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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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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 2/275:00 am
ORD
-
PHF
1 stop4h 44m
American Airlines
Sun 3/17:55 pm
PHF
-
ORD
1 stop5h 21m
American Airlines
Deal found 1/27$389
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/155:00 am
ORD
-
PHF
1 stop4h 44m
American Airlines
Thu 3/1911:11 am
PHF
-
ORD
1 stop7h 46m
American Airlines
Deal found 1/27$437
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/1111:50 am
ORD
-
PHF
1 stop6h 01m
American Airlines
Sun 2/1511:11 am
PHF
-
ORD
1 stop6h 10m
American Airlines
Deal found 1/27$465
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/2410:28 am
ORD
-
PHF
1 stop4h 43m
American Airlines
Fri 3/277:55 pm
PHF
-
ORD
1 stop5h 21m
American Airlines
Deal found 1/27$495
This American Airlines deal was found by Cheapflights users on 1/27. 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 10/3012:49 pm
ORD
-
PHF
1 stop5h 44m
American Airlines
Sun 11/88:12 pm
PHF
-
ORD
1 stop4h 28m
American Airlines
Deal found 1/27$505
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/96:05 am
ORD
-
PHF
1 stop4h 12m
American Airlines
Thu 2/125:00 am
PHF
-
ORD
1 stop5h 05m
American Airlines
Deal found 1/27$533
This American Airlines deal was found by Cheapflights users on 1/26. 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 1/298:12 am
ORD
-
PHF
1 stop6h 14m
American Airlines
Sat 1/317:28 am
PHF
-
ORD
1 stop6h 54m
American Airlines
Deal found 1/26$581
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/2511:18 am
ORD
-
PHF
2 stops6h 35m
American Airlines
Fri 2/277:55 pm
PHF
-
ORD
1 stop5h 21m
American Airlines
Deal found 1/26$763
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/262:55 pm
ORD
-
PHF
2 stops8h 04m
American Airlines
Sat 2/287:55 pm
PHF
-
ORD
1 stop5h 03m
American Airlines
Deal found 1/26$793

Find flight deals from Chicago to Williamsburg

Keep the following information in mind while searching for Chicago to Williamsburg flight deals. Data was last updated January 29, 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.
Search Deals
From Chicago (CHI) 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
Search Deals

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 January 29, 2026.
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

Wed 2/25

12:00 pm-6:53 pm

1 stop5h 53m

Newport News Intl

Fri 2/27

7:55 pm-12:16 am

1 stop5h 21m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Thu 2/26

7:10 am-3:14 pm

1 stop7h 04m

Newport News Intl

Sat 2/28

5:00 am-9:05 am

1 stop5h 05m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 2/27

5:00 am-10:44 am

1 stop4h 44m

Newport News Intl

Sun 3/1

7:55 pm-12:16 am

1 stop5h 21m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 2/27

7:10 am-3:14 pm

1 stop7h 04m

Newport News Intl

Fri 3/6

7:55 pm-12:16 am

1 stop5h 21m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Sun 3/15

5:00 am-10:44 am

1 stop4h 44m

Newport News Intl

Thu 3/19

11:11 am-5:57 pm

1 stop7h 46m

$437

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Wed 2/11

11:50 am-6:51 pm

1 stop6h 01m

Newport News Intl

Sun 2/15

11:11 am-4:21 pm

1 stop6h 10m

$465

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 2/13

5:00 am-10:44 am

1 stop4h 44m

Newport News Intl

Sun 2/15

5:00 am-9:05 am

1 stop5h 05m

$465

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Tue 3/24

10:28 am-4:11 pm

1 stop4h 43m

Newport News Intl

Fri 3/27

7:55 pm-12:16 am

1 stop5h 21m

$495

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Mon 2/9

6:05 am-11:17 am

1 stop4h 12m

Newport News Intl

Thu 2/12

5:00 am-9:05 am

1 stop5h 05m

$533

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 $134). Flying from Chicago 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 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 January 29, 2026.

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 morning, which can drop the price by up to 14% 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 January 24, 2026.

Travelers seeking maximum savings on their Chicago to Williamsburg flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon 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 January 29, 2026.

The most flights from CHI to W11 are scheduled on a Thursday (20 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (14 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 29, 2026.
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
11,206 reviews

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

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
11,206 reviews
American Airlines
7.2
Good
11,206 reviews

Crew

8.0

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Food

6.4

Overall

7.2

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 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 53m. 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 Envoy Air (78%), Republic Airways (66%) and ANA (62%).

  • What are the cheapest flights from Chicago to Williamsburg?

    While on average a flight from Chicago to Williamsburg is generally $383, our data shows the cheapest flight currently is $124. 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 $134). Flying from Chicago 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.

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
FrontierCheapest$102Average$234FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$207Average$396FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$213Average$372FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$237Average$414FlexibilityNo cancel feeOn-time71%

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