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.

Tue, Jun 10 - Sat, Jun 14

MDW

Midway Intl.

IAD

Washington Dulles Intl.

$158 Roundtrip, found 1 day ago

$158

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Tue, Jun 10 from Midway Intl. to Washington Dulles Intl., returning Sat, Jun 14, priced at $158 found 1 day ago

Tue, Jun 10 - Fri, Jun 13

MDW

Midway Intl.

IAD

Washington Dulles Intl.

$169 Roundtrip, found 1 day ago

$169

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Tue, Jun 10 from Midway Intl. to Washington Dulles Intl., returning Fri, Jun 13, priced at $169 found 1 day ago

Tue, Jun 17 - Tue, Jun 24

ORD

O'Hare Intl.

IAD

Washington Dulles Intl.

$208 Roundtrip, found 4 days ago

$208

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Washington Dulles Intl., returning Tue, Jun 24, priced at $208 found 4 days ago

Wed, Jul 30 - Tue, Aug 5

ORD

O'Hare Intl.

DCA

Ronald Reagan Washington National

$219 Roundtrip, found 3 days ago

$219

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Jul 30 from O'Hare Intl. to Ronald Reagan Washington National, returning Tue, Aug 5, priced at $219 found 3 days ago

Tue, Jun 17 - Sat, Jun 28

ORD

O'Hare Intl.

IAD

Washington Dulles Intl.

$221 Roundtrip, found 4 days ago

$221

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Washington Dulles Intl., returning Sat, Jun 28, priced at $221 found 4 days ago

Tue, Jun 17 - Mon, Jun 30

ORD

O'Hare Intl.

IAD

Washington Dulles Intl.

$228 Roundtrip, found 4 days ago

$228

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Washington Dulles Intl., returning Mon, Jun 30, priced at $228 found 4 days ago

Sat, Jun 21 - Sat, Jun 28

ORD

O'Hare Intl.

IAD

Washington Dulles Intl.

$232 Roundtrip, found 4 days ago

$232

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Washington Dulles Intl., returning Sat, Jun 28, priced at $232 found 4 days ago

Tue, Jul 29 - Tue, Aug 5

ORD

O'Hare Intl.

DCA

Ronald Reagan Washington National

$234 Roundtrip, found 3 days ago

$234

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Tue, Jul 29 from O'Hare Intl. to Ronald Reagan Washington National, returning Tue, Aug 5, priced at $234 found 3 days ago

Tue, Jul 29 - Mon, Aug 4

ORD

O'Hare Intl.

DCA

Ronald Reagan Washington National

$235 Roundtrip, found 3 days ago

$235

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Tue, Jul 29 from O'Hare Intl. to Ronald Reagan Washington National, returning Mon, Aug 4, priced at $235 found 3 days ago

Thu, Jul 31 - Mon, Aug 4

ORD

O'Hare Intl.

DCA

Ronald Reagan Washington National

$236 Roundtrip, found 3 days ago

$236

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Thu, Jul 31 from O'Hare Intl. to Ronald Reagan Washington National, returning Mon, Aug 4, priced at $236 found 3 days ago

Sun, May 25 - Sat, May 31

ORD

O'Hare Intl.

DCA

Ronald Reagan Washington National

$237 Roundtrip, found 16 hours ago

$237

Roundtrip

found 16 hours ago

Select Delta flight, departing Sun, May 25 from O'Hare Intl. to Ronald Reagan Washington National, returning Sat, May 31, priced at $237 found 16 hours ago

Tue, Jun 17 - Wed, Jun 25

ORD

O'Hare Intl.

IAD

Washington Dulles Intl.

$238 Roundtrip, found 4 days ago

$238

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Washington Dulles Intl., returning Wed, Jun 25, priced at $238 found 4 days ago

Fri, Aug 1 - Thu, Aug 7

ORD

O'Hare Intl.

DCA

Ronald Reagan Washington National

$239 Roundtrip, found 3 days ago

$239

Roundtrip

found 3 days ago

Select United flight, departing Fri, Aug 1 from O'Hare Intl. to Ronald Reagan Washington National, returning Thu, Aug 7, priced at $239 found 3 days ago

Sat, Jun 21 - Mon, Jun 30

ORD

O'Hare Intl.

IAD

Washington Dulles Intl.

$241 Roundtrip, found 4 days ago

$241

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Washington Dulles Intl., returning Mon, Jun 30, priced at $241 found 4 days ago

Fri, Aug 1 - Thu, Aug 7

ORD

O'Hare Intl.

DCA

Ronald Reagan Washington National

$244 Roundtrip, found 3 days ago

$244

Roundtrip

found 3 days ago

Select Delta flight, departing Fri, Aug 1 from O'Hare Intl. to Ronald Reagan Washington National, returning Thu, Aug 7, priced at $244 found 3 days ago

Fri, Jun 20 - Sun, Jun 22

ORD

O'Hare Intl.

IAD

Washington Dulles Intl.

$248 Roundtrip, found 4 days ago

$248

Roundtrip

found 4 days ago

Select United flight, departing Fri, Jun 20 from O'Hare Intl. to Washington Dulles Intl., returning Sun, Jun 22, priced at $248 found 4 days ago

Thu, Jun 19 - Mon, Jun 30

ORD

O'Hare Intl.

IAD

Washington Dulles Intl.

$248 Roundtrip, found 4 days ago

$248

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to Washington Dulles Intl., returning Mon, Jun 30, priced at $248 found 4 days ago

Fri, Jun 20 - Sun, Jun 22

MDW

Midway Intl.

DCA

Ronald Reagan Washington National

$249 Roundtrip, found 4 days ago

$249

Roundtrip

found 4 days ago

Select Delta flight, departing Fri, Jun 20 from Midway Intl. to Ronald Reagan Washington National, returning Sun, Jun 22, priced at $249 found 4 days ago

Wed, Jul 30 - Wed, Aug 6

ORD

O'Hare Intl.

DCA

Ronald Reagan Washington National

$249 Roundtrip, found 3 days ago

$249

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Jul 30 from O'Hare Intl. to Ronald Reagan Washington National, returning Wed, Aug 6, priced at $249 found 3 days ago

Sun, Jun 8 - Thu, Jun 12

ORD

O'Hare Intl.

DCA

Ronald Reagan Washington National

$264 Roundtrip, found 1 day ago

$264

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Jun 8 from O'Hare Intl. to Ronald Reagan Washington National, returning Thu, Jun 12, priced at $264 found 1 day ago