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$205+ 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
May 1 — May 81
Fri 5/1
Fri 5/8
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 April 1, 2026.

This American Airlines deal was found by Cheapflights users on 3/27. 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 5/157:59 pm
PHF
-
ORD
1 stop4h 55m
American Airlines
Mon 5/184:17 pm
ORD
-
PHF
1 stop6h 42m
American Airlines
Deal found 3/27$409
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/247:59 pm
PHF
-
ORD
1 stop4h 55m
American Airlines
Sun 5/35:00 am
ORD
-
PHF
1 stop4h 40m
American Airlines
Deal found 3/31$419
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Thu 7/98:01 pm
PHF
-
ORD
1 stop4h 58m
American Airlines
Mon 7/134:45 pm
ORD
-
PHF
1 stop6h 14m
American Airlines
Deal found 3/31$473
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/127:59 pm
PHF
-
ORD
1 stop4h 55m
American Airlines
Thu 4/164:17 pm
ORD
-
PHF
1 stop6h 42m
American Airlines
Deal found 3/27$485
This American Airlines deal was found by Cheapflights users on 3/29. 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 5/1611:12 am
PHF
-
ORD
1 stop6h 09m
American Airlines
Wed 5/208:39 am
ORD
-
PHF
1 stop5h 38m
American Airlines
Deal found 3/29$569
This American Airlines deal was found by Cheapflights users on 3/29. 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 5/157:59 pm
PHF
-
ORD
1 stop4h 55m
American Airlines
Wed 5/208:39 am
ORD
-
PHF
1 stop5h 38m
American Airlines
Deal found 3/29$586
This American Airlines deal was found by Cheapflights users on 3/29. 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 4/185:02 am
PHF
-
ORD
2 stops11h 45m
American Airlines
Mon 4/204:07 pm
ORD
-
PHF
2 stops17h 35m
American Airlines
Deal found 3/29$591
This American Airlines deal was found by Cheapflights users on 3/29. 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 5/1411:12 am
PHF
-
ORD
1 stop6h 09m
American Airlines
Wed 5/208:39 am
ORD
-
PHF
1 stop5h 38m
American Airlines
Deal found 3/29$599
This American Airlines deal was found by Cheapflights users on 3/29. 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 5/1411:12 am
PHF
-
ORD
1 stop6h 09m
American Airlines
Mon 5/183:26 pm
ORD
-
PHF
1 stop7h 33m
American Airlines
Deal found 3/29$616
This American Airlines deal was found by Cheapflights users on 3/29. 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 4/185:02 am
PHF
-
ORD
1 stop4h 28m
American Airlines
Tue 4/218:39 am
ORD
-
PHF
1 stop5h 35m
American Airlines
Deal found 3/29$623
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Wed 4/111:11 am
PHF
-
ORD
1 stop7h 46m
American Airlines
Mon 4/66:44 pm
ORD
-
PHF
1 stop4h 15m
American Airlines
Deal found 3/31$626

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 April 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$409
(American Airlines)

One-way from

$205
(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.
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From Williamsburg to Chicago (CHI)
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One-way flight from Williamsburg to Chicago (CHI)
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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 April 1, 2026.
Use the filters below to find and compare flights from Williamsburg to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Fri 5/15

7:59 pm-11:54 pm

1 stop4h 55m

Chicago O'Hare Intl

Mon 5/18

4:17 pm-11:59 pm

1 stop6h 42m

$409

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Fri 4/24

7:59 pm-11:54 pm

1 stop4h 55m

Chicago O'Hare Intl

Sun 5/3

5:00 am-10:40 am

1 stop4h 40m

$419

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Thu 7/9

8:01 pm-11:59 pm

1 stop4h 58m

Chicago O'Hare Intl

Mon 7/13

4:45 pm-11:59 pm

1 stop6h 14m

$473

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Sun 4/12

7:59 pm-11:54 pm

1 stop4h 55m

Chicago O'Hare Intl

Thu 4/16

4:17 pm-11:59 pm

1 stop6h 42m

$485
Quickest round-trip

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Mon 4/13

7:59 pm-11:54 pm

1 stop4h 55m

Chicago O'Hare Intl

Fri 4/17

6:41 pm-11:59 pm

1 stop4h 18m

$485

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Fri 5/15

7:59 pm-11:54 pm

1 stop4h 55m

Chicago O'Hare Intl

Wed 5/20

8:39 am-3:17 pm

1 stop5h 38m

$586

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Thu 5/14

11:12 am-5:58 pm

1 stop7h 46m

Chicago O'Hare Intl

Tue 5/19

8:39 am-3:14 pm

1 stop5h 35m

$599

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Sat 4/18

5:02 am-8:30 am

1 stop4h 28m

Chicago O'Hare Intl

Tue 4/21

8:39 am-3:14 pm

1 stop5h 35m

$623

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Fri 4/17

3:42 pm-7:22 pm

1 stop4h 40m

Chicago O'Hare Intl

Wed 4/22

1:54 pm-7:34 pm

1 stop4h 40m

$626

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Thu 4/16

5:02 am-8:30 am

1 stop4h 28m

Chicago O'Hare Intl

Tue 4/21

8:39 am-3:14 pm

1 stop5h 35m

$626

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 14 resultsSorted by cheapest first
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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 $108). 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 April 1, 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 10% on your trip compared to booking a flight in the morning.

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 March 28, 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 April 1, 2026.

The most flights from W11 to CHI are scheduled on a Tuesday (27 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 $409, American Airlines can have you in Chicago from Williamsburg in 4h 55m. 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 GoJet (100%), Avianca (82%) or ANA (80%) 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 $860, our data shows the cheapest flight currently is $166. When looking at the most popular route, (Newport News Intl - Chicago O'Hare Intl), you can expect to pay $409 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 $108). 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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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 April 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$92Average$303FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$260FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$154Average$261FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$362FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$406FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$395FlexibilityNo cancel feeOn-time69%

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