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.

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$181 Roundtrip, found 3 days ago

$181

Roundtrip

found 3 days ago

Select American Airlines flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $181 found 3 days ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$181 Roundtrip, found 3 days ago

$181

Roundtrip

found 3 days ago

Select United flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $181 found 3 days ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$191 Roundtrip, found 3 days ago

$191

Roundtrip

found 3 days ago

Select United flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $191 found 3 days ago

Sat, Sep 13 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$201 Roundtrip, found 17 hours ago

$201

Roundtrip

found 17 hours ago

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

Fri, Sep 12 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$203 Roundtrip, found 8 hours ago

$203

Roundtrip

found 8 hours ago

Select American Airlines flight, departing Fri, Sep 12 from Jacksonville Intl. to O'Hare Intl., returning Wed, Sep 17, priced at $203 found 8 hours ago

Fri, Sep 12 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$213 Roundtrip, found 8 hours ago

$213

Roundtrip

found 8 hours ago

Select United flight, departing Fri, Sep 12 from Jacksonville Intl. to O'Hare Intl., returning Wed, Sep 17, priced at $213 found 8 hours ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$216 Roundtrip, found 3 days ago

$216

Roundtrip

found 3 days ago

Select American Airlines flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $216 found 3 days ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$217 Roundtrip, found 5 hours ago

$217

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $217 found 5 hours ago

Thu, Sep 11 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$219 Roundtrip, found 17 hours ago

$219

Roundtrip

found 17 hours ago

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

Fri, Aug 22 - Sat, Aug 23

JAX

Jacksonville Intl.

MDW

Midway Intl.

$223 Roundtrip, found 5 days ago

$223

Roundtrip

found 5 days ago

Select Delta flight, departing Fri, Aug 22 from Jacksonville Intl. to Midway Intl., returning Sat, Aug 23, priced at $223 found 5 days ago

Fri, Sep 12 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$223 Roundtrip, found 8 hours ago

$223

Roundtrip

found 8 hours ago

Select Delta flight, departing Fri, Sep 12 from Jacksonville Intl. to O'Hare Intl., returning Wed, Sep 17, priced at $223 found 8 hours ago

Tue, Sep 9 - Fri, Sep 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$223 Roundtrip, found 17 hours ago

$223

Roundtrip

found 17 hours ago

Select JetBlue Airways flight, departing Tue, Sep 9 from Jacksonville Intl. to O'Hare Intl., returning Fri, Sep 19, priced at $223 found 17 hours ago

Fri, Sep 12 - Wed, Sep 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$224 Roundtrip, found 8 hours ago

$224

Roundtrip

found 8 hours ago

Select American Airlines flight, departing Fri, Sep 12 from Jacksonville Intl. to O'Hare Intl., returning Wed, Sep 17, priced at $224 found 8 hours ago

Mon, Aug 25 - Thu, Aug 28

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$225 Roundtrip, found 1 day ago

$225

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Aug 25 from Jacksonville Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $225 found 1 day ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$226 Roundtrip, found 3 days ago

$226

Roundtrip

found 3 days ago

Select United flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $226 found 3 days ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$227 Roundtrip, found 5 hours ago

$227

Roundtrip

found 5 hours ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $227 found 5 hours ago

Sun, Aug 24 - Sun, Aug 31

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$228 Roundtrip, found 2 days ago

$228

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sun, Aug 24 from Jacksonville Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $228 found 2 days ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$230 Roundtrip, found 3 days ago

$230

Roundtrip

found 3 days ago

Select Delta flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $230 found 3 days ago

Sat, Nov 1 - Tue, Nov 11

JAX

Jacksonville Intl.

TUL

Tulsa Intl.

$237 Roundtrip, found 1 day ago

$237

Roundtrip

found 1 day ago

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

Tue, Aug 5 - Sat, Aug 9

GNV

Gainesville Regional

ORD

O'Hare Intl.

$431 Roundtrip, found 1 day ago

$431

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from Gainesville Regional to O'Hare Intl., returning Sat, Aug 9, priced at $431 found 1 day ago