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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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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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 octubre 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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.
lun. 12/228:03 pmPHF - ORD
1 stop4h 39mAmerican Airlines
jue. 12/255:00 amORD - PHF
1 stop4h 54mAmerican Airlines
Deal found 10/28$459
This American Airlines deal was found by Cheapflights users on 10/30. 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.
vie. 11/147:16 pmPHF - ORD
1 stop5h 21mAmerican Airlines
mar. 11/183:44 pmORD - PHF
1 stop6h 21mAmerican Airlines
Deal found 10/30$465
This American Airlines deal was found by Cheapflights users on 10/28. 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. 12/2311:24 amPHF - ORD
1 stop5h 41mAmerican Airlines
jue. 12/255:00 amORD - PHF
1 stop4h 54mAmerican Airlines
Deal found 10/28$514
This American Airlines deal was found by Cheapflights users on 10/28. 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.
mié. 12/2411:24 amPHF - ORD
1 stop8h 58mAmerican Airlines
jue. 12/257:00 amORD - PHF
2 stops11h 33mAmerican Airlines
Deal found 10/28$551
This American Airlines deal was found by Cheapflights users on 10/29. 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.
dom. 11/236:10 amPHF - ORD
1 stop7h 46mAmerican Airlines
sáb. 11/295:00 amORD - PHF
1 stop4h 53mAmerican Airlines
Deal found 10/29$566
This American Airlines deal was found by Cheapflights users on 10/28. 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.
lun. 12/228:03 pmPHF - ORD
1 stop4h 39mAmerican Airlines
vie. 12/264:05 pmORD - PHF
1 stop6h 54mAmerican Airlines
Deal found 10/28$572
This KAYAK deal was found by Cheapflights users on 10/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/47:54 amPHF - ORD
1 stop5h 34mAmerican Airlines
jue. 11/67:10 amORD - PHF
1 stop7h 06mAmerican Airlines
Deal found 10/28$579
This American Airlines deal was found by Cheapflights users on 10/28. 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. 12/2311:24 amPHF - ORD
1 stop5h 41mAmerican Airlines
vie. 12/264:05 pmORD - PHF
1 stop6h 54mAmerican Airlines
Deal found 10/28$627
This American Airlines deal was found by Cheapflights users on 10/28. 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.
lun. 12/228:03 pmPHF - ORD
1 stop4h 39mAmerican Airlines
sáb. 12/277:11 amORD - PHF
1 stop7h 02mAmerican Airlines
Deal found 10/28$631
This American Airlines deal was found by Cheapflights users on 10/28. 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. 12/2311:24 amPHF - ORD
1 stop5h 41mAmerican Airlines
sáb. 12/277:11 amORD - PHF
1 stop7h 02mAmerican Airlines
Deal found 10/28$686

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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$437
(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.
Search Deals
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 octubre 30, 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

jue. 4/23

8:16 pm-11:50 pm

1 stop4h 34m

Chicago O'Hare Intl

dom. 4/26

5:10 am-10:37 am

1 stop4h 27m

$437

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

lun. 12/22

8:03 pm-11:42 pm

1 stop4h 39m

Chicago O'Hare Intl

jue. 12/25

5:00 am-10:54 am

1 stop4h 54m

$459

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

mié. 3/4

7:19 pm-10:49 pm

1 stop4h 30m

Chicago O'Hare Intl

sáb. 3/7

6:48 pm-11:57 pm

1 stop4h 09m

$459

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

vie. 11/14

7:16 pm-11:37 pm

1 stop5h 21m

Chicago O'Hare Intl

mar. 11/18

3:44 pm-11:05 pm

1 stop6h 21m

$465

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

mar. 12/23

11:24 am-4:05 pm

1 stop5h 41m

Chicago O'Hare Intl

jue. 12/25

5:00 am-10:54 am

1 stop4h 54m

$514

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

mié. 12/24

11:24 am-7:22 pm

1 stop8h 58m

Chicago O'Hare Intl

jue. 12/25

7:00 am-7:33 pm

2 stops11h 33m

$551

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

mié. 3/25

8:06 pm-12:13 am

1 stop5h 07m

Chicago O'Hare Intl

sáb. 3/28

1:30 pm-9:49 pm

1 stop7h 19m

$552

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

dom. 11/23

6:10 am-12:56 pm

1 stop7h 46m

Chicago O'Hare Intl

sáb. 11/29

5:00 am-10:53 am

1 stop4h 53m

$566

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

dom. 11/23

8:12 pm-11:40 pm

1 stop4h 28m

$205

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

jue. 11/13

8:12 pm-11:40 pm

1 stop4h 28m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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 December is currently the most expensive (average of $292). 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 octubre 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Williamsburg to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 4% 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 October 26, 2025.

Travelers seeking maximum savings on their Williamsburg to Chicago flight should consider departing on Monday evenings 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.

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 4h 34m. 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%), GoJet (94%) or ANA (93%) 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 $963, our data shows the cheapest flight currently is $128. 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 $108). Flying from Williamsburg to Chicago in December is currently the most expensive (average of $292). 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
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 5 airlines flying from Williamsburg to Chicago

Discover the top 5 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$283FlexibilityNo cancel feeOn-time65%
FrontierCheapest$168Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$383FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$392FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$229Average$381FlexibilityNo cancel feeOn-time63%

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