HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
janv. 22 — janv. 291
jeu. 1/22
jeu. 1/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Williamsburg with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 décembre 23, 2025.

This American Airlines deal was found by Cheapflights users on 12/21. 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.
mer. 12/241:54 pmORD - PHF
1 stop4h 39mAmerican Airlines
ven. 1/23:42 pmPHF - ORD
1 stop4h 40mAmerican Airlines
Deal found 12/21$509
This American Airlines deal was found by Cheapflights users on 12/22. 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.
ven. 12/266:37 pmORD - PHF
1 stop4h 22mAmerican Airlines
jeu. 1/87:16 pmPHF - ORD
1 stop5h 11mAmerican Airlines
Deal found 12/22$552
This American Airlines deal was found by Cheapflights users on 12/22. 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.
mar. 12/235:00 amORD - PHF
1 stop4h 54mAmerican Airlines
ven. 12/265:00 amPHF - ORD
1 stop5h 21mAmerican Airlines
Deal found 12/22$561
This American Airlines deal was found by Cheapflights users on 12/22. 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.
ven. 12/265:28 pmORD - PHF
1 stop5h 31mAmerican Airlines
lun. 12/293:42 pmPHF - ORD
1 stop4h 40mAmerican Airlines
Deal found 12/22$569
This American Airlines deal was found by Cheapflights users on 12/22. 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.
ven. 12/268:03 amORD - PHF
1 stop6h 10mAmerican Airlines
mer. 12/315:00 amPHF - ORD
2 stops15h 44mAmerican Airlines
Deal found 12/22$651
This American Airlines deal was found by Cheapflights users on 12/22. 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.
sam. 12/275:00 amORD - PHF
1 stop4h 54mAmerican Airlines
mer. 12/3111:24 amPHF - ORD
1 stop7h 25mAmerican Airlines
Deal found 12/22$688
This American Airlines deal was found by Cheapflights users on 12/22. 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.
ven. 12/265:00 amORD - PHF
1 stop4h 54mAmerican Airlines
jeu. 1/15:00 amPHF - ORD
2 stops14h 39mAmerican Airlines
Deal found 12/22$690
This American Airlines deal was found by Cheapflights users on 12/22. 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.
sam. 12/277:11 amORD - PHF
1 stop7h 02mAmerican Airlines
ven. 1/23:42 pmPHF - ORD
1 stop4h 40mAmerican Airlines
Deal found 12/22$696
This American Airlines deal was found by Cheapflights users on 12/22. 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.
ven. 12/268:03 amORD - PHF
1 stop6h 10mAmerican Airlines
mar. 12/305:00 amPHF - ORD
2 stops15h 44mAmerican Airlines
Deal found 12/22$765
This American Airlines deal was found by Cheapflights users on 12/22. 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.
sam. 12/278:26 pmORD - PHF
2 stops13h 28mAmerican Airlines
mar. 12/3011:24 amPHF - ORD
1 stop5h 41mAmerican Airlines
Deal found 12/22$796

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 décembre 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$389
(American Airlines)

Popular in

June

Cheapest in

July

Average price

$504
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. 0% potential increase in price ($2 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 December 2025
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 décembre 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

mar. 5/12

5:10 am-10:37 am

1 stop4h 27m

Newport News Intl

lun. 5/18

8:16 pm-11:50 pm

1 stop4h 34m

$389

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

mar. 5/12

6:30 pm-11:52 pm

1 stop4h 22m

Newport News Intl

dim. 5/17

8:16 pm-11:50 pm

1 stop4h 34m

$434

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

mer. 1/7

3:21 pm-11:02 pm

1 stop6h 41m

Newport News Intl

mer. 1/14

7:28 am-11:35 am

1 stop5h 07m

$437

ChicagoNewport News

ORD - PHF

ORDPHF

Chicago O'Hare Intl

ven. 1/2

1:54 pm-7:33 pm

1 stop4h 39m

Newport News Intl

mar. 1/6

11:42 am-6:01 pm

1 stop7h 19m

$523

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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 $121). Flying from Chicago to Williamsburg in December is currently the most expensive (average of $267). 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 décembre 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 19% 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 December 20, 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. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 décembre 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
11,054 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Boarding

7.5

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 27m. 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 GoJet (73%), United Airlines (69%) and Qatar Airways (65%).

  • What are the cheapest flights from Chicago to Williamsburg?

    While on average a flight from Chicago to Williamsburg is generally $390, our data shows the cheapest flight currently is $119. 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 $121). Flying from Chicago to Williamsburg in December is currently the most expensive (average of $267). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Williamsburg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Reagan-National flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Raleigh flights
Midway to Dulles Intl flights
St. Louis to Dulles Intl flights
Midway to Reagan-National flights
O'Hare Intl to Norfolk flights
St. Louis to Reagan-National flights
St. Louis to Raleigh flights
O'Hare Intl to Richmond flights
Midway to Raleigh flights
O'Hare Intl to Greensboro flights
O'Hare Intl to Charlottesville flights
Midway to Norfolk flights
O'Hare Intl to Roanoke flights
Midway to Richmond flights
St. Louis to Richmond flights
Peoria to Richmond flights
St. Louis to Norfolk flights
Peoria to Norfolk flights
O'Hare Intl to Blountville flights
Midway to Greensboro flights
Moline to Dulles Intl flights
Peoria to Dulles Intl flights
Peoria to Reagan-National flights
Midway to Charlottesville flights
St. Louis to Roanoke flights
Peoria to Raleigh flights
Moline to Norfolk flights
O'Hare Intl to Lynchburg flights
Moline to Reagan-National flights
Moline to Raleigh flights
O'Hare Intl to Salisbury flights
St. Louis to Charlottesville flights
Midway to Blountville flights
Evansville to Dulles Intl flights
St. Louis to Greensboro flights
Peoria to Greensboro flights
Evansville to Reagan-National flights
Champaign to Raleigh flights
Midway to Roanoke flights
Bloomington to Raleigh flights
O'Hare Intl to Staunton flights
O'Hare Intl to Newport News flights
Champaign to Reagan-National flights
Bloomington to Richmond flights
Bloomington to Reagan-National flights
Bloomington to Dulles Intl flights
Moline to Greensboro flights
Moline to Richmond flights

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 décembre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$78Average$224FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$207Average$400FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$213Average$371FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$234Average$414FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.