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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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Apr 28 — May 51
Tue 4/28
Tue 5/5
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 March 29, 2026.

This Delta deal was found by Cheapflights users on 3/25. 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.
Sat 4/185:45 am
ORF
-
MDW
1 stop4h 02m
Delta
Wed 4/296:00 am
MDW
-
ORF
1 stop4h 14m
Delta
Deal found 3/25$276
This Delta deal was found by Cheapflights users on 3/25. 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 4/214:58 pm
ORF
-
ORD
1 stop4h 42m
Delta
Sat 4/255:04 pm
ORD
-
ORF
1 stop4h 51m
Delta
Deal found 3/25$276
This Mytrip deal was found by Cheapflights users on 3/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:59 pm
ORF
-
ORD
1 stop16h 06m
Spirit Airlines
Sun 5/310:07 pm
ORD
-
ORF
2 stops18h 32m
Spirit Airlines
Deal found 3/28$278
This Southwest deal was found by Cheapflights users on 3/25. 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.
Mon 4/275:25 pm
ORF
-
MDW
1 stop5h 55m
Southwest
Tue 5/52:35 pm
MDW
-
ORF
2 stops6h 20m
Southwest
Deal found 3/25$281
This United Airlines deal was found by Cheapflights users on 3/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
ORF
-
ORD
Nonstop2h 28m
United Airlines
Mon 6/811:53 am
ORD
-
ORF
Nonstop2h 21m
United Airlines
Deal found 3/26$281
This Southwest deal was found by Cheapflights users on 3/25. 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.
Sat 6/66:35 pm
ORF
-
MDW
Nonstop2h 05m
Southwest
Mon 6/87:00 pm
MDW
-
ORF
Nonstop2h 00m
Southwest
Deal found 3/25$282
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Thu 4/168:01 pm
ORF
-
ORD
Nonstop2h 41m
American Airlines
Mon 4/207:16 pm
ORD
-
ORF
Nonstop2h 16m
American Airlines
Deal found 3/25$282
This CheapOair deal was found by Cheapflights users on 3/27. 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.
Thu 4/99:04 am
ORF
-
ORD
1 stop24h 13m
Multiple Airlines
Mon 4/138:58 am
ORD
-
ORF
1 stop7h 07m
Multiple Airlines
Deal found 3/27$283
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 5/111:27 am
ORF
-
MDW
1 stop9h 04m
Frontier
Sat 5/26:00 am
MDW
-
ORF
2 stops11h 21m
Frontier
Deal found 3/27$284
This CheapOair deal was found by Cheapflights users on 3/28. 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.
Wed 5/2012:06 pm
ORF
-
ORD
1 stop8h 45m
Multiple Airlines
Sun 5/245:05 am
ORD
-
ORF
1 stop11h 34m
Multiple Airlines
Deal found 3/28$286
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 7/2412:21 pm
ORF
-
MDW
1 stop10h 50m
Frontier
Mon 7/2712:04 pm
MDW
-
ORF
1 stop22h 22m
Frontier
Deal found 3/25$287
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Thu 7/3012:21 pm
ORF
-
ORD
1 stop8h 34m
Frontier
Fri 8/71:50 pm
ORD
-
ORF
1 stop20h 30m
Frontier
Deal found 3/27$287

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 March 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$276
(Delta)

One-way from

$70
(Frontier)

Popular in

June

Cheapest in

September

Average price

$373
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. 6% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 29, 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 - MDW

ORFMDW

Norfolk

Sat 5/9

5:20 pm-8:40 pm

1 stop4h 20m

Chicago Midway

Sat 5/16

7:50 am-10:50 am

Nonstop2h 00m

$302

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 4/28

8:40 am-2:05 pm

2 stops6h 25m

Chicago Midway

Tue 5/5

6:05 pm-9:10 pm

Nonstop2h 05m

$318

NorfolkChicago

ORF - RFD

ORFRFD

Norfolk

Fri 5/1

7:37 am-6:19 pm

1 stop11h 42m

Chicago Greater Rockford

Sun 5/3

10:37 am-5:39 pm

1 stop30h 02m

$327

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 4/25

1:15 pm-6:15 pm

1 stop6h 00m

Chicago Midway

Mon 4/27

7:00 pm-10:00 pm

Nonstop2h 00m

$339

NorfolkChicago

ORF - RFD

ORFRFD

Norfolk

Fri 6/26

9:56 pm-9:17 am

1 stop12h 21m

Chicago Greater Rockford

Mon 6/29

7:48 pm-11:26 am

2 stops14h 38m

$343

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 7/29

12:21 pm-8:03 am

1 stop20h 42m

Chicago O'Hare Intl

Sat 8/1

7:52 pm-12:14 pm

2 stops15h 22m

$348

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 4/21

6:00 am-11:05 am

1 stop6h 05m

Chicago O'Hare Intl

Mon 4/27

11:00 am-4:17 pm

1 stop4h 17m

$349

NorfolkChicago

ORF - RFD

ORFRFD

Norfolk

Wed 4/8

8:41 pm-9:47 am

1 stop14h 06m

Chicago Greater Rockford

Sun 4/12

10:37 am-9:47 pm

2 stops34h 10m

$355

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Thu 5/7

6:05 am-4:05 pm

2 stops11h 00m

Chicago O'Hare Intl

Tue 5/12

5:55 am-5:50 pm

2 stops10h 55m

$364

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Tue 6/16

4:57 pm-6:29 pm

Nonstop2h 32m

Chicago O'Hare Intl

Tue 6/23

6:45 am-10:07 am

Nonstop2h 22m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 50 resultsSorted by cheapest first
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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 March 13, 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 March 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 10% 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 March 28, 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 March 29, 2026.

The most flights from V1B to CHI are scheduled on a Sunday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 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 March 29, 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
4,329 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
4,329 reviews
Southwest
8.0
Very good
4,329 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
9,514 reviews
Southwest
8.0
Very good
4,329 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
11,531 reviews
Southwest
8.0
Very good
4,329 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
8,558 reviews
Southwest
8.0
Very good
4,329 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

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
3,010 reviews
Southwest
8.0
Very good
4,329 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

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 32m. 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 (100%), Avianca (82%) and ANA (80%).

  • 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 $895. The most popular route, (Norfolk - Chicago O'Hare Intl), can usually be booked for $150.

  • 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 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 March 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$92Average$303FlexibilityNo cancel feeOn-time65%
DeltaCheapest$108Average$260FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$154Average$261FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$178Average$362FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$371FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$395FlexibilityNo cancel feeOn-time69%

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