Flights from Jacksonville to Sleepy Hollow

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 2 days ago

$181

Roundtrip

found 2 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 2 days ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$181 Roundtrip, found 2 days ago

$181

Roundtrip

found 2 days ago

Select United flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $181 found 2 days ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$191 Roundtrip, found 2 days ago

$191

Roundtrip

found 2 days ago

Select United flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $191 found 2 days ago

Tue, Sep 23 - Wed, Sep 24

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$201 Roundtrip, found 2 days ago

$201

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Sep 23 from Jacksonville Intl. to O'Hare Intl., returning Wed, Sep 24, priced at $201 found 2 days ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$216 Roundtrip, found 2 days ago

$216

Roundtrip

found 2 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 2 days ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$224 Roundtrip, found 2 days ago

$224

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $224 found 2 days ago

Mon, Aug 25 - Thu, Aug 28

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$225 Roundtrip, found 2 hours ago

$225

Roundtrip

found 2 hours ago

Select American Airlines flight, departing Mon, Aug 25 from Jacksonville Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $225 found 2 hours ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$226 Roundtrip, found 2 days ago

$226

Roundtrip

found 2 days ago

Select United flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $226 found 2 days ago

Sun, Aug 24 - Sun, Aug 31

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$228 Roundtrip, found 1 day ago

$228

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sun, Aug 24 from Jacksonville Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $228 found 1 day ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$230 Roundtrip, found 2 days ago

$230

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $230 found 2 days ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$234 Roundtrip, found 2 days ago

$234

Roundtrip

found 2 days ago

Select United flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $234 found 2 days ago

Mon, Aug 25 - Thu, Aug 28

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$235 Roundtrip, found 2 hours ago

$235

Roundtrip

found 2 hours ago

Select United flight, departing Mon, Aug 25 from Jacksonville Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $235 found 2 hours ago

Mon, Aug 25 - Thu, Aug 28

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$236 Roundtrip, found 2 hours ago

$236

Roundtrip

found 2 hours ago

Select United flight, departing Mon, Aug 25 from Jacksonville Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $236 found 2 hours ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 2 days ago

$240

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $240 found 2 days ago

Wed, Sep 24 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$244 Roundtrip, found 2 days ago

$244

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Sep 24 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $244 found 2 days ago

Mon, Aug 25 - Thu, Aug 28

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$246 Roundtrip, found 2 hours ago

$246

Roundtrip

found 2 hours ago

Select American Airlines flight, departing Mon, Aug 25 from Jacksonville Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $246 found 2 hours ago

Thu, Sep 25 - Sat, Sep 27

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$250 Roundtrip, found 2 days ago

$250

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Sep 25 from Jacksonville Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $250 found 2 days ago

Thu, Jan 15 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$251 Roundtrip, found 10 hours ago

$251

Roundtrip

found 10 hours ago

Select JetBlue Airways flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $251 found 10 hours ago

Sat, Sep 27 - Mon, Sep 29

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$268 Roundtrip, found 2 days ago

$268

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sat, Sep 27 from Jacksonville Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $268 found 2 days ago

Sat, Aug 2 - Tue, Aug 5

GNV

Gainesville Regional

ORD

O'Hare Intl.

$389 Roundtrip, found 5 hours ago

$389

Roundtrip

found 5 hours ago

Select Delta flight, departing Sat, Aug 2 from Gainesville Regional to O'Hare Intl., returning Tue, Aug 5, priced at $389 found 5 hours ago