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$57+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$129
(CheapOair)

One-way from

$57
(Cheapflightsfares)

Popular in

January

Cheapest in

October

Average price

$361

Good round-trip deal

$286 or less

Good one-way deal

$139 or less
From Virginia to Chicago (CHI)
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One-way flight from Virginia to Chicago (CHI)
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Highest demand for flights based on searches. 4% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Virginia to Chicago (CHI).
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Price to beat on a one-way flight from Virginia to Chicago (CHI).
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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 September 15, 2025.

This CheapOair deal was found by Cheapflights users on 9/13. 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 10/23:35 pmRDU - ORD
Nonstop2h 16mFrontier
Fri 10/38:49 pmORD - RDU
1 stop20h 24mFrontier
Deal found 9/13$129
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:06 pmRDU - ORD
Nonstop2h 22mFrontier
Sun 11/91:50 pmORD - RDU
Nonstop2h 06mFrontier
Deal found 9/15$130
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/283:35 pmRDU - ORD
Nonstop2h 16mMultiple Airlines
Tue 9/3011:13 amORD - RDU
1 stop6h 51mMultiple Airlines
Deal found 9/13$131
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/16:45 amRDU - MDW
1 stop10h 13mFrontier
Mon 10/65:33 pmMDW - RDU
1 stop21h 04mFrontier
Deal found 9/13$131
This Trip.com deal was found by Cheapflights users on 9/13. 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.
Thu 9/253:35 pmRDU - ORD
Nonstop2h 16mFrontier
Sat 9/2712:22 pmORD - RDU
1 stop9h 25mFrontier
Deal found 9/13$132
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:30 pmRDU - MDW
Nonstop2h 00mSouthwest
Tue 10/2810:10 amMDW - RDU
2 stops5h 50mSouthwest
Deal found 9/12$132
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/242:27 pmRDU - ORD
Nonstop2h 22mFrontier
Mon 10/276:00 amORD - RDU
1 stop6h 32mFrontier
Deal found 9/14$133
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/14:55 pmRDU - MDW
Nonstop1h 55mSouthwest
Mon 11/31:40 pmMDW - RDU
Nonstop1h 45mSouthwest
Deal found 9/12$133
This Frontier deal was found by Cheapflights users on 9/14. 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 9/253:35 pmRDU - ORD
Nonstop2h 16mFrontier
Sun 9/288:49 pmORD - RDU
1 stop12h 04mFrontier
Deal found 9/14$135
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Sat 11/15:07 pmRDU - MDW
1 stop16h 23mFrontier
Mon 11/39:15 amMDW - RDU
1 stop5h 47mFrontier
Deal found 9/12$135
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/26:22 amRDU - ORD
1 stop5h 09mMultiple Airlines
Tue 10/711:13 amORD - RDU
1 stop6h 38mMultiple Airlines
Deal found 9/13$136
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:10 amRDU - ORD
1 stop5h 31mFrontier
Fri 11/141:50 pmORD - RDU
Nonstop2h 06mFrontier
Deal found 9/15$137

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 September 15, 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

Sat 10/25

5:27 pm-6:50 pm

Nonstop2h 23m

Chicago O'Hare Intl

Tue 10/28

7:10 am-10:14 am

Nonstop2h 04m

$139

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 10/4

7:25 am-8:39 am

Nonstop2h 14m

Chicago O'Hare Intl

Sat 10/4

1:42 pm-8:36 pm

1 stop5h 54m

$143

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 10/11

4:22 pm-10:47 pm

1 stop7h 25m

Chicago Midway

Wed 10/15

8:05 am-7:46 pm

1 stop10h 41m

$144

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 9/24

6:45 am-3:58 pm

1 stop10h 13m

Chicago Midway

Fri 10/3

6:21 am-5:11 pm

1 stop9h 50m

$145

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 11/1

1:30 pm-2:55 pm

Nonstop2h 25m

Chicago O'Hare Intl

Mon 11/3

2:20 pm-5:23 pm

Nonstop2h 03m

$158

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 10/22

6:15 am-7:38 am

Nonstop2h 23m

Chicago O'Hare Intl

Sun 10/26

7:10 am-10:14 am

Nonstop2h 04m

$158

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 11/15

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Mon 11/24

7:30 pm-10:20 pm

Nonstop1h 50m

$169

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sun 9/21

7:09 pm-7:23 am

1 stop13h 14m

Chicago Midway

Thu 9/25

6:20 am-12:55 pm

1 stop5h 35m

$169

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/11

4:55 pm-5:50 pm

Nonstop1h 55m

Chicago Midway

Wed 10/15

6:05 pm-8:55 pm

Nonstop1h 50m

$174

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 11/14

5:45 am-6:50 am

Nonstop2h 05m

Chicago Midway

Sun 11/16

9:45 am-12:40 pm

Nonstop1h 55m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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, August is the cheapest month in which you can book a flight from Virginia to Chicago (average of $245). Flying from Virginia to Chicago in March is currently the most expensive (average of $321). 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 September 15, 2025.

When flying from Virginia to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 15, 2025.

The most flights from USVA to CHI are scheduled on a Monday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

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?

    United Airlines, Frontier, and Southwest can get you from Virginia to Chicago in just under 2h 05m. Your travel time can differ by up to 5h 20m. 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 United Airlines, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from Frontier 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 Avianca (87%), United Airlines (85%) or Republic Airways (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 $916, our data shows the cheapest flight currently is $135. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $145 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 $245). Flying from Virginia to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$270FlexibilityNo cancel feeOn-time65%
DeltaCheapest$98Average$311FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$168Average$204FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$208Average$347FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$385FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$383FlexibilityNo cancel feeOn-time63%

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