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$91+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
May 18 — May 251
Sun 5/18
Sun 5/25
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 Wednesday 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 May 13, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$210
(Frontier)

One-way from

$91
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$375
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 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 ($15 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 May 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 May 13, 2025.

This Frontier deal was found by Cheapflights users on 5/12. 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.
Wed 5/285:12 pmORF - MDW
1 stop6h 24mFrontier
Fri 5/306:35 amMDW - ORF
1 stop8h 52mFrontier
Deal found 5/12$210
This Frontier deal was found by Cheapflights users on 5/12. 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 5/293:28 pmORF - ORD
1 stop9h 52mFrontier
Sat 5/318:04 amORD - ORF
1 stop7h 23mFrontier
Deal found 5/12$210
This Orbitz deal was found by Cheapflights users on 5/12. 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.
Wed 5/2812:13 pmORF - ORD
1 stop8h 50mMultiple Airlines
Fri 5/305:10 amORD - ORF
1 stop10h 17mMultiple Airlines
Deal found 5/12$215
This Mytrip deal was found by Cheapflights users on 5/11. 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 6/151:01 pmORF - ORD
2 stops33h 55mSpirit Airlines
Tue 6/175:51 amORD - ORF
1 stop5h 15mSpirit Airlines
Deal found 5/11$218
This Mytrip deal was found by Cheapflights users on 5/12. 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 6/133:19 pmORF - RFD
1 stop17h 45mMultiple Airlines
Sun 6/154:06 pmRFD - ORF
2 stops21h 00mMultiple Airlines
Deal found 5/12$264
This Southwest deal was found by Cheapflights users on 5/12. 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 5/286:15 amORF - MDW
Nonstop2h 10mSouthwest
Fri 5/301:20 pmMDW - ORF
Nonstop2h 00mSouthwest
Deal found 5/12$265
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 5/283:57 pmORF - ORD
1 stop4h 38mAmerican Airlines
Sat 6/77:55 pmORD - ORF
Nonstop2h 31mAmerican Airlines
Deal found 5/12$275
This United Airlines deal was found by Cheapflights users on 5/12. 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.
Mon 8/255:00 pmORF - ORD
Nonstop2h 25mUnited Airlines
Wed 8/275:55 pmORD - ORF
1 stop4h 55mUnited Airlines
Deal found 5/12$282
This Delta deal was found by Cheapflights users on 5/12. 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.
Wed 5/285:35 amORF - MDW
1 stop5h 05mDelta
Thu 5/2910:25 amMDW - ORF
1 stop7h 10mDelta
Deal found 5/12$285
This Southwest deal was found by Cheapflights users on 5/12. 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 5/286:40 amORF - ORD
2 stops7h 05mSouthwest
Fri 5/301:50 pmORD - ORF
1 stop3h 55mSouthwest
Deal found 5/12$290
This Delta deal was found by Cheapflights users on 5/12. 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.
Mon 6/93:29 pmORF - ORD
1 stop6h 13mDelta
Tue 6/102:25 pmORD - ORF
1 stop6h 44mDelta
Deal found 5/12$296

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 May 13, 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

Wed 5/28

5:12 pm-10:36 pm

1 stop6h 24m

Chicago Midway

Fri 5/30

6:35 am-4:27 pm

1 stop8h 52m

$210

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 5/29

3:28 pm-12:20 am

1 stop9h 52m

Chicago O'Hare Intl

Sat 5/31

8:04 am-4:27 pm

1 stop7h 23m

$210

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 5/28

12:13 pm-8:03 pm

1 stop8h 50m

Chicago O'Hare Intl

Fri 5/30

5:10 am-4:27 pm

1 stop10h 17m

$215

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sun 6/15

1:01 pm-9:56 pm

2 stops33h 55m

Chicago O'Hare Intl

Tue 6/17

5:51 am-12:06 pm

1 stop5h 15m

$218

NorfolkChicago

ORF - RFD

ORFRFD

Norfolk

Fri 6/13

3:19 pm-8:04 am

1 stop17h 45m

Chicago Greater Rockford

Sun 6/15

4:06 pm-2:06 pm

2 stops21h 00m

$264

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 5/28

6:15 am-7:25 am

Nonstop2h 10m

Chicago Midway

Fri 5/30

1:20 pm-4:20 pm

Nonstop2h 00m

$265

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 5/28

3:57 pm-7:35 pm

1 stop4h 38m

Chicago O'Hare Intl

Sat 6/7

7:55 pm-11:26 pm

Nonstop2h 31m

$275

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 8/25

5:00 pm-6:25 pm

Nonstop2h 25m

Chicago O'Hare Intl

Wed 8/27

5:55 pm-11:50 pm

1 stop4h 55m

$282

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 5/28

5:35 am-9:40 am

1 stop5h 05m

Chicago Midway

Thu 5/29

10:25 am-6:35 pm

1 stop7h 10m

$285

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 5/28

6:40 am-12:45 pm

2 stops7h 05m

Chicago O'Hare Intl

Fri 5/30

1:50 pm-6:45 pm

1 stop3h 55m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/12

Showing 1-10 of 25 results
1
2
3

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 May 9, 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 May 13, 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 May 11, 2025.

Travelers seeking maximum savings on their Virginia Beach to Chicago flight should consider departing on Thursday afternoons 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 May 13, 2025.

The most flights from V1B to CHI are scheduled on a Saturday (28 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 on average).

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 May 13, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Virginia Beach to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,290 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,290 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,724 reviews
Southwest
8.0
Very good
4,290 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,290 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,290 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Allegiant Air, which is currently one of the cheapest options available, starting at $91. Spirit Airlines flights start at $93 while deals on Frontier start at $100 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 Qatar Airways (78%), Royal Jordanian (77%) and Avianca (75%).

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

    The cheapest flight price from Virginia Beach to Chicago is $126. On average you can expect to pay $775. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $200.

  • 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
Hammond
Benton Harbor
Porter
Lansing
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 May 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$441FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$146Average$230FlexibilityNo cancel feeOn-time65%
FrontierCheapest$176Average$204FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$182Average$392FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$251Average$386FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$268Average$378FlexibilityNo cancel feeOn-time63%

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