$92+ Cheap flights from Chicago (CHI) to Virginia Beach, VA
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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
aug 29 — sep 51
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Virginia Beach with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago to Virginia Beach are usually found in December or January, booked 61 days in advance, depart on a Saturday or Tuesday and return on a Thursday
Cheap flight deals from Chicago to Virginia Beach
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to Virginia BeachExplore the most affordable flight options available from Chicago to Virginia Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juli 30, 2026.
Explore the most affordable flight options available from Chicago to Virginia Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juli 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lör 9/126:25 am
MDW
- ORF
1 stop8h 25m
Frontier
lör 9/194:45 pm
ORF
- MDW
1 stop26h 01m
Frontier
Deal found 7/29![Frontier logo]()
$277
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sön 9/133:50 pm
ORD
- ORF
1 stop25h 58m
Frontier
sön 9/207:43 pm
ORF
- ORD
1 stop28h 16m
Frontier
Deal found 7/30![Frontier logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre 8/288:11 pm
ORD
- ORF
2 stops15h 14m
Frontier
fre 9/41:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Deal found 7/30![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 7/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre 10/236:05 am
ORD
- ORF
1 stop10h 25m
Frontier
sön 10/2512:57 pm
ORF
- ORD
1 stop8h 31m
Frontier
Deal found 7/25![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
tis 9/12:41 pm
ORD
- ORF
2 stops20h 44m
Frontier
sön 9/61:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Deal found 7/28![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
tors 11/127:25 am
MDW
- ORF
2 stops12h 20m
Multiple Airlines
mån 11/1612:57 pm
ORF
- MDW
1 stop23h 01m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
tors 9/38:30 pm
ORD
- ORF
2 stops14h 55m
Frontier
sön 9/61:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Deal found 7/26![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
fre 8/216:05 am
MDW
- ORF
1 stop5h 20m
Frontier
sön 8/231:20 pm
ORF
- MDW
1 stop22h 35m
Frontier
Deal found 7/27![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
fre 8/141:50 pm
ORD
- ORF
1 stop20h 31m
Frontier
mån 8/1712:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Deal found 7/25![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
tors 8/208:05 am
ORD
- ORF
2 stops14h 48m
Multiple Airlines
sön 8/231:20 pm
ORF
- ORD
1 stop19h 33m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
mån 11/162:46 pm
ORD
- ORF
2 stops20h 16m
Frontier
tors 11/1912:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Deal found 7/25![Frontier logo]()
$286
This CheapOair deal was found by Cheapflights users on 7/28. 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.
tors 8/207:44 pm
ORD
- ORF
1 stop19h 27m
Frontier
sön 8/235:06 pm
ORF
- ORD
1 stop7h 02m
Frontier
Deal found 7/28![Frontier logo]()
$287
Best flights from Chicago to Virginia BeachDiscover carefully curated flight deals from Chicago to Virginia Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated juli 30, 2026.
Discover carefully curated flight deals from Chicago to Virginia Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated juli 30, 2026.
This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 9/96:25 pm
MDW
- ORF
Nonstop2h 10m
Southwest
ons 9/168:05 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/26![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/26. 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.
tors 9/310:55 am
ORD
- ORF
Nonstop2h 22m
United Airlines
sön 9/612:34 pm
ORF
- ORD
Nonstop2h 29m
United Airlines
Deal found 7/26![United Airlines logo]()
$322
This CheapOair deal was found by Cheapflights users on 7/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tis 8/119:35 am
ORD
- ORF
2 stops30h 35m
Multiple Airlines
sön 8/169:34 pm
ORF
- ORD
1 stop12h 37m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tors 8/201:00 pm
MDW
- ORF
1 stop3h 55m
Southwest
mån 8/248:00 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/27![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/26. 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.
fre 9/47:30 am
ORD
- ORF
Nonstop2h 30m
United Airlines
sön 9/67:59 pm
ORF
- ORD
1 stop4h 41m
United Airlines
Deal found 7/26![United Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 7/25. 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.
tors 10/296:45 pm
MDW
- ORF
Nonstop2h 00m
Southwest
sön 11/17:30 am
ORF
- MDW
Nonstop2h 15m
Southwest
Deal found 7/25![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tors 8/279:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
tors 9/310:10 am
ORF
- MDW
1 stop7h 05m
Southwest
Deal found 7/27![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tors 8/206:25 am
ORD
- ORF
1 stop6h 50m
United Airlines
mån 8/246:00 am
ORF
- ORD
Nonstop2h 34m
United Airlines
Deal found 7/27![United Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tors 9/39:20 am
MDW
- ORF
2 stops7h 35m
Southwest
tis 9/83:20 pm
ORF
- MDW
2 stops8h 05m
Southwest
Deal found 7/26![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 9/91:30 pm
ORD
- ORF
2 stops9h 13m
United Airlines
fre 9/111:00 pm
ORF
- ORD
Nonstop2h 34m
United Airlines
Deal found 7/29![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre 9/412:15 pm
MDW
- ORF
1 stop8h 00m
Southwest
tis 9/88:05 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 7/28![Southwest logo]()
$348
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre 8/286:15 pm
ORD
- ORF
Nonstop2h 33m
United Airlines
tors 9/35:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 7/29![United Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 7/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tors 9/2411:57 am
ORD
- ORF
Nonstop2h 19m
United Airlines
sön 9/276:20 am
ORF
- ORD
Nonstop2h 33m
United Airlines
Deal found 7/25![United Airlines logo]()
$456
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lör 8/1510:55 am
ORD
- ORF
Nonstop2h 22m
United Airlines
ons 8/195:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 7/27![United Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 7/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 8/1210:55 am
ORD
- ORF
Nonstop2h 22m
United Airlines
sön 8/165:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 7/25![United Airlines logo]()
$473
Last-minute flights from Chicago to Virginia BeachDiscover last-minute flight deals from Chicago to Virginia Beach. Data last updated juli 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Virginia Beach. Data last updated juli 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
fre 8/141:50 pm
ORD
- ORF
1 stop20h 31m
Frontier
mån 8/1712:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Deal found 7/25![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
lör 8/151:50 pm
ORD
- ORF
1 stop20h 25m
Frontier
ons 8/191:20 pm
ORF
- ORD
1 stop7h 48m
Frontier
Deal found 7/27![Frontier logo]()
$302
This Super.com deal was found by Cheapflights users on 7/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sön 8/165:13 pm
ORD
- ORF
1 stop26h 45m
Frontier
lör 8/221:20 pm
ORF
- ORD
1 stop7h 48m
Frontier
Deal found 7/29![Frontier logo]()
$299
This Super.com deal was found by Cheapflights users on 7/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sön 8/165:13 pm
ORD
- ORF
1 stop26h 45m
Frontier
fre 8/215:06 pm
ORF
- ORD
1 stop7h 02m
Frontier
Deal found 7/29![Frontier logo]()
$307
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 8/196:05 am
MDW
- ORF
1 stop5h 20m
Frontier
mån 8/241:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/30![Frontier logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 8/198:05 am
ORD
- ORF
2 stops9h 21m
Multiple Airlines
sön 8/231:20 pm
ORF
- ORD
1 stop19h 33m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
tors 8/208:05 am
ORD
- ORF
2 stops14h 48m
Multiple Airlines
sön 8/231:20 pm
ORF
- ORD
1 stop19h 33m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$284
This CheapOair deal was found by Cheapflights users on 7/28. 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.
tors 8/207:44 pm
ORD
- ORF
1 stop19h 27m
Frontier
sön 8/235:06 pm
ORF
- ORD
1 stop7h 02m
Frontier
Deal found 7/28![Frontier logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre 8/216:05 am
MDW
- ORF
1 stop5h 20m
Frontier
sön 8/231:20 pm
ORF
- MDW
1 stop22h 35m
Frontier
Deal found 7/30![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
tors 8/277:44 pm
ORD
- ORF
2 stops39h 41m
Frontier
tors 9/31:20 pm
ORF
- ORD
1 stop7h 44m
Frontier
Deal found 7/28![Frontier logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tors 8/279:26 pm
MDW
- ORF
2 stops37h 59m
Frontier
tors 9/31:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/30![Frontier logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre 8/288:11 pm
ORD
- ORF
2 stops15h 14m
Frontier
fre 9/41:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Deal found 7/30![Frontier logo]()
$279
One-way flights from Chicago to Virginia BeachSearch for one-way flight options from Chicago to Virginia Beach. Find affordable one-way fares based on user searches. Data last updated juli 30, 2026.
Search for one-way flight options from Chicago to Virginia Beach. Find affordable one-way fares based on user searches. Data last updated juli 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
ons 8/268:05 am
ORD
- ORF
2 stops9h 21m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
fre 8/281:59 pm
ORD
- ORF
1 stop21h 26m
Frontier
Deal found 7/28![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
sön 8/307:05 am
ORD
- ORF
1 stop28h 20m
Frontier
Deal found 7/28![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
ons 8/267:05 am
ORD
- ORF
1 stop28h 20m
Frontier
Deal found 7/28![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lör 8/291:59 pm
ORD
- ORF
1 stop21h 26m
Frontier
Deal found 7/30![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
mån 9/287:11 am
ORD
- ORF
2 stops27h 48m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mån 9/2810:26 am
ORD
- ORF
1 stop25h 03m
Frontier
Deal found 7/30![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
tis 8/251:59 pm
ORD
- ORF
1 stop21h 26m
Frontier
Deal found 7/27![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
mån 8/176:05 am
MDW
- ORF
1 stop29h 20m
Frontier
Deal found 7/28![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons 8/266:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/30![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tis 8/256:05 am
MDW
- ORF
1 stop29h 20m
Frontier
Deal found 7/29![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tis 8/1811:50 am
MDW
- ORF
1 stop23h 35m
Frontier
Deal found 7/30![Frontier logo]()
$121
Find flight deals from Chicago to Virginia Beach
Keep the following information in mind while searching for Chicago to Virginia Beach flight deals. Data was last updated juli 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $277 (Kiwi.com) |
One-way from | $92 (Kiwi.com) |
Popular in | March |
Cheapest in | December |
Average price | $443 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Virginia Beach 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 juli 30, 2026.
Use the filters below to find and compare flights from Chicago to Virginia Beach that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
ons 9/9
6:25 pm-9:35 pm
Nonstop2h 10m
Norfolk
ons 9/16
8:05 am-9:05 am
Nonstop2h 00m
$317
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
tors 9/3
10:55 am-2:17 pm
Nonstop2h 22m
Norfolk
sön 9/6
12:34 pm-2:03 pm
Nonstop2h 29m
$322
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
tors 8/20
1:00 pm-5:55 pm
1 stop3h 55m
Norfolk
mån 8/24
8:00 am-9:00 am
Nonstop2h 00m
$327
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
tors 10/29
6:45 pm-9:45 pm
Nonstop2h 00m
Norfolk
sön 11/1
7:30 am-8:45 am
Nonstop2h 15m
$345
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
tors 8/27
9:00 am-12:10 pm
Nonstop2h 10m
Norfolk
tors 9/3
10:10 am-4:15 pm
1 stop7h 05m
$347
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
tors 9/3
9:20 am-5:55 pm
2 stops7h 35m
Norfolk
tis 9/8
3:20 pm-10:25 pm
2 stops8h 05m
$347
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
fre 9/4
12:15 pm-9:15 pm
1 stop8h 00m
Norfolk
tis 9/8
8:05 am-9:05 am
Nonstop2h 00m
$348
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
fre 9/4
7:30 am-11:00 am
Nonstop2h 30m
Norfolk
sön 9/6
7:59 pm-11:40 pm
1 stop4h 41m
$353
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
tors 8/20
6:25 am-2:15 pm
1 stop6h 50m
Norfolk
mån 8/24
6:00 am-7:34 am
Nonstop2h 34m
$408
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
ons 9/9
1:30 pm-11:43 pm
2 stops9h 13m
Norfolk
fre 9/11
1:00 pm-2:34 pm
Nonstop2h 34m
$417
Showing 1-10 of 32 resultsSorted by cheapest first
Best time to book a flight from Chicago to Virginia Beach
Have a flexible travel schedule? Discover the best time to fly to Virginia Beach from Chicago with our price prediction graph.
MDW-ORF
ORD-ORF
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 Chicago to Virginia Beach
CHI-V1B
MDW-ORF
ORD-ORF
What is the cheapest time of day to fly from CHI to V1B?
Find hourly flight availability from Chicago to Virginia Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated juli 30, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Virginia Beach in the morning. If you’re flexible enough to do this you can expect to save up to 5% on your trip compared to booking a flight in the evening.
Weekly flight availability from Chicago to Virginia Beach
Explore weekly flight availability from Chicago to Virginia Beach. 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 juli 30, 2026.
The most flights from CHI to V1B are scheduled on a Thursday (26 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 Chicago to Virginia Beach?
Airfare is typical for this route at the moment.
Chicago to Virginia Beach flights typically cost between $277 and $520 in September.The cheapest round-trip price found within the last 5 days was $277 on Frontier (Sep 12-Sep 19).
What is the cheapest day to fly from Chicago to Virginia Beach?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Virginia Beach. Price data was last updated on July 25, 2026.
Travelers seeking maximum savings on their Chicago to Virginia Beach flight should consider departing on Wednesday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Virginia Beach
Get insights into the airlines that provide service to Virginia Beach. 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 Virginia Beach. Reviews last updated juli 30, 2026.
Read through reviews of airlines operating flights from Chicago to Virginia Beach, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Virginia Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Popular flights
Top destinations
Alternative routes for Chicago to Virginia Beach
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Virginia Beach by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Virginia Beach by cabin class
Find flights from Chicago to Virginia Beach, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Virginia Beach flights
Browse other Chicago and Virginia Beach flight options. Last updated on juli 30, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on juli 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Virginia Beach flights
Consider these flights traveling from Chicago to Virginia Beach.
Top 4 airlines flying from Chicago to Virginia Beach
Discover the top 4 airlines that operate flights from Chicago to Virginia Beach. 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 juli 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$102 | Average$267 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$174 | Average$383 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$219 | Average$411 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$389 | FlexibilityNo cancel fee | On-time71% |