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$271+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$389
(American Airlines)

One-way from

$271
(American Airlines)
From Williamsburg to Chicago (CHI)
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One-way flight from Williamsburg to Chicago (CHI)
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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 September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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 10/167:59 pmPHF - ORD
1 stop4h 54mAmerican Airlines
Wed 10/225:20 amORD - PHF
1 stop6h 01mAmerican Airlines
Deal found 9/14$389
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/204:03 pmPHF - ORD
1 stop5h 24mAmerican Airlines
Sat 9/275:00 amORD - PHF
1 stop6h 08mAmerican Airlines
Deal found 9/15$443
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/297:14 pmPHF - ORD
1 stop4h 58mAmerican Airlines
Fri 10/39:45 amORD - PHF
1 stop4h 53mAmerican Airlines
Deal found 9/14$445
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/204:03 pmPHF - ORD
1 stop5h 24mAmerican Airlines
Mon 9/225:00 amORD - PHF
1 stop6h 08mAmerican Airlines
Deal found 9/15$486
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/288:00 pmPHF - ORD
1 stop4h 39mAmerican Airlines
Thu 10/212:40 pmORD - PHF
1 stop5h 55mAmerican Airlines
Deal found 9/15$493
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/2311:24 amPHF - ORD
1 stop7h 25mAmerican Airlines
Fri 12/268:03 amORD - PHF
1 stop6h 10mAmerican Airlines
Deal found 9/15$679

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 September 16, 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

Thu 10/16

7:59 pm-11:53 pm

1 stop4h 54m

Chicago O'Hare Intl

Wed 10/22

5:20 am-12:21 pm

1 stop6h 01m

$389

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Mon 9/29

7:14 pm-11:12 pm

1 stop4h 58m

Chicago O'Hare Intl

Fri 10/3

9:45 am-3:38 pm

1 stop4h 53m

$445

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Sat 9/20

4:03 pm-8:27 pm

1 stop5h 24m

Chicago O'Hare Intl

Mon 9/22

5:00 am-12:08 pm

1 stop6h 08m

$486

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Sun 9/28

8:00 pm-11:39 pm

1 stop4h 39m

Chicago O'Hare Intl

Thu 10/2

12:40 pm-7:35 pm

1 stop5h 55m

$493

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Sat 9/20

12:33 pm-5:30 pm

1 stop5h 57m

Chicago O'Hare Intl

Sat 9/27

8:01 am-3:38 pm

2 stops6h 37m

$777

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Sat 9/20

4:03 pm-8:27 pm

1 stop5h 24m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

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 September 16, 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 September 14, 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 September 16, 2025.

The most flights from W11 to CHI are scheduled on a Monday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

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.

  • How long is the flight from Williamsburg to Chicago?

    For as low as $389, American Airlines can have you in Chicago from Williamsburg in 4h 54m. There are 693 mi between Williamsburg and Chicago.

  • 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 Emirates (100%), Avianca (89%) or United Airlines (86%) 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 $901, our data shows the cheapest flight currently is $135. When looking at the most popular route, (Newport News Intl - Chicago O'Hare Intl), you can expect to pay $389 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
Chesterton

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Alternative routes for Williamsburg to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$270FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$352FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$168Average$204FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$208Average$383FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$238Average$392FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$383FlexibilityNo cancel feeOn-time63%

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