Cheap flights from Williamsburg, VA to Chicago (CHI)

RIC — CHI
Aug 13 — Aug 201

What is the cheapest month to fly from Williamsburg to Chicago?

January is one of the best times of the year to fly to Chicago from Williamsburg. Prices for January average $365 per person but you can even find prices for as low as $244. The most expensive prices can be found in the month of June. Opting for a January flight can save you 40% on your journey compared to booking in June

When is the cheapest time to fly from Williamsburg to Chicago (W11 - CHI)?

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.

Cheap flights from Williamsburg to Chicago in August, September 2022

The best prices found for Williamsburg to CHI flights for August, September
Aug 31 - Sep 7
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

4h 37m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

1 stop

4h 15m
$357

American Airlines

Pick Dates

Deal found 8/7/22

Aug 26 - Aug 31
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

4h 37m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

1 stop

4h 07m
$368

American Airlines

Pick Dates

Deal found 8/6/22

Aug 26 - Aug 31
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

2 stops

12h 35m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

1 stop

4h 07m
$414

American Airlines

Pick Dates

Deal found 8/6/22

Williamsburg to Chicago 2022 flight deals

Cheap flights to Chicago from Williamsburg found for this year
Aug 31 - Sep 7
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

4h 37m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

1 stop

4h 15m
$357

American Airlines

Pick Dates

Deal found 8/7/22

Aug 26 - Aug 31
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

4h 37m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

1 stop

4h 07m
$368

American Airlines

Pick Dates

Deal found 8/6/22

Nov 30 - Dec 5
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

4h 14m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

1 stop

5h 57m
$387

American Airlines

Pick Dates

Deal found 8/7/22

Cheap American Airlines flights from Williamsburg to Chicago

Aug 31 - Sep 7
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

4h 37m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

1 stop

4h 15m
$357

American Airlines

Pick Dates

Deal found 8/7/22

Aug 26 - Aug 31
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

4h 37m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

1 stop

4h 07m
$368

American Airlines

Pick Dates

Deal found 8/6/22

Nov 30 - Dec 5
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

4h 14m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

1 stop

5h 57m
$387

American Airlines

Pick Dates

Deal found 8/7/22

Cheap Linear Air Taxi flights from Williamsburg to Chicago

Oct 12 - Oct 18
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

2 stops

9h 00m
ORD

Chicago O'Hare Intl

PHF

Newport News Intl

2 stops

17h 00m
$15,490

Linear Air Taxi

Pick Dates

Deal found 8/7/22

Oct 12 - Oct 18
PHF

Newport News Intl

MDW

Chicago Midway

1 stop

6h 23m
MDW

Chicago Midway

PHF

Newport News Intl

1 stop

6h 41m
$33,191

Linear Air Taxi

Pick Dates

Deal found 8/7/22

One-way flights to Chicago from Williamsburg

The cheapest one-way flights from Williamsburg to Chicago
Aug 29
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

6h 41m
$179

American Airlines

Pick Dates

Deal found 8/6/22

Aug 19
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

4h 37m
$190

American Airlines

Pick Dates

Deal found 8/5/22

Aug 14
PHF

Newport News Intl

ORD

Chicago O'Hare Intl

1 stop

6h 25m
$230

American Airlines

Pick Dates

Deal found 8/6/22

Related info for your journey

Useful info, stats and facts about Williamsburg to Chicago flights.

Which airlines flying from Williamsburg to Chicago have flexible cancellations due to COVID-19?

American Airlines and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Williamsburg to Chicago for under $400 on Cheapflights?

Yes, there are multiple flights from Williamsburg to Chicago for under $400. The cheapest flight booked recently is on American Airlines for just $357, but on average you can expect to pay $461.

What are the most popular airlines that fly from Williamsburg to Chicago?

When booking a flight from Williamsburg to Chicago, you may want to consider flying on American Airlines, JetBlue or Delta as they are the most popular for this route.

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 SkyWest Airlines (100%), Royal Jordanian (90%) or Envoy Air (88%) 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 $327, our data shows the cheapest flight currently is $122. When looking at the most popular route, (Newport News Intl - Chicago O'Hare Intl), you can expect to pay $387 for that flight.

Other flights to Chicago

Alternative routes for Williamsburg to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Williamsburg to Chicago

The chart below displays the airlines Cheapflights users traveling from Williamsburg to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$17Average$24FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Spirit AirlinesCheapest$39Average$102FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
FrontierCheapest$87Average$218FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
JetBlueCheapest$91Average$190FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search JetBlue flights
American AirlinesCheapest$98Average$362FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
DeltaCheapest$100Average$348FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$141Average$303FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Williamsburg to Chicago

See what time of day planes typically take off from Williamsburg to Chicago
21%of flight departuresEarly morningMidnight to 6 am
30%of flight departuresMorning6 am to noon
46%of flight departuresAfternoonNoon to 6 pm
3%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM