$71+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
May 30 — Jun 61
Round-trip
1 adult, Economy
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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 September, booked 72 days in advance, depart on a Wednesday or Saturday 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 April 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 April 30, 2026.
This CheapOair deal was found by Cheapflights users on 4/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:49 am
ORD
- ORF
1 stop24h 09m
Multiple Airlines
Sat 5/1611:42 am
ORF
- ORD
1 stop9h 09m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$298
This Priceline deal was found by Cheapflights users on 4/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:00 am
ORD
- ORF
1 stop9h 21m
Frontier
Tue 5/512:06 pm
ORF
- ORD
1 stop8h 45m
Frontier
Deal found 4/26![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Wed 6/101:50 pm
ORD
- ORF
1 stop20h 36m
Frontier
Fri 6/1212:21 pm
ORF
- ORD
1 stop8h 32m
Frontier
Deal found 4/25![Frontier logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Thu 7/237:07 pm
ORD
- ORF
1 stop13h 06m
Multiple Airlines
Tue 7/286:12 pm
ORF
- ORD
2 stops19h 13m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$304
This Southwest deal was found by Cheapflights users on 4/26. 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.
Sat 7/256:25 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Sat 8/16:55 pm
ORF
- MDW
1 stop5h 25m
Southwest
Deal found 4/26![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 6/121:50 pm
ORD
- ORF
1 stop20h 31m
Frontier
Mon 6/159:35 pm
ORF
- ORD
2 stops23h 18m
Frontier
Deal found 4/27![Frontier logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/154:52 pm
MDW
- ORF
2 stops17h 03m
Multiple Airlines
Sun 5/178:49 pm
ORF
- MDW
1 stop20h 08m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$306
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Wed 8/1912:21 pm
ORF
- ORD
1 stop8h 34m
Frontier
Deal found 4/29![Frontier logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 6/252:46 pm
MDW
- ORF
2 stops17h 27m
Multiple Airlines
Sun 6/2812:21 pm
ORF
- MDW
1 stop23h 48m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/96:55 am
ORD
- ORF
2 stops10h 34m
Frontier
Sun 5/178:49 pm
ORF
- ORD
1 stop27h 24m
Frontier
Deal found 4/28![Frontier logo]()
$307
This CheapOair deal was found by Cheapflights users on 4/28. 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 6/2410:27 am
ORD
- ORF
1 stop5h 36m
Multiple Airlines
Sun 6/289:35 pm
ORF
- ORD
1 stop12h 46m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Sat 7/2512:11 pm
MDW
- ORF
1 stop22h 10m
Multiple Airlines
Sat 8/110:31 pm
ORF
- MDW
2 stops46h 59m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$309
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 April 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 April 30, 2026.
This Southwest deal was found by Cheapflights users on 4/26. 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.
Sat 7/256:25 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Sat 8/18:15 am
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 4/26![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Wed 6/1712:22 pm
ORD
- ORF
Nonstop2h 21m
United Airlines
Sun 6/216:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 4/25![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1712:45 pm
MDW
- ORF
1 stop5h 43m
Delta
Mon 6/2210:16 am
ORF
- MDW
1 stop7h 00m
Delta
Deal found 4/29![Delta logo]()
$360
This Southwest deal was found by Cheapflights users on 4/28. 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.
Wed 7/17:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sat 7/47:10 am
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 4/28![Southwest logo]()
$340
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 6/176:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Thu 6/186:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 4/29![United Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 4/28. 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.
Wed 7/17:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Mon 7/63:30 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 4/28![Southwest logo]()
$340
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Wed 6/1712:22 pm
ORD
- ORF
Nonstop2h 21m
United Airlines
Mon 6/228:00 am
ORF
- ORD
Nonstop2h 32m
United Airlines
Deal found 4/25![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:00 am
ORD
- ORF
1 stop4h 17m
Delta
Sun 5/315:20 am
ORF
- ORD
1 stop5h 56m
Delta
Deal found 4/27![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 4/25. 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.
Wed 6/177:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sun 6/216:15 pm
ORF
- MDW
1 stop6h 25m
Southwest
Deal found 4/25![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Sun 7/199:35 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Sun 7/266:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 4/27![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 4/25. 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 5/237:50 am
MDW
- ORF
Nonstop2h 00m
Southwest
Sat 5/307:55 am
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 4/25![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Mon 7/133:53 pm
ORD
- ORF
1 stop6h 51m
United Airlines
Sat 7/186:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 4/26![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:05 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Wed 6/36:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Deal found 4/29![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Tue 7/146:15 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Tue 7/2110:45 am
ORF
- ORD
1 stop4h 55m
United Airlines
Deal found 4/25![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 4/25. 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.
Fri 7/317:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Sun 8/27:20 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 4/25![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Thu 7/26:15 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Mon 7/66:05 am
ORF
- ORD
1 stop4h 31m
United Airlines
Deal found 4/25![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 4/28. 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.
Sun 8/238:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Fri 8/288:00 am
ORF
- MDW
Nonstop2h 00m
Southwest
Deal found 4/28![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Mon 6/229:19 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Sun 6/287:59 pm
ORF
- ORD
1 stop4h 27m
United Airlines
Deal found 4/29![United Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 4/28. 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.
Fri 6/127:00 pm
MDW
- ORF
1 stop3h 35m
Southwest
Fri 6/197:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 4/28![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 4/27. 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.
Sun 7/197:45 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sun 7/267:45 pm
ORF
- MDW
1 stop5h 35m
Southwest
Deal found 4/27![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 6/69:19 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Mon 6/88:00 am
ORF
- ORD
Nonstop2h 32m
United Airlines
Deal found 4/27![United Airlines logo]()
$435
This Southwest deal was found by Cheapflights users on 4/25. 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.
Thu 6/42:40 pm
MDW
- ORF
2 stops7h 45m
Southwest
Sun 6/78:05 am
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 4/25![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Thu 8/206:45 am
ORD
- ORF
Nonstop2h 25m
United Airlines
Sun 8/236:30 am
ORF
- ORD
Nonstop2h 26m
United Airlines
Deal found 4/25![United Airlines logo]()
$443
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Fri 7/246:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Mon 7/276:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 4/26![United Airlines logo]()
$443
Last-minute flights from Chicago to Virginia BeachDiscover last-minute flight deals from Chicago to Virginia Beach. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Virginia Beach. Data last updated April 30, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:21 am
MDW
- ORF
1 stop10h 25m
Frontier
Tue 5/512:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 4/26![Frontier logo]()
$311
This Priceline deal was found by Cheapflights users on 4/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:00 am
ORD
- ORF
1 stop9h 21m
Frontier
Tue 5/512:06 pm
ORF
- ORD
1 stop8h 45m
Frontier
Deal found 4/26![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/96:55 am
ORD
- ORF
2 stops10h 34m
Frontier
Sun 5/178:49 pm
ORF
- ORD
1 stop27h 24m
Frontier
Deal found 4/28![Frontier logo]()
$307
This CheapOair deal was found by Cheapflights users on 4/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:30 pm
ORD
- ORF
1 stop25h 24m
Multiple Airlines
Sat 5/2310:50 am
ORF
- ORD
1 stop22h 10m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Sat 5/96:00 am
MDW
- ORF
2 stops34h 39m
Multiple Airlines
Tue 5/1212:06 pm
ORF
- MDW
1 stop10h 56m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$310
This CheapOair deal was found by Cheapflights users on 4/25. 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.
Sun 5/107:33 pm
ORD
- ORF
1 stop21h 06m
Spirit Airlines
Thu 5/146:34 pm
ORF
- ORD
1 stop14h 48m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$316
This CheapOair deal was found by Cheapflights users on 4/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:49 am
ORD
- ORF
1 stop24h 09m
Multiple Airlines
Sat 5/1611:42 am
ORF
- ORD
1 stop9h 09m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 5/154:52 pm
MDW
- ORF
2 stops17h 03m
Multiple Airlines
Sun 5/178:49 pm
ORF
- MDW
1 stop20h 08m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 5/211:50 pm
ORD
- ORF
1 stop20h 21m
Frontier
Sun 5/2412:06 pm
ORF
- ORD
2 stops12h 07m
Frontier
Deal found 4/29![Frontier logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/2212:04 pm
MDW
- ORF
1 stop22h 11m
Multiple Airlines
Mon 5/256:34 pm
ORF
- MDW
2 stops28h 28m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$312
This American Airlines deal was found by Cheapflights users on 4/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:40 pm
ORD
- ORF
Nonstop2h 27m
American Airlines
Tue 6/26:45 am
ORF
- ORD
Nonstop2h 42m
American Airlines
Deal found 4/26![American Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Wed 5/276:40 pm
ORD
- ORF
Nonstop2h 27m
American Airlines
Sat 5/301:17 pm
ORF
- ORD
Nonstop2h 31m
American Airlines
Deal found 4/25![American Airlines logo]()
$306
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 April 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 April 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/276:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 4/27![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Tue 5/266:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 4/29![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 5/286:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 4/29![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Wed 5/271:50 pm
ORD
- ORF
1 stop20h 21m
Frontier
Deal found 4/29![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Sat 6/206:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 4/25![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Sat 5/2311:59 am
MDW
- ORF
1 stop22h 12m
Frontier
Deal found 4/25![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Mon 5/256:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 4/29![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Sat 5/236:55 am
ORD
- ORF
1 stop27h 16m
Frontier
Deal found 4/27![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Mon 6/16:55 am
ORD
- ORF
1 stop27h 16m
Frontier
Deal found 4/29![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 7/2512:11 pm
MDW
- ORF
1 stop22h 10m
Frontier
Deal found 4/28![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Tue 6/2312:27 pm
MDW
- ORF
1 stop21h 59m
Frontier
Deal found 4/29![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Thu 6/256:55 am
ORD
- ORF
1 stop27h 31m
Frontier
Deal found 4/28![Frontier logo]()
$93
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 April 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $298 (CheapOair) |
One-way from | $71 (Kiwi.com) |
Popular in | March |
Cheapest in | December |
Average price | $469 |
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 April 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
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 7/25
6:25 pm-9:25 pm
Nonstop2h 00m
Norfolk
Sat 8/1
8:15 am-9:25 am
Nonstop2h 10m
$317
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Wed 6/17
12:22 pm-3:43 pm
Nonstop2h 21m
Norfolk
Sun 6/21
6:00 am-7:28 am
Nonstop2h 28m
$340
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 7/1
7:55 am-11:05 am
Nonstop2h 10m
Norfolk
Sat 7/4
7:10 am-8:15 am
Nonstop2h 05m
$340
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Wed 6/17
6:45 am-10:07 am
Nonstop2h 22m
Norfolk
Thu 6/18
6:00 am-7:28 am
Nonstop2h 28m
$340
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 7/1
7:55 am-11:05 am
Nonstop2h 10m
Norfolk
Mon 7/6
3:30 pm-4:35 pm
Nonstop2h 05m
$340
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Wed 6/17
12:22 pm-3:43 pm
Nonstop2h 21m
Norfolk
Mon 6/22
8:00 am-9:32 am
Nonstop2h 32m
$340
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 6/17
7:55 am-11:05 am
Nonstop2h 10m
Norfolk
Sun 6/21
6:15 pm-11:40 pm
1 stop6h 25m
$350
Quickest round-trip
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 5/23
7:50 am-10:50 am
Nonstop2h 00m
Norfolk
Sat 5/30
7:55 am-9:00 am
Nonstop2h 05m
$355
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 5/27
6:05 pm-9:10 pm
Nonstop2h 05m
Norfolk
Wed 6/3
6:25 pm-7:35 pm
Nonstop2h 10m
$357
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 6/17
12:45 pm-7:28 pm
1 stop5h 43m
Norfolk
Mon 6/22
10:16 am-4:16 pm
1 stop7h 00m
$360
Showing 1-10 of 45 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 April 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 6% on your trip compared to booking a flight at noon.
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 April 25, 2026.
Travelers seeking maximum savings on their Chicago to Virginia Beach flight should consider departing on Sunday mornings when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 30, 2026.
The most flights from CHI to V1B are scheduled on a Wednesday (29 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Chicago to Virginia Beach?
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 April 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.
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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Complete your trip
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Popular flights
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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 April 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 April 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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$265 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$174 | Average$354 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$392 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$236 | Average$403 | FlexibilityNo cancel fee | On-time71% |