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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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
May 5 — May 121
Mon 5/5
Mon 5/12
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 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$176
(Frontier)

One-way from

$57
(Cheapflightsfares)

Popular in

December

Cheapest in

March

Average price

$387

Good round-trip deal

$349 or less

Good one-way deal

$148 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)
Search Deals
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).
Search Deals
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 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Sat 5/313:06 pmRDU - ORD
1 stop5h 42mFrontier
Mon 6/211:32 amORD - RDU
Nonstop2h 07mFrontier
Deal found 4/29$176
This CheapOair deal was found by Cheapflights users on 4/29. 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.
Thu 8/73:26 pmRDU - ORD
Nonstop2h 25mMultiple Airlines
Sun 8/108:00 amORD - RDU
1 stop10h 48mMultiple Airlines
Deal found 4/29$177
This CheapOair deal was found by Cheapflights users on 4/29. 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.
Thu 5/157:31 amIAD - ORD
1 stop22h 39mFrontier
Sat 5/179:19 amORD - IAD
1 stop22h 25mFrontier
Deal found 4/29$181
This Frontier deal was found by Cheapflights users on 4/29. 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.
Thu 5/153:32 pmIAD - MDW
1 stop9h 07mFrontier
Sat 5/1710:48 amMDW - IAD
1 stop4h 46mFrontier
Deal found 4/29$181
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Thu 6/58:50 amRDU - ORD
1 stop6h 16mSpirit Airlines
Sun 6/87:35 pmORD - RDU
1 stop12h 37mSpirit Airlines
Deal found 4/29$181
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:50 pmDCA - MDW
1 stop4h 00mSouthwest
Sun 5/259:20 amMDW - DCA
1 stop4h 40mSouthwest
Deal found 4/28$181
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:09 pmRDU - ORD
Nonstop2h 33mAmerican Airlines
Wed 5/287:00 amORD - RDU
1 stop3h 55mAmerican Airlines
Deal found 4/29$185
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/46:15 amRDU - MDW
Nonstop2h 00mSouthwest
Mon 7/78:10 pmMDW - RDU
Nonstop1h 50mSouthwest
Deal found 4/28$189
This CheapOair deal was found by Cheapflights users on 4/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/51:00 pmDCA - MDW
1 stop7h 08mFrontier
Thu 5/158:03 pmMDW - DCA
1 stop24h 56mFrontier
Deal found 4/27$191
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Sat 5/247:11 pmDCA - ORD
Nonstop2h 16mUnited Airlines
Mon 5/266:00 amORD - DCA
Nonstop1h 57mUnited Airlines
Deal found 4/29$195
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Fri 5/2310:18 pmIAD - ORD
Nonstop2h 12mUnited Airlines
Sun 5/259:31 pmORD - IAD
Nonstop1h 59mUnited Airlines
Deal found 4/29$195
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2810:09 pmDCA - ORD
Nonstop2h 15mAmerican Airlines
Wed 7/27:17 pmORD - DCA
Nonstop1h 58mAmerican Airlines
Deal found 4/29$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 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

Sat 5/31

3:06 pm-7:48 pm

1 stop5h 42m

Chicago O'Hare Intl

Mon 6/2

11:32 am-2:39 pm

Nonstop2h 07m

$176

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 8/7

3:26 pm-4:51 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 8/10

8:00 am-7:48 pm

1 stop10h 48m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 6/5

8:50 am-2:06 pm

1 stop6h 16m

Chicago O'Hare Intl

Sun 6/8

7:35 pm-9:12 am

1 stop12h 37m

$181

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/24

6:50 pm-9:50 pm

1 stop4h 00m

Chicago Midway

Sun 5/25

9:20 am-3:00 pm

1 stop4h 40m

$181

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 5/15

7:31 am-5:10 am

1 stop22h 39m

Chicago O'Hare Intl

Sat 5/17

9:19 am-8:44 am

1 stop22h 25m

$181

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 5/15

3:32 pm-11:39 pm

1 stop9h 07m

Chicago Midway

Sat 5/17

10:48 am-4:34 pm

1 stop4h 46m

$181

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 5/24

4:09 pm-5:42 pm

Nonstop2h 33m

Chicago O'Hare Intl

Wed 5/28

7:00 am-11:55 am

1 stop3h 55m

$185

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 7/4

6:15 am-7:15 am

Nonstop2h 00m

Chicago Midway

Mon 7/7

8:10 pm-11:00 pm

Nonstop1h 50m

$189

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 5/11

7:00 am-7:08 pm

1 stop13h 08m

Chicago Midway

Thu 5/15

8:03 pm-4:59 pm

1 stop19h 56m

$191

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/24

7:11 pm-8:27 pm

Nonstop2h 16m

Chicago O'Hare Intl

Mon 5/26

6:00 am-8:57 am

Nonstop1h 57m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 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 April 30, 2025.

The most flights from USVA to CHI are scheduled on a Monday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 30, 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
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Avelo Airlines and Frontier, 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 (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 $755, our data shows the cheapest flight currently is $138. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $179 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.
LaGuardia to O'Hare Intl flights
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Reagan-National to Midway flights
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Boston to Midway flights
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Seattle to Midway flights
Minneapolis to O'Hare Intl flights
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John F Kennedy Intl to St. Louis flights
Tampa to Midway flights

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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$147Average$233FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$148Average$359FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$474FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$176Average$204FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$184Average$384FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$268Average$380FlexibilityNo cancel feeOn-time63%

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