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$258+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$389
(American Airlines)

One-way from

$258
(American Airlines)

Popular in

December

Cheapest in

July

Average price

$474
Provider with most accurate pricing for Chicago (CHI)-Newport News Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Newport News Intl flights.
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From Chicago (CHI) to Williamsburg
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One-way flight from Chicago (CHI) to Williamsburg
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 23, 2025.

This American Airlines deal was found by Cheapflights users on 10/21. 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 12/28:20 amORD - PHF
1 stop6h 02mAmerican Airlines
Sat 12/611:25 amPHF - ORD
1 stop5h 45mAmerican Airlines
Deal found 10/21$389
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/53:44 pmORD - PHF
1 stop6h 22mAmerican Airlines
Fri 12/127:16 pmPHF - ORD
1 stop5h 23mAmerican Airlines
Deal found 10/21$390
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/198:20 amORD - PHF
1 stop6h 02mAmerican Airlines
Sat 11/228:12 pmPHF - ORD
1 stop4h 28mAmerican Airlines
Deal found 10/22$399
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/1210:29 amORD - PHF
1 stop7h 21mAmerican Airlines
Sun 11/168:12 pmPHF - ORD
1 stop4h 28mAmerican Airlines
Deal found 10/22$409
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Fri 11/75:00 amORD - PHF
1 stop4h 43mAmerican Airlines
Mon 11/1011:26 amPHF - ORD
1 stop4h 31mAmerican Airlines
Deal found 10/23$445
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Fri 10/319:20 amORD - PHF
1 stop5h 42mAmerican Airlines
Mon 11/37:16 pmPHF - ORD
1 stop5h 21mAmerican Airlines
Deal found 10/23$489
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/48:20 amORD - PHF
1 stop6h 02mAmerican Airlines
Wed 11/511:26 amPHF - ORD
1 stop7h 26mAmerican Airlines
Deal found 10/22$498
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Mon 11/35:00 amORD - PHF
1 stop4h 43mAmerican Airlines
Mon 11/37:16 pmPHF - ORD
1 stop5h 21mAmerican Airlines
Deal found 10/23$551
This American Airlines deal was found by Cheapflights users on 10/22. 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 10/2812:52 pmORD - PHF
1 stop4h 57mAmerican Airlines
Thu 10/3012:46 pmPHF - ORD
1 stop7h 24mAmerican Airlines
Deal found 10/22$707
This American Airlines deal was found by Cheapflights users on 10/23. 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.
Mon 10/274:59 pmORD - PHF
1 stop6h 07mAmerican Airlines
Thu 10/306:00 amPHF - ORD
1 stop5h 32mAmerican Airlines
Deal found 10/23$736

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 October 23, 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

Fri 12/5

3:44 pm-11:06 pm

1 stop6h 22m

Newport News Intl

Fri 12/12

7:16 pm-11:39 pm

1 stop5h 23m

$390

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Wed 11/19

5:00 am-10:43 am

1 stop4h 43m

Newport News Intl

Sat 11/22

3:46 pm-7:18 pm

1 stop4h 32m

$399

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Wed 11/12

10:29 am-6:50 pm

1 stop7h 21m

Newport News Intl

Sun 11/16

8:12 pm-11:40 pm

1 stop4h 28m

$409

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Thu 11/6

2:03 pm-7:46 pm

1 stop4h 43m

Newport News Intl

Mon 11/10

11:26 am-3:56 pm

1 stop5h 30m

$445

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 11/7

5:00 am-10:43 am

1 stop4h 43m

Newport News Intl

Mon 11/10

11:26 am-3:56 pm

1 stop5h 30m

$445

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

8:06 pm-12:13 am

1 stop5h 07m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Tue 11/4

8:20 am-3:22 pm

1 stop6h 02m

Newport News Intl

Wed 11/5

11:26 am-5:52 pm

1 stop7h 26m

$498

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Tue 11/4

8:20 am-3:22 pm

1 stop6h 02m

$258

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 10/31

12:52 pm-6:49 pm

1 stop4h 57m

$285

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Sat 11/1

7:10 am-3:26 pm

1 stop7h 16m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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, February is the cheapest month in which you can book a flight from Chicago to Williamsburg (average of $149). Flying from Chicago to Williamsburg in January is currently the most expensive (average of $270). 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 October 23, 2025.

When flying from Chicago to Williamsburg, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 15% versus a flight in the afternoon.

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 October 19, 2025.

Travelers seeking maximum savings on their Chicago to Williamsburg flight should consider departing on Sunday mornings when fares are most often at their lowest. Saturday evenings 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 October 23, 2025.

The most flights from CHI to W11 are scheduled on a Thursday (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 October 23, 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
11,033 reviews

Food

6.4

Entertainment

6.9

Boarding

7.5

Crew

8.0

Comfort

7.2

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
11,033 reviews
American Airlines
7.2
Good
11,033 reviews

Food

6.4

Entertainment

6.9

Boarding

7.5

Crew

8.0

Comfort

7.2

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 6h 22m. 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 (92%), Envoy Air (88%) and United Airlines (83%).

  • What are the cheapest flights from Chicago to Williamsburg?

    While on average a flight from Chicago to Williamsburg is generally $322, our data shows the cheapest flight currently is $115. 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, February is the cheapest month in which you can book a flight from Chicago to Williamsburg (average of $149). Flying from Chicago to Williamsburg in January is currently the most expensive (average of $270). 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 4 airlines flying from Chicago to Williamsburg

Discover the top 4 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$218Average$425FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$230Average$363FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$237Average$415FlexibilityNo cancel feeOn-time71%

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