Flights from Gainesville to Chicago

Cheapest flights from Gainesville

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, Aug 14 - Thu, Aug 21

MCO

Orlando Intl.

ORD

O'Hare Intl.

$96 Roundtrip, found 2 days ago

$96

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Aug 14 from Orlando Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $96 found 2 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$100 Roundtrip, found 1 hour ago

$100

Roundtrip

found 1 hour ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $100 found 1 hour ago

Mon, Sep 15 - Tue, Sep 16

MCO

Orlando Intl.

ORD

O'Hare Intl.

$106 Roundtrip, found 4 days ago

$106

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Mon, Sep 15 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 16, priced at $106 found 4 days ago

Tue, Sep 16 - Mon, Sep 22

MCO

Orlando Intl.

ORD

O'Hare Intl.

$107 Roundtrip, found 3 days ago

$107

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, Sep 16 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $107 found 3 days ago

Fri, Aug 15 - Mon, Aug 18

MCO

Orlando Intl.

ORD

O'Hare Intl.

$108 Roundtrip, found 2 days ago

$108

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Fri, Aug 15 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $108 found 2 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$110 Roundtrip, found 1 hour ago

$110

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $110 found 1 hour ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$111 Roundtrip, found 1 hour ago

$111

Roundtrip

found 1 hour ago

Select Spirit Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $111 found 1 hour ago

Sun, Aug 31 - Thu, Sep 4

MCO

Orlando Intl.

ORD

O'Hare Intl.

$114 Roundtrip, found 4 days ago

$114

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sun, Aug 31 from Orlando Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $114 found 4 days ago

Thu, Sep 11 - Sun, Sep 14

MCO

Orlando Intl.

ORD

O'Hare Intl.

$116 Roundtrip, found 4 days ago

$116

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Sep 11 from Orlando Intl. to O'Hare Intl., returning Sun, Sep 14, priced at $116 found 4 days ago

Tue, Sep 16 - Mon, Sep 22

MCO

Orlando Intl.

ORD

O'Hare Intl.

$120 Roundtrip, found 3 days ago

$120

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, Sep 16 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $120 found 3 days ago

Sun, Sep 14 - Tue, Sep 16

MCO

Orlando Intl.

ORD

O'Hare Intl.

$126 Roundtrip, found 4 days ago

$126

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sun, Sep 14 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 16, priced at $126 found 4 days ago

Tue, Sep 2 - Sun, Sep 7

MCO

Orlando Intl.

ORD

O'Hare Intl.

$127 Roundtrip, found 4 days ago

$127

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Sep 2 from Orlando Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $127 found 4 days ago

Thu, Aug 14 - Mon, Aug 18

MCO

Orlando Intl.

ORD

O'Hare Intl.

$128 Roundtrip, found 2 days ago

$128

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Aug 14 from Orlando Intl. to O'Hare Intl., returning Mon, Aug 18, priced at $128 found 2 days ago

Sun, Aug 17 - Mon, Aug 18

MCO

Orlando Intl.

MDW

Midway Intl.

$136 Roundtrip, found 2 days ago

$136

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sun, Aug 17 from Orlando Intl. to Midway Intl., returning Mon, Aug 18, priced at $136 found 2 days ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 1 hour ago

$159

Roundtrip

found 1 hour ago

Select United flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $159 found 1 hour ago

Fri, Sep 5 - Mon, Sep 8

MCO

Orlando Intl.

ORD

O'Hare Intl.

$159 Roundtrip, found 1 hour ago

$159

Roundtrip

found 1 hour ago

Select American Airlines flight, departing Fri, Sep 5 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $159 found 1 hour ago

Mon, Aug 25 - Thu, Aug 28

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$179 Roundtrip, found 5 hours ago

$179

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Mon, Aug 25 from Jacksonville Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $179 found 5 hours ago

Tue, Sep 16 - Mon, Sep 22

MCO

Orlando Intl.

ORD

O'Hare Intl.

$197 Roundtrip, found 3 days ago

$197

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Sep 16 from Orlando Intl. to O'Hare Intl., returning Mon, Sep 22, priced at $197 found 3 days ago

Tue, Aug 19 - Fri, Aug 22

JAX

Jacksonville Intl.

MDW

Midway Intl.

$214 Roundtrip, found 23 hours ago

$214

Roundtrip

found 23 hours ago

Select Delta flight, departing Tue, Aug 19 from Jacksonville Intl. to Midway Intl., returning Fri, Aug 22, priced at $214 found 23 hours ago

Mon, Sep 8 - Thu, Sep 11

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$223 Roundtrip, found 3 days ago

$223

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Mon, Sep 8 from Jacksonville Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $223 found 3 days ago