Flights from Chesapeake

Cheapest flights from Chesapeake

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, Dec 8 - Tue, Dec 22

HTS

Tri-State

MCO

Orlando Intl.

$330 Roundtrip, found 1 day ago

$330

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Dec 8 from Tri-State to Orlando Intl., returning Tue, Dec 22, priced at $330 found 1 day ago

Wed, Jan 6 - Wed, Jan 13

HTS

Tri-State

MIA

Miami Intl.

$338 Roundtrip, found 1 day ago

$338

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Jan 6 from Tri-State to Miami Intl., returning Wed, Jan 13, priced at $338 found 1 day ago

Wed, Dec 23 - Thu, Jan 7

HTS

Tri-State

MCO

Orlando Intl.

$345 Roundtrip, found 1 day ago

$345

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Dec 23 from Tri-State to Orlando Intl., returning Thu, Jan 7, priced at $345 found 1 day ago

Thu, Dec 31 - Mon, Jan 11

HTS

Tri-State

MCO

Orlando Intl.

$360 Roundtrip, found 23 hours ago

$360

Roundtrip

found 23 hours ago

Select American Airlines flight, departing Thu, Dec 31 from Tri-State to Orlando Intl., returning Mon, Jan 11, priced at $360 found 23 hours ago

Wed, Dec 23 - Sat, Jan 9

HTS

Tri-State

MCO

Orlando Intl.

$372 Roundtrip, found 1 day ago

$372

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Dec 23 from Tri-State to Orlando Intl., returning Sat, Jan 9, priced at $372 found 1 day ago

Sat, Nov 14 - Thu, Nov 26

HTS

Tri-State

MCO

Orlando Intl.

$387 Roundtrip, found 2 days ago

$387

Roundtrip

found 2 days ago

Select American Airlines flight, departing Sat, Nov 14 from Tri-State to Orlando Intl., returning Thu, Nov 26, priced at $387 found 2 days ago

Tue, Dec 1 - Fri, Dec 18

HTS

Tri-State

MCO

Orlando Intl.

$389 Roundtrip, found 12 hours ago

$389

Roundtrip

found 12 hours ago

Select American Airlines flight, departing Tue, Dec 1 from Tri-State to Orlando Intl., returning Fri, Dec 18, priced at $389 found 12 hours ago

Wed, Dec 23 - Sat, Jan 9

HTS

Tri-State

MCO

Orlando Intl.

$390 Roundtrip, found 1 day ago

$390

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Dec 23 from Tri-State to Orlando Intl., returning Sat, Jan 9, priced at $390 found 1 day ago

Tue, Jan 5 - Mon, Jan 11

HTS

Tri-State

MIA

Miami Intl.

$400 Roundtrip, found 2 days ago

$400

Roundtrip

found 2 days ago

Select American Airlines flight, departing Tue, Jan 5 from Tri-State to Miami Intl., returning Mon, Jan 11, priced at $400 found 2 days ago

Fri, Nov 27 - Fri, Dec 18

HTS

Tri-State

MCO

Orlando Intl.

$404 Roundtrip, found 3 days ago

$404

Roundtrip

found 3 days ago

Select American Airlines flight, departing Fri, Nov 27 from Tri-State to Orlando Intl., returning Fri, Dec 18, priced at $404 found 3 days ago

Wed, Dec 23 - Thu, Jan 7

HTS

Tri-State

MCO

Orlando Intl.

$405 Roundtrip, found 1 day ago

$405

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Dec 23 from Tri-State to Orlando Intl., returning Thu, Jan 7, priced at $405 found 1 day ago

Tue, Dec 1 - Sat, Dec 19

HTS

Tri-State

MCO

Orlando Intl.

$408 Roundtrip, found 4 days ago

$408

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Dec 1 from Tri-State to Orlando Intl., returning Sat, Dec 19, priced at $408 found 4 days ago

Wed, Dec 23 - Sat, Jan 9

HTS

Tri-State

MCO

Orlando Intl.

$409 Roundtrip, found 2 days ago

$409

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Dec 23 from Tri-State to Orlando Intl., returning Sat, Jan 9, priced at $409 found 2 days ago

Thu, Dec 10 - Tue, Dec 22

HTS

Tri-State

MCO

Orlando Intl.

$410 Roundtrip, found 1 day ago

$410

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Dec 10 from Tri-State to Orlando Intl., returning Tue, Dec 22, priced at $410 found 1 day ago

Sat, Jan 2 - Sat, Jan 9

HTS

Tri-State

MCO

Orlando Intl.

$412 Roundtrip, found 1 day ago

$412

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Jan 2 from Tri-State to Orlando Intl., returning Sat, Jan 9, priced at $412 found 1 day ago

Tue, Dec 1 - Sat, Dec 19

HTS

Tri-State

MCO

Orlando Intl.

$414 Roundtrip, found 4 days ago

$414

Roundtrip

found 4 days ago

Select American Airlines flight, departing Tue, Dec 1 from Tri-State to Orlando Intl., returning Sat, Dec 19, priced at $414 found 4 days ago

Tue, Dec 8 - Sat, Dec 26

HTS

Tri-State

MCO

Orlando Intl.

$422 Roundtrip, found 14 hours ago

$422

Roundtrip

found 14 hours ago

Select American Airlines flight, departing Tue, Dec 8 from Tri-State to Orlando Intl., returning Sat, Dec 26, priced at $422 found 14 hours ago

Wed, Dec 23 - Thu, Jan 7

HTS

Tri-State

MCO

Orlando Intl.

$424 Roundtrip, found 1 day ago

$424

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Dec 23 from Tri-State to Orlando Intl., returning Thu, Jan 7, priced at $424 found 1 day ago

Fri, Nov 27 - Sun, Dec 13

HTS

Tri-State

MCO

Orlando Intl.

$425 Roundtrip, found 3 days ago

$425

Roundtrip

found 3 days ago

Select American Airlines flight, departing Fri, Nov 27 from Tri-State to Orlando Intl., returning Sun, Dec 13, priced at $425 found 3 days ago

Sat, Jan 2 - Mon, Jan 11

HTS

Tri-State

MCO

Orlando Intl.

$427 Roundtrip, found 2 days ago

$427

Roundtrip

found 2 days ago

Select American Airlines flight, departing Sat, Jan 2 from Tri-State to Orlando Intl., returning Mon, Jan 11, priced at $427 found 2 days ago