Flights from Chicago to Madison

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.

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$229 Roundtrip, found 5 days ago

$229

Roundtrip

found 5 days ago

Select American Airlines flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $229 found 5 days ago

Tue, Aug 19 - Tue, Aug 26

MDW

Midway Intl.

CHO

Charlottesville-Albemarle

$229 Roundtrip, found 1 day ago

$229

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 19 from Midway Intl. to Charlottesville-Albemarle, returning Tue, Aug 26, priced at $229 found 1 day ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$229 Roundtrip, found 5 days ago

$229

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $229 found 5 days ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$239 Roundtrip, found 5 days ago

$239

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $239 found 5 days ago

Sat, Aug 23 - Mon, Aug 25

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$259 Roundtrip, found 1 day ago

$259

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Charlottesville-Albemarle, returning Mon, Aug 25, priced at $259 found 1 day ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$260 Roundtrip, found 5 days ago

$260

Roundtrip

found 5 days ago

Select United flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $260 found 5 days ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$264 Roundtrip, found 5 days ago

$264

Roundtrip

found 5 days ago

Select American Airlines flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $264 found 5 days ago

Wed, Aug 20 - Sat, Aug 23

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$269 Roundtrip, found 1 day ago

$269

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Charlottesville-Albemarle, returning Sat, Aug 23, priced at $269 found 1 day ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$279 Roundtrip, found 5 days ago

$279

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $279 found 5 days ago

Tue, Aug 19 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$299 Roundtrip, found 1 day ago

$299

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Aug 19 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $299 found 1 day ago

Tue, Aug 19 - Sat, Aug 30

MDW

Midway Intl.

CHO

Charlottesville-Albemarle

$304 Roundtrip, found 1 day ago

$304

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 19 from Midway Intl. to Charlottesville-Albemarle, returning Sat, Aug 30, priced at $304 found 1 day ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$309 Roundtrip, found 5 days ago

$309

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $309 found 5 days ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$310 Roundtrip, found 5 days ago

$310

Roundtrip

found 5 days ago

Select United flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $310 found 5 days ago

Sat, Aug 23 - Sun, Aug 31

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$319 Roundtrip, found 1 day ago

$319

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Charlottesville-Albemarle, returning Sun, Aug 31, priced at $319 found 1 day ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$324 Roundtrip, found 5 days ago

$324

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $324 found 5 days ago

Mon, Aug 25 - Sun, Aug 31

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$324 Roundtrip, found 1 day ago

$324

Roundtrip

found 1 day ago

Select United flight, departing Mon, Aug 25 from O'Hare Intl. to Charlottesville-Albemarle, returning Sun, Aug 31, priced at $324 found 1 day ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$329 Roundtrip, found 5 days ago

$329

Roundtrip

found 5 days ago

Select American Airlines flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $329 found 5 days ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$330 Roundtrip, found 5 days ago

$330

Roundtrip

found 5 days ago

Select United flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $330 found 5 days ago

Thu, Aug 21 - Sat, Aug 23

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$334 Roundtrip, found 1 day ago

$334

Roundtrip

found 1 day ago

Select United flight, departing Thu, Aug 21 from O'Hare Intl. to Charlottesville-Albemarle, returning Sat, Aug 23, priced at $334 found 1 day ago

Wed, Aug 13 - Wed, Aug 20

ORD

O'Hare Intl.

CHO

Charlottesville-Albemarle

$339 Roundtrip, found 5 days ago

$339

Roundtrip

found 5 days ago

Select Delta flight, departing Wed, Aug 13 from O'Hare Intl. to Charlottesville-Albemarle, returning Wed, Aug 20, priced at $339 found 5 days ago