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$72+ Cheap flights from Virginia Beach, VA 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Virginia Beach to Chicago are usually found in September or March, booked 10 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap flight deals from Virginia Beach to Chicago

Keep the following information in mind while searching for Virginia Beach to Chicago flight deals. Data was last updated July 29, 2025.

Round-trip from

$239
(American Airlines)

One-way from

$72
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$375
From Virginia Beach to Chicago (CHI)
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One-way flight from Virginia Beach 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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Find flight deals from Virginia Beach to Chicago

Cheapest flights from Virginia Beach to Chicago
Explore the most affordable flight options available from Virginia Beach to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This CheapOair deal was found by Cheapflights users on 7/28. 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 8/77:39 pmORF - ORD
1 stop28h 52mMultiple Airlines
Mon 8/115:05 amORD - ORF
1 stop10h 20mMultiple Airlines
Deal found 7/28$239
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/285:34 pmORF - ORD
1 stop5h 48mSpirit Airlines
Thu 9/411:48 amORD - ORF
1 stop10h 00mSpirit Airlines
Deal found 7/29$241
This Southwest deal was found by Cheapflights users on 7/28. 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 8/276:05 amORF - MDW
1 stop6h 40mSouthwest
Wed 9/31:00 pmMDW - ORF
2 stops7h 40mSouthwest
Deal found 7/28$242
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.
Mon 8/257:28 pmORF - ORD
1 stop4h 31mAmerican Airlines
Tue 8/262:32 pmORD - ORF
Nonstop2h 18mAmerican Airlines
Deal found 7/29$249
This Frontier deal was found by Cheapflights users on 7/27. 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 8/294:12 pmORF - MDW
1 stop8h 15mFrontier
Sun 8/319:17 amMDW - ORF
1 stop10h 50mFrontier
Deal found 7/27$258
This Southwest deal was found by Cheapflights users on 7/28. 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 10/16:05 amORF - ORD
1 stop6h 45mSouthwest
Sat 10/412:40 pmORD - ORF
2 stops7h 40mSouthwest
Deal found 7/28$277
This Delta deal was found by Cheapflights users on 7/28. 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.
Thu 9/47:00 amORF - ORD
1 stop11h 37mDelta
Sat 9/67:15 amORD - ORF
1 stop4h 11mDelta
Deal found 7/28$286
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Tue 9/25:00 pmORF - ORD
Nonstop2h 25mUnited Airlines
Tue 9/96:30 pmORD - ORF
Nonstop2h 22mUnited Airlines
Deal found 7/28$287
This Delta deal was found by Cheapflights users on 7/28. 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.
Sun 9/286:00 amORF - MDW
1 stop7h 28mDelta
Tue 10/712:48 pmMDW - ORF
1 stop4h 49mDelta
Deal found 7/28$311

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia Beach 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 29, 2025.
Use the filters below to find and compare flights from Virginia Beach to Chicago that are best for you.

Fly from

Virginia Beach

Fly to

Chicago

Route

Depart

Return

Price

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 8/25

6:12 pm-7:50 pm

Nonstop2h 38m

Chicago O'Hare Intl

Tue 8/26

2:32 pm-5:50 pm

Nonstop2h 18m

$239

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 8/28

5:34 pm-10:22 pm

1 stop5h 48m

Chicago O'Hare Intl

Thu 9/4

11:48 am-10:48 pm

1 stop10h 00m

$241

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 8/27

6:05 am-11:45 am

1 stop6h 40m

Chicago Midway

Wed 9/3

1:00 pm-9:40 pm

2 stops7h 40m

$242

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 8/29

4:12 pm-11:27 pm

1 stop8h 15m

Chicago Midway

Sun 8/31

9:17 am-9:07 pm

1 stop10h 50m

$258

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 10/1

6:05 am-11:50 am

1 stop6h 45m

Chicago O'Hare Intl

Sat 10/4

12:40 pm-9:20 pm

2 stops7h 40m

$277

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 9/4

7:00 am-5:37 pm

1 stop11h 37m

Chicago O'Hare Intl

Wed 9/10

7:05 am-12:52 pm

1 stop4h 47m

$286

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 9/2

5:00 pm-6:25 pm

Nonstop2h 25m

Chicago O'Hare Intl

Tue 9/9

6:30 pm-9:52 pm

Nonstop2h 22m

$287

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sun 9/28

6:00 am-12:28 pm

1 stop7h 28m

Chicago Midway

Tue 10/7

12:48 pm-6:37 pm

1 stop4h 49m

$311

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 10/15

3:27 pm-10:58 pm

1 stop8h 31m

$72

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 10/15

3:27 pm-12:10 am

1 stop9h 43m

$86

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 20 results
1
2

Best time to book a flight from Virginia Beach to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Virginia Beach 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 Beach to Chicago

How far ahead should I book a flight from Virginia Beach to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Virginia Beach to Chicago. Price data was last updated on July 25, 2025.

Booking 10 days in advance of your planned departure date is, on average, the best time to get cheap flights from Virginia Beach to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Virginia Beach to Chicago?

Currently, August is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $245). Flying from Virginia Beach 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 V1B to CHI?

Find hourly flight availability from Virginia Beach 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 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Virginia Beach to Chicago as you normally would.

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

Use this chart to determine the cheapest time to fly round-trip from Virginia Beach to Chicago. Price data was last updated on July 27, 2025.

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

Weekly flight availability from Virginia Beach to Chicago

Explore weekly flight availability from Virginia Beach 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 29, 2025.

The most flights from V1B to CHI are scheduled on a Monday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 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 29, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Virginia Beach to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
8,896 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
4,238 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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 Beach 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 Beach to Chicago one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $72. Spirit Airlines flights start at $92 while deals on Southwest start at $109 one-way.

  • What are the most popular routes from Virginia Beach to Chicago?

    The most popular route from Virginia Beach to Chicago is Norfolk - Chicago O'Hare Intl. You may also consider Norfolk - Chicago Midway or Norfolk - Chicago Greater Rockford.

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

    The top 3 most reliable airlines when flying from Virginia Beach to Chicago are Avianca (93%), Piedmont Airlines (85%) and ANA (84%).

  • What are the cheapest flights from Virginia Beach to Chicago?

    The cheapest flight price from Virginia Beach to Chicago is $90. On average you can expect to pay $1,233. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $178.

  • Can I find deals for flights from Virginia Beach to Chicago that include hotel bookings?

    Yes. In addition to deals on Virginia Beach to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Virginia Beach to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Virginia Beach to Chicago.

  • Can I find deals for business class flights from Virginia Beach to Chicago?

    Yes. Cheapflights offers flight deals from Virginia Beach 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 Beach to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $245). Flying from Virginia Beach 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for Virginia Beach to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Reagan-National to O'Hare Intl flights
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Top 6 airlines flying from Virginia Beach to Chicago

Discover the top 6 airlines that operate flights from Virginia Beach 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$287FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$449FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$191Average$390FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$382FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$231Average$374FlexibilityNo cancel feeOn-time63%

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