Flights from Chicago to Middleburg

Cheapest flights from Chicago

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.

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$321 Roundtrip, found 6 days ago

$321

Roundtrip

found 6 days ago

Select United flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $321 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$331 Roundtrip, found 6 days ago

$331

Roundtrip

found 6 days ago

Select United flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $331 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$356 Roundtrip, found 6 days ago

$356

Roundtrip

found 6 days ago

Select United flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $356 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$366 Roundtrip, found 6 days ago

$366

Roundtrip

found 6 days ago

Select United flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $366 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$386 Roundtrip, found 6 days ago

$386

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $386 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$391 Roundtrip, found 6 days ago

$391

Roundtrip

found 6 days ago

Select United flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $391 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$396 Roundtrip, found 6 days ago

$396

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $396 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$400 Roundtrip, found 6 days ago

$400

Roundtrip

found 6 days ago

Select United flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $400 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$401 Roundtrip, found 6 days ago

$401

Roundtrip

found 6 days ago

Select United flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $401 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$406 Roundtrip, found 6 days ago

$406

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $406 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$414 Roundtrip, found 6 days ago

$414

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $414 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$417 Roundtrip, found 6 days ago

$417

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $417 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$422 Roundtrip, found 6 days ago

$422

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $422 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$426 Roundtrip, found 6 days ago

$426

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $426 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$457 Roundtrip, found 6 days ago

$457

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Dec 13 from Midway Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $457 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$457 Roundtrip, found 6 days ago

$457

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Dec 13 from O'Hare Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $457 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$477 Roundtrip, found 6 days ago

$477

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Dec 13 from Midway Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $477 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$527 Roundtrip, found 6 days ago

$527

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Dec 13 from Midway Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $527 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$547 Roundtrip, found 6 days ago

$547

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Dec 13 from Midway Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $547 found 6 days ago

Sat, Dec 13 - Sat, Dec 20

MDW

Midway Intl.

JAX

Jacksonville Intl.

$587 Roundtrip, found 6 days ago

$587

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Dec 13 from Midway Intl. to Jacksonville Intl., returning Sat, Dec 20, priced at $587 found 6 days ago