Flights from Jacksonville to Historic Route 66

Cheapest flights from Jacksonville

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, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$173 Roundtrip, found 1 day ago

$173

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $173 found 1 day ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$182 Roundtrip, found 1 day ago

$182

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $182 found 1 day ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$183 Roundtrip, found 1 day ago

$183

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $183 found 1 day ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$187 Roundtrip, found 1 day ago

$187

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $187 found 1 day ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$196 Roundtrip, found 1 day ago

$196

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $196 found 1 day ago

Wed, Nov 12 - Tue, Nov 18

JAX

Jacksonville Intl.

STL

Lambert-St. Louis Intl.

$197 Roundtrip, found 2 hours ago

$197

Roundtrip

found 2 hours ago

Select Delta flight, departing Wed, Nov 12 from Jacksonville Intl. to Lambert-St. Louis Intl., returning Tue, Nov 18, priced at $197 found 2 hours ago

Tue, Oct 14 - Sat, Oct 18

JAX

Jacksonville Intl.

MDW

Midway Intl.

$201 Roundtrip, found 1 day ago

$201

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Oct 14 from Jacksonville Intl. to Midway Intl., returning Sat, Oct 18, priced at $201 found 1 day ago

Sat, Sep 13 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$201 Roundtrip, found 4 days ago

$201

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Sep 13 from Jacksonville Intl. to O'Hare Intl., returning Wed, Sep 17, priced at $201 found 4 days ago

Fri, Sep 12 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$203 Roundtrip, found 4 days ago

$203

Roundtrip

found 4 days ago

Select American Airlines flight, departing Fri, Sep 12 from Jacksonville Intl. to O'Hare Intl., returning Wed, Sep 17, priced at $203 found 4 days ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$206 Roundtrip, found 1 day ago

$206

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $206 found 1 day ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$208 Roundtrip, found 1 day ago

$208

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $208 found 1 day ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$210 Roundtrip, found 1 day ago

$210

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $210 found 1 day ago

Fri, Sep 12 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$213 Roundtrip, found 4 days ago

$213

Roundtrip

found 4 days ago

Select United flight, departing Fri, Sep 12 from Jacksonville Intl. to O'Hare Intl., returning Wed, Sep 17, priced at $213 found 4 days ago

Thu, Sep 11 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$219 Roundtrip, found 4 days ago

$219

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Sep 11 from Jacksonville Intl. to O'Hare Intl., returning Wed, Sep 17, priced at $219 found 4 days ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$219 Roundtrip, found 1 day ago

$219

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $219 found 1 day ago

Fri, Nov 14 - Mon, Nov 17

JAX

Jacksonville Intl.

STL

Lambert-St. Louis Intl.

$222 Roundtrip, found 2 hours ago

$222

Roundtrip

found 2 hours ago

Select American Airlines flight, departing Fri, Nov 14 from Jacksonville Intl. to Lambert-St. Louis Intl., returning Mon, Nov 17, priced at $222 found 2 hours ago

Tue, Sep 9 - Fri, Sep 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$223 Roundtrip, found 4 days ago

$223

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Sep 9 from Jacksonville Intl. to O'Hare Intl., returning Fri, Sep 19, priced at $223 found 4 days ago

Thu, Oct 16 - Sun, Oct 19

JAX

Jacksonville Intl.

MDW

Midway Intl.

$223 Roundtrip, found 1 day ago

$223

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Oct 16 from Jacksonville Intl. to Midway Intl., returning Sun, Oct 19, priced at $223 found 1 day ago

Sat, Nov 1 - Tue, Nov 11

JAX

Jacksonville Intl.

TUL

Tulsa Intl.

$237 Roundtrip, found 5 days ago

$237

Roundtrip

found 5 days ago

Select Delta flight, departing Sat, Nov 1 from Jacksonville Intl. to Tulsa Intl., returning Tue, Nov 11, priced at $237 found 5 days ago

Fri, Aug 8 - Sun, Aug 10

GNV

Gainesville Regional

ORD

O'Hare Intl.

$625 Roundtrip, found 5 days ago

$625

Roundtrip

found 5 days ago

Select American Airlines flight, departing Fri, Aug 8 from Gainesville Regional to O'Hare Intl., returning Sun, Aug 10, priced at $625 found 5 days ago