Flights from Chicago to Highlandville

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, Sep 20 - Mon, Sep 22

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$209 Roundtrip, found 5 days ago

$209

Roundtrip

found 5 days ago

Select Delta flight, departing Sat, Sep 20 from O'Hare Intl. to Springfield-Branson National, returning Mon, Sep 22, priced at $209 found 5 days ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$219 Roundtrip, found 22 hours ago

$219

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $219 found 22 hours ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$229 Roundtrip, found 22 hours ago

$229

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $229 found 22 hours ago

Wed, Dec 31 - Thu, Jan 1

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$249 Roundtrip, found 1 day ago

$249

Roundtrip

found 1 day ago

Select United flight, departing Wed, Dec 31 from O'Hare Intl. to Springfield-Branson National, returning Thu, Jan 1, priced at $249 found 1 day ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$252 Roundtrip, found 22 hours ago

$252

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $252 found 22 hours ago

Sat, Sep 20 - Wed, Sep 24

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$254 Roundtrip, found 5 days ago

$254

Roundtrip

found 5 days ago

Select United flight, departing Sat, Sep 20 from O'Hare Intl. to Springfield-Branson National, returning Wed, Sep 24, priced at $254 found 5 days ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$259 Roundtrip, found 22 hours ago

$259

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $259 found 22 hours ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$261 Roundtrip, found 22 hours ago

$261

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $261 found 22 hours ago

Wed, Sep 24 - Sat, Sep 27

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$265 Roundtrip, found 5 days ago

$265

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Sep 24 from O'Hare Intl. to Springfield-Branson National, returning Sat, Sep 27, priced at $265 found 5 days ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$269 Roundtrip, found 22 hours ago

$269

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $269 found 22 hours ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$271 Roundtrip, found 22 hours ago

$271

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $271 found 22 hours ago

Thu, Dec 25 - Mon, Jan 5

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$279 Roundtrip, found 1 day ago

$279

Roundtrip

found 1 day ago

Select United flight, departing Thu, Dec 25 from O'Hare Intl. to Springfield-Branson National, returning Mon, Jan 5, priced at $279 found 1 day ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$281 Roundtrip, found 22 hours ago

$281

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $281 found 22 hours ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$281 Roundtrip, found 22 hours ago

$281

Roundtrip

found 22 hours ago

Select United flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $281 found 22 hours ago

Mon, Sep 22 - Sat, Sep 27

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$289 Roundtrip, found 5 days ago

$289

Roundtrip

found 5 days ago

Select American Airlines flight, departing Mon, Sep 22 from O'Hare Intl. to Springfield-Branson National, returning Sat, Sep 27, priced at $289 found 5 days ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$291 Roundtrip, found 22 hours ago

$291

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $291 found 22 hours ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$294 Roundtrip, found 22 hours ago

$294

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $294 found 22 hours ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$298 Roundtrip, found 22 hours ago

$298

Roundtrip

found 22 hours ago

Select United flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $298 found 22 hours ago

Thu, Dec 25 - Sat, Jan 3

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$300 Roundtrip, found 1 day ago

$300

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Dec 25 from O'Hare Intl. to Springfield-Branson National, returning Sat, Jan 3, priced at $300 found 1 day ago

Sat, May 23 - Thu, May 28

ORD

O'Hare Intl.

SGF

Springfield-Branson National

$301 Roundtrip, found 22 hours ago

$301

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Sat, May 23 from O'Hare Intl. to Springfield-Branson National, returning Thu, May 28, priced at $301 found 22 hours ago