$407+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
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
Keep the following information in mind while searching for Williamsburg to Chicago flight deals. Data was last updated February 20, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $407 (American Airlines) |
Popular in | August |
Cheapest in | September |
Average price | $378 |
Find flight deals from Williamsburg to Chicago
Cheapest flights from Williamsburg to ChicagoExplore 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 February 20, 2025.
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 February 20, 2025.
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Find flights from Williamsburg to Chicago within your budget
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 February 20, 2025.
Fly from
Fly to
Route
Depart
Return
Price
Newport NewsChicago
PHF - ORD
PHFORD
Newport News Intl
Fri 3/7
11:19 am-3:40 pm
1 stop5h 21m
Chicago O'Hare Intl
Mon 3/17
8:05 am-3:28 pm
1 stop6h 23m
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.
Travel insights for flights from Williamsburg to Chicago
Get recent, data-driven insights about flights from Williamsburg to Chicago including ideal travel times, pricing trends, and more.
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 February 20, 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 February 16, 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 February 20, 2025.
The most flights from W11 to CHI are scheduled on a Thursday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 20, 2025.
Crew
Comfort
Entertainment
Overall
Boarding
Food
Reviews
Anonymous,Oct 2024
LAX - ORD
Crew
Comfort
Entertainment
Overall
Boarding
Food
Reviews
Anonymous,Oct 2024
LAX - ORD
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.
Traveling to a place near Williamsburg?
Book flights to Williamsburg if you plan to visit one of these locationsBrowse 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.
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 February 20, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$105 | Average$227 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$175 | Average$489 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$390 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$251 | Average$388 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$268 | Average$391 | FlexibilityNo cancel fee | On-time63% |