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$65+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jun 11 — Jun 181
Thu 6/11
Thu 6/18
1 adult, Economy
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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 May 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/712:54 pm
RDU
-
ORD
1 stop20h 01m
Multiple Airlines
Tue 6/96:55 am
ORD
-
RDU
2 stops14h 48m
Multiple Airlines
Deal found 5/7$213
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Thu 7/212:54 pm
RDU
-
ORD
1 stop20h 09m
Frontier
Tue 7/71:50 pm
ORD
-
RDU
1 stop9h 35m
Frontier
Deal found 5/8$215
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Tue 5/266:21 pm
RDU
-
ORD
1 stop29h 52m
Frontier
Sat 5/306:55 am
ORD
-
RDU
1 stop16h 31m
Frontier
Deal found 5/10$216
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/710:15 pm
RDU
-
MDW
2 stops17h 33m
Multiple Airlines
Tue 6/912:27 pm
MDW
-
RDU
1 stop11h 02m
Multiple Airlines
Deal found 5/7$216
This Kiwi.com deal was found by Cheapflights users on 5/9. 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.
Fri 8/712:26 pm
RDU
-
ORD
1 stop9h 26m
Frontier
Wed 8/121:50 pm
ORD
-
RDU
1 stop9h 35m
Frontier
Deal found 5/9$217
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Wed 6/36:15 am
RDU
-
MDW
1 stop5h 54m
Frontier
Mon 6/812:04 pm
MDW
-
RDU
1 stop11h 20m
Frontier
Deal found 5/10$217
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Wed 5/279:46 am
RDU
-
ORD
2 stops10h 55m
Frontier
Tue 6/21:29 pm
ORD
-
RDU
1 stop10h 04m
Frontier
Deal found 5/11$218
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Tue 6/26:15 am
RDU
-
MDW
1 stop5h 57m
Frontier
Mon 6/812:04 pm
MDW
-
RDU
1 stop11h 20m
Frontier
Deal found 5/10$218
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 6/1112:54 pm
RDU
-
ORD
1 stop20h 09m
Frontier
Thu 6/181:29 pm
ORD
-
RDU
1 stop9h 41m
Frontier
Deal found 5/12$219
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Sun 8/26:15 am
RDU
-
MDW
1 stop5h 52m
Frontier
Thu 8/1312:11 pm
MDW
-
RDU
1 stop11h 14m
Frontier
Deal found 5/8$219
This Frontier deal was found by Cheapflights users on 5/12. 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.
Wed 5/2712:33 pm
RDU
-
ORD
1 stop8h 08m
Frontier
Thu 6/41:29 pm
ORD
-
RDU
1 stop9h 55m
Frontier
Deal found 5/12$220
This Frontier deal was found by Cheapflights users on 5/11. 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 5/2912:33 pm
RDU
-
MDW
1 stop10h 29m
Frontier
Tue 6/26:00 am
MDW
-
RDU
1 stop4h 59m
Frontier
Deal found 5/11$220

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 May 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$213
(Kiwi.com)

One-way from

$65
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$363

Good round-trip deal

$307 or less

Good one-way deal

$178 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. 6% potential increase in price ($25 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 May 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 May 12, 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

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 8/11

9:39 am-1:13 pm

1 stop4h 34m

Chicago O'Hare Intl

Sat 8/15

7:05 am-12:42 pm

1 stop4h 37m

$238

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 6/23

6:00 am-9:14 am

1 stop4h 14m

Chicago Midway

Mon 6/29

1:26 pm-6:59 pm

1 stop4h 33m

$238

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 7/15

10:20 pm-11:31 pm

Nonstop2h 11m

Chicago O'Hare Intl

Sat 7/18

8:40 am-11:52 am

Nonstop2h 12m

$247

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 6/22

6:55 pm-8:05 pm

Nonstop2h 10m

Chicago Midway

Wed 6/24

5:05 pm-7:55 pm

Nonstop1h 50m

$247
Quickest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 6/2

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago Midway

Wed 6/3

7:40 am-10:30 am

Nonstop1h 50m

$257

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sun 5/24

5:40 am-8:45 am

1 stop4h 05m

Chicago O'Hare Intl

Wed 5/27

8:10 am-3:10 pm

1 stop6h 00m

$257

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 6/20

5:31 pm-10:17 pm

1 stop5h 46m

Chicago Midway

Tue 6/23

11:05 am-4:47 pm

1 stop4h 42m

$258

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/1

12:23 pm-6:07 pm

1 stop6h 44m

Chicago Midway

Sat 8/8

6:42 pm-11:09 pm

1 stop3h 27m

$259

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sun 5/24

7:00 am-1:55 pm

2 stops7h 55m

Chicago O'Hare Intl

Wed 5/27

1:35 pm-9:35 pm

1 stop7h 00m

$262

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 7/3

1:30 pm-6:00 pm

1 stop5h 30m

Chicago O'Hare Intl

Wed 7/8

7:00 am-12:42 pm

1 stop4h 42m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 60 resultsSorted by cheapest first
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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

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

Booking 88 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 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 $65). Flying from Virginia to Chicago in November is currently the most expensive (average of $929). 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 May 12, 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 5% versus a flight in the morning.

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 May 9, 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 mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 May 12, 2026.

The most flights from USVA to CHI are scheduled on a Monday (30 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (28 on average).

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

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 10m. Your travel time can differ by up to 2h 24m. The distance from Virginia to Chicago is about 599 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 United Airlines and Delta, 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. Dulles Intl - Chicago O'Hare Intl, Washington, D.C. Reagan-National - 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 GoJet (83%), United Airlines (81%) or ANA (81%) 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 $1,158, our data shows the cheapest flight currently is $190. When looking at the most popular route, (Washington, D.C. Dulles Intl - 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 $65). Flying from Virginia to Chicago in November is currently the most expensive (average of $929). 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
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Virginia to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
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Denver to O'Hare Intl flights
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Dallas/Fort Worth to Midway flights
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Miami to O'Hare Intl flights
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LaGuardia to Midway flights
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Hobby to Midway flights
San Francisco to Midway flights
Austin to O'Hare Intl flights
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Atlanta to Midway flights
Philadelphia to Midway flights
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Portland to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
San Jose to O'Hare Intl flights
New Orleans to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Reagan-National to Midway flights
Orlando to Midway flights
Jacksonville to O'Hare Intl flights
Minneapolis to Midway flights

Top 7 airlines flying from Virginia to Chicago

Discover the top 7 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 May 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$354FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$92Average$303FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$244FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$126Average$352FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$375FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$203Average$335FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$378FlexibilityNo cancel feeOn-time69%

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