$248+ Cheap flights from Chicago (CHI) to Williamsburg, VA
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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Williamsburg 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 Chicago to Williamsburg
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Cheapest flights from Chicago to WilliamsburgExplore the most affordable flight options available from Chicago to Williamsburg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Chicago to Williamsburg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Thu 9/244:45 pm -
1 stop5h 38m
Sun 9/275:00 am -
1 stop6h 45m
Deal found 8/17![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/175:20 am -
1 stop5h 41m
Fri 9/187:16 pm -
1 stop5h 43m
Deal found 8/19![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/45:05 am -
1 stop6h 04m
Mon 9/76:07 am -
1 stop5h 44m
Deal found 8/18![American Airlines logo]()
$495
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Thu 9/176:29 am -
1 stop4h 32m
Fri 9/256:00 am -
1 stop7h 14m
Deal found 8/18![American Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Sat 8/224:53 pm -
1 stop5h 39m
Sat 8/296:07 am -
1 stop7h 08m
Deal found 8/17![American Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/168:59 am -
1 stop5h 38m
Thu 9/247:16 pm -
1 stop5h 43m
Deal found 8/18![American Airlines logo]()
$509
This KAYAK deal was found by Cheapflights users on 8/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:54 am -
1 stop7h 29m
Thu 8/2712:36 pm -
1 stop6h 06m
Deal found 8/17![American Airlines logo]()
$559
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/2211:15 am -
2 stops11h 08m
Thu 9/247:16 pm -
1 stop5h 43m
Deal found 8/18![American Airlines logo]()
$656
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Mon 9/2111:15 am -
2 stops11h 08m
Fri 9/256:00 am -
1 stop7h 14m
Deal found 8/18![American Airlines logo]()
$700
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Sun 9/205:18 am -
1 stop4h 15m
Thu 9/246:00 am -
2 stops11h 58m
Deal found 8/18![American Airlines logo]()
$791
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/197:47 am -
2 stops6h 50m
Sat 9/2612:27 pm -
1 stop4h 33m
Deal found 8/16![American Airlines logo]()
$798
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Sun 11/299:00 am -
1 stop6h 11m
Sat 12/512:39 pm -
1 stop5h 50m
Deal found 8/18![American Airlines logo]()
$821
Best flights from Chicago to WilliamsburgDiscover carefully curated flight deals from Chicago to Williamsburg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Chicago to Williamsburg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/198:05 am -
1 stop6h 32m
Sat 9/267:16 pm -
1 stop5h 45m
Deal found 8/16![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/16. 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 10/299:02 am -
1 stop6h 06m
Mon 11/212:34 pm -
1 stop8h 01m
Deal found 8/16![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/20. 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 10/38:05 am -
1 stop6h 32m
Sat 10/105:00 am -
1 stop5h 10m
Deal found 8/20![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/256:29 am -
1 stop4h 32m
Sun 9/277:54 pm -
1 stop5h 05m
Deal found 8/19![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/248:05 am -
1 stop6h 32m
Sat 10/34:25 pm -
1 stop7h 06m
Deal found 8/20![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Thu 9/244:45 pm -
1 stop5h 38m
Sun 9/275:00 am -
1 stop6h 45m
Deal found 8/17![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Fri 2/125:18 am -
1 stop4h 25m
Mon 2/157:58 pm -
1 stop5h 04m
Deal found 8/17![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/175:20 am -
1 stop5h 41m
Fri 9/187:16 pm -
1 stop5h 43m
Deal found 8/19![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/45:05 am -
1 stop6h 04m
Mon 9/76:07 am -
1 stop5h 44m
Deal found 8/18![American Airlines logo]()
$495
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Sat 9/195:20 am -
1 stop5h 41m
Thu 9/247:16 pm -
1 stop5h 43m
Deal found 8/18![American Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/225:20 am -
1 stop5h 41m
Sat 9/264:25 pm -
1 stop7h 06m
Deal found 8/18![American Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/165:20 am -
1 stop5h 41m
Mon 9/286:00 am -
1 stop7h 14m
Deal found 8/18![American Airlines logo]()
$509
Last-minute flights from Chicago to WilliamsburgDiscover last-minute flight deals from Chicago to Williamsburg. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Williamsburg. Data last updated August 21, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Sat 8/224:53 pm -
1 stop5h 39m
Sat 8/296:07 am -
1 stop7h 08m
Deal found 8/17![American Airlines logo]()
$501
This KAYAK deal was found by Cheapflights users on 8/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:54 am -
1 stop7h 29m
Thu 8/2712:36 pm -
1 stop6h 06m
Deal found 8/17![American Airlines logo]()
$559
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/45:05 am -
1 stop6h 04m
Mon 9/76:07 am -
1 stop5h 44m
Deal found 8/18![American Airlines logo]()
$495
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/168:59 am -
1 stop5h 38m
Thu 9/247:16 pm -
1 stop5h 43m
Deal found 8/18![American Airlines logo]()
$509
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/175:20 am -
1 stop5h 41m
Fri 9/187:16 pm -
1 stop5h 43m
Deal found 8/19![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Thu 9/176:29 am -
1 stop4h 32m
Fri 9/256:00 am -
1 stop7h 14m
Deal found 8/18![American Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/197:47 am -
2 stops6h 50m
Sat 9/2612:27 pm -
1 stop4h 33m
Deal found 8/16![American Airlines logo]()
$798
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Sun 9/205:18 am -
1 stop4h 15m
Thu 9/246:00 am -
2 stops11h 58m
Deal found 8/18![American Airlines logo]()
$791
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Mon 9/2111:15 am -
2 stops11h 08m
Fri 9/256:00 am -
1 stop7h 14m
Deal found 8/18![American Airlines logo]()
$700
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 9/2211:15 am -
2 stops11h 08m
Thu 9/247:16 pm -
1 stop5h 43m
Deal found 8/18![American Airlines logo]()
$656
This American Airlines deal was found by Cheapflights users on 8/17. 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.
Thu 9/244:45 pm -
1 stop5h 38m
Sun 9/275:00 am -
1 stop6h 45m
Deal found 8/17![American Airlines logo]()
$419
One-way flights from Chicago to WilliamsburgSearch for one-way flight options from Chicago to Williamsburg. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Chicago to Williamsburg. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This American Airlines deal was found by Cheapflights users on 8/16. 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.
Tue 9/15:05 am -
1 stop6h 04m
Deal found 8/16![American Airlines logo]()
$248
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Thu 9/176:29 am -
1 stop4h 32m
Deal found 8/18![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/168:59 am -
1 stop5h 38m
Deal found 8/18![American Airlines logo]()
$260
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Sat 9/1911:15 am -
2 stops11h 08m
Deal found 8/18![American Airlines logo]()
$413
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/187:09 am -
2 stops15h 14m
Deal found 8/18![American Airlines logo]()
$423
Find flight deals from Chicago to Williamsburg
Keep the following information in mind while searching for Chicago to Williamsburg flight deals. Data was last updated August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $419 (American Airlines) |
One-way from | $248 (American Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Williamsburg 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 7,457,451 searches. Data last updated August 21, 2026.
Use the filters below to find and compare flights from Chicago to Williamsburg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Sat 9/19
8:05 am-3:37 pm
1 stop6h 32m
Newport News Intl
Sat 9/26
7:16 pm-12:01 am
1 stop5h 45m
$419
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Thu 10/29
9:02 am-4:08 pm
1 stop6h 06m
Newport News Intl
Mon 11/2
12:34 pm-7:35 pm
1 stop8h 01m
$419
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Sat 10/3
8:05 am-3:37 pm
1 stop6h 32m
Newport News Intl
Sat 10/10
5:00 am-9:10 am
1 stop5h 10m
$419
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Fri 9/25
6:29 am-12:01 pm
1 stop4h 32m
Newport News Intl
Sun 9/27
7:54 pm-11:59 pm
1 stop5h 05m
$419
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Thu 9/24
8:05 am-3:37 pm
1 stop6h 32m
Newport News Intl
Sat 10/3
4:25 pm-10:31 pm
1 stop7h 06m
$419
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Thu 9/24
4:45 pm-11:23 pm
1 stop5h 38m
Newport News Intl
Sun 9/27
5:00 am-10:45 am
1 stop6h 45m
$419
Quickest round-trip
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Fri 2/12
5:18 am-10:43 am
1 stop4h 25m
Newport News Intl
Mon 2/15
7:58 pm-12:02 am
1 stop5h 04m
$429
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Thu 9/17
5:20 am-12:01 pm
1 stop5h 41m
Newport News Intl
Fri 9/18
7:16 pm-11:59 pm
1 stop5h 43m
$429
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Fri 9/4
5:05 am-12:09 pm
1 stop6h 04m
Newport News Intl
Mon 9/7
6:07 am-10:51 am
1 stop5h 44m
$495
ChicagoNewport News
ORD Chicago O'Hare Intl - PHF Newport News Intl
ORDPHF
Chicago O'Hare Intl
Sat 9/19
5:20 am-12:01 pm
1 stop5h 41m
Newport News Intl
Thu 9/24
7:16 pm-11:59 pm
1 stop5h 43m
$499
Showing 1-10 of 18 resultsSorted by cheapest first
Best time to book a flight from Chicago to Williamsburg
Have a flexible travel schedule? Discover the best time to fly to Williamsburg from Chicago with our price prediction graph.
ORD-PHF
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 Chicago to Williamsburg
CHI-W11
ORD-PHF
What is the cheapest time of day to fly from CHI to W11?
Find hourly flight availability from Chicago to Williamsburg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2026.
When flying from Chicago to Williamsburg, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 3% versus a flight in the evening.
Weekly flight availability from Chicago to Williamsburg
Explore weekly flight availability from Chicago to Williamsburg. 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 August 21, 2026.
The most flights from CHI to W11 are scheduled on a Wednesday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).
What is the cheapest day to fly from Chicago to Williamsburg?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Williamsburg. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Chicago to Williamsburg flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday 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 Chicago to Williamsburg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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.
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Alternative routes for Chicago to Williamsburg
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Williamsburg by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Williamsburg by cabin class
Find flights from Chicago to Williamsburg, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Williamsburg flights
Browse other Chicago and Williamsburg flight options. Last updated on August 21, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Williamsburg flights
Consider these flights traveling from Chicago to Williamsburg.
Top 4 airlines flying from Chicago to Williamsburg
Discover the top 4 airlines that operate flights from Chicago to Williamsburg. 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 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$394 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$219 | Average$416 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$234 | Average$349 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$263 | Average$392 | FlexibilityNo cancel fee | On-time71% |