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$55+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:00 amRDU - ORD
1 stop17h 24mFrontier
Sat 1/106:11 pmORD - RDU
1 stop16h 47mFrontier
Deal found 10/28$128
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/236:00 amRDU - MDW
1 stop17h 12mFrontier
Tue 12/306:14 amMDW - RDU
1 stop16h 59mFrontier
Deal found 10/27$128
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/14:05 pmRDU - ORD
Nonstop2h 25mFrontier
Sat 12/61:24 pmORD - RDU
1 stop9h 48mFrontier
Deal found 10/29$129
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:10 amRDU - MDW
1 stop7h 31mFrontier
Fri 11/149:15 amMDW - RDU
1 stop5h 14mFrontier
Deal found 10/30$129
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:30 pmRDU - ORD
1 stop17h 43mFrontier
Mon 11/2412:17 pmORD - RDU
Nonstop2h 03mFrontier
Deal found 10/28$130
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:14 pmRDU - MDW
1 stop26h 44mFrontier
Mon 12/86:15 amMDW - RDU
1 stop4h 45mFrontier
Deal found 10/29$130
This Frontier deal was found by Cheapflights users on 10/28. 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.
Mon 11/1010:06 pmRDU - ORD
Nonstop2h 22mFrontier
Thu 11/131:50 pmORD - RDU
Nonstop2h 06mFrontier
Deal found 10/28$131
This Expedia deal was found by Cheapflights users on 10/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1410:06 pmRDU - ORD
Nonstop2h 22mFrontier
Sun 11/161:50 pmORD - RDU
Nonstop2h 06mFrontier
Deal found 10/29$132
This Frontier deal was found by Cheapflights users on 10/28. 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.
Sun 11/910:06 pmRDU - ORD
Nonstop2h 22mFrontier
Mon 11/171:50 pmORD - RDU
Nonstop2h 06mFrontier
Deal found 10/28$135
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:58 pmRDU - ORD
Nonstop2h 25mFrontier
Sun 11/2312:17 pmORD - RDU
Nonstop2h 03mFrontier
Deal found 10/30$136
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:12 pmRDU - MDW
1 stop15h 00mFrontier
Mon 11/179:15 amMDW - RDU
1 stop5h 47mFrontier
Deal found 10/29$136
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/127:14 pmRDU - ORD
Nonstop2h 28mFrontier
Mon 12/156:30 pmORD - RDU
2 stops28h 42mFrontier
Deal found 10/27$137

Cheap flight deals from Virginia to Chicago

Keep the following information in mind while searching for Virginia to Chicago flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$128
(Kiwi.com)

One-way from

$55
(Priceline)

Popular in

December

Cheapest in

September

Average price

$313

Good round-trip deal

$300 or less

Good one-way deal

$137 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 ($23 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 October 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 October 30, 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

Thu 11/13

7:05 pm-12:11 am

1 stop6h 06m

Chicago O'Hare Intl

Fri 11/14

7:34 pm-1:19 pm

1 stop16h 45m

$131

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Sat 12/13

9:50 am-12:45 pm

Nonstop1h 55m

$139

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 1/17

6:15 am-1:10 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 1/31

2:05 pm-10:47 pm

1 stop7h 42m

$153

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Mon 11/24

6:30 am-7:56 am

Nonstop2h 26m

Chicago O'Hare Intl

Tue 12/2

7:10 am-10:14 am

Nonstop2h 04m

$154

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 1/10

6:15 am-1:10 pm

1 stop7h 55m

Chicago O'Hare Intl

Thu 1/15

2:05 pm-10:47 pm

1 stop7h 42m

$154

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 11/12

8:40 am-12:41 pm

1 stop5h 01m

Chicago Midway

Fri 11/14

1:37 pm-12:11 am

1 stop9h 34m

$167

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

1:09 pm-6:06 pm

1 stop5h 57m

Chicago Midway

Sat 12/13

1:14 pm-5:40 pm

1 stop3h 26m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 1/15

10:00 am-11:26 am

Nonstop2h 26m

Chicago O'Hare Intl

Thu 1/15

6:35 pm-9:46 pm

Nonstop2h 11m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/4

1:40 pm-2:45 pm

Nonstop2h 05m

Chicago Midway

Sun 12/7

7:30 pm-10:20 pm

Nonstop1h 50m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

5:45 am-1:59 pm

1 stop9h 14m

Chicago Midway

Sat 12/13

6:00 am-4:44 pm

2 stops9h 44m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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 October 30, 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 in the afternoon, which can drop the price by up to 15% 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. Monday at noon 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?

    Southwest, JetBlue, and United Airlines can get you from Virginia to Chicago in just under 2h 05m. Your travel time can differ by up to 5h 50m. 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 $68. However, be on the lookout for offers from United Airlines and Southwest, 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 Emirates (100%), GoJet (94%) or ANA (93%) 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 $963, our data shows the cheapest flight currently is $128. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $110 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
Merrillville
Lansing
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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$283FlexibilityNo cancel feeOn-time65%
FrontierCheapest$168Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$209Average$347FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$210Average$380FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$228FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$229Average$381FlexibilityNo cancel feeOn-time63%

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