$103+ Cheap flights from Virginia Beach, VA to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Oct 17 — Oct 241
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 29 days in advance, depart on a Wednesday or Thursday 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 September 17, 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 September 17, 2026.
This Priceline deal was found by Cheapflights users on 9/13. 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.
Thu 10/221:23 pm -
1 stop5h 22m
Sun 10/256:24 am -
1 stop5h 10m
Deal found 9/13![Frontier logo]()
$280
This Delta deal was found by Cheapflights users on 9/14. 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 10/86:00 am -
1 stop4h 32m
Mon 10/126:44 pm -
1 stop3h 48m
Deal found 9/14![Delta logo]()
$317
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:59 pm -
1 stop5h 09m
Mon 10/199:02 am -
1 stop7h 25m
Deal found 9/14![American Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 9/16. 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 12/33:05 pm -
2 stops5h 40m
Mon 12/78:50 am -
1 stop3h 40m
Deal found 9/16![Southwest logo]()
$318
This deal was found by Cheapflights users on 9/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:19 pm -
1 stop5h 26m
Thu 10/296:16 am -
1 stop5h 30m
Deal found 9/14![Frontier logo]()
$319
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:23 pm -
1 stop6h 08m
Sun 10/258:26 am -
1 stop9h 20m
Deal found 9/14![Frontier logo]()
$319
This Frontier deal was found by Cheapflights users on 9/12. 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.
Sun 9/271:18 pm -
1 stop11h 26m
Thu 10/16:25 am -
1 stop5h 04m
Deal found 9/12![Frontier logo]()
$320
This Priceline deal was found by Cheapflights users on 9/16. 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.
Thu 10/11:18 pm -
1 stop6h 05m
Wed 11/49:51 am -
1 stop7h 53m
Deal found 9/16![Frontier logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/103:50 pm -
1 stop8h 53m
Mon 10/126:15 am -
2 stops17h 03m
Deal found 9/13![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/217:41 pm -
1 stop12h 50m
Tue 10/277:50 pm -
2 stops21h 54m
Deal found 9/12![Frontier logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 11/143:50 pm -
1 stop18h 06m
Tue 11/177:28 pm -
2 stops25h 42m
Deal found 9/13![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/33:47 pm -
1 stop18h 33m
Mon 10/57:28 pm -
2 stops16h 45m
Deal found 9/13![Multiple Airlines logo]()
$325
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 September 17, 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 September 17, 2026.
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:25 pm -
1 stop5h 55m
Mon 11/92:37 pm -
1 stop6h 28m
Deal found 9/15![Delta logo]()
$336
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/276:10 am -
Nonstop2h 42m
Wed 10/2810:59 am -
Nonstop2h 23m
Deal found 9/16![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 9/14. 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.
Wed 11/183:05 pm -
1 stop4h 50m
Fri 11/207:05 pm -
Nonstop2h 05m
Deal found 9/14![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 11/97:00 am -
1 stop12h 13m
Thu 11/129:30 am -
2 stops12h 26m
Deal found 9/15![Multiple Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 9/15. 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 10/1612:10 pm -
2 stops8h 05m
Sat 10/178:05 am -
Nonstop2h 00m
Deal found 9/15![Southwest logo]()
$351
This United Airlines deal was found by Cheapflights users on 9/16. 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 11/26:10 am -
Nonstop2h 42m
Sat 11/79:00 am -
1 stop7h 21m
Deal found 9/16![United Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/229:55 am -
1 stop6h 40m
Mon 10/268:00 am -
Nonstop2h 00m
Deal found 9/14![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 9/13. 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 32m
Sun 11/16:44 pm -
1 stop3h 48m
Deal found 9/13![Delta logo]()
$433
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 12/186:15 am -
1 stop4h 25m
Fri 1/16:10 pm -
1 stop4h 20m
Deal found 9/14![United Airlines logo]()
$394
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 10/176:25 am -
2 stops10h 00m
Sat 10/248:10 am -
2 stops6h 05m
Deal found 9/16![Southwest logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/87:41 pm -
1 stop13h 21m
Mon 10/126:13 pm -
2 stops17h 21m
Deal found 9/12![Multiple Airlines logo]()
$482
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/215:01 pm -
Nonstop2h 29m
Tue 10/2710:59 am -
Nonstop2h 23m
Deal found 9/12![United Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 10/166:05 pm -
1 stop4h 55m
Sun 10/187:40 am -
Nonstop2h 00m
Deal found 9/14![Southwest logo]()
$384
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/171:00 pm -
Nonstop2h 34m
Wed 10/2111:57 am -
Nonstop2h 19m
Deal found 9/13![United Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 9/16. 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.
Mon 10/125:50 pm -
1 stop7h 05m
Wed 10/141:35 pm -
2 stops5h 20m
Deal found 9/16![Southwest logo]()
$398
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/226:20 am -
Nonstop2h 33m
Sun 10/257:29 am -
Nonstop2h 24m
Deal found 9/12![United Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 9/277:43 pm -
1 stop14h 49m
Mon 9/284:50 pm -
1 stop23h 53m
Deal found 9/16![Multiple Airlines logo]()
$560
This Southwest deal was found by Cheapflights users on 9/15. 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.
Sat 10/175:00 pm -
Nonstop2h 10m
Mon 10/198:00 am -
Nonstop2h 00m
Deal found 9/15![Southwest logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 10/67:43 pm -
1 stop14h 01m
Thu 10/89:03 pm -
1 stop22h 39m
Deal found 9/15![Multiple Airlines logo]()
$570
This Southwest deal was found by Cheapflights users on 9/12. 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 11/257:20 pm -
Nonstop2h 15m
Fri 11/277:05 pm -
Nonstop2h 05m
Deal found 9/12![Southwest logo]()
$413
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/86:20 am -
Nonstop2h 33m
Sun 10/118:45 am -
Nonstop2h 30m
Deal found 9/16![United Airlines logo]()
$458
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/97:00 am -
1 stop13h 12m
Mon 10/126:13 pm -
2 stops17h 21m
Deal found 9/12![Multiple Airlines logo]()
$587
This Southwest deal was found by Cheapflights users on 9/12. 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 10/227:00 pm -
Nonstop2h 10m
Tue 10/277:45 am -
2 stops7h 25m
Deal found 9/12![Southwest logo]()
$428
This United Airlines deal was found by Cheapflights users on 9/13. 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 11/266:00 am -
1 stop8h 09m
Sat 11/287:29 am -
Nonstop2h 24m
Deal found 9/13![United Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/307:50 pm -
1 stop5h 11m
Sun 11/17:50 pm -
2 stops17h 22m
Deal found 9/15![United Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/148:00 am -
2 stops29h 22m
Sun 10/189:33 pm -
1 stop22h 09m
Deal found 9/15![Multiple Airlines logo]()
$692
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/127:00 am -
1 stop11h 23m
Wed 10/1411:04 am -
1 stop10h 25m
Deal found 9/16![Multiple Airlines logo]()
$713
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated September 17, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 9/12. 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.
Sun 9/271:18 pm -
1 stop11h 26m
Thu 10/16:25 am -
1 stop5h 04m
Deal found 9/12![Frontier logo]()
$320
This Super.com deal was found by Cheapflights users on 9/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/271:18 pm -
1 stop6h 05m
Wed 9/303:50 pm -
1 stop25h 58m
Deal found 9/14![Frontier logo]()
$327
This Priceline deal was found by Cheapflights users on 9/16. 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.
Thu 10/11:18 pm -
1 stop6h 05m
Wed 11/49:51 am -
1 stop7h 53m
Deal found 9/16![Frontier logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/33:47 pm -
1 stop18h 33m
Mon 10/57:28 pm -
2 stops16h 45m
Deal found 9/13![Multiple Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 9/14. 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 10/86:00 am -
1 stop4h 32m
Mon 10/126:44 pm -
1 stop3h 48m
Deal found 9/14![Delta logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/103:50 pm -
1 stop8h 53m
Mon 10/126:15 am -
2 stops17h 03m
Deal found 9/13![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:00 am -
2 stops30h 32m
Mon 10/197:44 pm -
1 stop15h 50m
Deal found 9/14![Multiple Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/217:41 pm -
1 stop12h 50m
Tue 10/277:50 pm -
2 stops21h 54m
Deal found 9/12![Frontier logo]()
$322
This Priceline deal was found by Cheapflights users on 9/13. 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.
Thu 10/221:23 pm -
1 stop5h 22m
Sun 10/256:24 am -
1 stop5h 10m
Deal found 9/13![Frontier logo]()
$280
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:23 pm -
1 stop6h 08m
Sun 10/258:26 am -
1 stop9h 20m
Deal found 9/14![Frontier logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:21 am -
Nonstop2h 39m
Thu 10/221:22 pm -
1 stop5h 35m
Deal found 9/14![American Airlines logo]()
$326
This deal was found by Cheapflights users on 9/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/251:19 pm -
1 stop5h 26m
Thu 10/296:16 am -
1 stop5h 30m
Deal found 9/14![Frontier logo]()
$319
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 September 17, 2026.
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Super.com deal was found by Cheapflights users on 9/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:50 pm -
1 stop8h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 11/171:44 pm -
1 stop24h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/131:19 pm -
1 stop23h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$106
This Frontier deal was found by Cheapflights users on 9/16. 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.
Tue 11/171:44 pm -
1 stop5h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$108
This Super.com deal was found by Cheapflights users on 9/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:18 pm -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$108
This Super.com deal was found by Cheapflights users on 9/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:18 pm -
1 stop5h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 9/15. 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 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$113
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:23 pm -
1 stop5h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 10/131:19 pm -
1 stop11h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 9/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:43 pm -
1 stop12h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$115
This Frontier deal was found by Cheapflights users on 9/16. 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.
Wed 10/147:41 pm -
1 stop12h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 11/121:31 pm -
1 stop6h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$118
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $280 (Priceline) |
One-way from | $103 (Super.com) |
Popular in | July |
Cheapest in | December |
Average price | $382 |
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 September 17, 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 - RFD Chicago Greater Rockford
ORFRFD
Norfolk
Tue 10/6
7:43 pm-8:44 am
1 stop14h 01m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Sat 10/10
6:20 am-7:53 am
Nonstop2h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Wed 10/7
6:20 am-7:53 am
Nonstop2h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$130
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Wed 10/14
11:00 am-4:14 pm
1 stop6h 14m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$140
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Tue 10/13
4:45 pm-7:25 pm
1 stop3h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$140
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Sat 12/12
8:00 am-1:42 pm
1 stop6h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$140
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Sat 10/10
12:30 pm-4:26 pm
1 stop4h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$140
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Tue 12/15
3:00 pm-7:05 pm
1 stop5h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$140
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Tue 12/15
6:15 am-2:30 pm
2 stops9h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$145
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Wed 11/18
8:30 am-12:46 pm
1 stop5h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Showing 1-10 of 55 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-MDW
ORF-ORD
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-MDW
ORF-ORD
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 September 17, 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 8% 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 September 17, 2026.
The most flights from V1B to CHI are scheduled on a Monday (29 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 on average).
How much does it cost to fly round-trip from Virginia Beach to Chicago?
Airfare is below average for this route at the moment.
Virginia Beach to Chicago flights typically cost between $314 and $418 in October.The cheapest round-trip price found within the last 5 days was $280 on Frontier (Oct 22-Oct 25).
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 September 12, 2026.
Travelers seeking maximum savings on their Virginia Beach to Chicago flight should consider departing on Friday 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 September 17, 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
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 September 17, 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 September 17, 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 September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$154 | Average$369 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$399 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$220 | Average$352 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$253 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$253 | Average$395 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$260 | Average$260 | FlexibilityNo cancel fee | On-timeN/A |