HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$39+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Mrz 10 — Mrz 171
Di 3/10
Di 3/17
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 Februar 8, 2026.

This Mytrip deal was found by Cheapflights users on 2/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 3/248:41 pm
ORF
-
ORD
1 stop15h 36m
Spirit Airlines
Di 3/315:05 am
ORD
-
ORF
1 stop13h 41m
Spirit Airlines
Deal found 2/8$141
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Sa 5/166:05 am
ORF
-
ORD
1 stop10h 20m
Multiple Airlines
Mi 5/201:27 pm
ORD
-
ORF
1 stop29h 02m
Multiple Airlines
Deal found 2/8$152
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Fr 3/134:07 pm
RDU
-
MDW
1 stop7h 12m
Multiple Airlines
Di 3/177:30 am
MDW
-
RDU
1 stop8h 59m
Multiple Airlines
Deal found 2/6$158
This Frontier deal was found by Cheapflights users on 2/8. 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.
Do 3/124:22 pm
RDU
-
ORD
Nonstop2h 30m
Frontier
Mi 3/189:28 am
ORD
-
RDU
1 stop4h 49m
Frontier
Deal found 2/8$159
This United Airlines deal was found by Cheapflights users on 2/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 3/77:30 am
DCA
-
ORD
Nonstop2h 20m
United Airlines
Di 3/107:40 pm
ORD
-
DCA
Nonstop2h 12m
United Airlines
Deal found 2/8$160
This United Airlines deal was found by Cheapflights users on 2/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/188:20 am
IAD
-
ORD
Nonstop2h 18m
United Airlines
Mi 4/222:25 pm
ORD
-
IAD
Nonstop2h 03m
United Airlines
Deal found 2/8$160
This Frontier deal was found by Cheapflights users on 2/7. 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.
Sa 4/1810:51 am
IAD
-
MDW
1 stop9h 40m
Frontier
Sa 4/252:20 pm
MDW
-
IAD
1 stop9h 16m
Frontier
Deal found 2/7$160
This Expedia deal was found by Cheapflights users on 2/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/154:07 pm
RDU
-
ORD
1 stop7h 32m
Frontier
Mo 5/185:11 am
ORD
-
RDU
1 stop12h 41m
Frontier
Deal found 2/7$160
This Priceline deal was found by Cheapflights users on 2/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/154:07 pm
RDU
-
MDW
1 stop7h 12m
Frontier
So 5/172:20 pm
MDW
-
RDU
1 stop8h 55m
Frontier
Deal found 2/8$160
This Orbitz deal was found by Cheapflights users on 2/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/156:43 pm
ORF
-
ORD
1 stop21h 42m
Frontier
Mo 5/186:57 am
ORD
-
ORF
1 stop9h 52m
Frontier
Deal found 2/8$160
This Frontier deal was found by Cheapflights users on 2/8. 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.
Fr 5/18:09 am
IAD
-
ORD
1 stop7h 08m
Frontier
Mo 5/44:28 pm
ORD
-
IAD
1 stop7h 08m
Frontier
Deal found 2/8$161
This Frontier deal was found by Cheapflights users on 2/8. 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.
Fr 5/19:51 am
IAD
-
MDW
1 stop10h 40m
Frontier
Mo 5/42:20 pm
MDW
-
IAD
1 stop9h 16m
Frontier
Deal found 2/8$161

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 Februar 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$141
(Mytrip)

One-way from

$39
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$318

Good round-trip deal

$286 or less

Good one-way deal

$202 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. 2% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 Februar 8, 2026.
Use the filters below to find and compare flights from Virginia to Chicago that are best for you.

Fly from

Virginia

Fly to

Chicago

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sa 4/18

8:09 am-4:13 pm

1 stop9h 04m

Chicago Midway

Sa 4/25

2:20 pm-12:36 am

1 stop9h 16m

$160

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Do 4/23

9:51 am-7:31 pm

1 stop10h 40m

Chicago Midway

So 4/26

9:14 am-7:27 am

1 stop21h 13m

$160

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Do 4/30

6:00 am-10:44 am

1 stop5h 44m

Chicago O'Hare Intl

So 5/3

8:24 pm-9:56 am

1 stop12h 32m

$160

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Mi 3/4

6:15 am-12:04 pm

1 stop6h 49m

Chicago O'Hare Intl

Sa 3/7

6:04 am-2:47 pm

1 stop7h 43m

$161

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Di 3/24

6:15 am-11:25 am

1 stop6h 10m

Chicago O'Hare Intl

Mi 3/25

6:45 am-3:36 pm

1 stop7h 51m

$161

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fr 3/6

6:15 am-11:48 am

1 stop6h 33m

Chicago O'Hare Intl

Mo 3/9

6:04 am-2:47 pm

1 stop7h 43m

$174

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mi 3/4

3:30 pm-4:51 pm

Nonstop2h 21m

Chicago O'Hare Intl

Sa 3/7

7:00 am-9:54 am

Nonstop1h 54m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Di 4/14

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago Midway

Mi 4/15

6:05 pm-8:55 pm

Nonstop1h 50m

$177

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sa 2/28

10:30 pm-11:43 pm

Nonstop2h 13m

Chicago O'Hare Intl

Di 3/3

1:02 pm-4:05 pm

Nonstop2h 03m

$177

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fr 5/1

9:51 am-7:31 pm

1 stop10h 40m

Chicago Midway

So 5/3

2:20 pm-12:36 am

1 stop9h 16m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 60 results
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, May is the cheapest month in which you can book a flight from Virginia to Chicago (average of $108). Flying from Virginia to Chicago in March is currently the most expensive (average of $236). 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 Februar 8, 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 at noon, which can drop the price by up to 16% versus a flight in the evening.

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 February 7, 2026.

Travelers seeking maximum savings on their Virginia to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday afternoons 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?

    Frontier, JetBlue, and United Airlines can get you from Virginia to Chicago in just under 2h 21m. Your travel time can differ by up to 6h 43m. 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 $72. However, be on the lookout for offers from Southwest and American 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 Raleigh-Durham - Chicago O'Hare Intl as they are the most popular.

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

    Consider Avianca (87%), GoJet (84%) or Air New Zealand (83%) 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 $1,259, our data shows the cheapest flight currently is $159. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $197 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, May is the cheapest month in which you can book a flight from Virginia to Chicago (average of $108). Flying from Virginia to Chicago in March is currently the most expensive (average of $236). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Newark to Midway flights
Boston to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
John F Kennedy Intl to Midway flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Seattle to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Los Angeles to Midway flights
Ontario to O'Hare Intl flights
LaGuardia to Midway flights
Raleigh to O'Hare Intl flights
Dulles Intl to Midway flights
Santa Ana to O'Hare Intl flights
Orlando to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Atlanta to Midway flights
Austin to O'Hare Intl flights
Hobby to O'Hare Intl flights
Minneapolis to Midway flights
George Bush Intcntl to O'Hare Intl flights
Baltimore to Midway flights
LaGuardia to St. Louis flights
Newark to St. Louis flights
San Diego to O'Hare Intl flights
Love Field to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Philadelphia to Midway flights
Cleveland to O'Hare Intl flights
Raleigh to Midway flights
Hartford to O'Hare Intl flights
San Francisco to Midway flights
Salt Lake City to O'Hare Intl flights
Tampa to O'Hare Intl flights
Reagan-National to Midway flights
Denver to Midway flights
Sacramento to O'Hare Intl flights
Seattle to Midway 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 Februar 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$92Average$303FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$244FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$172Average$208FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$363FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$191Average$373FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$209Average$324FlexibilityNo cancel feeOn-time71%

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.