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$54+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
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 diciembre 18, 2024.

Round-trip from

$153
(Southwest)

One-way from

$54
(Frontier)
From Virginia to Chicago (CHI)
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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 diciembre 18, 2024.

This Frontier deal was found by Cheapflights users on 12/17. 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.
mar. 12/3111:34 amIAD - MDW
1 stop11h 59mFrontier
vie. 1/32:35 pmMDW - IAD
1 stop5h 30mFrontier
Deal found 12/17$158
This Frontier deal was found by Cheapflights users on 12/17. 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.
mié. 12/258:45 pmRDU - MDW
1 stop10h 54mFrontier
mié. 1/18:25 amMDW - RDU
1 stop8h 15mFrontier
Deal found 12/17$198
This American Airlines deal was found by Cheapflights users on 12/18. 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.
mié. 12/258:45 pmDCA - ORD
Nonstop2h 20mAmerican Airlines
mié. 1/88:25 pmORD - DCA
Nonstop1h 55mAmerican Airlines
Deal found 12/18$225
This Frontier deal was found by Cheapflights users on 12/17. 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.
mar. 12/249:57 pmRDU - ORD
1 stop12h 27mFrontier
mié. 1/110:22 pmORD - RDU
1 stop7h 37mFrontier
Deal found 12/17$228
This CheapOair deal was found by Cheapflights users on 12/18. 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.
mar. 12/3112:10 pmRDU - ORD
1 stop8h 41mMultiple Airlines
jue. 1/210:15 pmORD - RDU
1 stop9h 57mMultiple Airlines
Deal found 12/18$239
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/255:42 pmDCA - ORD
1 stop4h 35mDelta
mié. 1/86:45 amORD - DCA
1 stop4h 15mDelta
Deal found 12/18$244
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/256:00 amIAD - ORD
1 stop4h 21mDelta
mié. 1/85:45 amORD - IAD
1 stop6h 01mDelta
Deal found 12/18$244
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/2512:30 pmIAD - MDW
1 stop4h 40mDelta
mié. 1/86:00 amMDW - IAD
1 stop5h 46mDelta
Deal found 12/18$244
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/2512:31 pmDCA - MDW
1 stop4h 39mDelta
mié. 1/86:00 amMDW - DCA
1 stop5h 49mDelta
Deal found 12/18$244
This Frontier deal was found by Cheapflights users on 12/17. 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.
mié. 12/251:01 pmDCA - MDW
1 stop9h 31mFrontier
mié. 1/88:15 amMDW - DCA
1 stop7h 47mFrontier
Deal found 12/17$258
This United Airlines deal was found by Cheapflights users on 12/18. 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.
mié. 12/258:35 amIAD - ORD
Nonstop2h 20mUnited Airlines
mar. 12/319:05 pmORD - IAD
Nonstop1h 54mUnited Airlines
Deal found 12/18$259
This United deal was found by Cheapflights users on 12/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/257:00 pmDCA - ORD
Nonstop2h 25mUnited Airlines
mié. 1/86:30 amORD - DCA
Nonstop2h 02mUnited Airlines
Deal found 12/17$304

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 diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

vie. 2/28

8:20 pm-9:25 pm

Nonstop2h 05m

Chicago Midway

dom. 3/2

8:10 pm-11:00 pm

Nonstop1h 50m

$153

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

lun. 1/20

4:27 pm-12:39 am

1 stop9h 12m

Chicago O'Hare Intl

mié. 1/22

3:56 pm-1:21 pm

1 stop20h 25m

$154

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

lun. 1/6

1:01 pm-11:46 pm

1 stop11h 45m

Chicago O'Hare Intl

vie. 1/10

7:25 am-9:56 pm

1 stop13h 31m

$158

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

dom. 2/9

11:34 am-10:27 pm

1 stop11h 53m

Chicago O'Hare Intl

vie. 2/14

7:18 pm-5:13 pm

1 stop20h 55m

$158

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

mar. 12/31

11:34 am-10:33 pm

1 stop11h 59m

Chicago Midway

vie. 1/3

2:35 pm-9:05 pm

1 stop5h 30m

$158

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

vie. 1/17

3:39 pm-8:45 pm

1 stop6h 06m

Chicago O'Hare Intl

lun. 1/20

8:38 am-3:27 pm

1 stop5h 49m

$158

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

jue. 1/9

1:01 pm-12:13 am

1 stop12h 12m

Chicago Midway

dom. 1/12

7:15 am-5:02 pm

1 stop8h 47m

$158

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

dom. 1/12

6:30 am-8:02 am

Nonstop2h 32m

Chicago O'Hare Intl

dom. 1/19

6:30 am-2:09 pm

1 stop6h 39m

$161

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

sáb. 2/1

3:07 pm-11:29 pm

1 stop9h 22m

Chicago Midway

sáb. 2/8

7:30 am-7:58 am

2 stops23h 28m

$161

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

vie. 1/24

2:26 pm-8:13 pm

1 stop6h 47m

Chicago O'Hare Intl

dom. 1/26

5:11 am-1:21 pm

1 stop7h 10m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

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 diciembre 18, 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.

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 diciembre 18, 2024.
To help decide which airline to fly from Virginia to Chicago, see what other customers have to say about Frontier, American Airlines and JetBlue. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

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
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

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
9,554 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

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
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

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.

United Airlines
7.4
Good
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

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 $54. However, be on the lookout for offers from Spirit Airlines and JetBlue, 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 Envoy Air (96%), ANA (95%) or Avianca (90%) 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 $906, our data shows the cheapest flight currently is $185. When looking at the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), you can expect to pay $147 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.

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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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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 diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$105Average$211FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$148Average$339FlexibilityNo cancel feeOn-time71%
DeltaCheapest$175Average$387FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$189Average$387FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$268Average$391FlexibilityNo cancel feeOn-time63%
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