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$369+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
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 August 21, 2025.

Round-trip from

$369
(American Airlines)
From Chicago (CHI) to Williamsburg
Search Deals

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 August 21, 2025.

This American Airlines deal was found by Cheapflights users on 8/20. 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 8/20$369
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/175:00 amORD - PHF
1 stop6h 08mAmerican Airlines
Sun 9/218:00 pmPHF - ORD
1 stop4h 39mAmerican Airlines
Deal found 8/20$379
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/95:08 pmORD - PHF
1 stop4h 57mAmerican Airlines
Thu 9/116:25 amPHF - ORD
1 stop5h 22mAmerican Airlines
Deal found 8/20$407
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/49:51 amORD - PHF
1 stop4h 47mAmerican Airlines
Mon 9/87:14 pmPHF - ORD
1 stop4h 58mAmerican Airlines
Deal found 8/20$425
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 8/234:56 pmORD - PHF
1 stop6h 10mAmerican Airlines
Sat 8/3011:05 amPHF - ORD
1 stop5h 50mAmerican Airlines
Deal found 8/21$443
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 8/2312:41 pmORD - PHF
1 stop5h 48mAmerican Airlines
Thu 8/287:59 pmPHF - ORD
1 stop4h 49mAmerican Airlines
Deal found 8/21$482
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Sun 8/245:20 amORD - PHF
1 stop4h 20mAmerican Airlines
Sat 8/303:40 pmPHF - ORD
1 stop4h 28mAmerican Airlines
Deal found 8/21$486
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/195:00 amORD - PHF
1 stop6h 08mAmerican Airlines
Mon 9/227:14 pmPHF - ORD
1 stop4h 58mAmerican Airlines
Deal found 8/21$497
This American Airlines deal was found by Cheapflights users on 8/20. 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 8/236:25 pmORD - PHF
1 stop4h 41mAmerican Airlines
Tue 8/2612:23 pmPHF - ORD
1 stop7h 06mAmerican Airlines
Deal found 8/20$513
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Thu 8/285:20 amORD - PHF
1 stop4h 20mAmerican Airlines
Thu 8/287:59 pmPHF - ORD
1 stop4h 49mAmerican Airlines
Deal found 8/21$521
This American Airlines deal was found by Cheapflights users on 8/21. 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 8/2210:26 amORD - PHF
1 stop4h 58mAmerican Airlines
Thu 8/287:59 pmPHF - ORD
1 stop4h 49mAmerican Airlines
Deal found 8/21$525
This American Airlines deal was found by Cheapflights users on 8/20. 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 8/236:25 pmORD - PHF
1 stop4h 41mAmerican Airlines
Fri 8/297:59 pmPHF - ORD
1 stop4h 43mAmerican Airlines
Deal found 8/20$534

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 August 21, 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

Wed 10/8

9:20 am-4:02 pm

1 stop5h 42m

Newport News Intl

Sun 10/12

7:59 pm-11:53 pm

1 stop4h 54m

$369

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

Wed 9/17

5:00 am-12:08 pm

1 stop6h 08m

Newport News Intl

Sun 9/21

8:00 pm-11:39 pm

1 stop4h 39m

$379

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Tue 9/9

5:08 pm-11:05 pm

1 stop4h 57m

Newport News Intl

Thu 9/11

6:25 am-10:47 am

1 stop5h 22m

$407

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 9/5

5:00 am-12:08 pm

1 stop6h 08m

Newport News Intl

Tue 9/9

6:00 am-10:43 am

1 stop5h 43m

$425

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Thu 9/4

9:51 am-3:38 pm

1 stop4h 47m

Newport News Intl

Mon 9/8

7:14 pm-11:12 pm

1 stop4h 58m

$425

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

Fri 9/19

5:08 pm-11:05 pm

1 stop4h 57m

Newport News Intl

Mon 9/22

7:14 pm-11:12 pm

1 stop4h 58m

$497

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

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 August 21, 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 August 17, 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 August 21, 2025.

The most flights from CHI to W11 are scheduled on a Thursday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 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 21, 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

Food

6.5

Overall

7.2

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Overall

7.2

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 42m. 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 (100%), GoJet (86%) and Republic Airways (76%).

  • What are the cheapest flights from Chicago to Williamsburg?

    While on average a flight from Chicago to Williamsburg is generally $285, our data shows the cheapest flight currently is $90. When looking at the most popular route, (Chicago O'Hare Intl - Newport News Intl), you can expect to pay $369 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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$245FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$366FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$206Average$430FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$213Average$370FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$233Average$423FlexibilityNo cancel feeOn-time71%

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