$102+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Sep 9 — Sep 161
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 September, 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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Best
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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 10, 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 10, 2026.
This CheapOair deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 8/271:20 pm -
1 stop10h 27m
Mon 8/316:05 am -
1 stop5h 20m
Deal found 8/9![Frontier logo]()
$316
This CheapOair deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 11/612:57 pm -
1 stop7h 47m
Sun 11/84:44 pm -
1 stop23h 31m
Deal found 8/7![Frontier logo]()
$316
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/54:00 pm -
Nonstop2h 05m
Sun 9/68:40 am -
Nonstop2h 15m
Deal found 8/5![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/55:02 pm -
Nonstop2h 29m
Sun 9/611:59 am -
Nonstop2h 18m
Deal found 8/5![United Airlines logo]()
$317
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/3012:57 pm -
1 stop7h 47m
Sun 11/19:26 am -
1 stop6h 49m
Deal found 8/7![Frontier logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/271:20 pm -
1 stop10h 27m
Sun 8/306:05 am -
1 stop5h 20m
Deal found 8/8![Frontier logo]()
$319
This Frontier deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/21:20 pm -
1 stop10h 27m
Mon 9/76:05 am -
1 stop5h 20m
Deal found 8/8![Frontier logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/31:20 pm -
1 stop19h 33m
Sat 9/58:45 am -
2 stops12h 00m
Deal found 8/6![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/131:18 pm -
1 stop5h 28m
Wed 9/166:25 am -
2 stops15h 04m
Deal found 8/7![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 -
2 stops29h 51m
Mon 10/57:28 pm -
1 stop16h 01m
Deal found 8/5![Multiple Airlines logo]()
$321
This Justfly.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:25 am -
1 stop7h 20m
Sun 9/133:00 pm -
1 stop6h 41m
Deal found 8/5![JetBlue logo]()
$322
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/41:20 pm -
1 stop10h 27m
Mon 9/76:05 am -
1 stop5h 20m
Deal found 8/7![Frontier 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 August 10, 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 10, 2026.
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/53:35 pm -
1 stop6h 00m
Sun 9/68:40 am -
Nonstop2h 15m
Deal found 8/5![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/36:00 am -
Nonstop2h 34m
Mon 9/77:30 am -
Nonstop2h 30m
Deal found 8/5![United Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/67:00 am -
1 stop13h 08m
Mon 11/910:38 am -
1 stop29h 37m
Deal found 8/8![Multiple Airlines logo]()
$387
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/116:45 pm -
Nonstop2h 05m
Tue 9/156:25 pm -
Nonstop2h 10m
Deal found 8/9![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/155:02 pm -
Nonstop2h 28m
Tue 9/226:15 pm -
Nonstop2h 26m
Deal found 8/7![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/194:00 pm -
Nonstop2h 05m
Sat 9/263:15 pm -
Nonstop2h 05m
Deal found 8/5![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/135:02 pm -
Nonstop2h 28m
Wed 9/166:59 am -
Nonstop2h 30m
Deal found 8/7![United Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/318:00 am -
Nonstop2h 00m
Wed 9/26:25 pm -
Nonstop2h 05m
Deal found 8/6![Southwest logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 8/287:20 am -
1 stop10h 03m
Sun 8/303:59 pm -
2 stops28h 42m
Deal found 8/7![Multiple Airlines logo]()
$437
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 10/26:15 am -
1 stop6h 31m
Mon 10/58:45 am -
Nonstop2h 30m
Deal found 8/5![United Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/106:45 pm -
Nonstop2h 05m
Tue 9/156:25 pm -
Nonstop2h 10m
Deal found 8/7![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 10/141:00 pm -
Nonstop2h 34m
Tue 10/2011:57 am -
Nonstop2h 19m
Deal found 8/9![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/156:15 pm -
Nonstop2h 05m
Tue 9/228:50 am -
Nonstop2h 15m
Deal found 8/6![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/286:20 am -
Nonstop2h 33m
Tue 9/296:06 pm -
1 stop4h 38m
Deal found 8/8![United Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/28:05 am -
Nonstop2h 00m
Mon 9/79:00 am -
Nonstop2h 10m
Deal found 8/6![Southwest logo]()
$352
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/176:10 pm -
1 stop7h 18m
Sat 9/196:26 pm -
Nonstop2h 26m
Deal found 8/8![United Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 10/49:36 pm -
1 stop22h 06m
Deal found 8/5![Multiple Airlines logo]()
$561
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/286:45 pm -
Nonstop2h 05m
Tue 9/296:25 pm -
Nonstop2h 10m
Deal found 8/8![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/41:00 pm -
Nonstop2h 34m
Mon 9/77:30 am -
Nonstop2h 30m
Deal found 8/6![United Airlines logo]()
$432
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/210:31 pm -
2 stops23h 08m
Mon 9/76:02 pm -
1 stop18h 28m
Deal found 8/6![Multiple Airlines logo]()
$983
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated August 10, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 8/1410:02 pm -
1 stop26h 08m
Mon 8/1710:16 am -
1 stop28h 55m
Deal found 8/5![Frontier logo]()
$342
This CheapOair deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:10 pm -
1 stop8h 43m
Thu 8/207:44 pm -
1 stop19h 27m
Deal found 8/7![Frontier logo]()
$352
This CheapOair deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 8/271:20 pm -
1 stop10h 27m
Mon 8/316:05 am -
1 stop5h 20m
Deal found 8/9![Frontier logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 8/271:20 pm -
1 stop10h 27m
Sun 8/306:05 am -
1 stop5h 20m
Deal found 8/8![Frontier logo]()
$319
This Frontier deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/21:20 pm -
1 stop10h 27m
Mon 9/76:05 am -
1 stop5h 20m
Deal found 8/8![Frontier logo]()
$320
This Trip.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:20 pm -
1 stop10h 27m
Fri 9/46:05 am -
1 stop5h 20m
Deal found 8/5![Frontier logo]()
$333
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/41:20 pm -
1 stop10h 27m
Mon 9/76:05 am -
1 stop5h 20m
Deal found 8/7![Frontier logo]()
$325
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/54:00 pm -
Nonstop2h 05m
Sun 9/68:40 am -
Nonstop2h 15m
Deal found 8/5![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/54:00 pm -
Nonstop2h 05m
Sat 9/127:45 am -
Nonstop2h 10m
Deal found 8/6![Southwest logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/104:57 pm -
2 stops7h 47m
Tue 9/156:25 am -
1 stop5h 04m
Deal found 8/5![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/131:18 pm -
1 stop5h 28m
Wed 9/166:25 am -
2 stops15h 04m
Deal found 8/7![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/171:18 pm -
1 stop5h 28m
Sat 9/196:25 am -
2 stops15h 04m
Deal found 8/8![Multiple Airlines logo]()
$336
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 10, 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 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/311:20 pm -
1 stop19h 33m
Deal found 8/6![Frontier logo]()
$102
This Trip.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:20 pm -
1 stop7h 48m
Deal found 8/9![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/11:20 pm -
1 stop19h 33m
Deal found 8/6![Frontier logo]()
$108
This Trip.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:57 pm -
1 stop8h 31m
Deal found 8/9![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 10/61:18 pm -
1 stop6h 05m
Deal found 8/7![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/41:20 pm -
1 stop19h 33m
Deal found 8/7![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/51:20 pm -
1 stop7h 48m
Deal found 8/5![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/61:20 pm -
1 stop7h 44m
Deal found 8/7![Frontier logo]()
$117
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/96:15 pm -
Nonstop2h 05m
Deal found 8/9![Southwest logo]()
$118
This Super.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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.
Thu 9/171:18 pm -
1 stop5h 28m
Deal found 8/5![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 10/61:18 pm -
1 stop5h 28m
Deal found 8/5![Frontier logo]()
$123
This Trip.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:20 pm -
1 stop10h 27m
Deal found 8/6![Frontier logo]()
$124
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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $316 (CheapOair) |
One-way from | $102 (Kiwi.com) |
Popular in | July |
Cheapest in | December |
Average price | $377 |
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 2,558,603 searches. Data last updated August 10, 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 - MDW Chicago Midway
ORFMDW
Norfolk
Sat 9/5
3:35 pm-8:35 pm
1 stop6h 00m
Chicago Midway
Sun 9/6
8:40 am-11:55 am
Nonstop2h 15m
$327
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Thu 9/3
6:00 am-7:34 am
Nonstop2h 34m
Chicago O'Hare Intl
Mon 9/7
7:30 am-11:00 am
Nonstop2h 30m
$345
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Fri 9/11
6:45 pm-7:50 pm
Nonstop2h 05m
Chicago Midway
Tue 9/15
6:25 pm-9:35 pm
Nonstop2h 10m
$345
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Tue 9/15
5:02 pm-6:30 pm
Nonstop2h 28m
Chicago O'Hare Intl
Tue 9/22
6:15 pm-9:41 pm
Nonstop2h 26m
$345
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Sat 9/19
4:00 pm-5:05 pm
Nonstop2h 05m
Chicago Midway
Sat 9/26
3:15 pm-6:20 pm
Nonstop2h 05m
$345
Quickest round-trip
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Mon 8/31
8:00 am-9:00 am
Nonstop2h 00m
Chicago Midway
Wed 9/2
6:25 pm-9:30 pm
Nonstop2h 05m
$345
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Thu 9/10
6:45 pm-7:50 pm
Nonstop2h 05m
Chicago Midway
Tue 9/15
6:25 pm-9:35 pm
Nonstop2h 10m
$345
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Tue 9/15
6:15 pm-7:20 pm
Nonstop2h 05m
Chicago Midway
Tue 9/22
8:50 am-12:05 pm
Nonstop2h 15m
$345
NorfolkChicago
ORF Norfolk - MDW Chicago Midway
ORFMDW
Norfolk
Wed 9/2
8:05 am-9:05 am
Nonstop2h 00m
Chicago Midway
Mon 9/7
9:00 am-12:10 pm
Nonstop2h 10m
$352
NorfolkChicago
ORF Norfolk - ORD Chicago O'Hare Intl
ORFORD
Norfolk
Sun 9/13
5:02 pm-6:30 pm
Nonstop2h 28m
Chicago O'Hare Intl
Wed 9/16
6:59 am-10:29 am
Nonstop2h 30m
$359
Showing 1-10 of 44 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 August 10, 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 10, 2026.
The most flights from V1B to CHI are scheduled on a Sunday (30 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 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 $327 and $468 in August.The cheapest round-trip price found within the last 5 days was $316 on Frontier (Aug 27-Aug 31).
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 8, 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 10, 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.
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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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 10, 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 10, 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 2,558,603 searches. Data last updated August 10, 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$397 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$388 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$243 | Average$437 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$260 | Average$260 | FlexibilityNo cancel fee | On-timeN/A |