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$48+ 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This Frontier deal was found by Cheapflights users on 11/20. 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 12/62:13 pmRDU - ORD
1 stop10h 34mFrontier
Sun 12/87:25 amORD - RDU
1 stop7h 52mFrontier
Deal found 11/20$128
This Frontier deal was found by Cheapflights users on 11/19. 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 12/62:13 pmRDU - MDW
1 stop11h 07mFrontier
Sun 12/87:15 amMDW - RDU
1 stop8h 02mFrontier
Deal found 11/19$128
This FlightHub deal was found by Cheapflights users on 11/20. 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.
Wed 12/115:30 amRDU - ORD
1 stop11h 36mMultiple Airlines
Fri 12/1310:59 amORD - RDU
1 stop23h 51mMultiple Airlines
Deal found 11/20$146
This Frontier deal was found by Cheapflights users on 11/20. 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 12/127:00 amDCA - ORD
1 stop8h 00mFrontier
Mon 12/167:25 amORD - DCA
1 stop13h 31mFrontier
Deal found 11/20$148
This CheapOair deal was found by Cheapflights users on 11/20. 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.
Sun 12/155:57 pmIAD - ORD
1 stop16h 57mFrontier
Wed 12/186:55 amORD - IAD
1 stop8h 33mFrontier
Deal found 11/20$148
This Frontier deal was found by Cheapflights users on 11/20. 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.
Wed 12/183:25 pmIAD - MDW
1 stop6h 52mFrontier
Wed 12/258:25 amMDW - IAD
1 stop5h 00mFrontier
Deal found 11/20$148
This Trip.com deal was found by Cheapflights users on 11/20. 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 12/127:00 amDCA - MDW
1 stop18h 13mFrontier
Sun 12/157:15 amMDW - DCA
1 stop8h 44mFrontier
Deal found 11/20$149
This Priceline deal was found by Cheapflights users on 11/20. 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.
Wed 12/45:30 amRDU - ORD
1 stop11h 36mSpirit Airlines
Fri 12/611:45 amORD - RDU
1 stop9h 51mSpirit Airlines
Deal found 11/20$157
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/186:00 amRDU - ORD
Nonstop2h 24mAmerican Airlines
Wed 12/252:20 pmORD - RDU
Nonstop2h 02mAmerican Airlines
Deal found 11/20$177
This JetBlue deal was found by Cheapflights users on 11/20. 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.
Wed 12/1111:00 amDCA - ORD
1 stop5h 53mJetBlue
Sat 12/148:51 amORD - DCA
1 stop5h 22mJetBlue
Deal found 11/20$182
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Mon 12/166:00 pmGSO - ORD
Nonstop2h 16mAmerican Airlines
Wed 12/186:30 pmORD - GSO
Nonstop2h 02mAmerican Airlines
Deal found 11/19$187
This Southwest deal was found by Cheapflights users on 11/20. 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 12/148:15 amRDU - MDW
Nonstop2h 05mSouthwest
Tue 12/178:30 amMDW - RDU
Nonstop1h 55mSouthwest
Deal found 11/20$188

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sun 2/9

5:20 pm-12:32 am

1 stop8h 12m

Chicago O'Hare Intl

Wed 2/12

6:01 pm-11:59 pm

1 stop4h 58m

$122

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 1/13

4:27 pm-10:45 pm

1 stop7h 18m

Chicago Midway

Thu 1/16

4:08 pm-12:11 pm

1 stop19h 03m

$126

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 12/11

5:30 am-4:06 pm

1 stop11h 36m

Chicago O'Hare Intl

Fri 12/13

10:59 am-11:50 am

1 stop23h 51m

$146

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 12/12

7:00 am-2:00 pm

1 stop8h 00m

Chicago O'Hare Intl

Mon 12/16

7:25 am-9:56 pm

1 stop13h 31m

$148

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 12/15

5:57 pm-9:54 am

1 stop16h 57m

Chicago O'Hare Intl

Wed 12/18

6:55 am-4:28 pm

1 stop8h 33m

$148

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 12/18

3:25 pm-9:17 pm

1 stop6h 52m

Chicago Midway

Wed 12/25

8:25 am-2:25 pm

1 stop5h 00m

$148

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 1/10

1:01 pm-12:13 am

1 stop12h 12m

Chicago Midway

Mon 1/13

7:15 am-5:02 pm

1 stop8h 47m

$148

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 12/4

5:30 am-4:06 pm

1 stop11h 36m

Chicago O'Hare Intl

Fri 12/6

11:45 am-10:36 pm

1 stop9h 51m

$157

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 12/18

6:00 am-7:24 am

Nonstop2h 24m

Chicago O'Hare Intl

Wed 12/25

2:20 pm-5:22 pm

Nonstop2h 02m

$177

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 1/1

7:35 am-8:40 am

Nonstop2h 05m

Chicago Midway

Wed 1/8

10:10 am-1:00 pm

Nonstop1h 50m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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, September is the cheapest month in which you can book a flight from Virginia to Chicago (average of $232). Flying from Virginia to Chicago in June is currently the most expensive (average of $308). 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 November 21, 2024.

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 November 21, 2024.

The most flights from USVA to CHI are scheduled on a Monday (18 on average). You will have fewer flight options on Tuesday, 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 November 21, 2024.
To help decide which airline to fly from Virginia to Chicago, see what other customers have to say about Frontier, Spirit Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,458 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Porter Airlines
7.8
Good
286 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $48. However, be on the lookout for offers from United Airlines and Spirit 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. 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 (100%), Republic Airways (100%) or ANA (98%) 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 $1,211, our data shows the cheapest flight currently is $159. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $163 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, September is the cheapest month in which you can book a flight from Virginia to Chicago (average of $232). Flying from Virginia to Chicago in June is currently the most expensive (average of $308). 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

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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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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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$206FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$148Average$341FlexibilityNo cancel feeOn-time71%
DeltaCheapest$175Average$399FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$190Average$386FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$369FlexibilityNo cancel feeOn-time63%
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