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Williamsburg

$195+ Cheap flights from Chicago (CHI) to Williamsburg, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Chicago to Williamsburg

Keep the following information in mind while searching for Chicago to Williamsburg flight deals. Data was last updated September 16, 2025.

Round-trip from

$389
(American Airlines)

One-way from

$195
(American Airlines)

Popular in

December

Cheapest in

July

Average price

$411
From Chicago (CHI) to Williamsburg
Search Deals
One-way flight from Chicago (CHI) to Williamsburg
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Highest demand for flights based on searches. 6% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Williamsburg

Cheapest flights from Chicago to Williamsburg
Explore the most affordable flight options available from Chicago to Williamsburg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/16. 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 10/259:15 amORD - PHF
1 stop5h 11mAmerican Airlines
Sat 11/811:18 amPHF - ORD
1 stop7h 37mAmerican Airlines
Deal found 9/16$389
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 9/308:38 amORD - PHF
1 stop6h 00mAmerican Airlines
Sat 10/44:03 pmPHF - ORD
1 stop5h 24mAmerican Airlines
Deal found 9/15$443
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/18:38 amORD - PHF
1 stop6h 00mAmerican Airlines
Sun 10/56:25 amPHF - ORD
1 stop5h 22mAmerican Airlines
Deal found 9/16$444
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/287:02 amORD - PHF
1 stop7h 11mAmerican Airlines
Thu 10/26:25 amPHF - ORD
1 stop5h 22mAmerican Airlines
Deal found 9/14$445
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 11/265:34 pmORD - PHF
1 stop5h 50mAmerican Airlines
Mon 12/18:12 pmPHF - ORD
1 stop4h 44mAmerican Airlines
Deal found 9/15$457
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/177:10 amORD - PHF
1 stop7h 16mAmerican Airlines
Sun 10/197:59 pmPHF - ORD
1 stop4h 54mAmerican Airlines
Deal found 9/13$493
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/2212:33 pmPHF - ORD
1 stop5h 12mAmerican Airlines
Deal found 9/15$529
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 11/264:05 pmORD - PHF
1 stop7h 19mAmerican Airlines
Sun 11/308:12 pmPHF - ORD
1 stop4h 44mAmerican Airlines
Deal found 9/15$617
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/268:03 amORD - PHF
1 stop6h 10mAmerican Airlines
Tue 12/305:00 amPHF - ORD
1 stop6h 45mAmerican Airlines
Deal found 9/15$705
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/84:15 pmORD - PHF
2 stops6h 43mAmerican Airlines
Sun 11/96:10 amPHF - ORD
1 stop5h 32mAmerican Airlines
Deal found 9/15$715

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 September 16, 2025.
Use the filters below to find and compare flights from Chicago to Williamsburg that are best for you.

Fly from

Chicago

Fly to

Williamsburg

Route

Depart

Return

Price

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Sat 10/25

9:15 am-3:26 pm

1 stop5h 11m

Newport News Intl

Sat 11/8

11:18 am-5:55 pm

1 stop7h 37m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Sat 11/8

5:30 pm-11:58 pm

1 stop5h 28m

Newport News Intl

Sun 11/9

6:10 am-10:42 am

1 stop5h 32m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Wed 10/1

8:38 am-3:38 pm

1 stop6h 00m

Newport News Intl

Sun 10/5

6:25 am-10:47 am

1 stop5h 22m

$444

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Sun 9/28

7:02 am-3:13 pm

1 stop7h 11m

Newport News Intl

Thu 10/2

6:25 am-10:47 am

1 stop5h 22m

$445

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Mon 9/29

12:33 pm-6:49 pm

1 stop5h 16m

Newport News Intl

Fri 10/3

6:00 am-10:43 am

1 stop5h 43m

$445

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Wed 11/26

5:34 pm-12:24 am

1 stop5h 50m

Newport News Intl

Mon 12/1

8:12 pm-11:56 pm

1 stop4h 44m

$457

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Sat 3/7

1:54 pm-9:46 pm

1 stop6h 52m

Newport News Intl

Tue 3/10

12:15 pm-3:45 pm

1 stop4h 30m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 10/17

7:10 am-3:26 pm

1 stop7h 16m

Newport News Intl

Sun 10/19

7:59 pm-11:53 pm

1 stop4h 54m

$493

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 3/6

1:54 pm-9:46 pm

1 stop6h 52m

Newport News Intl

Sat 3/14

12:15 pm-3:45 pm

1 stop4h 30m

$499

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Thu 10/16

5:22 am-10:56 am

1 stop4h 34m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 11 results
1
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Best time to book a flight from Chicago to Williamsburg

Have a flexible travel schedule? Discover the best time to fly to Williamsburg from Chicago 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 to Williamsburg

What is the cheapest month to book a flight from Chicago to Williamsburg?

Currently, January is the cheapest month in which you can book a flight from Chicago to Williamsburg (average of $281). Flying from Chicago 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 CHI to W11?

Find hourly flight availability from Chicago 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 September 16, 2025.

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

What is the cheapest day to fly from Chicago to Williamsburg?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Williamsburg. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Chicago to Williamsburg flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Williamsburg

Explore weekly flight availability from Chicago 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 September 16, 2025.

The most flights from CHI to W11 are scheduled on a Sunday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 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 September 16, 2025.
Peruse reviews from past customers who have flown with American Airlines from Chicago to Williamsburg to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Food

6.4

Crew

8.0

Entertainment

6.9

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Food

6.4

Crew

8.0

Entertainment

6.9

Boarding

7.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 to Williamsburg?

    Departing from Chicago to Williamsburg will take you 5h 11m. Chicago and Williamsburg are separated by a distance of 693 mi.

  • What are the most reliable airlines from Chicago to Williamsburg?

    The top 3 most reliable airlines when flying from Chicago to Williamsburg are Republic Airways (80%), GoJet (77%) and United Airlines (75%).

  • What are the cheapest flights from Chicago to Williamsburg?

    While on average a flight from Chicago to Williamsburg is generally $337, our data shows the cheapest flight currently is $135. When looking at the most popular route, (Chicago O'Hare Intl - Newport News Intl), you can expect to pay $389 for that flight.

  • Can I find deals for flights from Chicago to Williamsburg that include hotel bookings?

    Yes. In addition to deals on Chicago to Williamsburg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Williamsburg?

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

  • Can I find deals for business class flights from Chicago to Williamsburg?

    Yes. Cheapflights offers flight deals from Chicago 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 to Williamsburg?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Williamsburg (average of $281). Flying from Chicago 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.

See more FAQs

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Alternative routes for Chicago to Williamsburg

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Williamsburg

Discover the top 5 airlines that operate flights from Chicago 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$245FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$366FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$213Average$369FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$217Average$435FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$415FlexibilityNo cancel feeOn-time71%

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