$106+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — RIC
Jul 18 — Jul 251
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 61 days in advance, depart on a Saturday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to Virginia Beach
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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 June 18, 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 June 18, 2026.
This Southwest deal was found by Cheapflights users on 6/18. 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 8/299:05 am
MDW
- ORF
1 stop4h 55m
Southwest
Sun 9/66:05 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 6/18![Southwest logo]()
$331
This CheapOair deal was found by Cheapflights users on 6/18. 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 8/16:00 am
ORD
- ORF
2 stops10h 12m
Multiple Airlines
Sat 8/159:34 pm
ORF
- ORD
1 stop26h 36m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 6/17. 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.
Tue 6/307:25 am
MDW
- ORF
1 stop3h 35m
Southwest
Tue 7/144:30 pm
ORF
- MDW
2 stops7h 45m
Southwest
Deal found 6/17![Southwest logo]()
$332
This CheapOair deal was found by Cheapflights users on 6/17. 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 9/249:26 am
ORD
- ORF
1 stop6h 49m
Multiple Airlines
Mon 9/287:05 pm
ORF
- ORD
2 stops17h 42m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/75:13 pm
ORD
- ORF
2 stops17h 02m
Frontier
Thu 7/912:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Deal found 6/17![Frontier logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 8/36:05 am
MDW
- ORF
2 stops13h 34m
Frontier
Sat 8/812:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 6/18![Frontier logo]()
$334
This CheapOair deal was found by Cheapflights users on 6/17. 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
Multiple Airlines
Wed 8/196:00 pm
ORF
- ORD
2 stops28h 55m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 6/16. 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 8/69:20 am
MDW
- ORF
2 stops7h 35m
Southwest
Mon 8/101:55 pm
ORF
- MDW
2 stops6h 35m
Southwest
Deal found 6/16![Southwest logo]()
$335
This American Airlines deal was found by Cheapflights users on 6/18. 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 7/282:52 pm
ORD
- ORF
Nonstop2h 24m
American Airlines
Sat 8/16:50 am
ORF
- ORD
Nonstop2h 40m
American Airlines
Deal found 6/18![American Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/75:13 pm
ORD
- ORF
2 stops17h 02m
Frontier
Sat 7/1112:16 pm
ORF
- ORD
1 stop8h 37m
Frontier
Deal found 6/17![Frontier logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/16. 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 6/306:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Wed 7/16:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 6/16![United Airlines logo]()
$337
This CheapOair deal was found by Cheapflights users on 6/18. 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 7/165:13 pm
ORD
- ORF
1 stop26h 26m
Multiple Airlines
Tue 7/216:00 pm
ORF
- ORD
2 stops24h 34m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$338
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 June 18, 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 June 18, 2026.
This Southwest deal was found by Cheapflights users on 6/18. 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 9/238:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Sun 9/276:20 am
ORF
- MDW
2 stops8h 45m
Southwest
Deal found 6/18![Southwest logo]()
$335
This United Airlines deal was found by Cheapflights users on 6/16. 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 8/66:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Sun 8/96:15 am
ORF
- ORD
1 stop4h 21m
United Airlines
Deal found 6/16![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 6/16. 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.
Fri 9/412:46 pm
MDW
- ORF
1 stop6h 35m
Delta
Thu 9/1012:50 pm
ORF
- MDW
1 stop5h 07m
Delta
Deal found 6/16![Delta logo]()
$354
This KAYAK deal was found by Cheapflights users on 6/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:14 pm
ORD
- ORF
Nonstop2h 25m
American Airlines
Fri 7/248:20 pm
ORF
- ORD
1 stop4h 41m
American Airlines
Deal found 6/17![American Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 6/18. 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 8/2911:00 am
MDW
- ORF
2 stops8h 55m
Southwest
Sun 9/64:30 pm
ORF
- MDW
1 stop7h 05m
Southwest
Deal found 6/18![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 6/17. 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 7/16:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Sat 7/46:05 am
ORF
- ORD
1 stop4h 31m
United Airlines
Deal found 6/17![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 6/14. 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.
Thu 10/87:10 am
ORD
- ORF
1 stop4h 37m
Delta
Sun 10/117:40 pm
ORF
- ORD
1 stop5h 10m
Delta
Deal found 6/14![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 6/17. 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 7/157:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sun 7/198:05 pm
ORF
- MDW
1 stop5h 20m
Southwest
Deal found 6/17![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 6/15. 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 9/16:15 pm
ORD
- ORF
Nonstop2h 26m
United Airlines
Wed 9/25:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 6/15![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 6/15. 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 7/2911:25 am
MDW
- ORF
2 stops5h 55m
Southwest
Sun 8/22:45 pm
ORF
- MDW
2 stops8h 00m
Southwest
Deal found 6/15![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/17. 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 9/46:15 pm
ORD
- ORF
Nonstop2h 26m
United Airlines
Sun 9/136:05 am
ORF
- ORD
Nonstop2h 29m
United Airlines
Deal found 6/17![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 6/17. 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 10/267:45 am
MDW
- ORF
2 stops9h 45m
Southwest
Fri 11/64:35 pm
ORF
- MDW
1 stop8h 20m
Southwest
Deal found 6/17![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 6/14. 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 8/912:22 pm
ORD
- ORF
Nonstop2h 28m
United Airlines
Thu 8/136:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 6/14![United Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 6/16. 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 8/68:10 am
MDW
- ORF
2 stops8h 45m
Southwest
Sun 8/96:20 am
ORF
- MDW
2 stops8h 45m
Southwest
Deal found 6/16![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 6/15. 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 9/259:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Sun 9/276:30 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 6/15![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 6/14. 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 7/277:00 am
MDW
- ORF
1 stop3h 40m
Southwest
Sat 8/19:55 am
ORF
- MDW
2 stops6h 05m
Southwest
Deal found 6/14![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 6/16. 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 7/242:40 pm
MDW
- ORF
2 stops7h 50m
Southwest
Sun 7/268:05 pm
ORF
- MDW
1 stop5h 20m
Southwest
Deal found 6/16![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 6/18. 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 8/37:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Sat 8/88:10 am
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 6/18![Southwest logo]()
$389
Last-minute flights from Chicago to Virginia BeachDiscover last-minute flight deals from Chicago to Virginia Beach. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Virginia Beach. Data last updated June 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/17. 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.
Tue 6/307:25 am
MDW
- ORF
1 stop3h 35m
Southwest
Tue 7/144:30 pm
ORF
- MDW
2 stops7h 45m
Southwest
Deal found 6/17![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 6/16. 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 6/306:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Wed 7/16:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Deal found 6/16![United Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:29 pm
ORD
- ORF
1 stop20h 57m
Frontier
Sat 7/412:06 pm
ORF
- ORD
1 stop8h 44m
Frontier
Deal found 6/18![Frontier logo]()
$339
This Travelocity deal was found by Cheapflights users on 6/17. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:59 pm
ORD
- ORF
1 stop25h 14m
Frontier
Mon 7/69:34 pm
ORF
- ORD
1 stop26h 36m
Frontier
Deal found 6/17![Frontier logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/75:13 pm
ORD
- ORF
2 stops17h 02m
Frontier
Thu 7/912:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Deal found 6/17![Frontier logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/75:13 pm
ORD
- ORF
2 stops17h 02m
Frontier
Sat 7/1112:16 pm
ORF
- ORD
1 stop8h 37m
Frontier
Deal found 6/17![Frontier logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:05 am
ORD
- ORF
2 stops9h 21m
Multiple Airlines
Sat 7/1112:16 pm
ORF
- ORD
1 stop8h 37m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/128:05 am
ORD
- ORF
2 stops26h 10m
Frontier
Sun 7/1912:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Deal found 6/17![Frontier logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/127:05 am
ORD
- ORF
1 stop27h 10m
Multiple Airlines
Thu 7/1612:59 pm
ORF
- ORD
2 stops24h 16m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$335
This CheapOair deal was found by Cheapflights users on 6/18. 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 7/165:13 pm
ORD
- ORF
1 stop26h 26m
Multiple Airlines
Tue 7/216:00 pm
ORF
- ORD
2 stops24h 34m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 6/18. 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 7/286:00 am
MDW
- ORF
1 stop5h 45m
Delta
Fri 7/3112:43 pm
ORF
- MDW
1 stop6h 42m
Delta
Deal found 6/18![Delta logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:45 pm
MDW
- ORF
2 stops26h 54m
Frontier
Mon 8/312:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/17![Frontier logo]()
$343
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 June 18, 2026.
Search for one-way flight options from Chicago to Virginia Beach. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 10/1912:03 pm
MDW
- ORF
1 stop22h 59m
Frontier
Deal found 6/18![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 9/1512:03 pm
MDW
- ORF
1 stop22h 59m
Frontier
Deal found 6/17![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 9/142:03 pm
ORD
- ORF
1 stop20h 59m
Frontier
Deal found 6/17![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 9/147:25 am
MDW
- ORF
1 stop27h 37m
Frontier
Deal found 6/17![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 9/152:03 pm
ORD
- ORF
1 stop20h 59m
Frontier
Deal found 6/17![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 8/197:55 am
ORD
- ORF
2 stops9h 31m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$118
This Frontier deal was found by Cheapflights users on 6/18. 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.
Tue 8/186:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 6/18![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:26 am
ORD
- ORF
1 stop6h 49m
Frontier
Deal found 6/16![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 9/127:25 am
MDW
- ORF
1 stop27h 37m
Frontier
Deal found 6/17![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 9/122:03 pm
ORD
- ORF
1 stop20h 59m
Frontier
Deal found 6/17![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Deal found 6/18![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/912:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Deal found 6/17![Frontier logo]()
$127
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 June 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $331 (Southwest) |
One-way from | $106 (Kiwi.com) |
Popular in | March |
Cheapest in | December |
Average price | $397 |
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 June 18, 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
Wed 9/23
8:50 am-12:05 pm
Nonstop2h 15m
Norfolk
Sun 9/27
6:20 am-2:05 pm
2 stops8h 45m
$335
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Thu 8/6
6:45 am-10:07 am
Nonstop2h 22m
Norfolk
Sun 8/9
6:15 am-9:36 am
1 stop4h 21m
$344
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Sat 8/29
11:00 am-8:55 pm
2 stops8h 55m
Norfolk
Sun 9/6
4:30 pm-10:35 pm
1 stop7h 05m
$346
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Wed 7/1
6:45 am-10:07 am
Nonstop2h 22m
Norfolk
Sat 7/4
6:05 am-9:36 am
1 stop4h 31m
$347
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 7/15
7:55 am-11:05 am
Nonstop2h 10m
Norfolk
Sun 7/19
8:05 pm-12:25 am
1 stop5h 20m
$347
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Wed 7/29
11:25 am-6:20 pm
2 stops5h 55m
Norfolk
Sun 8/2
2:45 pm-9:45 pm
2 stops8h 00m
$350
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Fri 9/4
12:46 pm-8:21 pm
1 stop6h 35m
Norfolk
Thu 9/10
12:50 pm-4:57 pm
1 stop5h 07m
$354
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Thu 10/8
7:10 am-12:47 pm
1 stop4h 37m
Norfolk
Sun 10/11
7:40 pm-11:50 pm
1 stop5h 10m
$354
ChicagoNorfolk
ORD - ORF
ORDORF
Chicago O'Hare Intl
Tue 9/1
6:15 pm-9:41 pm
Nonstop2h 26m
Norfolk
Wed 9/2
5:02 pm-6:30 pm
Nonstop2h 28m
$357
ChicagoNorfolk
MDW - ORF
MDWORF
Chicago Midway
Mon 10/26
7:45 am-6:30 pm
2 stops9h 45m
Norfolk
Fri 11/6
4:35 pm-11:55 pm
1 stop8h 20m
$359
Showing 1-10 of 38 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 June 18, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Virginia Beach at noon. 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 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 June 18, 2026.
The most flights from CHI to V1B are scheduled on a Monday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).
How much does it cost to fly round-trip from Chicago to Virginia Beach?
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 June 13, 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. Monday afternoons 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 June 18, 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
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 June 18, 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 June 18, 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 3 airlines flying from Chicago to Virginia Beach
Discover the top 3 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 June 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$361 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$406 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$236 | Average$401 | FlexibilityNo cancel fee | On-time71% |