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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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$161
(American Airlines)

One-way from

$57
(FlightHub)

Popular in

June

Cheapest in

March

Average price

$376

Good round-trip deal

$354 or less

Good one-way deal

$169 or less
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
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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. 2% potential increase in price ($10 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 April 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 April 17, 2025.

This Frontier deal was found by Cheapflights users on 4/16. 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.
Fri 7/113:26 pmRDU - ORD
Nonstop2h 32mFrontier
Sun 7/1311:32 amORD - RDU
Nonstop2h 10mFrontier
Deal found 4/16$160
This American Airlines deal was found by Cheapflights users on 4/15. 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.
Sat 5/2411:55 amDCA - ORD
Nonstop2h 14mAmerican Airlines
Sun 5/257:50 amORD - DCA
Nonstop1h 54mAmerican Airlines
Deal found 4/15$161
This American Airlines deal was found by Cheapflights users on 4/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/317:20 amRDU - ORD
Nonstop2h 21mAmerican Airlines
Tue 6/37:29 pmORD - RDU
Nonstop2h 00mAmerican Airlines
Deal found 4/16$169
This Frontier deal was found by Cheapflights users on 4/17. 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.
Sat 5/241:00 pmDCA - ORD
1 stop11h 52mFrontier
Sat 5/316:00 amORD - DCA
1 stop9h 59mFrontier
Deal found 4/17$178
This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/25:26 pmIAD - ORD
1 stop7h 06mFrontier
Sat 5/310:22 amORD - IAD
1 stop5h 12mFrontier
Deal found 4/17$178
This Frontier deal was found by Cheapflights users on 4/17. 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.
Sat 5/244:49 pmIAD - MDW
1 stop6h 13mFrontier
Wed 5/286:40 amMDW - IAD
1 stop8h 34mFrontier
Deal found 4/17$178
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Thu 5/296:48 amIAD - ORD
Nonstop2h 14mUnited Airlines
Sat 5/3111:23 amORD - IAD
Nonstop2h 05mUnited Airlines
Deal found 4/17$179
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/286:30 pmDCA - MDW
Nonstop2h 05mSouthwest
Thu 5/293:15 pmMDW - DCA
Nonstop1h 50mSouthwest
Deal found 4/16$179
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/26:05 amDCA - ORD
1 stop7h 40mSouthwest
Fri 7/47:30 amORD - DCA
1 stop8h 45mSouthwest
Deal found 4/16$181
This CheapOair deal was found by Cheapflights users on 4/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/17:00 amDCA - MDW
1 stop13h 08mFrontier
Fri 5/28:03 pmMDW - DCA
1 stop24h 56mFrontier
Deal found 4/16$181
This United Airlines deal was found by Cheapflights users on 4/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:11 pmDCA - ORD
Nonstop2h 16mUnited Airlines
Sun 5/256:00 amORD - DCA
1 stop5h 25mUnited Airlines
Deal found 4/16$186
This Priceline deal was found by Cheapflights users on 4/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:29 amRDU - ORD
1 stop7h 58mMultiple Airlines
Sun 5/41:01 pmORD - RDU
Nonstop2h 04mMultiple Airlines
Deal found 4/17$196

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 April 17, 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

Fri 7/11

3:26 pm-4:58 pm

Nonstop2h 32m

Chicago O'Hare Intl

Sun 7/13

11:32 am-2:42 pm

Nonstop2h 10m

$160

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/24

11:55 am-1:09 pm

Nonstop2h 14m

Chicago O'Hare Intl

Sun 5/25

7:50 am-10:44 am

Nonstop1h 54m

$161

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 5/31

7:20 am-8:41 am

Nonstop2h 21m

Chicago O'Hare Intl

Tue 6/3

7:29 pm-10:29 pm

Nonstop2h 00m

$169

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/24

1:00 pm-11:52 pm

1 stop11h 52m

Chicago O'Hare Intl

Sat 5/31

6:00 am-4:59 pm

1 stop9h 59m

$178

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Fri 5/2

5:26 pm-11:32 pm

1 stop7h 06m

Chicago O'Hare Intl

Sat 5/3

10:22 am-4:34 pm

1 stop5h 12m

$178

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 5/24

4:49 pm-10:02 pm

1 stop6h 13m

Chicago Midway

Wed 5/28

6:40 am-4:14 pm

1 stop8h 34m

$178

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 5/29

6:48 am-8:02 am

Nonstop2h 14m

Chicago O'Hare Intl

Sat 5/31

11:23 am-2:28 pm

Nonstop2h 05m

$179

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 5/28

6:30 pm-7:35 pm

Nonstop2h 05m

Chicago Midway

Thu 5/29

3:15 pm-6:05 pm

Nonstop1h 50m

$179

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 7/2

6:05 am-12:45 pm

1 stop7h 40m

Chicago O'Hare Intl

Fri 7/4

7:30 am-5:15 pm

1 stop8h 45m

$181

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/1

7:00 am-7:08 pm

1 stop13h 08m

Chicago Midway

Fri 5/2

8:03 pm-9:59 pm

1 stop24h 56m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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 April 17, 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 April 17, 2025.

The most flights from USVA to CHI are scheduled on a Monday (23 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (17 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 17, 2025.
To help decide which airline to fly from Virginia to Chicago, see what other customers have to say about Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,887 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,916 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

  • What are the cheapest airlines to fly from Virginia to Chicago one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $57. However, be on the lookout for offers from American Airlines and United 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. 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 ANA (75%), Qatar Airways (74%) or Royal Jordanian (73%) 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 $885, our data shows the cheapest flight currently is $138. When looking at the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), you can expect to pay $161 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 Virginia?

Book flights to Virginia if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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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Boston to Midway flights
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Top 5 airlines flying from Virginia to Chicago

Discover the top 5 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$230FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$148Average$358FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$474FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$187Average$383FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$268Average$382FlexibilityNo cancel feeOn-time63%

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