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$70+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Virginia Beach to Chicago are usually found in September or March, booked 88 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 1, 2025.

Round-trip from

$227
(Southwest)

One-way from

$70
(Priceline)

Popular in

June

Cheapest in

September

Average price

$375
From Virginia Beach to Chicago (CHI)
Search Deals
One-way flight from Virginia Beach to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 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 1, 2025.

This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 8/73:00 pmORF - MDW
2 stops5h 30mSouthwest
Tue 8/121:00 pmMDW - ORF
2 stops7h 40mSouthwest
Deal found 6/30$227
This Booking.com deal was found by Cheapflights users on 6/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/285:50 amORF - ORD
1 stop13h 08mSpirit Airlines
Mon 8/45:05 amORD - ORF
1 stop10h 20mSpirit Airlines
Deal found 6/30$227
This Southwest deal was found by Cheapflights users on 7/1. 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.
Tue 9/26:05 amORF - ORD
2 stops12h 50mSouthwest
Mon 9/81:50 pmORD - ORF
1 stop3h 50mSouthwest
Deal found 7/1$228
This FlightHub deal was found by Cheapflights users on 6/30. 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.
Fri 8/110:25 amORF - MDW
1 stop13h 52mFrontier
Thu 8/72:55 pmMDW - ORF
1 stop17h 18mFrontier
Deal found 6/30$229
This FlightHub deal was found by Cheapflights users on 7/1. 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.
Fri 8/110:25 amORF - ORD
1 stop14h 57mMultiple Airlines
Mon 8/45:05 amORD - ORF
1 stop10h 20mMultiple Airlines
Deal found 7/1$230
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/295:05 pmORF - ORD
Nonstop2h 25mUnited Airlines
Tue 8/54:46 pmORD - ORF
1 stop5h 55mUnited Airlines
Deal found 6/30$241
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Fri 8/159:58 amORF - ORD
1 stop15h 24mFrontier
Sun 8/175:01 amORD - ORF
1 stop27h 12mFrontier
Deal found 6/30$245
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/156:12 pmORF - ORD
Nonstop2h 38mAmerican Airlines
Tue 8/262:32 pmORD - ORF
Nonstop2h 18mAmerican Airlines
Deal found 6/30$250
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/296:27 amORF - MDW
1 stop4h 18mDelta
Tue 8/512:43 pmMDW - ORF
1 stop5h 50mDelta
Deal found 6/30$251
This Mytrip deal was found by Cheapflights users on 6/29. 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.
Sun 7/279:05 amORF - MDW
2 stops25h 36mMultiple Airlines
Fri 8/11:11 pmMDW - ORF
3 stops21h 05mMultiple Airlines
Deal found 6/29$330
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Fri 7/49:52 pmORF - RFD
2 stops19h 35mMultiple Airlines
Sun 7/612:44 pmRFD - ORF
2 stops24h 22mMultiple Airlines
Deal found 6/30$762

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 1, 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 - MDW

ORFMDW

Norfolk

Thu 8/7

3:00 pm-7:30 pm

2 stops5h 30m

Chicago Midway

Tue 8/12

1:00 pm-9:40 pm

2 stops7h 40m

$227

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 7/28

5:50 am-5:58 pm

1 stop13h 08m

Chicago O'Hare Intl

Mon 8/4

5:05 am-4:25 pm

1 stop10h 20m

$227

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 9/2

6:05 am-5:55 pm

2 stops12h 50m

Chicago O'Hare Intl

Mon 9/8

1:50 pm-6:40 pm

1 stop3h 50m

$228

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 8/1

10:25 am-11:17 pm

1 stop13h 52m

Chicago Midway

Thu 8/7

2:55 pm-9:13 am

1 stop17h 18m

$229

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 8/1

10:25 am-12:22 am

1 stop14h 57m

Chicago O'Hare Intl

Mon 8/4

5:05 am-4:25 pm

1 stop10h 20m

$230

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 7/29

5:05 pm-6:30 pm

Nonstop2h 25m

Chicago O'Hare Intl

Tue 8/5

4:46 pm-11:41 pm

1 stop5h 55m

$241

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 8/15

9:58 am-12:22 am

1 stop15h 24m

Chicago O'Hare Intl

Sun 8/17

5:01 am-9:13 am

1 stop27h 12m

$245

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 8/15

6:12 pm-7:50 pm

Nonstop2h 38m

Chicago O'Hare Intl

Tue 8/26

2:32 pm-5:50 pm

Nonstop2h 18m

$250

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 7/29

6:27 am-9:45 am

1 stop4h 18m

Chicago Midway

Tue 8/5

12:43 pm-7:33 pm

1 stop5h 50m

$251

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sun 7/27

9:05 am-9:41 am

2 stops25h 36m

Chicago Midway

Fri 8/1

1:11 pm-11:16 am

3 stops21h 05m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 22 results
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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 June 27, 2025.

Booking 88 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 1, 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 June 29, 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 1, 2025.

The most flights from V1B to CHI are scheduled on a Tuesday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 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 1, 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
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,974 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.2
Good
710 reviews
Southwest
8.0
Very good
4,275 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $70. Spirit Airlines flights start at $93 while deals on Southwest start at $99 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%), Japan Airlines (91%) and Piedmont Airlines (90%).

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

    The cheapest flight price from Virginia Beach to Chicago is $169. On average you can expect to pay $1,543. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $155.

  • 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 Virginia Beach?

Book flights to Virginia Beach if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
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.
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Blountville to Midway flights
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Greensboro to Peoria flights

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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$410FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$146Average$284FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$174Average$389FlexibilityNo cancel feeOn-time69%
FrontierCheapest$198Average$208FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$239Average$383FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$268Average$375FlexibilityNo cancel feeOn-time63%

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