HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$99+ Cheap flights from Virginia to Chicago (CHI)

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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jul 31 — Aug 71
Fri 7/31
Fri 8/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Virginia 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 Virginia to Chicago

Cheapest flights from Virginia to Chicago
Explore the most affordable flight options available from Virginia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2026.

This American Airlines deal was found by Cheapflights users on 6/30. 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 8/18:06 pm
DCA
-
ORD
Nonstop2h 36m
American Airlines
Mon 8/35:07 am
ORD
-
DCA
1 stop4h 43m
American Airlines
Deal found 6/30$247
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:49 am
IAD
-
ORD
2 stops17h 21m
Frontier
Wed 7/298:05 am
ORD
-
IAD
1 stop10h 33m
Frontier
Deal found 6/29$247
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:30 pm
DCA
-
MDW
Nonstop2h 05m
Southwest
Thu 7/305:00 am
MDW
-
DCA
1 stop7h 15m
Southwest
Deal found 6/29$247
This JetBlue deal was found by Cheapflights users on 6/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/32:25 pm
DCA
-
ORD
1 stop6h 30m
JetBlue
Tue 9/810:56 am
ORD
-
DCA
1 stop6h 00m
JetBlue
Deal found 6/30$248
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/204:52 pm
IAD
-
ORD
1 stop7h 16m
Frontier
Sat 8/228:05 am
ORD
-
IAD
1 stop10h 39m
Frontier
Deal found 6/26$248
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:47 pm
IAD
-
MDW
1 stop5h 49m
Delta
Sat 8/296:11 am
MDW
-
IAD
1 stop6h 32m
Delta
Deal found 6/29$248
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am
DCA
-
MDW
1 stop4h 52m
Delta
Thu 10/156:45 pm
MDW
-
DCA
1 stop3h 24m
Delta
Deal found 6/29$248
This JetBlue deal was found by Cheapflights users on 6/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:25 pm
DCA
-
ORD
1 stop6h 02m
JetBlue
Mon 8/2411:01 am
ORD
-
DCA
1 stop7h 04m
JetBlue
Deal found 6/26$249
This Frontier deal was found by Cheapflights users on 6/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:33 pm
IAD
-
ORD
1 stop12h 20m
Frontier
Tue 7/287:05 am
ORD
-
IAD
1 stop8h 35m
Frontier
Deal found 6/30$249
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2412:26 pm
IAD
-
MDW
1 stop4h 50m
Delta
Sat 9/264:30 pm
MDW
-
IAD
1 stop7h 10m
Delta
Deal found 6/28$249
This Southwest deal was found by Cheapflights users on 6/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:00 pm
DCA
-
MDW
2 stops5h 50m
Southwest
Mon 8/318:55 am
MDW
-
DCA
Nonstop1h 55m
Southwest
Deal found 6/28$249
This Frontier deal was found by Cheapflights users on 6/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:59 pm
DCA
-
ORD
1 stop8h 36m
Frontier
Sun 9/2010:40 pm
ORD
-
DCA
1 stop13h 09m
Frontier
Deal found 6/28$250

Find flight deals from Virginia to Chicago

Keep the following information in mind while searching for Virginia to Chicago flight deals. Data was last updated July 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$246
(JetBlue)

One-way from

$99
(Delta)

Popular in

May

Cheapest in

October

Average price

$376

Good round-trip deal

$308 or less

Good one-way deal

$209 or less
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
Search Deals
From Virginia to Chicago (CHI)
Search Deals
One-way flight from Virginia to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Virginia to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Virginia to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia 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 July 1, 2026.
Use the filters below to find and compare flights from Virginia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/19

6:09 pm-10:45 pm

1 stop5h 36m

Chicago Midway

Thu 9/24

10:48 am-4:17 pm

1 stop4h 29m

$248

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 9/1

8:10 pm-9:30 pm

Nonstop2h 20m

Chicago O'Hare Intl

Wed 9/2

2:00 pm-5:09 pm

Nonstop2h 09m

$257

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 8/1

7:10 pm-8:32 pm

Nonstop2h 22m

Chicago O'Hare Intl

Sat 8/8

10:05 am-1:09 pm

Nonstop2h 04m

$257

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 8/27

5:47 pm-10:36 pm

1 stop5h 49m

Chicago Midway

Sat 8/29

6:42 pm-11:26 pm

1 stop3h 44m

$257

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 7/28

7:15 am-8:28 am

Nonstop2h 13m

Chicago O'Hare Intl

Tue 7/28

6:00 pm-9:10 pm

Nonstop2h 10m

$257

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 7/22

6:00 am-9:13 am

1 stop4h 13m

Chicago Midway

Mon 7/27

6:00 am-2:01 pm

1 stop7h 01m

$257

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 8/4

1:15 pm-2:29 pm

Nonstop2h 14m

Chicago O'Hare Intl

Sat 8/8

8:43 am-11:55 am

Nonstop2h 12m

$257

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 8/3

5:47 pm-10:36 pm

1 stop5h 49m

Chicago Midway

Tue 8/4

6:05 am-11:33 am

1 stop4h 28m

$257

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 9/9

6:15 am-7:29 am

Nonstop2h 14m

Chicago O'Hare Intl

Sat 9/12

8:45 am-11:52 am

Nonstop2h 07m

$257

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 9/8

6:00 am-11:50 am

2 stops6h 50m

Chicago Midway

Tue 9/8

4:40 pm-9:30 pm

1 stop3h 50m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/27

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from Virginia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Virginia 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.

Cheapflights Insights

Everything you need to know about your flight from Virginia to Chicago

What is the cheapest month to book a flight from Virginia to Chicago?

Currently, August is the cheapest month in which you can book a flight from Virginia to Chicago (average of $70). Flying from Virginia to Chicago in November is currently the most expensive (average of $960). 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 VA to CHI?

Find hourly flight availability from Virginia 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 July 1, 2026.

When flying from Virginia to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 6% versus a flight at noon.

Weekly flight availability from Virginia to Chicago

Explore weekly flight availability from Virginia 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 July 1, 2026.

The most flights from USVA to CHI are scheduled on a Wednesday (27 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 on average).

How much does it cost to fly round-trip from Virginia to Chicago?

How far ahead should I book a flight from Virginia to Chicago?

Booking 90 days in advance of your planned departure date is, on average, the best time to get cheap flights from Virginia to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from Virginia to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Virginia to Chicago. Price data was last updated on June 27, 2026.

Travelers seeking maximum savings on their Virginia to Chicago flight should consider departing on Sunday afternoons 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.

Related info for your journey

Find useful and relevant information for your journey from Virginia to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Virginia to Chicago?

    Delta, United Airlines, and Southwest can get you from Virginia to Chicago in just under 2h 20m. Your travel time can differ by up to 4h 30m. The distance from Virginia to Chicago is about 610 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Virginia to Chicago one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Virginia to Chicago for a low price.

  • What are the most popular routes from Virginia to Chicago?

    When deciding which route to take from Virginia to Chicago consider Washington, D.C. Reagan-National - Chicago O'Hare Intl, Washington, D.C. Dulles Intl - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago Midway as they are the most popular.

  • What are the most reliable airlines from Virginia to Chicago?

    Consider Royal Jordanian (90%), Japan Airlines (89%) or Republic Airways (88%) when booking your flight. These represent the most reliable airlines when flying from Virginia to Chicago.

  • What are the cheapest flights from Virginia to Chicago?

    While on average a flight from Virginia to Chicago is generally $1,178, our data shows the cheapest flight currently is $174. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $177 for that flight.

  • Can I find deals for flights from Virginia to Chicago that include hotel bookings?

    Yes. In addition to deals on Virginia to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Virginia to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Virginia to Chicago.

  • Can I find deals for business class flights from Virginia to Chicago?

    Yes. Cheapflights offers flight deals from Virginia 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 Virginia to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Virginia to Chicago (average of $70). Flying from Virginia to Chicago in November is currently the most expensive (average of $960). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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 for Virginia to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Seattle to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Newark to Midway flights
Baltimore to O'Hare Intl flights
Hobby to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Denver to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Boston to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Ontario to O'Hare Intl flights
Orlando to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Tampa to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to Midway flights
Charlotte to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
Miami to O'Hare Intl flights
Dulles Intl to Midway flights
Austin to O'Hare Intl flights
San Francisco to Midway flights
John F Kennedy Intl to Midway flights
Baltimore to Midway flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Fort Lauderdale to O'Hare Intl flights
Minneapolis to Midway flights
Portland to O'Hare Intl flights
Newark to St. Louis flights
Minneapolis to O'Hare Intl flights
Reagan-National to Midway flights
Hobby to Midway flights
Seattle to Midway flights
Salt Lake City to O'Hare Intl flights
LaGuardia to St. Louis flights
San Jose to O'Hare Intl flights
Philadelphia to Midway flights
New Orleans to O'Hare Intl flights
Kansas City to O'Hare Intl flights
Hartford to O'Hare Intl flights

Top 6 airlines flying from Virginia to Chicago

Discover the top 6 airlines that operate flights from Virginia 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 July 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$369FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$126Average$314FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$388FlexibilityNo cancel feeOn-time63%
DeltaCheapest$200Average$244FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$203Average$363FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$390FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.