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$368+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Dec 28 — Jan 41
Sat 12/28
Sat 1/4
1 adult, Economy
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Cheap flight deals from Williamsburg to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Williamsburg (W11) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 2024.

Round-trip from

$368
(American Airlines)
From Williamsburg to Chicago (CHI)
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Find 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 December 23, 2024.

This American Airlines deal was found by Cheapflights users on 12/21. 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.
Mon 1/278:13 pmPHF - ORD
1 stop4h 56mAmerican Airlines
Fri 1/314:30 pmORD - PHF
1 stop6h 28mAmerican Airlines
Deal found 12/21$368

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 December 23, 2024.

Fly from

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Route

Depart

Return

Price

Newport NewsChicago

PHF - ORD

PHFORD

Newport News Intl

Mon 1/27

8:13 pm-12:09 am

1 stop4h 56m

Chicago O'Hare Intl

Fri 1/31

4:30 pm-11:58 pm

1 stop6h 28m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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.

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 $317). 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 December 23, 2024.

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 December 16, 2024.

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 December 23, 2024.

The most flights from W11 to CHI are scheduled on a Friday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 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 December 23, 2024.
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Entertainment

7.0

Overall

7.2

Comfort

7.2

Boarding

7.6

Crew

8.0

Reviews

1 / 10

The seats are just SO UNCOMFORTABLE it completely ruins the experience, especially on a redeye. I was so exhausted but couldn’t sleep a wink because it was just so incredibly uncomfortable. I don’t know who designs airplane seats, but they’re curved forward, forcing your body into a slouching position. Please. Please please get new seats. Also ones that actually extent to the bulkhead so that when you try to lean against the wall, you don’t just fall through the gap

American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Entertainment

7.0

Overall

7.2

Comfort

7.2

Boarding

7.6

Crew

8.0

Reviews

1 / 10

The seats are just SO UNCOMFORTABLE it completely ruins the experience, especially on a redeye. I was so exhausted but couldn’t sleep a wink because it was just so incredibly uncomfortable. I don’t know who designs airplane seats, but they’re curved forward, forcing your body into a slouching position. Please. Please please get new seats. Also ones that actually extent to the bulkhead so that when you try to lean against the wall, you don’t just fall through the gap

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.

  • 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 Envoy Air (96%), ANA (95%) or Avianca (90%) 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 $906, our data shows the cheapest flight currently is $185. When looking at the most popular route, (Newport News Intl - Chicago O'Hare Intl), you can expect to pay $368 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, 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 $317). 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.

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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 December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$387FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$189Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$248Average$383FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$268Average$391FlexibilityNo cancel feeOn-time63%
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