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$63+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Virginia Beach to Chicago are usually found in September or October, booked 78 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap 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 January 29, 2026.

This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:39 am
ORF
-
ORD
1 stop12h 00m
Multiple Airlines
Wed 2/255:15 am
ORD
-
ORF
1 stop12h 11m
Multiple Airlines
Deal found 1/28$133
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:39 am
ORF
-
ORD
1 stop24h 12m
Frontier
Wed 2/256:02 pm
ORD
-
ORF
1 stop15h 49m
Frontier
Deal found 1/28$138
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/257:31 pm
ORF
-
ORD
1 stop28h 34m
Multiple Airlines
Sat 2/284:42 pm
ORD
-
ORF
1 stop16h 55m
Multiple Airlines
Deal found 1/26$142
This Mytrip deal was found by Cheapflights users on 1/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:31 pm
ORF
-
ORD
1 stop16h 51m
Spirit Airlines
Tue 3/36:51 pm
ORD
-
ORF
2 stops22h 35m
Spirit Airlines
Deal found 1/27$143
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2211:32 am
ORF
-
ORD
1 stop24h 19m
Frontier
Wed 2/256:02 pm
ORD
-
ORF
1 stop15h 49m
Frontier
Deal found 1/28$146
This Frontier deal was found by Cheapflights users on 1/27. 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.
Mon 2/2311:39 am
ORF
-
MDW
1 stop9h 08m
Frontier
Thu 2/267:30 am
MDW
-
ORF
1 stop9h 58m
Frontier
Deal found 1/27$148
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:31 pm
ORF
-
ORD
1 stop29h 16m
Spirit Airlines
Mon 3/94:43 pm
ORD
-
ORF
1 stop24h 43m
Spirit Airlines
Deal found 1/27$148
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:31 pm
ORF
-
ORD
1 stop16h 51m
Spirit Airlines
Mon 3/98:16 pm
ORD
-
ORF
1 stop21h 10m
Spirit Airlines
Deal found 1/27$149
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2211:32 am
ORF
-
ORD
1 stop24h 19m
Multiple Airlines
Mon 2/238:16 pm
ORD
-
ORF
1 stop21h 10m
Multiple Airlines
Deal found 1/27$153
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/611:43 am
ORF
-
ORD
1 stop12h 03m
Frontier
Sun 2/85:40 am
ORD
-
ORF
1 stop28h 08m
Frontier
Deal found 1/28$154
This CheapOair deal was found by Cheapflights users on 1/28. 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 3/57:31 pm
ORF
-
ORD
1 stop29h 16m
Spirit Airlines
Mon 3/94:43 pm
ORD
-
ORF
1 stop24h 43m
Spirit Airlines
Deal found 1/28$155
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/611:43 am
ORF
-
MDW
1 stop22h 00m
Multiple Airlines
Mon 2/95:01 pm
MDW
-
ORF
2 stops24h 37m
Multiple Airlines
Deal found 1/27$158

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$133
(Expedia)

One-way from

$63
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$345
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. 4% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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 2/23

11:39 am-10:51 am

1 stop24h 12m

Chicago O'Hare Intl

Wed 2/25

6:02 pm-10:51 am

1 stop15h 49m

$138

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Mon 2/23

7:31 pm-11:22 am

1 stop16h 51m

Chicago O'Hare Intl

Wed 2/25

6:51 pm-10:51 am

2 stops15h 00m

$170

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sun 2/22

11:32 am-10:51 am

1 stop24h 19m

Chicago O'Hare Intl

Wed 2/25

6:51 pm-10:51 am

2 stops15h 00m

$170

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 2/13

6:45 am-5:46 pm

1 stop12h 01m

Chicago O'Hare Intl

Mon 2/23

5:15 am-6:26 pm

1 stop12h 11m

$172

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 2/23

11:39 am-7:47 pm

1 stop9h 08m

Chicago Midway

Thu 2/26

7:30 am-6:28 pm

1 stop9h 58m

$175

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 2/12

11:46 am-10:39 pm

1 stop11h 53m

Chicago O'Hare Intl

Sun 2/15

5:15 am-6:26 pm

1 stop12h 11m

$205

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 2/21

12:29 pm-7:47 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 2/25

6:02 pm-10:51 am

1 stop15h 49m

$207

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 3/14

3:26 pm-11:38 pm

1 stop9h 12m

Chicago O'Hare Intl

Mon 3/16

5:01 am-11:38 am

1 stop5h 37m

$210

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 3/14

6:45 am-1:08 pm

1 stop7h 23m

Chicago Midway

Mon 3/16

7:25 am-10:32 pm

1 stop14h 07m

$216

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 3/13

8:41 pm-7:46 pm

1 stop24h 05m

Chicago O'Hare Intl

Sun 3/15

8:41 pm-7:46 pm

1 stop22h 05m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 54 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 January 23, 2026.

Booking 78 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, May is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $114). Flying from Virginia Beach to Chicago in July is currently the most expensive (average of $266). 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 January 29, 2026.

A simple way to save on the total cost of your ticket is to fly from Virginia Beach to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the evening.

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 January 24, 2026.

Travelers seeking maximum savings on their Virginia Beach to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday evenings 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 January 29, 2026.

The most flights from V1B to CHI are scheduled on a Thursday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 January 29, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,394 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Virginia Beach to Chicago?

    Departing from Virginia Beach to Chicago will take you 5h 56m. The distance between Virginia Beach and Chicago is about 702 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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. American Airlines flights start at $98 while deals on United Airlines start at $132 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 (87%), ANA (83%) and United Airlines (79%).

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

    The cheapest flight price from Virginia Beach to Chicago is $149. On average you can expect to pay $1,196. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $133.

  • 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, May is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $114). Flying from Virginia Beach to Chicago in July is currently the most expensive (average of $266). 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 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
Dulles Intl to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Reagan-National to Midway flights
Dulles Intl to St. Louis flights
Richmond to O'Hare Intl flights
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Raleigh to Midway flights
Norfolk to O'Hare Intl flights
Reagan-National to St. Louis flights
Richmond to Midway flights
Charlottesville to O'Hare Intl flights
Raleigh to St. Louis flights
Norfolk to Midway flights
Greensboro to St. Louis flights
Greensboro to Midway flights
Roanoke to O'Hare Intl flights
Richmond to St. Louis flights
Charlottesville to Midway flights
Blountville to O'Hare Intl flights
Norfolk to St. Louis flights
Richmond to Peoria flights
Dulles Intl to Peoria flights
Reagan-National to Peoria flights
Roanoke to St. Louis flights
Lynchburg to O'Hare Intl flights
Dulles Intl to Moline flights
Norfolk to Moline flights
Roanoke to Midway flights
Dulles Intl to Evansville flights
Reagan-National to Evansville flights
Blountville to Midway flights
Raleigh to Peoria flights
Charlottesville to St. Louis flights
Reagan-National to Moline flights
Raleigh to Moline flights
Staunton to O'Hare Intl flights
Raleigh to Evansville flights
Richmond to Bloomington flights
Norfolk to Peoria flights
Newport News to O'Hare Intl flights
Raleigh to Dubuque flights
Richmond to Evansville flights
Reagan-National to Springfield flights
Dulles Intl to Springfield flights
Norfolk to Rockford flights
Roanoke to Moline 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$65Average$244FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$260FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$172Average$208FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$363FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$191Average$384FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$209Average$362FlexibilityNo cancel feeOn-time71%

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