HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$437+ Cheap flights from Williamsburg, VA to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
janv. 17 — janv. 241
sam. 1/17
sam. 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Williamsburg to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Williamsburg to Chicago

Best flights from Williamsburg to Chicago
Discover carefully curated flight deals from Williamsburg to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated décembre 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/17. 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. 1/611:42 amPHF - ORD
1 stop7h 19mAmerican Airlines
lun. 1/126:05 amORD - PHF
1 stop4h 12mAmerican Airlines
Deal found 12/17$437
This American Airlines deal was found by Cheapflights users on 12/17. 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.
jeu. 1/15:00 amPHF - ORD
1 stop5h 21mAmerican Airlines
lun. 1/55:28 pmORD - PHF
1 stop5h 31mAmerican Airlines
Deal found 12/17$447

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 décembre 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$437
(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

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 décembre 18, 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

mar. 1/6

11:42 am-6:01 pm

1 stop7h 19m

Chicago O'Hare Intl

lun. 1/12

6:05 am-11:17 am

1 stop4h 12m

$437

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

jeu. 1/1

5:00 am-9:21 am

1 stop5h 21m

Chicago O'Hare Intl

lun. 1/5

5:28 pm-11:59 pm

1 stop5h 31m

$447

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

sam. 3/28

7:55 pm-9:05 am

1 stop14h 10m

$505

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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 $265). 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 décembre 18, 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 16% 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 December 13, 2025.

Travelers seeking maximum savings on their Williamsburg to Chicago flight should consider departing on Saturday mornings 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 7h 19m. 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 ANA (80%), Avianca (75%) or GoJet (74%) 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 $1,129, our data shows the cheapest flight currently is $154. When looking at the most popular route, (Newport News Intl - Chicago O'Hare Intl), you can expect to pay $465 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 $265). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Williamsburg to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Dulles Intl to Midway flights
Dulles Intl to St. Louis flights
Reagan-National to Midway flights
Norfolk to O'Hare Intl flights
Reagan-National to St. Louis flights
Richmond to O'Hare Intl flights
Raleigh to Midway flights
Charlottesville to O'Hare Intl flights
Greensboro to O'Hare Intl flights
Norfolk to Midway flights
Raleigh to St. Louis flights
Richmond to Midway flights
Roanoke to O'Hare Intl flights
Greensboro to Midway flights
Richmond to St. Louis flights
Greensboro to St. Louis flights
Roanoke to St. Louis flights
Charlottesville to Midway flights
Dulles Intl to Moline flights
Raleigh to Peoria flights
Roanoke to Midway flights
Reagan-National to Peoria flights
Dulles Intl to Peoria flights
Blountville to O'Hare Intl flights
Raleigh to Evansville flights
Raleigh to Moline flights
Lynchburg to O'Hare Intl flights
Norfolk to St. Louis flights
Norfolk to Peoria flights
Reagan-National to Moline flights
Richmond to Rockford flights
Staunton to O'Hare Intl flights
Norfolk to Moline flights
Charlottesville to St. Louis flights
Richmond to Champaign flights
Raleigh to Dubuque flights
Richmond to Peoria flights
Reagan-National to Bloomington flights
Dulles Intl to Bloomington flights
Greensboro to Peoria flights
Richmond to Moline flights
Blountville to St. Louis flights
Roanoke to Peoria flights
Blountville to Midway flights
Reagan-National to Evansville flights

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 décembre 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$249FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$260FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$176Average$208FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$181Average$364FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$214Average$385FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$217Average$362FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.