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Williamsburg

$389+ Cheap flights from Chicago (CHI) 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
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 noviembre 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$389
(KAYAK)

Popular in

December

Cheapest in

July

Average price

$388
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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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 November 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 noviembre 6, 2025.

This KAYAK deal was found by Cheapflights users on 11/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/75:00 amORD - PHF
1 stop5h 00mAmerican Airlines
mar. 12/911:26 amPHF - ORD
1 stop7h 36mAmerican Airlines
Deal found 11/6$389
This American Airlines deal was found by Cheapflights users on 11/6. 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.
mar. 12/237:11 amORD - PHF
1 stop7h 02mAmerican Airlines
vie. 12/268:03 pmPHF - ORD
1 stop4h 39mAmerican Airlines
Deal found 11/6$454
This American Airlines deal was found by Cheapflights users on 11/6. 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.
jue. 12/181:54 pmORD - PHF
1 stop4h 39mAmerican Airlines
jue. 12/253:42 pmPHF - ORD
1 stop4h 40mAmerican Airlines
Deal found 11/6$459
This American Airlines deal was found by Cheapflights users on 11/6. 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.
vie. 11/218:20 amORD - PHF
1 stop5h 56mAmerican Airlines
mar. 11/258:12 pmPHF - ORD
1 stop4h 28mAmerican Airlines
Deal found 11/6$465
This American Airlines deal was found by Cheapflights users on 11/6. 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.
jue. 12/181:54 pmORD - PHF
1 stop4h 39mAmerican Airlines
mié. 12/315:00 amPHF - ORD
2 stops15h 32mAmerican Airlines
Deal found 11/6$472
This American Airlines deal was found by Cheapflights users on 11/6. 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.
jue. 12/1810:30 amORD - PHF
1 stop4h 24mAmerican Airlines
lun. 12/298:03 pmPHF - ORD
2 stops11h 48mAmerican Airlines
Deal found 11/6$482
This American Airlines deal was found by Cheapflights users on 11/6. 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.
sáb. 12/205:00 amORD - PHF
1 stop4h 54mAmerican Airlines
vie. 12/268:03 pmPHF - ORD
1 stop4h 39mAmerican Airlines
Deal found 11/6$497
This American Airlines deal was found by Cheapflights users on 11/6. 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.
sáb. 12/205:00 amORD - PHF
1 stop4h 54mAmerican Airlines
mié. 12/315:00 amPHF - ORD
2 stops15h 32mAmerican Airlines
Deal found 11/6$510
This American Airlines deal was found by Cheapflights users on 11/6. 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.
jue. 12/181:54 pmORD - PHF
1 stop4h 39mAmerican Airlines
jue. 1/15:00 amPHF - ORD
2 stops15h 28mAmerican Airlines
Deal found 11/6$516
This American Airlines deal was found by Cheapflights users on 11/6. 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.
sáb. 12/205:00 amORD - PHF
1 stop4h 54mAmerican Airlines
lun. 12/298:03 pmPHF - ORD
2 stops13h 37mAmerican Airlines
Deal found 11/6$520
This American Airlines deal was found by Cheapflights users on 11/5. 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.
mar. 11/183:44 pmORD - PHF
1 stop6h 21mAmerican Airlines
mié. 11/1911:26 amPHF - ORD
1 stop7h 26mAmerican Airlines
Deal found 11/5$523
This American Airlines deal was found by Cheapflights users on 11/6. 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.
jue. 12/1810:30 amORD - PHF
1 stop4h 24mAmerican Airlines
sáb. 12/278:03 pmPHF - ORD
1 stop4h 56mAmerican Airlines
Deal found 11/6$524

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 noviembre 6, 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

lun. 12/8

5:00 am-10:57 am

1 stop4h 57m

Newport News Intl

lun. 12/8

7:16 pm-11:39 pm

1 stop5h 23m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

dom. 12/7

7:10 am-3:18 pm

1 stop7h 08m

Newport News Intl

lun. 12/8

7:16 pm-11:39 pm

1 stop5h 23m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

dom. 12/7

5:00 am-11:00 am

1 stop5h 00m

Newport News Intl

mar. 12/9

11:26 am-6:02 pm

1 stop7h 36m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

lun. 12/8

5:40 pm-11:06 pm

1 stop4h 26m

Newport News Intl

mar. 12/9

11:26 am-3:04 pm

1 stop4h 38m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

mar. 12/23

7:11 am-3:13 pm

1 stop7h 02m

Newport News Intl

vie. 12/26

8:03 pm-11:42 pm

1 stop4h 39m

$454

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

sáb. 3/7

6:48 pm-11:57 pm

1 stop4h 09m

Newport News Intl

mar. 3/10

8:06 pm-12:13 am

1 stop5h 07m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

jue. 12/18

8:03 am-3:54 pm

1 stop6h 51m

Newport News Intl

vie. 12/26

8:03 pm-11:42 pm

1 stop4h 39m

$459

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

jue. 12/18

1:54 pm-7:33 pm

1 stop4h 39m

Newport News Intl

mié. 12/31

5:00 am-7:32 pm

2 stops15h 32m

$472

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

jue. 12/18

10:30 am-3:54 pm

1 stop4h 24m

Newport News Intl

lun. 12/29

8:03 pm-6:51 am

2 stops11h 48m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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, November is the cheapest month in which you can book a flight from Chicago to Williamsburg (average of $129). 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 noviembre 6, 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 20% 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 November 2, 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 noviembre 6, 2025.

The most flights from CHI to W11 are scheduled on a Thursday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 noviembre 6, 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
11,040 reviews

Overall

7.2

Food

6.4

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,040 reviews
American Airlines
7.2
Good
11,040 reviews

Overall

7.2

Food

6.4

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

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 4h 57m. 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 (93%), GoJet (90%) and United Airlines (90%).

  • What are the cheapest flights from Chicago to Williamsburg?

    While on average a flight from Chicago to Williamsburg is generally $349, 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, November is the cheapest month in which you can book a flight from Chicago to Williamsburg (average of $129). 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 noviembre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$217Average$424FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$230Average$363FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$237Average$415FlexibilityNo cancel feeOn-time71%

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