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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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
May 9 — May 161
Sat 5/9
Sat 5/16
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 60 days in advance, depart on a Thursday or Friday and return on a Wednesday

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 April 9, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/5. 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 6/812:06 pm
ORF
-
ORD
1 stop20h 57m
Frontier
Fri 6/121:50 pm
ORD
-
ORF
1 stop20h 30m
Frontier
Deal found 4/5$276
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 6/812:06 pm
ORF
-
ORD
1 stop8h 45m
Frontier
Thu 6/111:50 pm
ORD
-
ORF
1 stop20h 36m
Frontier
Deal found 4/6$278
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/206:02 pm
ORF
-
MDW
2 stops26h 29m
Frontier
Thu 4/238:26 am
MDW
-
ORF
1 stop10h 20m
Frontier
Deal found 4/6$281
This CheapOair deal was found by Cheapflights users on 4/6. 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.
Fri 6/199:56 pm
ORF
-
ORD
1 stop26h 18m
Frontier
Fri 6/265:30 pm
ORD
-
ORF
1 stop26h 31m
Frontier
Deal found 4/6$281
This Mytrip deal was found by Cheapflights users on 4/6. 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 5/18:57 pm
ORF
-
ORD
3 stops27h 10m
Spirit Airlines
Sun 5/35:05 am
ORD
-
ORF
1 stop13h 57m
Spirit Airlines
Deal found 4/6$282
This CheapOair deal was found by Cheapflights users on 4/6. 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 6/185:48 pm
ORF
-
ORD
1 stop7h 11m
Multiple Airlines
Mon 6/225:30 pm
ORD
-
ORF
1 stop26h 31m
Multiple Airlines
Deal found 4/6$283
This Mytrip deal was found by Cheapflights users on 4/5. 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.
Thu 4/238:57 pm
ORF
-
ORD
3 stops27h 10m
Spirit Airlines
Thu 4/307:50 am
ORD
-
ORF
3 stops35h 12m
Spirit Airlines
Deal found 4/5$284
This Frontier deal was found by Cheapflights users on 4/8. 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 4/911:31 am
ORF
-
ORD
1 stop12h 13m
Frontier
Mon 4/135:25 am
ORD
-
ORF
1 stop6h 12m
Frontier
Deal found 4/8$285
This CheapOair deal was found by Cheapflights users on 4/8. 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.
Sun 5/246:34 pm
ORF
-
ORD
1 stop14h 48m
Spirit Airlines
Sun 5/315:05 am
ORD
-
ORF
1 stop11h 34m
Spirit Airlines
Deal found 4/8$286
This Kiwi.com deal was found by Cheapflights users on 4/5. 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.
Thu 6/119:56 pm
ORF
-
MDW
2 stops17h 11m
Frontier
Mon 6/1512:04 pm
MDW
-
ORF
1 stop22h 22m
Frontier
Deal found 4/5$287
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/229:12 pm
ORF
-
MDW
2 stops25h 50m
Frontier
Thu 5/286:00 am
MDW
-
ORF
1 stop28h 11m
Frontier
Deal found 4/6$288
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 7/2912:21 pm
ORF
-
ORD
1 stop8h 34m
Frontier
Fri 7/316:55 am
ORD
-
ORF
1 stop27h 25m
Frontier
Deal found 4/6$288

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 April 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$276
(Kiwi.com)

One-way from

$70
(Frontier)

Popular in

March

Cheapest in

September

Average price

$374
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. 7% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 9, 2026.
Use the filters below to find and compare flights from Virginia Beach to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkChicago

ORF - RFD

ORFRFD

Norfolk

Thu 6/11

9:56 pm-7:03 pm

1 stop22h 07m

Chicago Greater Rockford

Mon 6/15

7:53 pm-11:26 am

2 stops14h 33m

$296

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 5/28

2:30 pm-8:20 pm

1 stop6h 50m

Chicago Midway

Tue 6/2

6:05 pm-9:10 pm

Nonstop2h 05m

$307

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 5/23

6:00 am-8:43 am

1 stop3h 43m

Chicago Midway

Tue 5/26

6:23 am-12:58 pm

1 stop5h 35m

$317

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 5/21

6:00 am-8:43 am

1 stop3h 43m

Chicago Midway

Tue 5/26

6:36 pm-11:15 pm

1 stop3h 39m

$317

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 6/11

6:17 pm-10:17 pm

1 stop5h 00m

Chicago Midway

Mon 6/15

9:17 am-4:24 pm

1 stop6h 07m

$317

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 5/23

7:55 am-9:00 am

Nonstop2h 05m

Chicago Midway

Tue 5/26

6:05 pm-9:10 pm

Nonstop2h 05m

$326
Quickest round-trip

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 5/2

7:55 am-9:00 am

Nonstop2h 05m

Chicago Midway

Mon 5/4

7:00 pm-10:00 pm

Nonstop2h 00m

$329

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 5/5

11:10 am-5:05 pm

2 stops6h 55m

Chicago Midway

Sat 5/9

12:45 pm-11:05 pm

2 stops9h 20m

$333

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 5/13

6:00 am-7:30 am

Nonstop2h 30m

Chicago O'Hare Intl

Sun 5/17

11:05 am-2:24 pm

Nonstop2h 19m

$356

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 6/4

6:00 am-8:43 am

1 stop3h 43m

Chicago Midway

Mon 6/8

5:11 pm-12:42 am

1 stop6h 31m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

Showing 1-10 of 46 resultsSorted by cheapest first
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5

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 April 3, 2026.

Booking 60 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 $108). 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 April 9, 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 9% on your trip compared to booking a flight in the morning.

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 April 4, 2026.

Travelers seeking maximum savings on their Virginia Beach to Chicago flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings 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 April 9, 2026.

The most flights from V1B to CHI are scheduled on a Wednesday (27 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (17 on average).

How much does it cost to fly round-trip from Virginia Beach to Chicago?

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 April 9, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican 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
4,337 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,337 reviews
Southwest
8.0
Very good
4,337 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,555 reviews
Southwest
8.0
Very good
4,337 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,563 reviews
Southwest
8.0
Very good
4,337 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.3
Okay
8,606 reviews
Southwest
8.0
Very good
4,337 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,995 reviews
Southwest
8.0
Very good
4,337 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 2h 30m. The distance between Virginia Beach and Chicago is about 715 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 GoJet (89%), ANA (86%) and Air Canada (86%).

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

    The cheapest flight price from Virginia Beach to Chicago is $166. On average you can expect to pay $880. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $162.

  • 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 $108). 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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Top 7 airlines flying from Virginia Beach to Chicago

Discover the top 7 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 April 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$92Average$303FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$260FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$116Average$352FlexibilityNo cancel feeOn-time62%
FrontierCheapest$154Average$261FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$362FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$374FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$396FlexibilityNo cancel feeOn-time69%

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