 27

ORD

O'Hare Intl.

MCO

Orlando Intl.

$127 Roundtrip, found 5 days ago

$127

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Fri, Sep 12 from O'Hare Intl. to Orlando Intl., returning Sat, Sep 27, priced at $127 found 5 days ago

Sat, Sep 6 - Thu, Sep 11

ORD

O'Hare Intl.

MCO

Orlando Intl.

$158 Roundtrip, found 3 days ago

$158

Roundtrip

found 3 days ago

Select United flight, departing Sat, Sep 6 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 11, priced at $158 found 3 days ago

Sat, Sep 6 - Thu, Sep 11

ORD

O'Hare Intl.

MCO

Orlando Intl.

$158 Roundtrip, found 3 days ago

$158

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Sep 6 from O'Hare Intl. to Orlando Intl., returning Thu, Sep 11, priced at $158 found 3 days ago

Tue, Oct 28 - Tue, Oct 28

MDW

Midway Intl.

TPA

Tampa Intl.

$191 Roundtrip, found 2 hours ago

$191

Roundtrip

found 2 hours ago

Select Delta flight, departing Tue, Oct 28 from Midway Intl. to Tampa Intl., returning Tue, Oct 28, priced at $191 found 2 hours ago

Fri, Sep 5 - Mon, Sep 8

ORD

O'Hare Intl.

TPA

Tampa Intl.

$275 Roundtrip, found 3 hours ago

$275

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Fri, Sep 5 from O'Hare Intl. to Tampa Intl., returning Mon, Sep 8, priced at $275 found 3 hours ago

Tue, Aug 12 - Tue, Aug 19

ORD

O'Hare Intl.

GNV

Gainesville Regional

$383 Roundtrip, found 2 days ago

$383

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Aug 12 from O'Hare Intl. to Gainesville Regional, returning Tue, Aug 19, priced at $383 found 2 days ago

Fri, Nov 14 - Wed, Nov 19

MDW

Midway Intl.

MCO

Orlando Intl.

$403 Roundtrip, found 2 days ago

$403

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Nov 14 from Midway Intl. to Orlando Intl., returning Wed, Nov 19, priced at $403 found 2 days ago