$95+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Aug 12 — Aug 191
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
Last-minute
One-way
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 July 13, 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 July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:45 pm
ORF
- MDW
2 stops7h 35m
Southwest
Mon 8/178:10 am
MDW
- ORF
2 stops8h 45m
Southwest
Deal found 7/10![Southwest logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 9/2512:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Sun 9/272:03 pm
ORD
- ORF
1 stop20h 59m
Frontier
Deal found 7/12![Frontier logo]()
$326
This Southwest deal was found by Cheapflights users on 7/12. 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 8/2610:05 am
ORF
- MDW
1 stop8h 35m
Southwest
Wed 9/26:25 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/12![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:15 am
ORF
- ORD
1 stop4h 23m
United Airlines
Thu 9/37:30 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 7/11![United Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 10/3012:57 pm
ORF
- MDW
1 stop9h 56m
Multiple Airlines
Sun 11/17:25 am
MDW
- ORF
2 stops12h 20m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$328
This CheapOair deal was found by Cheapflights users on 7/9. 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.
Sat 8/112:16 pm
ORF
- ORD
1 stop8h 37m
Frontier
Mon 8/35:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 7/9![Frontier logo]()
$328
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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.
Fri 9/116:17 pm
ORF
- ORD
Nonstop2h 51m
American Airlines
Sun 9/138:44 pm
ORD
- ORF
Nonstop2h 26m
American Airlines
Deal found 7/10![American Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 8/512:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Sat 8/86:05 am
MDW
- ORF
2 stops13h 34m
Frontier
Deal found 7/12![Frontier logo]()
$330
This CheapOair deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Wed 8/55:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 7/10![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 7/12. 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.
Sun 11/13:49 pm
ORF
- MDW
2 stops20h 09m
Multiple Airlines
Thu 11/512:03 pm
MDW
- ORF
1 stop22h 59m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 7/12. 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.
Tue 8/46:15 am
ORF
- MDW
2 stops6h 35m
Southwest
Tue 8/46:25 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/12![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Tue 8/48:45 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 7/10![Southwest logo]()
$333
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 July 13, 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 July 13, 2026.
This Southwest deal was found by Cheapflights users on 7/12. 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 8/2610:05 am
ORF
- MDW
1 stop8h 35m
Southwest
Wed 9/26:25 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/12![Southwest logo]()
$327
This American Airlines deal was found by Cheapflights users on 7/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:22 am
ORF
- ORD
Nonstop2h 38m
American Airlines
Sat 8/85:05 am
ORD
- ORF
1 stop5h 55m
American Airlines
Deal found 7/12![American Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
ORF
- ORD
1 stop6h 59m
United Airlines
Wed 9/28:45 am
ORD
- ORF
1 stop4h 30m
United Airlines
Deal found 7/10![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am
ORF
- MDW
1 stop4h 18m
Delta
Tue 10/276:45 pm
MDW
- ORF
1 stop3h 41m
Delta
Deal found 7/12![Delta logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 9/106:10 pm
ORF
- RFD
1 stop15h 42m
Multiple Airlines
Mon 9/145:20 pm
RFD
- ORF
1 stop23h 23m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 7/12. 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 8/268:50 am
ORF
- MDW
1 stop3h 45m
Southwest
Mon 8/319:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/12![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 7/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:30 am
ORF
- MDW
1 stop5h 22m
Delta
Wed 10/2810:58 am
MDW
- ORF
1 stop4h 19m
Delta
Deal found 7/12![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 7/12. 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.
Tue 8/186:15 am
ORF
- ORD
1 stop6h 38m
United Airlines
Fri 8/217:30 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 7/12![United Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:25 am
ORF
- MDW
2 stops7h 00m
Southwest
Sat 8/87:40 am
MDW
- ORF
2 stops8h 15m
Southwest
Deal found 7/11![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 7/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:20 am
ORF
- ORD
1 stop7h 31m
Delta
Sun 8/305:30 am
ORD
- ORF
1 stop5h 09m
Delta
Deal found 7/8![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 7/8. 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 9/35:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Fri 9/46:15 pm
ORD
- ORF
1 stop4h 28m
United Airlines
Deal found 7/8![United Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:20 am
ORF
- RFD
1 stop10h 03m
Multiple Airlines
Sun 8/233:59 pm
RFD
- ORF
2 stops28h 42m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$420
This Southwest deal was found by Cheapflights users on 7/12. 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 9/33:45 pm
ORF
- MDW
1 stop4h 30m
Southwest
Fri 9/46:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/12![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:14 pm
ORF
- ORD
1 stop6h 41m
Delta
Tue 9/159:30 am
ORD
- ORF
1 stop7h 10m
Delta
Deal found 7/11![Delta logo]()
$360
This United Airlines deal was found by Cheapflights users on 7/12. 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.
Fri 10/307:59 pm
ORF
- ORD
1 stop4h 38m
United Airlines
Sun 11/17:20 am
ORD
- ORF
Nonstop2h 24m
United Airlines
Deal found 7/12![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 7/12. 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 8/201:55 pm
ORF
- MDW
1 stop4h 00m
Southwest
Sun 8/238:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 7/12![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 9/105:02 pm
ORF
- MDW
1 stop6h 43m
Delta
Mon 9/146:05 am
MDW
- ORF
1 stop7h 04m
Delta
Deal found 7/11![Delta logo]()
$368
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 12/296:15 am
ORF
- ORD
1 stop6h 05m
United Airlines
Sat 1/25:50 pm
ORD
- ORF
Nonstop2h 14m
United Airlines
Deal found 7/10![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 7/12. 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.
Tue 8/183:20 pm
ORF
- MDW
1 stop4h 25m
Southwest
Fri 8/219:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/12![Southwest logo]()
$350
This Southwest deal was found by Cheapflights users on 7/9. 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 8/281:05 pm
ORF
- MDW
2 stops8h 05m
Southwest
Sun 8/301:10 pm
MDW
- ORF
2 stops8h 30m
Southwest
Deal found 7/9![Southwest logo]()
$360
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Thu 8/610:48 am
ORF
- ORD
Nonstop2h 39m
United Airlines
Sun 8/96:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 7/9![United Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” 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 11/36:10 pm
ORF
- RFD
1 stop21h 34m
Multiple Airlines
Sun 11/88:37 pm
RFD
- ORF
1 stop23h 05m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$565
This Southwest deal was found by Cheapflights users on 7/9. 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 8/213:45 pm
ORF
- MDW
2 stops7h 35m
Southwest
Sun 8/236:05 am
MDW
- ORF
2 stops8h 55m
Southwest
Deal found 7/9![Southwest logo]()
$360
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Fri 10/95:01 pm
ORF
- ORD
Nonstop2h 29m
United Airlines
Tue 10/1311:57 am
ORD
- ORF
Nonstop2h 19m
United Airlines
Deal found 7/9![United Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Thu 7/306:00 am
ORF
- ORD
Nonstop2h 29m
United Airlines
Sun 8/96:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 7/9![United Airlines logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:20 am
ORF
- RFD
1 stop10h 03m
Multiple Airlines
Sun 8/309:35 pm
RFD
- ORF
1 stop20h 51m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$637
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/17:59 pm
ORF
- ORD
1 stop4h 32m
United Airlines
Wed 8/53:53 pm
ORD
- ORF
1 stop6h 51m
United Airlines
Deal found 7/10![United Airlines logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 9/39:16 pm
ORF
- RFD
1 stop11h 46m
Multiple Airlines
Sun 9/69:29 pm
RFD
- ORF
1 stop20h 57m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$787
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated July 13, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated July 13, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Wed 8/55:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 7/10![Frontier logo]()
$330
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Tue 8/48:45 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 7/10![Southwest logo]()
$333
This CheapOair deal was found by Cheapflights users on 7/9. 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.
Sat 8/112:16 pm
ORF
- ORD
1 stop8h 37m
Frontier
Mon 8/35:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 7/9![Frontier logo]()
$328
This American Airlines deal was found by Cheapflights users on 7/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:40 am
ORF
- ORD
Nonstop2h 40m
American Airlines
Wed 8/58:45 am
ORD
- ORF
Nonstop2h 19m
American Airlines
Deal found 7/9![American Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 7/12. 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.
Tue 8/46:15 am
ORF
- MDW
2 stops6h 35m
Southwest
Tue 8/46:25 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/12![Southwest logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 8/512:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Sat 8/86:05 am
MDW
- ORF
2 stops13h 34m
Frontier
Deal found 7/12![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 7/12. 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.
Sat 8/89:34 pm
ORF
- MDW
2 stops25h 29m
Frontier
Sun 8/1611:06 am
MDW
- ORF
1 stop23h 09m
Frontier
Deal found 7/12![Frontier logo]()
$337
This American Airlines deal was found by Cheapflights users on 7/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:24 am
ORF
- ORD
Nonstop2h 36m
American Airlines
Fri 8/148:45 am
ORD
- ORF
Nonstop2h 19m
American Airlines
Deal found 7/9![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 7/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:17 pm
ORF
- ORD
Nonstop2h 44m
American Airlines
Sat 8/155:05 am
ORD
- ORF
1 stop5h 55m
American Airlines
Deal found 7/11![American Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:45 pm
ORF
- MDW
2 stops7h 35m
Southwest
Mon 8/178:10 am
MDW
- ORF
2 stops8h 45m
Southwest
Deal found 7/10![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/136:14 pm
ORF
- MDW
1 stop5h 22m
Delta
Sat 8/156:11 am
MDW
- ORF
1 stop5h 34m
Delta
Deal found 7/10![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 7/12. 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 8/2610:05 am
ORF
- MDW
1 stop8h 35m
Southwest
Wed 9/26:25 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/12![Southwest logo]()
$327
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 July 13, 2026.
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated July 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/301:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/10![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Deal found 7/9![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/9![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” 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 8/812:16 pm
ORF
- ORD
1 stop8h 37m
Frontier
Deal found 7/10![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/9![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/612:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Deal found 7/8![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Wed 10/712:57 pm
ORF
- MDW
1 stop10h 01m
Frontier
Deal found 7/8![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:20 pm
ORF
- ORD
1 stop7h 48m
Frontier
Deal found 7/9![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Mon 8/312:10 pm
ORF
- MDW
1 stop23h 57m
Frontier
Deal found 7/8![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Mon 8/312:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Deal found 7/8![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 7/7. 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.
Wed 9/912:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Deal found 7/7![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Wed 10/712:57 pm
ORF
- ORD
1 stop20h 18m
Frontier
Deal found 7/8![Frontier logo]()
$101
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 July 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $326 (Southwest) |
One-way from | $95 (Kiwi.com) |
Popular in | July |
Cheapest in | December |
Average price | $439 |
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 July 13, 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 - MDW
ORFMDW
Norfolk
Wed 8/26
10:05 am-5:40 pm
1 stop8h 35m
Chicago Midway
Wed 9/2
6:25 pm-9:30 pm
Nonstop2h 05m
$327
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Wed 8/5
6:22 am-8:00 am
Nonstop2h 38m
Chicago O'Hare Intl
Sat 8/8
5:05 am-12:00 pm
1 stop5h 55m
$327
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 8/26
8:50 am-11:35 am
1 stop3h 45m
Chicago Midway
Mon 8/31
9:00 am-12:10 pm
Nonstop2h 10m
$327
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Tue 9/1
6:00 am-11:59 am
1 stop6h 59m
Chicago O'Hare Intl
Wed 9/2
8:45 am-2:15 pm
1 stop4h 30m
$329
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 10/22
6:00 am-9:18 am
1 stop4h 18m
Chicago Midway
Tue 10/27
6:45 pm-11:26 pm
1 stop3h 41m
$337
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 10/21
5:30 am-9:52 am
1 stop5h 22m
Chicago Midway
Wed 10/28
10:58 am-4:17 pm
1 stop4h 19m
$337
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 8/6
6:25 am-12:25 pm
2 stops7h 00m
Chicago Midway
Sat 8/8
7:40 am-4:55 pm
2 stops8h 15m
$347
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Fri 8/28
10:20 am-4:51 pm
1 stop7h 31m
Chicago O'Hare Intl
Sun 8/30
5:30 am-11:39 am
1 stop5h 09m
$349
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Tue 8/18
6:15 am-11:53 am
1 stop6h 38m
Chicago O'Hare Intl
Fri 8/21
7:30 am-11:00 am
Nonstop2h 30m
$350
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 9/3
3:45 pm-7:15 pm
1 stop4h 30m
Chicago Midway
Fri 9/4
6:50 pm-9:55 pm
Nonstop2h 05m
$350
Showing 1-10 of 54 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 July 13, 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 11% 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 July 13, 2026.
The most flights from V1B to CHI are scheduled on a Saturday (29 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost to fly round-trip from Virginia Beach to Chicago?
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 July 11, 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 July 13, 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.
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
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 July 13, 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 July 13, 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 July 13, 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$200 | Average$260 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$386 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$431 | FlexibilityNo cancel fee | On-time69% |