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$56+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/311:05 pmRDU - ORD
1 stop10h 19mMultiple Airlines
Wed 1/76:05 pmORD - RDU
1 stop19h 45mMultiple Airlines
Deal found 12/17$158
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/311:05 pmRDU - ORD
1 stop10h 19mFrontier
Tue 1/62:26 pmORD - RDU
1 stop8h 46mFrontier
Deal found 12/17$163
This Frontier deal was found by Cheapflights users on 12/17. 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 12/316:00 amRDU - MDW
1 stop8h 21mFrontier
Mon 1/56:12 amMDW - RDU
1 stop5h 08mFrontier
Deal found 12/17$163
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/316:05 amIAD - ORD
1 stop17h 19mFrontier
Tue 1/62:26 pmORD - IAD
1 stop25h 24mFrontier
Deal found 12/17$183
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/247:40 pmRDU - ORD
1 stop5h 04mUnited Airlines
Thu 12/256:37 pmORD - RDU
Nonstop2h 11mUnited Airlines
Deal found 12/15$187
This Southwest deal was found by Cheapflights users on 12/17. 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 12/241:50 pmRDU - MDW
1 stop7h 25mSouthwest
Thu 1/110:00 amMDW - RDU
Nonstop2h 00mSouthwest
Deal found 12/17$187
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/318:31 amRDU - ORD
1 stop12h 35mFrontier
Mon 1/56:00 amORD - RDU
1 stop5h 20mFrontier
Deal found 12/17$189
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/247:40 pmRDU - ORD
1 stop5h 04mUnited Airlines
Thu 1/18:51 amORD - RDU
1 stop4h 19mUnited Airlines
Deal found 12/17$197
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/247:00 pmRDU - ORD
Nonstop2h 41mAmerican Airlines
Thu 12/257:00 amORD - RDU
Nonstop2h 08mAmerican Airlines
Deal found 12/15$202
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/248:31 amRDU - ORD
1 stop12h 35mFrontier
Wed 12/316:05 amORD - RDU
1 stop4h 55mFrontier
Deal found 12/17$212
This Frontier deal was found by Cheapflights users on 12/16. 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.
Mon 12/299:58 pmIAD - ORD
1 stop12h 04mFrontier
Mon 1/59:47 amORD - IAD
1 stop10h 16mFrontier
Deal found 12/16$213
This Expedia deal was found by Cheapflights users on 12/15. 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.
Tue 12/309:58 pmIAD - MDW
1 stop25h 00mFrontier
Thu 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/15$213

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$111
(Kiwi.com)

One-way from

$56
(Priceline)

Popular in

December

Cheapest in

September

Average price

$390

Good round-trip deal

$233 or less

Good one-way deal

$184 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 ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 18, 2025.
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

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Tue 1/27

7:10 am-1:58 pm

1 stop7h 48m

Chicago O'Hare Intl

Mon 2/2

3:22 pm-12:33 pm

1 stop20h 11m

$127

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 1/24

10:00 am-5:43 pm

1 stop8h 43m

Chicago O'Hare Intl

Mon 2/2

7:27 am-1:50 pm

1 stop5h 23m

$161

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 5/14

1:25 pm-7:26 pm

1 stop7h 01m

Chicago O'Hare Intl

Sun 5/17

10:35 am-7:34 pm

1 stop7h 59m

$161

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 2/28

6:15 am-11:58 am

1 stop6h 43m

Chicago O'Hare Intl

Thu 3/5

6:04 am-2:46 pm

1 stop7h 42m

$161

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/29

5:37 pm-10:19 pm

1 stop5h 42m

Chicago Midway

Thu 2/5

6:20 am-4:28 pm

1 stop9h 08m

$163

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 12/31

6:00 am-1:21 pm

1 stop8h 21m

Chicago Midway

Wed 1/7

5:10 pm-12:12 am

1 stop6h 02m

$163

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 1/12

6:16 pm-10:17 pm

1 stop5h 01m

Chicago Midway

Thu 1/22

5:01 pm-12:11 am

1 stop6h 10m

$163

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 1/18

7:19 pm-12:02 am

1 stop5h 43m

Chicago Midway

Sat 1/24

9:38 am-11:56 pm

1 stop13h 18m

$171

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 1/29

6:10 am-11:45 am

1 stop6h 35m

Chicago Midway

Sat 2/14

8:00 am-8:30 pm

1 stop11h 30m

$183

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 12/24

1:50 pm-8:15 pm

1 stop7h 25m

Chicago Midway

Thu 1/1

10:00 am-1:00 pm

Nonstop2h 00m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 60 results
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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

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 $214). 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 December 18, 2025.

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 17% 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 December 16, 2024.

Travelers seeking maximum savings on their Virginia to Chicago flight should consider departing on Friday mornings 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.

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?

    Frontier, JetBlue, and Southwest can get you from Virginia to Chicago in just under 7h 25m. Your travel time can differ by up to 1h 18m. The distance from Virginia to Chicago is about 631 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 American 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. 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 ANA (80%), Avianca (75%) or GoJet (74%) 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 $1,129, our data shows the cheapest flight currently is $154. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $168 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 $214). 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

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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.
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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$249FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$244FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$176Average$208FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$181Average$364FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$209Average$326FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$375FlexibilityNo cancel feeOn-time69%

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