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Williamsburg

$369+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — RIC
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap 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 August 14, 2025.

Round-trip from

$369
(American Airlines)

Popular in

October

Cheapest in

November

Average price

$399
From Chicago O'Hare Intl to Williamsburg
Search Deals
High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. 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 9/185:00 amORD - PHF
1 stop4h 53mAmerican Airlines
Mon 9/227:14 pmPHF - ORD
1 stop4h 58mAmerican Airlines
Deal found 8/14$369
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/75:00 amORD - PHF
1 stop4h 53mAmerican Airlines
Mon 9/87:14 pmPHF - ORD
1 stop4h 58mAmerican Airlines
Deal found 8/14$389
This American Airlines deal was found by Cheapflights users on 8/13. 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 8/294:56 pmORD - PHF
1 stop6h 03mAmerican Airlines
Mon 9/15:00 amPHF - ORD
1 stop5h 23mAmerican Airlines
Deal found 8/13$425
This American Airlines deal was found by Cheapflights users on 8/13. 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 8/287:13 amORD - PHF
1 stop6h 42mAmerican Airlines
Mon 9/17:59 pmPHF - ORD
1 stop4h 43mAmerican Airlines
Deal found 8/13$495
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/15:20 amORD - PHF
1 stop4h 19mAmerican Airlines
Mon 9/87:14 pmPHF - ORD
1 stop4h 58mAmerican Airlines
Deal found 8/14$507
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/198:00 amORD - PHF
2 stops6h 38mAmerican Airlines
Mon 9/227:14 pmPHF - ORD
1 stop4h 58mAmerican Airlines
Deal found 8/14$793

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 August 14, 2025.
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 9/18

5:00 am-10:53 am

1 stop4h 53m

Newport News Intl

Mon 9/22

7:14 pm-11:12 pm

1 stop4h 58m

$369

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 9/19

5:00 am-12:08 pm

1 stop6h 08m

Newport News Intl

Mon 9/22

7:14 pm-11:12 pm

1 stop4h 58m

$369

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Sun 9/7

5:00 am-10:53 am

1 stop4h 53m

Newport News Intl

Mon 9/8

7:14 pm-11:12 pm

1 stop4h 58m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 8/29

4:56 pm-11:59 pm

1 stop6h 03m

Newport News Intl

Mon 9/1

5:00 am-9:23 am

1 stop5h 23m

$425

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Thu 8/28

7:13 am-2:55 pm

1 stop6h 42m

Newport News Intl

Mon 9/1

7:59 pm-11:42 pm

1 stop4h 43m

$495

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Mon 9/1

5:20 am-10:39 am

1 stop4h 19m

Newport News Intl

Mon 9/8

7:14 pm-11:12 pm

1 stop4h 58m

$507

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Sun 8/17

5:20 am-10:40 am

1 stop4h 20m

$435

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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 $281). Flying from Chicago O'Hare Intl Airport to Williamsburg in March is currently the most expensive (average of $351). 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 August 14, 2025.

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 August 10, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Williamsburg flight should consider departing on Friday at noon when fares are most often at their lowest. Friday mornings 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 August 14, 2025.

The most flights from ORD to W11 are scheduled on a Thursday (23 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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 August 14, 2025.
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
10,000 reviews

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.5

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.5

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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.

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

    Consider Envoy Air (92%), Republic Airways (83%) or GoJet (81%) 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 $287, our data indicates the cheapest price to be $90. The most popular route (Chicago O'Hare Intl - Newport News Intl), is priced around $369.

  • 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 $281). Flying from Chicago O'Hare Intl Airport to Williamsburg in March is currently the most expensive (average of $351). 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$79Average$245FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$366FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$213Average$423FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$214Average$430FlexibilityNo cancel feeOn-time69%

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