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$213+ Cheap flights from Williamsburg, VA to Chicago (CHI)

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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Williamsburg to Chicago

Keep the following information in mind while searching for Williamsburg to Chicago flight deals. Data was last updated July 31, 2025.

Round-trip from

$425
(American Airlines)

One-way from

$213
(American Airlines)

Popular in

August

Cheapest in

May

Average price

$419
From Williamsburg to Chicago (CHI)
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One-way flight from Williamsburg to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Williamsburg to Chicago

Cheapest flights from Williamsburg to Chicago
Explore the most affordable flight options available from Williamsburg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/31. 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 8/157:16 pmPHF - ORD
1 stop4h 43mAmerican Airlines
Tue 8/195:54 pmORD - PHF
1 stop4h 08mAmerican Airlines
Deal found 7/31$425

Cheapflights Fare Finder

 
Customize your flight search to find flights from Williamsburg to Chicago 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 July 31, 2025.
Use the filters below to find and compare flights from Williamsburg to Chicago that are best for you.

Fly from

Williamsburg

Fly to

Chicago

Route

Depart

Return

Price

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Fri 8/15

7:16 pm-10:59 pm

1 stop4h 43m

Chicago O'Hare Intl

Tue 8/19

5:54 pm-11:02 pm

1 stop4h 08m

$425

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Fri 8/15

7:16 pm-10:59 pm

1 stop4h 43m

$213

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Best time to book a flight from Williamsburg to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Williamsburg 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 Williamsburg to Chicago

What is the cheapest month to book a flight from Williamsburg to Chicago?

Currently, August is the cheapest month in which you can book a flight from Williamsburg to Chicago (average of $245). Flying from Williamsburg to Chicago in March is currently the most expensive (average of $321). 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 W11 to CHI?

Find hourly flight availability from Williamsburg to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Williamsburg to Chicago as you normally would.

What is the cheapest day to fly from Williamsburg to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Williamsburg to Chicago. Price data was last updated on July 27, 2025.

Travelers seeking maximum savings on their Williamsburg to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Williamsburg to Chicago

Explore weekly flight availability from Williamsburg to Chicago. 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 July 31, 2025.

The most flights from W11 to CHI are scheduled on a Thursday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 31, 2025.
Read reviews from past customers who have flown American Airlines from Williamsburg to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2024

LAX - ORD

The seats are just SO UNCOMFORTABLE it completely ruins the experience, especially on a redeye. I was so exhausted but couldn’t sleep a wink because it was just so incredibly uncomfortable. I don’t know who designs airplane seats, but they’re curved forward, forcing your body into a slouching position. Please. Please please get new seats. Also ones that actually extent to the bulkhead so that when you try to lean against the wall, you don’t just fall through the gap
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Entertainment

6.9

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2024

LAX - ORD

The seats are just SO UNCOMFORTABLE it completely ruins the experience, especially on a redeye. I was so exhausted but couldn’t sleep a wink because it was just so incredibly uncomfortable. I don’t know who designs airplane seats, but they’re curved forward, forcing your body into a slouching position. Please. Please please get new seats. Also ones that actually extent to the bulkhead so that when you try to lean against the wall, you don’t just fall through the gap

Related info for your journey

Find useful and relevant information for your journey from Williamsburg to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most reliable airlines from Williamsburg to Chicago?

    No one likes to see their flight delayed. When booking a flight from Williamsburg to Chicago consider choosing Avianca (93%), Piedmont Airlines (85%) or ANA (84%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Williamsburg to Chicago?

    While on average a flight from Williamsburg to Chicago is generally $1,233, our data shows the cheapest flight currently is $90. When looking at the most popular route, (Newport News Intl - Chicago O'Hare Intl), you can expect to pay $437 for that flight.

  • Can I find deals for flights from Williamsburg to Chicago that include hotel bookings?

    Yes. In addition to deals on Williamsburg to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Williamsburg to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Williamsburg to Chicago.

  • Can I find deals for business class flights from Williamsburg to Chicago?

    Yes. Cheapflights offers flight deals from Williamsburg to Chicago 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 Williamsburg to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Williamsburg to Chicago (average of $245). Flying from Williamsburg to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Top 6 airlines flying from Williamsburg to Chicago

Discover the top 6 airlines that operate flights from Williamsburg to Chicago. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$287FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$449FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$191Average$390FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$398FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$231Average$374FlexibilityNo cancel feeOn-time63%

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