$82+ Cheap flights from Virginia Beach, VA to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Virginia Beach to Chicago 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 Virginia Beach to Chicago are usually found in December or January, booked 2 days in advance, depart on a Thursday or Wednesday and return on a Saturday
Cheap flight deals from Virginia Beach to Chicago
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Cheapest flights from Virginia Beach to ChicagoExplore the most affordable flight options available from Virginia Beach to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Virginia Beach to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This JetBlue deal was found by Cheapflights users on 8/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:25 am -
1 stop7h 20m
Thu 10/19:38 am -
1 stop7h 55m
Deal found 8/17![JetBlue logo]()
$313
This CheapOair deal was found by Cheapflights users on 8/17. 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.
Tue 8/251:20 pm -
1 stop10h 27m
Tue 9/16:05 am -
1 stop5h 20m
Deal found 8/17![Frontier logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 10/27:43 pm -
2 stops23h 44m
Mon 10/57:28 pm -
1 stop16h 01m
Deal found 8/20![Frontier logo]()
$314
This Southwest deal was found by Cheapflights users on 8/19. 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 9/186:45 pm -
Nonstop2h 05m
Fri 9/256:50 pm -
Nonstop2h 10m
Deal found 8/19![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/21. 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 9/185:02 pm -
Nonstop2h 28m
Fri 9/2511:57 am -
Nonstop2h 19m
Deal found 8/21![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 8/20. 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 10/25:50 pm -
1 stop7h 05m
Mon 10/56:25 pm -
1 stop4h 10m
Deal found 8/20![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 8/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:25 pm -
1 stop7h 18m
Mon 11/96:45 am -
1 stop4h 40m
Deal found 8/17![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:40 am -
Nonstop2h 50m
Tue 12/88:33 pm -
Nonstop2h 26m
Deal found 8/21![American Airlines logo]()
$317
This KAYAK deal was found by Cheapflights users on 8/20. 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 9/216:00 am -
1 stop4h 07m
Wed 9/231:00 pm -
1 stop6h 13m
Deal found 8/20![Delta logo]()
$318
This KAYAK deal was found by Cheapflights users on 8/20. 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 9/217:19 pm -
1 stop5h 40m
Wed 9/236:00 am -
1 stop6h 44m
Deal found 8/20![Delta logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/101:18 pm -
1 stop6h 05m
Sun 9/137:28 pm -
2 stops27h 50m
Deal found 8/17![Multiple Airlines logo]()
$319
This Frontier deal was found by Cheapflights users on 8/16. 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.
Fri 8/281:20 pm -
1 stop10h 27m
Mon 8/316:05 am -
1 stop5h 20m
Deal found 8/16![Frontier logo]()
$320
Best flights from Virginia Beach to ChicagoDiscover carefully curated flight deals from Virginia Beach to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Virginia Beach to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This United Airlines deal was found by Cheapflights users on 8/21. 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 9/185:02 pm -
Nonstop2h 28m
Fri 9/2511:57 am -
Nonstop2h 19m
Deal found 8/21![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 8/17. 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.
Fri 11/65:55 pm -
2 stops5h 45m
Mon 11/97:50 am -
2 stops8h 25m
Deal found 8/17![Southwest logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 11/56:10 pm -
1 stop15h 28m
Mon 11/97:03 pm -
2 stops15h 59m
Deal found 8/17![Multiple Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 8/21. 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 9/1012:15 pm -
1 stop5h 44m
Mon 9/145:10 pm -
1 stop5h 23m
Deal found 8/21![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 8/16. 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 9/246:20 am -
Nonstop2h 28m
Sun 9/2711:57 am -
Nonstop2h 19m
Deal found 8/16![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 8/21. 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 10/512:10 pm -
2 stops7h 45m
Mon 10/126:45 pm -
Nonstop2h 00m
Deal found 8/21![Southwest logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 10/307:00 am -
1 stop13h 06m
Mon 11/25:55 pm -
2 stops17h 07m
Deal found 8/17![Multiple Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 8/18. 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.
Fri 10/306:00 am -
1 stop4h 17m
Sun 11/16:44 pm -
1 stop3h 48m
Deal found 8/18![Delta logo]()
$364
This KAYAK deal was found by Cheapflights users on 8/19. 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.
Wed 9/306:15 am -
3 stops8h 15m
Wed 9/308:35 pm -
2 stops16h 00m
Deal found 8/19![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:15 pm -
Nonstop2h 44m
Wed 10/287:29 am -
Nonstop2h 24m
Deal found 8/18![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 8/19. 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 11/247:45 am -
Nonstop2h 10m
Fri 11/276:10 pm -
1 stop4h 20m
Deal found 8/19![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Sat 11/712:26 pm -
Nonstop2h 44m
Tue 11/177:29 am -
Nonstop2h 24m
Deal found 8/16![United Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 8/16. 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 9/171:00 pm -
Nonstop2h 34m
Sat 9/1911:55 am -
Nonstop2h 18m
Deal found 8/16![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 8/20. 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 10/87:00 pm -
Nonstop2h 10m
Sun 10/117:40 am -
Nonstop2h 00m
Deal found 8/20![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Wed 11/412:04 pm -
Nonstop2h 44m
Tue 11/177:29 am -
Nonstop2h 24m
Deal found 8/16![United Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/17:43 pm -
1 stop13h 16m
Sun 10/411:12 am -
2 stops22h 30m
Deal found 8/19![Multiple Airlines logo]()
$495
This Southwest deal was found by Cheapflights users on 8/20. 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 10/112:10 pm -
2 stops7h 45m
Sun 10/410:00 am -
2 stops6h 05m
Deal found 8/20![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:20 am -
Nonstop2h 33m
Sun 9/278:45 am -
Nonstop2h 30m
Deal found 8/18![United Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 10/27:00 am -
1 stop13h 12m
Sun 10/411:12 am -
2 stops22h 30m
Deal found 8/17![Multiple Airlines logo]()
$500
This Southwest deal was found by Cheapflights users on 8/20. 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 9/101:05 pm -
1 stop4h 10m
Mon 9/149:20 am -
2 stops7h 35m
Deal found 8/20![Southwest logo]()
$387
This United Airlines deal was found by Cheapflights users on 8/16. 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 11/106:15 am -
1 stop4h 30m
Sat 11/1412:28 pm -
Nonstop2h 22m
Deal found 8/16![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 8/17. 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 11/237:30 am -
Nonstop2h 15m
Mon 11/307:00 am -
1 stop9h 30m
Deal found 8/17![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Mon 11/96:02 pm -
1 stop6h 59m
Wed 11/187:29 am -
Nonstop2h 24m
Deal found 8/16![United Airlines logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 9/257:00 am -
1 stop10h 15m
Sun 9/279:29 pm -
1 stop22h 13m
Deal found 8/18![Multiple Airlines logo]()
$557
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/107:59 pm -
1 stop4h 41m
Mon 9/146:15 pm -
Nonstop2h 26m
Deal found 8/20![United Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 8/17. 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 11/66:15 am -
1 stop4h 30m
Tue 11/107:29 am -
Nonstop2h 24m
Deal found 8/17![United Airlines logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/47:00 am -
1 stop13h 07m
Mon 9/76:02 pm -
1 stop18h 28m
Deal found 8/19![Multiple Airlines logo]()
$715
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated August 21, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/17. 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.
Tue 8/251:20 pm -
1 stop10h 27m
Tue 9/16:05 am -
1 stop5h 20m
Deal found 8/17![Frontier logo]()
$314
This Expedia deal was found by Cheapflights users on 8/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:20 pm -
1 stop10h 27m
Mon 8/316:05 am -
1 stop5h 20m
Deal found 8/16![Frontier logo]()
$320
This Priceline deal was found by Cheapflights users on 8/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:20 pm -
1 stop7h 39m
Mon 8/316:05 am -
1 stop9h 06m
Deal found 8/16![Frontier logo]()
$320
This CheapOair deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:06 pm -
1 stop7h 02m
Tue 9/85:29 pm -
1 stop24h 19m
Deal found 8/20![Frontier logo]()
$321
This Delta deal was found by Cheapflights users on 8/19. 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 9/912:15 pm -
1 stop5h 44m
Fri 9/115:10 pm -
1 stop5h 23m
Deal found 8/19![Delta logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/101:18 pm -
1 stop6h 05m
Sun 9/137:28 pm -
2 stops27h 50m
Deal found 8/17![Multiple Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 8/18. 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 9/146:25 am -
2 stops7h 00m
Wed 9/233:05 pm -
1 stop4h 50m
Deal found 8/18![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 8/19. 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 9/186:45 pm -
Nonstop2h 05m
Fri 9/256:50 pm -
Nonstop2h 10m
Deal found 8/19![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/186:05 am -
Nonstop2h 29m
Fri 9/186:15 pm -
Nonstop2h 26m
Deal found 8/17![United Airlines logo]()
$315
This KAYAK deal was found by Cheapflights users on 8/20. 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 9/216:00 am -
1 stop4h 07m
Wed 9/231:00 pm -
1 stop6h 13m
Deal found 8/20![Delta logo]()
$318
This KAYAK deal was found by Cheapflights users on 8/20. 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 9/217:19 pm -
1 stop5h 40m
Wed 9/236:00 am -
1 stop6h 44m
Deal found 8/20![Delta logo]()
$318
This JetBlue deal was found by Cheapflights users on 8/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:25 am -
1 stop7h 20m
Thu 10/19:38 am -
1 stop7h 55m
Deal found 8/17![JetBlue logo]()
$313
One-way flights from Virginia Beach to ChicagoSearch for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 11/1612:57 pm -
1 stop24h 05m
Deal found 8/16![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Tue 9/151:18 pm -
1 stop29h 33m
Deal found 8/16![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Tue 9/151:18 pm -
1 stop6h 05m
Deal found 8/16![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Tue 9/1512:39 pm -
2 stops27h 41m
Deal found 8/18![Multiple Airlines logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/131:19 pm -
1 stop11h 24m
Deal found 8/17![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Wed 11/1812:57 pm -
1 stop7h 47m
Deal found 8/16![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 8/16. 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 9/171:18 pm -
1 stop5h 28m
Deal found 8/16![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:19 pm -
1 stop6h 12m
Deal found 8/17![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 11/1612:57 pm -
1 stop23h 01m
Deal found 8/16![Frontier logo]()
$100
This Super.com deal was found by Cheapflights users on 8/19. 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.
Wed 9/97:43 pm -
1 stop15h 37m
Deal found 8/19![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:50 pm -
1 stop8h 53m
Deal found 8/17![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:41 pm -
1 stop12h 50m
Deal found 8/17![Frontier logo]()
$105
Find flight deals from Virginia Beach to Chicago
Keep the following information in mind while searching for Virginia Beach to Chicago flight deals. Data was last updated August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $313 (JetBlue) |
One-way from | $82 (Kiwi.com) |
Popular in | July |
Cheapest in | December |
Average price | $367 |
Cheapflights Fare Finder
Customize your flight search to find flights from Virginia Beach to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
Use the filters below to find and compare flights from Virginia Beach to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Fri 9/18
5:02 pm-6:30 pm
Nonstop2h 28m
Chicago O'Hare Intl
Fri 9/25
11:57 am-3:16 pm
Nonstop2h 19m
$315
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Thu 9/24
6:20 am-7:48 am
Nonstop2h 28m
Chicago O'Hare Intl
Sun 9/27
11:57 am-3:16 pm
Nonstop2h 19m
$325
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Fri 11/6
5:55 pm-10:40 pm
2 stops5h 45m
Chicago Midway
Mon 11/9
7:50 am-5:15 pm
2 stops8h 25m
$326
NorfolkChicago
ORF Norfolk - RFD Chicago Greater Rockford
ORFRFD
Norfolk
Thu 11/5
6:10 pm-8:38 am
1 stop15h 28m
Chicago Greater Rockford
Mon 11/9
7:03 pm-12:02 pm
2 stops15h 59m
$329
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Mon 10/5
12:10 pm-6:55 pm
2 stops7h 45m
Chicago Midway
Mon 10/12
6:45 pm-9:45 pm
Nonstop2h 00m
$330
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Wed 9/30
6:15 am-1:30 pm
3 stops8h 15m
Chicago Midway
Wed 9/30
8:35 pm-1:35 pm
2 stops16h 00m
$347
NorfolkChicago
ORF Norfolk - RFD Chicago Greater Rockford
ORFRFD
Norfolk
Fri 10/30
7:00 am-7:06 pm
1 stop13h 06m
Chicago Greater Rockford
Mon 11/2
5:55 pm-12:02 pm
2 stops17h 07m
$349
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Tue 11/24
7:45 am-8:55 am
Nonstop2h 10m
Chicago Midway
Fri 11/27
6:10 pm-11:30 pm
1 stop4h 20m
$354
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Tue 10/27
12:15 pm-1:59 pm
Nonstop2h 44m
Chicago O'Hare Intl
Wed 10/28
7:29 am-10:53 am
Nonstop2h 24m
$357
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Sat 11/7
12:26 pm-2:10 pm
Nonstop2h 44m
Chicago O'Hare Intl
Tue 11/17
7:29 am-10:53 am
Nonstop2h 24m
$357
Showing 1-10 of 52 resultsSorted by cheapest first
Best time to book a flight from Virginia Beach to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Virginia Beach with our price prediction graph.
ORF-ORD
ORF-MDW
ORF-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Virginia Beach to Chicago
V1B-CHI
ORF-ORD
ORF-MDW
ORF-RFD
What is the cheapest time of day to fly from V1B to CHI?
Find hourly flight availability from Virginia Beach to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2026.
A simple way to save on the total cost of your ticket is to fly from Virginia Beach to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 9% on your trip compared to booking a flight in the morning.
Weekly flight availability from Virginia Beach to Chicago
Explore weekly flight availability from Virginia Beach to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 21, 2026.
The most flights from V1B to CHI are scheduled on a Wednesday (32 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 Virginia Beach to Chicago?
Airfare is typical for this route at the moment.
Virginia Beach to Chicago flights typically cost between $300 and $439 in September.The cheapest round-trip price found within the last 5 days was $313 on JetBlue (Sep 30-Oct 1).
What is the cheapest day to fly from Virginia Beach to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Virginia Beach to Chicago. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Virginia Beach to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 21, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Virginia Beach to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Virginia Beach to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Virginia Beach to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 21, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Virginia Beach to Chicago by cabin class
Find flights from Virginia Beach to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Virginia Beach and Chicago flights
Browse other Virginia Beach and Chicago flight options. Last updated on August 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Virginia Beach to Chicago flights
Consider these flights traveling from Virginia Beach to Chicago.
Top 6 airlines flying from Virginia Beach to Chicago
Discover the top 6 airlines that operate flights from Virginia Beach to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$369 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$352 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$399 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$389 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$442 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$260 | Average$260 | FlexibilityNo cancel fee | On-timeN/A |