$409+ Cheap flights from Chicago (CHI) to Williamsburg, VA
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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
May 3 — May 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 April 3, 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 April 3, 2026.
This American Airlines deal was found by Cheapflights users on 3/31. 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 6/66:47 pm
ORD
- PHF
1 stop4h 38m
American Airlines
Mon 6/88:01 pm
PHF
- ORD
1 stop4h 58m
American Airlines
Deal found 3/31![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 4/288:39 am
ORD
- PHF
1 stop5h 35m
American Airlines
Wed 5/135:02 am
PHF
- ORD
1 stop4h 28m
American Airlines
Deal found 3/30![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/246:41 pm
ORD
- PHF
1 stop4h 18m
American Airlines
Sun 4/267:59 pm
PHF
- ORD
1 stop4h 55m
American Airlines
Deal found 4/2![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 3/31. 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 6/165:34 pm
ORD
- PHF
1 stop5h 51m
American Airlines
Sun 6/218:01 pm
PHF
- ORD
1 stop4h 58m
American Airlines
Deal found 3/31![American Airlines logo]()
$473
This American Airlines deal was found by Cheapflights users on 4/1. 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 10/235:22 am
ORD
- PHF
1 stop4h 24m
American Airlines
Sun 10/258:14 pm
PHF
- ORD
1 stop4h 39m
American Airlines
Deal found 4/1![American Airlines logo]()
$479
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 4/145:00 am
ORD
- PHF
1 stop4h 42m
American Airlines
Sat 4/1811:12 am
PHF
- ORD
1 stop7h 46m
American Airlines
Deal found 3/30![American Airlines logo]()
$485
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/75:00 am
ORD
- PHF
1 stop4h 42m
American Airlines
Wed 4/1511:12 am
PHF
- ORD
1 stop5h 09m
American Airlines
Deal found 4/2![American Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/2312:33 pm
ORD
- PHF
1 stop6h 03m
American Airlines
Tue 5/265:05 am
PHF
- ORD
1 stop4h 57m
American Airlines
Deal found 4/2![American Airlines logo]()
$569
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/217:58 am
ORD
- PHF
1 stop5h 46m
American Airlines
Tue 5/265:05 am
PHF
- ORD
1 stop4h 57m
American Airlines
Deal found 4/2![American Airlines logo]()
$586
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/156:41 pm
ORD
- PHF
1 stop4h 18m
American Airlines
Mon 5/187:59 pm
PHF
- ORD
1 stop4h 55m
American Airlines
Deal found 4/2![American Airlines logo]()
$592
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/225:10 am
ORD
- PHF
1 stop4h 37m
American Airlines
Tue 5/265:05 am
PHF
- ORD
1 stop4h 57m
American Airlines
Deal found 4/2![American Airlines logo]()
$599
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/216:55 am
ORD
- PHF
1 stop6h 49m
American Airlines
Mon 5/258:01 pm
PHF
- ORD
1 stop4h 58m
American Airlines
Deal found 4/2![American Airlines logo]()
$603
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 April 3, 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 April 3, 2026.
This American Airlines deal was found by Cheapflights users on 3/28. 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.
Tue 6/166:55 am
ORD
- PHF
1 stop6h 49m
American Airlines
Sun 6/218:01 pm
PHF
- ORD
1 stop4h 58m
American Airlines
Deal found 3/28![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/98:39 am
ORD
- PHF
1 stop5h 38m
American Airlines
Fri 5/157:59 pm
PHF
- ORD
1 stop4h 55m
American Airlines
Deal found 4/1![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 3/29. 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.
Sat 6/66:55 am
ORD
- PHF
1 stop6h 49m
American Airlines
Mon 6/88:01 pm
PHF
- ORD
1 stop4h 58m
American Airlines
Deal found 3/29![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Sat 5/26:41 pm
ORD
- PHF
1 stop4h 18m
American Airlines
Sat 5/1611:12 am
PHF
- ORD
1 stop5h 18m
American Airlines
Deal found 3/30![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 4/2. 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 6/247:58 am
ORD
- PHF
1 stop5h 46m
American Airlines
Wed 7/111:12 am
PHF
- ORD
1 stop7h 28m
American Airlines
Deal found 4/2![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Fri 5/16:41 pm
ORD
- PHF
1 stop4h 18m
American Airlines
Fri 5/87:59 pm
PHF
- ORD
1 stop4h 55m
American Airlines
Deal found 3/30![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/98:39 am
ORD
- PHF
1 stop5h 38m
American Airlines
Sat 5/1611:12 am
PHF
- ORD
1 stop6h 09m
American Airlines
Deal found 4/1![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 4/288:39 am
ORD
- PHF
1 stop5h 35m
American Airlines
Wed 5/135:02 am
PHF
- ORD
1 stop4h 28m
American Airlines
Deal found 3/30![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/153:26 pm
ORD
- PHF
1 stop7h 33m
American Airlines
Sun 4/195:02 am
PHF
- ORD
1 stop6h 09m
American Airlines
Deal found 3/31![American Airlines logo]()
$485
Last-minute flights from Chicago to WilliamsburgDiscover last-minute flight deals from Chicago to Williamsburg. Data last updated April 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Williamsburg. Data last updated April 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/75:00 am
ORD
- PHF
1 stop4h 42m
American Airlines
Wed 4/1511:12 am
PHF
- ORD
1 stop5h 09m
American Airlines
Deal found 4/2![American Airlines logo]()
$543
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 4/145:00 am
ORD
- PHF
1 stop4h 42m
American Airlines
Sat 4/1811:12 am
PHF
- ORD
1 stop7h 46m
American Airlines
Deal found 3/30![American Airlines logo]()
$485
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/246:41 pm
ORD
- PHF
1 stop4h 18m
American Airlines
Sun 4/267:59 pm
PHF
- ORD
1 stop4h 55m
American Airlines
Deal found 4/2![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 4/288:39 am
ORD
- PHF
1 stop5h 35m
American Airlines
Wed 5/135:02 am
PHF
- ORD
1 stop4h 28m
American Airlines
Deal found 3/30![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/98:39 am
ORD
- PHF
1 stop5h 38m
American Airlines
Sat 5/1611:12 am
PHF
- ORD
1 stop6h 09m
American Airlines
Deal found 4/1![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/94:21 pm
ORD
- PHF
1 stop6h 38m
American Airlines
Sun 5/177:59 pm
PHF
- ORD
1 stop4h 55m
American Airlines
Deal found 4/1![American Airlines logo]()
$473
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/156:41 pm
ORD
- PHF
1 stop4h 18m
American Airlines
Mon 5/187:59 pm
PHF
- ORD
1 stop4h 55m
American Airlines
Deal found 4/2![American Airlines logo]()
$592
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/217:58 am
ORD
- PHF
1 stop5h 46m
American Airlines
Tue 5/265:05 am
PHF
- ORD
1 stop4h 57m
American Airlines
Deal found 4/2![American Airlines logo]()
$586
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/216:55 am
ORD
- PHF
1 stop6h 49m
American Airlines
Mon 5/258:01 pm
PHF
- ORD
1 stop4h 58m
American Airlines
Deal found 4/2![American Airlines logo]()
$603
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/225:10 am
ORD
- PHF
1 stop4h 37m
American Airlines
Tue 5/265:05 am
PHF
- ORD
1 stop4h 57m
American Airlines
Deal found 4/2![American Airlines logo]()
$599
This American Airlines deal was found by Cheapflights users on 4/2. 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 5/2312:33 pm
ORD
- PHF
1 stop6h 03m
American Airlines
Tue 5/265:05 am
PHF
- ORD
1 stop4h 57m
American Airlines
Deal found 4/2![American Airlines logo]()
$569
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 April 3, 2026.
Search for one-way flight options from Chicago to Williamsburg. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
This American Airlines deal was found by Cheapflights users on 4/3. 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 6/195:34 pm
ORD
- PHF
1 stop5h 51m
American Airlines
Deal found 4/3![American Airlines logo]()
$416
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 April 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $409 (American Airlines) |
Popular in | February |
Cheapest in | January |
Average price | $528 |
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 2,558,603 searches. Data last updated April 3, 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 - PHF
ORDPHF
Chicago O'Hare Intl
Tue 6/16
6:55 am-2:44 pm
1 stop6h 49m
Newport News Intl
Sun 6/21
8:01 pm-11:59 pm
1 stop4h 58m
$409
ChicagoNewport News
ORD - PHF
ORDPHF
Chicago O'Hare Intl
Sat 5/9
8:39 am-3:17 pm
1 stop5h 38m
Newport News Intl
Fri 5/15
7:59 pm-11:54 pm
1 stop4h 55m
$409
ChicagoNewport News
ORD - PHF
ORDPHF
Chicago O'Hare Intl
Sat 6/6
6:55 am-2:44 pm
1 stop6h 49m
Newport News Intl
Mon 6/8
8:01 pm-11:59 pm
1 stop4h 58m
$409
ChicagoNewport News
ORD - PHF
ORDPHF
Chicago O'Hare Intl
Sat 5/2
6:41 pm-11:59 pm
1 stop4h 18m
Newport News Intl
Sat 5/16
11:12 am-3:30 pm
1 stop5h 18m
$409
ChicagoNewport News
ORD - PHF
ORDPHF
Chicago O'Hare Intl
Wed 6/24
7:58 am-2:44 pm
1 stop5h 46m
Newport News Intl
Wed 7/1
11:12 am-5:40 pm
1 stop7h 28m
$409
Quickest round-trip
ChicagoNewport News
ORD - PHF
ORDPHF
Chicago O'Hare Intl
Fri 5/1
6:41 pm-11:59 pm
1 stop4h 18m
Newport News Intl
Fri 5/8
7:59 pm-11:54 pm
1 stop4h 55m
$409
ChicagoNewport News
ORD - PHF
ORDPHF
Chicago O'Hare Intl
Sat 5/9
8:39 am-3:17 pm
1 stop5h 38m
Newport News Intl
Sat 5/16
11:12 am-4:21 pm
1 stop6h 09m
$409
ChicagoNewport News
ORD - PHF
ORDPHF
Chicago O'Hare Intl
Tue 4/28
8:39 am-3:14 pm
1 stop5h 35m
Newport News Intl
Wed 5/13
5:02 am-8:30 am
1 stop4h 28m
$419
ChicagoNewport News
ORD - PHF
ORDPHF
Chicago O'Hare Intl
Wed 4/15
3:26 pm-11:59 pm
1 stop7h 33m
Newport News Intl
Sun 4/19
5:02 am-10:11 am
1 stop6h 09m
$485
Cheapest one-way
Quickest one-way
ChicagoNewport News
ORD - PHF
ORDPHF
Chicago O'Hare Intl
Fri 6/19
5:34 pm-12:25 am
1 stop5h 51m
$416
Sorted 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 month to book a flight from Chicago to Williamsburg?
Currently, January is the cheapest month in which you can book a flight from Chicago to Williamsburg (average of $130). Flying from Chicago to Williamsburg in December 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 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 April 3, 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 6% versus a flight at noon.
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 March 28, 2026.
Travelers seeking maximum savings on their Chicago to Williamsburg flight should consider departing on Sunday mornings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 3, 2026.
The most flights from CHI to W11 are scheduled on a Thursday (25 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).
Reviews of airlines servicing Williamsburg
Get insights into the airlines that provide service to Williamsburg. 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 Williamsburg. Reviews last updated April 3, 2026.
Peruse reviews from past customers who have flown with American Airlines from Chicago to Williamsburg to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.1
Crew
7.9
Comfort
7.2
Food
6.4
Boarding
7.5
Entertainment
6.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Overall
7.1
Crew
7.9
Comfort
7.2
Food
6.4
Boarding
7.5
Entertainment
6.9
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Top destinations
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 April 3, 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 April 3, 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 3 airlines flying from Chicago to Williamsburg
Discover the top 3 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 2,558,603 searches. Data last updated April 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$355 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$390 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$236 | Average$417 | FlexibilityNo cancel fee | On-time71% |