Flights from Jacksonville to Northwest Chicago

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.

Mon, Jun 2 - Fri, Jun 13

JAX

Jacksonville Intl.

MDW

Midway Intl.

$216 Roundtrip, found 9 hours ago

$216

Roundtrip

found 9 hours ago

Select Frontier Airlines flight, departing Mon, Jun 2 from Jacksonville Intl. to Midway Intl., returning Fri, Jun 13, priced at $216 found 9 hours ago

Mon, Jun 2 - Mon, Jun 9

JAX

Jacksonville Intl.

MDW

Midway Intl.

$220 Roundtrip, found 9 hours ago

$220

Roundtrip

found 9 hours ago

Select Frontier Airlines flight, departing Mon, Jun 2 from Jacksonville Intl. to Midway Intl., returning Mon, Jun 9, priced at $220 found 9 hours ago

Sat, May 31 - Tue, Jun 10

JAX

Jacksonville Intl.

MDW

Midway Intl.

$300 Roundtrip, found 9 hours ago

$300

Roundtrip

found 9 hours ago

Select Delta flight, departing Sat, May 31 from Jacksonville Intl. to Midway Intl., returning Tue, Jun 10, priced at $300 found 9 hours ago

Sat, May 31 - Thu, Jun 12

JAX

Jacksonville Intl.

MDW

Midway Intl.

$311 Roundtrip, found 9 hours ago

$311

Roundtrip

found 9 hours ago

Select Delta flight, departing Sat, May 31 from Jacksonville Intl. to Midway Intl., returning Thu, Jun 12, priced at $311 found 9 hours ago

Sat, May 31 - Fri, Jun 13

JAX

Jacksonville Intl.

MDW

Midway Intl.

$322 Roundtrip, found 9 hours ago

$322

Roundtrip

found 9 hours ago

Select Delta flight, departing Sat, May 31 from Jacksonville Intl. to Midway Intl., returning Fri, Jun 13, priced at $322 found 9 hours ago

Fri, Jan 16 - Tue, Jan 20

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$327 Roundtrip, found 3 days ago

$327

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Tue, Jan 20, priced at $327 found 3 days ago

Fri, Jan 16 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$332 Roundtrip, found 2 days ago

$332

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $332 found 2 days ago

Thu, Jan 15 - Sat, Jan 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$338 Roundtrip, found 2 days ago

$338

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Sat, Jan 17, priced at $338 found 2 days ago

Fri, Jan 16 - Tue, Jan 20

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$352 Roundtrip, found 3 days ago

$352

Roundtrip

found 3 days ago

Select United flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Tue, Jan 20, priced at $352 found 3 days ago

Fri, Jan 16 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$357 Roundtrip, found 2 days ago

$357

Roundtrip

found 2 days ago

Select American Airlines flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $357 found 2 days ago

Fri, Jan 16 - Tue, Jan 20

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$362 Roundtrip, found 3 days ago

$362

Roundtrip

found 3 days ago

Select American Airlines flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Tue, Jan 20, priced at $362 found 3 days ago

Thu, Jan 15 - Sat, Jan 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$364 Roundtrip, found 2 days ago

$364

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Sat, Jan 17, priced at $364 found 2 days ago

Fri, Jan 16 - Sun, Jan 18

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$366 Roundtrip, found 2 days ago

$366

Roundtrip

found 2 days ago

Select United flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Sun, Jan 18, priced at $366 found 2 days ago

Fri, Jan 16 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$367 Roundtrip, found 2 days ago

$367

Roundtrip

found 2 days ago

Select American Airlines flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $367 found 2 days ago

Fri, Jan 16 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$370 Roundtrip, found 2 days ago

$370

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $370 found 2 days ago

Fri, Jan 16 - Tue, Jan 20

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$372 Roundtrip, found 3 days ago

$372

Roundtrip

found 3 days ago

Select Delta flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Tue, Jan 20, priced at $372 found 3 days ago

Fri, Jan 16 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$372 Roundtrip, found 2 days ago

$372

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $372 found 2 days ago

Fri, Jan 16 - Mon, Jan 19

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$377 Roundtrip, found 2 days ago

$377

Roundtrip

found 2 days ago

Select American Airlines flight, departing Fri, Jan 16 from Jacksonville Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $377 found 2 days ago

Thu, Jan 15 - Sat, Jan 17

JAX

Jacksonville Intl.

ORD

O'Hare Intl.

$377 Roundtrip, found 2 days ago

$377

Roundtrip

found 2 days ago

Select United flight, departing Thu, Jan 15 from Jacksonville Intl. to O'Hare Intl., returning Sat, Jan 17, priced at $377 found 2 days ago

Tue, Jun 3 - Tue, Jun 10

JAX

Jacksonville Intl.

MDW

Midway Intl.

$381 Roundtrip, found 9 hours ago

$381

Roundtrip

found 9 hours ago

Select Delta flight, departing Tue, Jun 3 from Jacksonville Intl. to Midway Intl., returning Tue, Jun 10, priced at $381 found 9 hours ago