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$72+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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Cheap 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 March 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
RDU
-
ORD
1 stop5h 02m
Frontier
Wed 4/156:08 pm
ORD
-
RDU
1 stop13h 15m
Frontier
Deal found 3/22$164
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:42 pm
RDU
-
MDW
1 stop7h 37m
Frontier
Sun 4/196:00 am
MDW
-
RDU
1 stop25h 46m
Frontier
Deal found 3/20$164
This CheapOair deal was found by Cheapflights users on 3/23. 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.
Fri 4/179:47 pm
RDU
-
ORD
Nonstop2h 19m
Frontier
Sun 4/193:52 pm
ORD
-
RDU
1 stop15h 26m
Frontier
Deal found 3/23$165
This Mytrip deal was found by Cheapflights users on 3/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/43:42 pm
RDU
-
MDW
1 stop7h 37m
Frontier
Mon 5/114:52 pm
MDW
-
RDU
1 stop15h 29m
Frontier
Deal found 3/20$165
This Super.com deal was found by Cheapflights users on 3/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:47 pm
RDU
-
ORD
Nonstop2h 19m
Frontier
Mon 4/202:10 pm
ORD
-
RDU
Nonstop2h 07m
Frontier
Deal found 3/23$166
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:10 am
RDU
-
MDW
1 stop14h 21m
Frontier
Mon 4/276:00 am
MDW
-
RDU
1 stop16h 25m
Frontier
Deal found 3/20$166
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:28 am
RDU
-
ORD
1 stop7h 14m
Frontier
Sat 4/184:28 pm
ORD
-
RDU
1 stop5h 27m
Frontier
Deal found 3/22$167
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:33 pm
RDU
-
MDW
1 stop23h 31m
Frontier
Sun 5/106:00 am
MDW
-
RDU
1 stop4h 59m
Frontier
Deal found 3/22$167
This Frontier deal was found by Cheapflights users on 3/23. 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 4/164:08 pm
RDU
-
ORD
Nonstop2h 19m
Frontier
Mon 4/202:10 pm
ORD
-
RDU
Nonstop2h 07m
Frontier
Deal found 3/23$168
This Trip.com deal was found by Cheapflights users on 3/20. 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.
Fri 5/13:49 pm
RDU
-
MDW
1 stop7h 37m
Frontier
Mon 5/42:15 pm
MDW
-
RDU
1 stop7h 45m
Frontier
Deal found 3/20$169
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/144:00 pm
RDU
-
ORD
1 stop19h 02m
Multiple Airlines
Fri 4/1711:28 am
ORD
-
RDU
1 stop10h 27m
Multiple Airlines
Deal found 3/19$170
This Kiwi.com deal was found by Cheapflights users on 3/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/273:42 pm
RDU
-
MDW
1 stop7h 37m
Frontier
Thu 4/302:15 pm
MDW
-
RDU
1 stop8h 05m
Frontier
Deal found 3/19$170

Find flight deals from Virginia to Chicago

Keep the following information in mind while searching for Virginia to Chicago flight deals. Data was last updated March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$164
(Kiwi.com)

One-way from

$72
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$373

Good round-trip deal

$253 or less

Good one-way deal

$183 or less
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
Search Deals
From Virginia to Chicago (CHI)
Search Deals
One-way flight from Virginia to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
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).
Search Deals

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 March 24, 2026.
Use the filters below to find and compare flights from Virginia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Wed 5/20

7:55 pm-11:44 pm

1 stop4h 49m

Chicago O'Hare Intl

Sat 5/23

7:26 am-10:46 am

Nonstop2h 20m

$218
Quickest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 5/17

8:00 am-9:00 am

Nonstop2h 00m

Chicago Midway

Tue 5/19

7:40 am-10:30 am

Nonstop1h 50m

$219

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 5/26

10:30 am-11:48 am

Nonstop2h 18m

Chicago O'Hare Intl

Mon 6/1

6:00 am-8:54 am

Nonstop1h 54m

$224

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 5/1

7:45 pm-8:45 pm

Nonstop2h 00m

Chicago Midway

Mon 5/4

7:45 am-10:35 am

Nonstop1h 50m

$226

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 5/1

7:45 pm-8:45 pm

Nonstop2h 00m

Chicago Midway

Tue 5/5

6:05 pm-8:55 pm

Nonstop1h 50m

$227

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 5/15

7:45 pm-8:45 pm

Nonstop2h 00m

Chicago Midway

Sat 5/16

3:45 pm-6:35 pm

Nonstop1h 50m

$227

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 4/18

6:10 am-2:35 pm

2 stops9h 25m

Chicago Midway

Wed 4/22

10:10 am-6:20 pm

2 stops7h 10m

$234

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/30

6:40 am-7:45 am

Nonstop2h 05m

Chicago Midway

Mon 6/1

5:40 pm-10:40 pm

1 stop4h 00m

$235

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 4/25

6:00 am-8:47 am

1 stop3h 47m

Chicago Midway

Mon 4/27

6:38 pm-11:03 pm

1 stop3h 25m

$243

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/14

9:35 pm-10:35 pm

Nonstop2h 00m

Chicago Midway

Fri 5/15

5:00 pm-7:55 pm

Nonstop1h 55m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/23

Showing 1-10 of 60 resultsSorted by cheapest first
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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, May is the cheapest month in which you can book a flight from Virginia to Chicago (average of $108). Flying from Virginia to Chicago in March is currently the most expensive (average of $220). 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 March 24, 2026.

When flying from Virginia to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 5% versus a flight in the morning.

What is the cheapest day to fly from Virginia to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Virginia to Chicago. Price data was last updated on March 14, 2026.

Travelers seeking maximum savings on their Virginia to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 March 24, 2026.

The most flights from USVA to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).

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.

  • How long is the flight from Virginia to Chicago?

    United Airlines, Southwest, and Delta can get you from Virginia to Chicago in just under 2h. Your travel time can differ by up to 2h 49m. The distance from Virginia to Chicago is about 631 mi. This flight may include one or multiple stops.

  • 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 $72. However, be on the lookout for offers from Southwest 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 GoJet (100%), Avianca (82%) 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 $895, our data shows the cheapest flight currently is $166. When looking at the most popular route, (Washington, D.C. Dulles Intl - Chicago O'Hare Intl), you can expect to pay $171 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, May is the cheapest month in which you can book a flight from Virginia to Chicago (average of $108). Flying from Virginia to Chicago in March is currently the most expensive (average of $220). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$92Average$303FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$244FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$154Average$274FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$362FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$209Average$328FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$374FlexibilityNo cancel feeOn-time69%

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