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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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$152
(Gotogate)

One-way from

$79
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$375

Good round-trip deal

$224 or less

Good one-way deal

$165 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 ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Gotogate deal was found by Cheapflights users on 7/31. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/143:13 pmRDU - ORD
Nonstop2h 25mFrontier
Mon 8/1811:15 amORD - RDU
Nonstop2h 13mFrontier
Deal found 7/31$152
This Orbitz deal was found by Cheapflights users on 7/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/259:23 amRDU - ORD
1 stop9h 16mMultiple Airlines
Sun 9/2811:36 amORD - RDU
Nonstop2h 14mMultiple Airlines
Deal found 7/29$153
This American Airlines deal was found by Cheapflights users on 7/29. 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 10/48:51 amRDU - ORD
Nonstop2h 17mAmerican Airlines
Sat 10/411:55 amORD - RDU
Nonstop2h 11mAmerican Airlines
Deal found 7/29$168
This FlightHub deal was found by Cheapflights users on 7/30. 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.
Sun 8/103:26 pmRDU - ORD
1 stop7h 23mSpirit Airlines
Sat 8/165:05 amORD - RDU
1 stop12h 26mSpirit Airlines
Deal found 7/30$171
This Southwest deal was found by Cheapflights users on 7/30. 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 10/114:55 pmRDU - MDW
Nonstop1h 55mSouthwest
Sat 10/189:55 amMDW - RDU
Nonstop1h 50mSouthwest
Deal found 7/30$173
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/181:22 pmIAD - MDW
1 stop5h 55mAllegiant Air
Fri 8/229:32 amMDW - IAD
1 stop4h 51mAllegiant Air
Deal found 7/29$174
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
Fri 8/298:58 amRDU - MDW
1 stop5h 12mFrontier
Sun 8/316:45 amMDW - RDU
1 stop6h 13mFrontier
Deal found 7/29$176
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Sat 9/137:14 pmIAD - MDW
1 stop15h 04mFrontier
Sat 9/2010:51 amMDW - IAD
1 stop6h 33mFrontier
Deal found 7/30$177
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/196:30 amRDU - ORD
Nonstop2h 23mUnited Airlines
Sun 9/217:10 amORD - RDU
Nonstop2h 11mUnited Airlines
Deal found 7/31$177
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Sun 9/149:24 pmRIC - ORD
2 stops21h 15mMultiple Airlines
Fri 9/196:30 amORD - RIC
1 stop14h 40mMultiple Airlines
Deal found 7/30$190
This United Airlines deal was found by Cheapflights users on 7/29. 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 8/306:24 pmRIC - ORD
1 stop6h 01mUnited Airlines
Sat 9/66:30 pmORD - RIC
Nonstop2h 16mUnited Airlines
Deal found 7/29$191
This FlightHub deal was found by Cheapflights users on 7/30. 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.
Mon 10/201:08 pmRIC - ORD
1 stop9h 50mSpirit Airlines
Wed 10/225:05 amORD - RIC
1 stop11h 30mSpirit Airlines
Deal found 7/30$192

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 July 31, 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

Thu 8/14

3:13 pm-4:38 pm

Nonstop2h 25m

Chicago O'Hare Intl

Mon 8/18

11:15 am-2:28 pm

Nonstop2h 13m

$152

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Thu 9/25

9:23 am-5:39 pm

1 stop9h 16m

Chicago O'Hare Intl

Sun 9/28

11:36 am-2:50 pm

Nonstop2h 14m

$153

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sat 10/4

8:51 am-10:08 am

Nonstop2h 17m

Chicago O'Hare Intl

Sat 10/4

11:55 am-3:06 pm

Nonstop2h 11m

$168

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Sun 8/10

3:26 pm-9:49 pm

1 stop7h 23m

Chicago O'Hare Intl

Sat 8/16

5:05 am-6:31 pm

1 stop12h 26m

$171

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/11

4:55 pm-5:50 pm

Nonstop1h 55m

Chicago Midway

Sat 10/18

9:55 am-12:45 pm

Nonstop1h 50m

$173

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 8/18

1:22 pm-6:17 pm

1 stop5h 55m

Chicago Midway

Fri 8/22

9:32 am-3:23 pm

1 stop4h 51m

$174

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 8/29

8:58 am-1:10 pm

1 stop5h 12m

Chicago Midway

Sun 8/31

6:45 am-1:58 pm

1 stop6h 13m

$176

RaleighChicago

RDU - ORD

RDUORD

Raleigh-Durham

Fri 9/19

6:30 am-7:53 am

Nonstop2h 23m

Chicago O'Hare Intl

Sun 9/21

7:10 am-10:21 am

Nonstop2h 11m

$177

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 9/13

7:14 pm-9:18 am

1 stop15h 04m

Chicago Midway

Sat 9/20

10:51 am-6:24 pm

1 stop6h 33m

$177

RichmondChicago

RIC - ORD

RICORD

Richmond Byrd Intl

Sun 9/14

9:24 pm-5:39 pm

2 stops21h 15m

Chicago O'Hare Intl

Fri 9/19

6:30 am-10:10 pm

1 stop14h 40m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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 July 31, 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 July 31, 2025.

The most flights from USVA to CHI are scheduled on a Thursday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

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 July 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Avelo Airlines from Virginia to Chicago to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $79. However, be on the lookout for offers from Frontier 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. 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 (93%), Piedmont Airlines (85%) or ANA (84%) 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 $1,233, our data shows the cheapest flight currently is $90. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $203 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Lansing
Hammond
Benton Harbor
Porter
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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.
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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$287FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$449FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$191Average$389FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$209Average$353FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$231Average$374FlexibilityNo cancel feeOn-time63%

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