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$79+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$162
(KAYAK)

One-way from

$79
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$387

Good round-trip deal

$343 or less

Good one-way deal

$187 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 ($15 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 June 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 June 12, 2025.

This KAYAK deal was found by Cheapflights users on 6/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/43:10 pmRDU - ORD
Nonstop2h 30mFrontier
Fri 8/811:15 amORD - RDU
Nonstop2h 13mFrontier
Deal found 6/12$162
This Southwest deal was found by Cheapflights users on 6/11. 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 8/96:25 amRDU - MDW
Nonstop1h 55mSouthwest
Mon 8/1110:00 amMDW - RDU
2 stops7h 55mSouthwest
Deal found 6/11$163
This Southwest deal was found by Cheapflights users on 6/11. 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.
Mon 10/276:00 amDCA - MDW
Nonstop2h 00mSouthwest
Tue 10/287:40 amMDW - DCA
1 stop4h 10mSouthwest
Deal found 6/11$163
This United Airlines deal was found by Cheapflights users on 6/9. 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 7/301:28 pmRDU - ORD
Nonstop2h 24mUnited Airlines
Wed 8/610:37 amORD - RDU
Nonstop2h 07mUnited Airlines
Deal found 6/9$164
This United Airlines deal was found by Cheapflights users on 6/11. 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 8/146:25 amDCA - ORD
Nonstop2h 14mUnited Airlines
Tue 8/198:50 amORD - DCA
1 stop4h 32mUnited Airlines
Deal found 6/11$167
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 8/272:15 pmDCA - ORD
Nonstop2h 13mAmerican Airlines
Sun 8/316:06 amORD - DCA
Nonstop1h 54mAmerican Airlines
Deal found 6/10$168
This United Airlines deal was found by Cheapflights users on 6/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/285:10 pmIAD - ORD
Nonstop2h 15mUnited Airlines
Sun 8/3110:43 amORD - IAD
Nonstop2h 06mUnited Airlines
Deal found 6/12$168
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/307:24 amRDU - ORD
Nonstop2h 20mAmerican Airlines
Tue 9/28:45 pmORD - RDU
Nonstop2h 14mAmerican Airlines
Deal found 6/11$169
This Southwest deal was found by Cheapflights users on 6/11. 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 8/132:10 pmDCA - ORD
1 stop8h 20mSouthwest
Wed 8/203:10 pmORD - DCA
1 stop6h 50mSouthwest
Deal found 6/11$177
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 8/148:40 amRDU - ORD
1 stop6h 11mSpirit Airlines
Mon 8/188:00 amORD - RDU
1 stop10h 48mSpirit Airlines
Deal found 6/10$182
This CheapOair deal was found by Cheapflights users on 6/10. 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 9/1112:20 pmRDU - MDW
1 stop20h 19mFrontier
Sun 9/148:15 amMDW - RDU
1 stop4h 23mFrontier
Deal found 6/10$185
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/176:10 amIAD - MDW
1 stop5h 31mFrontier
Wed 6/1811:39 amMDW - IAD
1 stop11h 25mFrontier
Deal found 6/10$186

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 June 12, 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

Sun 8/24

3:32 pm-4:57 pm

Nonstop2h 25m

Chicago O'Hare Intl

Thu 8/28

11:34 am-2:47 pm

Nonstop2h 13m

$162

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 8/9

6:25 am-7:20 am

Nonstop1h 55m

Chicago Midway

Mon 8/11

10:00 am-6:55 pm

2 stops7h 55m

$163

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 7/30

1:28 pm-2:52 pm

Nonstop2h 24m

Chicago O'Hare Intl

Wed 8/6

10:37 am-1:44 pm

Nonstop2h 07m

$164

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 8/14

6:25 am-7:39 am

Nonstop2h 14m

Chicago O'Hare Intl

Tue 8/19

8:50 am-2:22 pm

1 stop4h 32m

$167

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/14

9:00 pm-10:00 pm

Nonstop2h 00m

Chicago Midway

Tue 8/19

9:55 am-2:25 pm

1 stop3h 30m

$167

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 8/27

2:15 pm-3:28 pm

Nonstop2h 13m

Chicago O'Hare Intl

Sun 8/31

6:06 am-9:00 am

Nonstop1h 54m

$168

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 8/28

5:10 pm-6:25 pm

Nonstop2h 15m

Chicago O'Hare Intl

Sun 8/31

10:43 am-1:49 pm

Nonstop2h 06m

$168

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 8/30

7:24 am-8:44 am

Nonstop2h 20m

Chicago O'Hare Intl

Tue 9/2

8:45 pm-11:59 pm

Nonstop2h 14m

$169

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 8/13

2:10 pm-9:30 pm

1 stop8h 20m

Chicago O'Hare Intl

Wed 8/20

3:10 pm-11:00 pm

1 stop6h 50m

$177

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 8/14

8:40 am-1:51 pm

1 stop6h 11m

Chicago O'Hare Intl

Mon 8/18

8:00 am-7:48 pm

1 stop10h 48m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 12, 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 June 12, 2025.

The most flights from USVA to CHI are scheduled on a Thursday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 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 June 12, 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
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

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 American Airlines, with whom users have recently found tickets for as low as $79. 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 Washington, D.C. Dulles Intl - Chicago Midway as they are the most popular.

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

    Consider Japan Airlines (93%), Avianca (90%) or ANA (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 $1,169, our data shows the cheapest flight currently is $139. When looking at the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), you can expect to pay $157 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
Lansing
Benton Harbor
Porter
Hammond
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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Dallas/Fort Worth to Midway flights
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LaGuardia to Midway flights
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Dulles Intl to Midway flights
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George Bush Intcntl to O'Hare Intl flights
Atlanta to Midway flights
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Los Angeles to Midway flights
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Boston to Midway flights
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Baltimore to Midway flights
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Seattle to Midway flights
Newark to St. Louis flights
Salt Lake City to O'Hare Intl flights
Dulles Intl to St. Louis 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$251FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$443FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$148Average$356FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$177Average$382FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$208FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$268Average$376FlexibilityNo cancel feeOn-time63%

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