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$195+ 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 6/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
mar 4 — mar 111
qua 3/4
qua 3/11
1 adult, Economy
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Cheap 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 fevereiro 2, 2026.

This American Airlines deal was found by Cheapflights users on 2/2. 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.
sex 3/67:55 pm
PHF
-
ORD
1 stop5h 21m
American Airlines
dom 3/85:00 pm
ORD
-
PHF
1 stop5h 59m
American Airlines
Deal found 2/2$389
This American Airlines deal was found by Cheapflights users on 2/1. 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.
qui 4/27:55 pm
PHF
-
ORD
1 stop5h 21m
American Airlines
seg 4/66:44 pm
ORD
-
PHF
1 stop4h 15m
American Airlines
Deal found 2/1$437
This American Airlines deal was found by Cheapflights users on 2/1. 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.
qui 6/118:00 pm
PHF
-
ORD
1 stop4h 59m
American Airlines
dom 6/145:20 am
ORD
-
PHF
1 stop4h 26m
American Airlines
Deal found 2/1$457
This American Airlines deal was found by Cheapflights users on 1/30. 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.
sex 2/137:55 pm
PHF
-
ORD
1 stop5h 21m
American Airlines
seg 2/161:39 pm
ORD
-
PHF
1 stop4h 51m
American Airlines
Deal found 1/30$465
This American Airlines deal was found by Cheapflights users on 2/2. 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.
sáb 2/1411:21 am
PHF
-
ORD
1 stop7h 37m
American Airlines
qua 2/181:39 pm
ORD
-
PHF
1 stop4h 14m
American Airlines
Deal found 2/2$484
This American Airlines deal was found by Cheapflights users on 2/1. 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.
sex 6/128:00 pm
PHF
-
ORD
1 stop4h 59m
American Airlines
sáb 6/135:20 am
ORD
-
PHF
1 stop4h 26m
American Airlines
Deal found 2/1$509
This American Airlines deal was found by Cheapflights users on 2/1. 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.
qua 6/108:00 pm
PHF
-
ORD
1 stop4h 59m
American Airlines
dom 6/145:20 am
ORD
-
PHF
1 stop4h 26m
American Airlines
Deal found 2/1$527
This American Airlines deal was found by Cheapflights users on 1/31. 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.
qui 2/1211:11 am
PHF
-
ORD
1 stop7h 47m
American Airlines
dom 2/155:00 pm
ORD
-
PHF
1 stop5h 59m
American Airlines
Deal found 1/31$533
This American Airlines deal was found by Cheapflights users on 2/1. 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.
qua 6/108:00 pm
PHF
-
ORD
1 stop4h 59m
American Airlines
seg 6/155:20 am
ORD
-
PHF
1 stop4h 26m
American Airlines
Deal found 2/1$539
This American Airlines deal was found by Cheapflights users on 2/1. 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.
sex 6/128:00 pm
PHF
-
ORD
1 stop4h 59m
American Airlines
dom 6/145:20 am
ORD
-
PHF
1 stop4h 26m
American Airlines
Deal found 2/1$552
This American Airlines deal was found by Cheapflights users on 2/1. 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.
sex 6/128:00 pm
PHF
-
ORD
1 stop4h 59m
American Airlines
seg 6/155:43 pm
ORD
-
PHF
1 stop5h 42m
American Airlines
Deal found 2/1$564
This American Airlines deal was found by Cheapflights users on 2/1. 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.
qua 6/108:00 pm
PHF
-
ORD
2 stops11h 31m
American Airlines
sáb 6/136:40 pm
ORD
-
PHF
1 stop4h 45m
American Airlines
Deal found 2/1$616

Find flight deals from Williamsburg to Chicago

Keep the following information in mind while searching for Williamsburg to Chicago flight deals. Data was last updated fevereiro 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$437
(American Airlines)

One-way from

$195
(American Airlines)
Provider with most accurate pricing for Newport News Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Newport News Intl-Chicago (CHI) flights.
Search Deals
From Williamsburg to Chicago (CHI)
Search Deals
One-way flight from Williamsburg to Chicago (CHI)
Search Deals

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 fevereiro 2, 2026.
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

sex 3/6

7:55 pm-12:16 am

1 stop5h 21m

Chicago O'Hare Intl

dom 3/8

5:00 pm-11:59 pm

1 stop5h 59m

$389

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

qui 4/2

7:55 pm-12:16 am

1 stop5h 21m

Chicago O'Hare Intl

seg 4/6

5:00 pm-11:59 pm

1 stop5h 59m

$437

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

qui 6/11

8:00 pm-11:59 pm

1 stop4h 59m

Chicago O'Hare Intl

dom 6/14

5:20 am-10:46 am

1 stop4h 26m

$457

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

sáb 2/14

3:41 pm-7:40 pm

1 stop4h 59m

Chicago O'Hare Intl

qua 2/18

5:00 am-12:00 pm

1 stop6h 00m

$465

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

sex 2/13

7:55 pm-12:16 am

1 stop5h 21m

Chicago O'Hare Intl

seg 2/16

1:39 pm-7:30 pm

1 stop4h 51m

$465

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

seg 2/16

7:55 pm-12:06 am

1 stop5h 11m

Chicago O'Hare Intl

sex 2/20

5:00 am-10:44 am

1 stop4h 44m

$465

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

sex 6/12

8:00 pm-11:59 pm

1 stop4h 59m

Chicago O'Hare Intl

sáb 6/13

5:20 am-10:46 am

1 stop4h 26m

$509

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

qui 2/12

11:11 am-5:58 pm

1 stop7h 47m

Chicago O'Hare Intl

dom 2/15

5:00 pm-11:59 pm

1 stop5h 59m

$533

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

qui 6/11

8:00 pm-11:59 pm

1 stop4h 59m

Chicago O'Hare Intl

seg 6/15

6:40 pm-12:25 am

1 stop4h 45m

$539

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

sáb 6/27

8:00 pm-11:59 pm

1 stop4h 59m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

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, May is the cheapest month in which you can book a flight from Williamsburg to Chicago (average of $114). Flying from Williamsburg to Chicago in July is currently the most expensive (average of $266). 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 fevereiro 2, 2026.

A simple way to save on the total cost of your ticket is to fly from Williamsburg to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the evening.

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 January 31, 2026.

Travelers seeking maximum savings on their Williamsburg to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday evenings 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 fevereiro 2, 2026.

The most flights from W11 to CHI are scheduled on a Friday (25 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (16 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 $437, American Airlines can have you in Chicago from Williamsburg in 5h 21m. 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 Avianca (87%), ANA (83%) or United Airlines (79%) 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 $1,076, our data shows the cheapest flight currently is $149. 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, May is the cheapest month in which you can book a flight from Williamsburg to Chicago (average of $114). Flying from Williamsburg to Chicago in July is currently the most expensive (average of $266). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 fevereiro 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$92Average$303FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$260FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$172Average$208FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$363FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$191Average$385FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$210Average$391FlexibilityNo cancel feeOn-time71%

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