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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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Virginia to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Virginia (USVA) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$165
(Frontier)

One-way from

$55
(Frontier)

Popular in

June

Cheapest in

March

Average price

$391

Good round-trip deal

$359 or less

Good one-way deal

$205 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. 3% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 30, 2025.

This Frontier deal was found by Cheapflights users on 1/28. 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.
Thu 5/18:31 pmRDU - ORD
1 stop11h 35mFrontier
Sun 5/41:01 pmORD - RDU
Nonstop2h 05mFrontier
Deal found 1/28$165
This Booking.com deal was found by Cheapflights users on 1/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/278:00 amRDU - MDW
1 stop15h 46mFrontier
Sun 3/24:08 pmMDW - RDU
1 stop5h 38mFrontier
Deal found 1/29$169
This CheapOair deal was found by Cheapflights users on 1/30. 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.
Wed 3/56:25 amRDU - ORD
1 stop11h 06mMultiple Airlines
Sun 3/97:42 pmORD - RDU
1 stop23h 47mMultiple Airlines
Deal found 1/30$173
This Trip.com deal was found by Cheapflights users on 1/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/47:00 amDCA - ORD
1 stop7h 25mFrontier
Sun 3/96:45 amORD - DCA
1 stop28h 18mFrontier
Deal found 1/30$175
This Frontier deal was found by Cheapflights users on 1/28. 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 2/95:57 pmIAD - ORD
1 stop6h 36mFrontier
Thu 2/208:04 amORD - IAD
1 stop7h 59mFrontier
Deal found 1/28$176
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/201:00 pmDCA - ORD
Nonstop2h 21mUnited Airlines
Thu 2/209:05 pmORD - DCA
Nonstop1h 52mUnited Airlines
Deal found 1/30$177
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/268:30 amIAD - ORD
Nonstop2h 18mUnited Airlines
Wed 3/54:10 pmORD - IAD
Nonstop1h 51mUnited Airlines
Deal found 1/29$177
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2011:55 amDCA - MDW
Nonstop2h 10mSouthwest
Mon 2/246:25 amMDW - DCA
Nonstop1h 50mSouthwest
Deal found 1/30$177
This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/72:26 pmRDU - ORD
1 stop10h 06mSpirit Airlines
Sun 2/165:00 amORD - RDU
1 stop7h 12mSpirit Airlines
Deal found 1/29$181
This Frontier deal was found by Cheapflights users on 1/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/91:03 pmDCA - MDW
1 stop12h 16mFrontier
Thu 3/136:40 amMDW - DCA
1 stop9h 19mFrontier
Deal found 1/29$181
This JetBlue deal was found by Cheapflights users on 1/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/17:00 amDCA - ORD
1 stop6h 29mJetBlue
Wed 4/21:24 pmORD - DCA
1 stop6h 35mJetBlue
Deal found 1/30$183
This Gotogate deal was found by Cheapflights users on 1/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/85:41 pmIAD - MDW
1 stop5h 15mFrontier
Mon 3/172:51 pmMDW - IAD
1 stop21h 25mFrontier
Deal found 1/30$189

Find flights from Virginia to Chicago within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 2/20

2:22 pm-9:27 am

1 stop20h 05m

Chicago O'Hare Intl

Mon 2/24

4:58 pm-5:34 pm

1 stop23h 36m

$150

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Mon 2/24

5:20 pm-12:44 am

1 stop8h 24m

Chicago O'Hare Intl

Fri 2/28

11:46 am-10:04 am

1 stop21h 18m

$165

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 4/11

5:24 pm-12:42 am

1 stop8h 18m

Chicago O'Hare Intl

Sun 4/13

6:45 am-6:42 pm

1 stop10h 57m

$169

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 2/27

8:00 am-10:46 pm

1 stop15h 46m

Chicago Midway

Sun 3/2

4:08 pm-10:46 pm

1 stop5h 38m

$169

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 3/1

7:16 pm-7:09 am

1 stop12h 53m

Chicago O'Hare Intl

Tue 3/4

7:13 pm-7:27 pm

1 stop23h 14m

$171

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 3/4

7:00 am-1:25 pm

1 stop7h 25m

Chicago O'Hare Intl

Sun 3/9

6:45 am-12:03 pm

1 stop28h 18m

$175

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 2/10

10:39 am-3:43 pm

1 stop6h 04m

Chicago Midway

Wed 2/19

8:12 am-2:39 pm

1 stop5h 27m

$175

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 2/9

5:57 pm-11:33 pm

1 stop6h 36m

Chicago O'Hare Intl

Thu 2/20

8:04 am-5:03 pm

1 stop7h 59m

$176

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 2/20

6:25 am-7:45 am

Nonstop2h 20m

Chicago O'Hare Intl

Thu 2/20

9:05 pm-11:57 pm

Nonstop1h 52m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 2/20

11:55 am-1:05 pm

Nonstop2h 10m

Chicago Midway

Mon 2/24

9:15 am-12:00 pm

Nonstop1h 45m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

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.

Travel insights for flights from Virginia to Chicago

Get recent, data-driven insights about flights from Virginia to Chicago including ideal travel times, pricing trends, and more.

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 $325). 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 January 30, 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 January 30, 2025.

The most flights from USVA to CHI are scheduled on a Monday (17 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 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 January 30, 2025.
To help decide which airline to fly from Virginia to Chicago, see what other customers have to say about Southwest, Alaska Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,686 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,450 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Avelo Airlines
7.5
Good
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,153 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, with whom users have recently found tickets for as low as $55. However, be on the lookout for offers from Spirit 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 Raleigh-Durham - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Virginia to Chicago?

    Consider Avianca (87%), ANA (84%) or Royal Jordanian (80%) 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 $1,030, our data shows the cheapest flight currently is $167. When looking at the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), you can expect to pay $165 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 $325). 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
New Buffalo
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.
John F Kennedy Intl to O'Hare Intl flights
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Dulles Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
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Newark to St. Louis flights
Hobby to Midway flights

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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$228FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$148Average$341FlexibilityNo cancel feeOn-time71%
DeltaCheapest$175Average$395FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$189Average$387FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$268Average$394FlexibilityNo cancel feeOn-time63%
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