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Williamsburg

$389+ Cheap flights from O'Hare Intl (ORD) to Williamsburg, VA

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Williamsburg

Cheapest flights from O'Hare Intl to Williamsburg
Explore the most affordable flight options available from O'Hare Intl to Williamsburg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:00 am
ORD
-
PHF
1 stop4h 44m
American Airlines
Fri 3/67:55 pm
PHF
-
ORD
1 stop5h 21m
American Airlines
Deal found 1/24$389
This American Airlines deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:10 am
ORD
-
PHF
1 stop6h 04m
American Airlines
Sun 2/227:55 pm
PHF
-
ORD
1 stop5h 21m
American Airlines
Deal found 1/23$399
This American Airlines deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/151:39 pm
ORD
-
PHF
1 stop4h 51m
American Airlines
Sat 2/215:00 am
PHF
-
ORD
1 stop5h 05m
American Airlines
Deal found 1/23$409
This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:40 pm
ORD
-
PHF
1 stop4h 19m
American Airlines
Sun 5/107:59 pm
PHF
-
ORD
1 stop4h 58m
American Airlines
Deal found 1/24$459
This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/78:20 am
ORD
-
PHF
1 stop6h 07m
American Airlines
Wed 2/117:28 am
PHF
-
ORD
1 stop6h 54m
American Airlines
Deal found 1/24$465
This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:25 pm
ORD
-
PHF
1 stop4h 41m
American Airlines
Sun 8/237:59 pm
PHF
-
ORD
1 stop4h 49m
American Airlines
Deal found 1/24$479
This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:20 am
ORD
-
PHF
1 stop4h 26m
American Airlines
Sat 7/118:00 pm
PHF
-
ORD
1 stop4h 59m
American Airlines
Deal found 1/24$484
This American Airlines deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:20 am
ORD
-
PHF
1 stop4h 20m
American Airlines
Sun 9/65:00 am
PHF
-
ORD
1 stop6h 43m
American Airlines
Deal found 1/25$499
This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:00 am
ORD
-
PHF
1 stop4h 40m
American Airlines
Sun 5/107:59 pm
PHF
-
ORD
1 stop4h 58m
American Airlines
Deal found 1/24$504
This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:00 am
ORD
-
PHF
1 stop4h 40m
American Airlines
Sat 5/97:59 pm
PHF
-
ORD
1 stop4h 58m
American Airlines
Deal found 1/24$507
This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:20 am
ORD
-
PHF
1 stop4h 26m
American Airlines
Fri 6/128:00 pm
PHF
-
ORD
1 stop4h 59m
American Airlines
Deal found 1/24$509
This American Airlines deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:43 pm
ORD
-
PHF
1 stop5h 42m
American Airlines
Mon 7/68:00 pm
PHF
-
ORD
1 stop4h 59m
American Airlines
Deal found 1/24$514

Find flight deals from O'Hare Intl to Williamsburg

Keep the following information in mind while searching for O'Hare Intl to Williamsburg flight deals. Data was last updated January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$389
(American Airlines)

Popular in

June

Cheapest in

July

Average price

$406
Provider with most accurate pricing for Chicago (CHI)-Newport News Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Newport News Intl flights.
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From Chicago O'Hare Intl to Williamsburg
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Williamsburg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Williamsburg that are best for you.

Fly from

O'Hare Intl

Fly to

Williamsburg

Route

Depart

Return

Price

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Thu 2/19

8:10 am-3:14 pm

1 stop6h 04m

Newport News Intl

Sun 2/22

7:55 pm-12:16 am

1 stop5h 21m

$399

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Mon 2/16

5:00 am-10:44 am

1 stop4h 44m

Newport News Intl

Fri 2/20

3:41 pm-7:40 pm

1 stop4h 59m

$409

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Sun 2/15

1:39 pm-7:30 pm

1 stop4h 51m

Newport News Intl

Sat 2/21

5:00 am-9:05 am

1 stop5h 05m

$409

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Wed 6/17

5:20 am-10:46 am

1 stop4h 26m

Newport News Intl

Wed 6/24

8:00 pm-11:59 pm

1 stop4h 59m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Wed 7/15

5:20 am-10:46 am

1 stop4h 26m

Newport News Intl

Tue 7/21

8:00 pm-11:59 pm

1 stop4h 59m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Tue 6/9

6:40 pm-12:25 am

1 stop4h 45m

Newport News Intl

Tue 6/16

8:00 pm-11:59 pm

1 stop4h 59m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Wed 6/24

5:20 am-10:46 am

1 stop4h 26m

Newport News Intl

Tue 6/30

8:00 pm-11:59 pm

1 stop4h 59m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Tue 6/30

5:20 am-10:46 am

1 stop4h 26m

Newport News Intl

Tue 7/7

5:05 am-9:04 am

1 stop4h 59m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Tue 7/21

5:43 pm-12:25 am

1 stop5h 42m

Newport News Intl

Tue 7/28

5:05 am-9:04 am

1 stop4h 59m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Wed 5/27

5:20 am-10:46 am

1 stop4h 26m

Newport News Intl

Wed 6/3

8:00 pm-11:59 pm

1 stop4h 59m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 12 results
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Best time to book a flight from O'Hare Intl to Williamsburg

Have a flexible travel schedule? Discover the best time to fly to Williamsburg from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Williamsburg

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Williamsburg?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Williamsburg (average of $134). Flying from Chicago O'Hare Intl Airport to Williamsburg in December is currently the most expensive (average of $265). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to W11?

Find hourly flight availability from O'Hare Intl to Williamsburg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 26, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to Williamsburg as you normally would.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Williamsburg?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Williamsburg. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Williamsburg flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Williamsburg

Explore weekly flight availability from O'Hare Intl to Williamsburg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 26, 2026.

The most flights from ORD to W11 are scheduled on a Sunday (21 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (17 on average).

Reviews of airlines servicing Williamsburg

Get insights into the airlines that provide service to Williamsburg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Williamsburg. Reviews last updated January 26, 2026.
Read reviews from past customers who have flown American Airlines from Chicago O'Hare Intl Airport to Williamsburg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,189 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,189 reviews
American Airlines
7.2
Good
11,189 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Williamsburg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago O'Hare Intl Airport to Williamsburg?

    There are many flights that can get you from Chicago O'Hare Intl Airport to Williamsburg in 6h 04m. Fly via American Airlines to get the fastest option. The distance from Chicago O'Hare Intl Airport to Williamsburg is about 693 mi.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Williamsburg?

    Consider Envoy Air (78%), Republic Airways (66%) or ANA (62%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Williamsburg.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Williamsburg?

    Looking for the cheapest flight from Chicago O'Hare Intl Airport to Williamsburg? While on average our users pay $383, our data indicates the cheapest price to be $124. The most popular route (Chicago O'Hare Intl - Newport News Intl), is priced around $387.

  • Can I find deals for flights from O'Hare Intl to Williamsburg that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Williamsburg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Williamsburg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Williamsburg.

  • Can I find deals for business class flights from O'Hare Intl to Williamsburg?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Williamsburg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Williamsburg?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Williamsburg (average of $134). Flying from Chicago O'Hare Intl Airport to Williamsburg in December is currently the most expensive (average of $265). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for O'Hare Intl to Williamsburg

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from O'Hare Intl to Williamsburg

Discover the top 4 airlines that operate flights from O'Hare Intl to Williamsburg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
FrontierCheapest$102Average$234FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$207Average$396FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$237Average$414FlexibilityNo cancel feeOn-time71%

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