$103+ 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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jul 11 — Jul 181
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 October or December, booked 2 days in advance, depart on a Thursday or Wednesday and return on a Wednesday
Cheap flight deals from Virginia Beach to Chicago
Cheapest
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 June 11, 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 June 11, 2026.
This CheapOair deal was found by Cheapflights users on 6/7. 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.
Thu 7/29:35 pm
ORF
- ORD
1 stop26h 44m
Multiple Airlines
Wed 7/86:00 am
ORD
- ORF
2 stops10h 10m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$333
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 pm
ORF
- ORD
2 stops28h 55m
Multiple Airlines
Mon 8/245:30 pm
ORD
- ORF
1 stop26h 31m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$334
This CheapOair deal was found by Cheapflights users on 6/7. 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 7/319:34 pm
ORF
- ORD
1 stop26h 36m
Multiple Airlines
Wed 8/59:37 am
ORD
- ORF
2 stops30h 28m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 6/9. 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 7/17:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sat 7/48:00 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 6/9![Southwest logo]()
$337
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 7/46:24 pm
ORF
- ORD
Nonstop2h 46m
American Airlines
Tue 7/72:52 pm
ORD
- ORF
Nonstop2h 24m
American Airlines
Deal found 6/9![American Airlines logo]()
$337
This Expedia deal was found by Cheapflights users on 6/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:21 pm
ORF
- ORD
1 stop8h 29m
Multiple Airlines
Sat 7/46:00 am
ORD
- ORF
2 stops10h 19m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/2812:10 pm
ORF
- MDW
1 stop10h 53m
Multiple Airlines
Mon 8/36:05 am
MDW
- ORF
2 stops34h 27m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Mon 7/1312:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Sat 7/189:57 pm
ORD
- ORF
2 stops36h 18m
Frontier
Deal found 6/9![Frontier logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 6/2912:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Sat 7/411:59 am
MDW
- ORF
1 stop22h 16m
Frontier
Deal found 6/6![Frontier logo]()
$340
This CheapOair deal was found by Cheapflights users on 6/10. 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 7/309:34 pm
ORF
- ORD
1 stop26h 36m
Multiple Airlines
Wed 8/56:00 am
ORD
- ORF
2 stops10h 10m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 6/8. 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.
Thu 8/1312:38 pm
ORF
- MDW
1 stop6h 55m
Delta
Sun 8/166:42 pm
MDW
- ORF
1 stop4h 00m
Delta
Deal found 6/8![Delta logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/312:21 pm
ORF
- ORD
1 stop8h 29m
Frontier
Mon 7/67:05 am
ORD
- ORF
1 stop27h 10m
Frontier
Deal found 6/8![Frontier logo]()
$341
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 June 11, 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 June 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Thu 8/66:00 am
ORF
- RFD
1 stop26h 49m
Multiple Airlines
Sun 8/911:37 am
RFD
- ORF
2 stops22h 38m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 6/6. 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.
Wed 7/16:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Tue 7/76:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/6![United Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 6/9. 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.
Thu 9/103:45 pm
ORF
- MDW
2 stops7h 35m
Southwest
Sun 9/138:10 am
MDW
- ORF
2 stops6h 50m
Southwest
Deal found 6/9![Southwest logo]()
$352
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:06 pm
ORF
- ORD
1 stop4h 25m
Delta
Tue 7/142:28 pm
ORD
- ORF
1 stop7h 24m
Delta
Deal found 6/9![Delta logo]()
$370
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Tue 8/116:15 am
ORF
- ORD
1 stop6h 38m
United Airlines
Wed 8/128:45 am
ORD
- ORF
1 stop4h 30m
United Airlines
Deal found 6/9![United Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 6/10. 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 9/113:45 pm
ORF
- MDW
2 stops7h 35m
Southwest
Sun 9/136:55 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/10![Southwest logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Sat 7/187:06 pm
ORF
- RFD
2 stops16h 31m
Multiple Airlines
Fri 7/248:39 am
RFD
- ORF
1 stop13h 29m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 6/11. 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 8/2012:38 pm
ORF
- ORD
1 stop4h 39m
Delta
Sun 8/237:00 am
ORD
- ORF
1 stop3h 52m
Delta
Deal found 6/11![Delta logo]()
$382
This Southwest deal was found by Cheapflights users on 6/7. 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.
Sat 8/224:00 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Tue 8/256:25 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/7![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 6/6. 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.
Mon 8/35:00 pm
ORF
- ORD
Nonstop2h 41m
United Airlines
Sat 8/86:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/6![United Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Tue 6/3012:21 pm
ORF
- RFD
2 stops21h 52m
Multiple Airlines
Sat 7/410:05 am
RFD
- ORF
1 stop10h 40m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 6/6. 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 9/158:05 am
ORF
- MDW
Nonstop2h 00m
Southwest
Tue 9/228:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 6/6![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 6/6. 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.
Thu 8/610:48 am
ORF
- ORD
Nonstop2h 39m
United Airlines
Sun 8/96:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/6![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 6/9. 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.
Sat 7/410:00 am
ORF
- MDW
2 stops5h 35m
Southwest
Tue 7/77:50 am
MDW
- ORF
2 stops5h 35m
Southwest
Deal found 6/9![Southwest logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Wed 7/17:06 pm
ORF
- RFD
2 stops16h 31m
Multiple Airlines
Sat 7/410:05 am
RFD
- ORF
1 stop10h 40m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 8/126:02 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Sun 8/167:15 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 6/11![United Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 6/7. 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.
Sun 7/126:15 pm
ORF
- MDW
1 stop6h 30m
Southwest
Mon 7/137:00 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/7![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/16:05 am
ORF
- ORD
1 stop6h 47m
United Airlines
Wed 8/56:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/10![United Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 6/6. 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 7/410:00 am
ORF
- MDW
1 stop5h 55m
Southwest
Sat 7/112:10 pm
MDW
- ORF
2 stops8h 00m
Southwest
Deal found 6/6![Southwest logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 10/127:00 am
ORF
- RFD
1 stop11h 23m
Multiple Airlines
Wed 10/1411:04 am
RFD
- ORF
1 stop10h 25m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 6/8. 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 7/65:00 pm
ORF
- ORD
Nonstop2h 41m
United Airlines
Mon 7/136:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/8![United Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 6/9. 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.
Thu 7/96:00 pm
ORF
- MDW
2 stops7h 45m
Southwest
Thu 7/165:20 pm
MDW
- ORF
1 stop5h 20m
Southwest
Deal found 6/9![Southwest logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Fri 7/109:34 pm
ORF
- RFD
1 stop12h 41m
Multiple Airlines
Mon 7/137:50 pm
RFD
- ORF
2 stops14h 25m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$481
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 7/910:45 am
ORF
- ORD
1 stop7h 17m
United Airlines
Sun 7/126:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/10![United Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 6/9. 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 7/106:00 pm
ORF
- MDW
2 stops7h 10m
Southwest
Fri 7/172:40 pm
MDW
- ORF
2 stops8h 00m
Southwest
Deal found 6/9![Southwest logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Fri 9/117:00 am
ORF
- RFD
1 stop10h 15m
Multiple Airlines
Sun 9/133:53 pm
RFD
- ORF
2 stops17h 49m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$532
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Sat 7/47:06 pm
ORF
- RFD
2 stops16h 31m
Multiple Airlines
Sun 7/51:14 pm
RFD
- ORF
1 stop29h 12m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$565
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Wed 7/17:00 am
ORF
- RFD
1 stop9h 57m
Multiple Airlines
Mon 7/67:50 pm
RFD
- ORF
2 stops14h 25m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$601
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Fri 9/187:00 am
ORF
- RFD
1 stop10h 15m
Multiple Airlines
Sun 9/209:29 pm
RFD
- ORF
1 stop22h 13m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$856
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated June 11, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 6/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:35 pm
ORF
- ORD
1 stop28h 44m
Frontier
Fri 6/264:59 pm
ORD
- ORF
1 stop24h 41m
Frontier
Deal found 6/10![Frontier logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 6/2912:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Sat 7/411:59 am
MDW
- ORF
1 stop22h 16m
Frontier
Deal found 6/6![Frontier logo]()
$340
This Southwest deal was found by Cheapflights users on 6/9. 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 7/17:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sat 7/48:00 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 6/9![Southwest logo]()
$337
This Expedia deal was found by Cheapflights users on 6/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/112:21 pm
ORF
- ORD
1 stop8h 29m
Multiple Airlines
Sat 7/46:00 am
ORD
- ORF
2 stops10h 19m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$338
This CheapOair deal was found by Cheapflights users on 6/7. 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.
Thu 7/29:35 pm
ORF
- ORD
1 stop26h 44m
Multiple Airlines
Wed 7/86:00 am
ORD
- ORF
2 stops10h 10m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/312:21 pm
ORF
- ORD
1 stop8h 29m
Frontier
Mon 7/67:05 am
ORD
- ORF
1 stop27h 10m
Frontier
Deal found 6/8![Frontier logo]()
$341
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 7/46:24 pm
ORF
- ORD
Nonstop2h 46m
American Airlines
Wed 7/82:52 pm
ORD
- ORF
Nonstop2h 24m
American Airlines
Deal found 6/9![American Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Mon 7/1312:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Sat 7/189:57 pm
ORD
- ORF
2 stops36h 18m
Frontier
Deal found 6/9![Frontier logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Mon 7/2012:10 pm
ORF
- MDW
1 stop10h 53m
Multiple Airlines
Fri 7/243:28 pm
MDW
- ORF
2 stops28h 11m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/2812:10 pm
ORF
- MDW
1 stop10h 53m
Multiple Airlines
Mon 8/36:05 am
MDW
- ORF
2 stops34h 27m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$339
This CheapOair deal was found by Cheapflights users on 6/10. 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 7/309:34 pm
ORF
- ORD
1 stop26h 36m
Multiple Airlines
Wed 8/56:00 am
ORD
- ORF
2 stops10h 10m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$340
This CheapOair deal was found by Cheapflights users on 6/7. 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 7/319:34 pm
ORF
- ORD
1 stop26h 36m
Multiple Airlines
Wed 8/59:37 am
ORD
- ORF
2 stops30h 28m
Multiple Airlines
Deal found 6/7![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 June 11, 2026.
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Trip.com deal was found by Cheapflights users on 6/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/10![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 8/412:10 pm
ORF
- MDW
1 stop22h 41m
Frontier
Deal found 6/10![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 7/712:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Deal found 6/10![Frontier logo]()
$111
This Southwest deal was found by Cheapflights users on 6/7. 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.
Tue 8/46:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Deal found 6/7![Southwest logo]()
$115
This Trip.com deal was found by Cheapflights users on 6/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Deal found 6/8![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Wed 8/512:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/9![Frontier logo]()
$116
This American Airlines deal was found by Cheapflights users on 6/8. 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 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
Deal found 6/8![American Airlines logo]()
$116
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier 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 6/9![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:10 pm
ORF
- ORD
1 stop6h 45m
Frontier
Deal found 6/10![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Mon 9/712:21 pm
ORF
- ORD
1 stop20h 42m
Frontier
Deal found 6/10![Frontier logo]()
$122
This Trip.com deal was found by Cheapflights users on 6/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:00 pm
ORF
- MDW
1 stop11h 11m
Frontier
Deal found 6/8![Frontier logo]()
$124
This Delta deal was found by Cheapflights users on 6/11. 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.
Tue 12/85:50 am
ORF
- MDW
1 stop3h 55m
Delta
Deal found 6/11![Delta logo]()
$125
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 June 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $333 (CheapOair) |
One-way from | $103 (Trip.com) |
Popular in | May |
Cheapest in | October |
Average price | $392 |
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 June 11, 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 - RFD
ORFRFD
Norfolk
Thu 8/6
6:00 am-7:49 am
1 stop26h 49m
Chicago Greater Rockford
Sun 8/9
11:37 am-11:15 am
2 stops22h 38m
$345
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Wed 7/1
6:00 am-7:28 am
Nonstop2h 28m
Chicago O'Hare Intl
Tue 7/7
6:45 am-10:07 am
Nonstop2h 22m
$350
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 9/10
3:45 pm-10:20 pm
2 stops7h 35m
Chicago Midway
Sun 9/13
8:10 am-4:00 pm
2 stops6h 50m
$352
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Tue 8/11
6:15 am-11:53 am
1 stop6h 38m
Chicago O'Hare Intl
Wed 8/12
8:45 am-2:15 pm
1 stop4h 30m
$355
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 9/11
3:45 pm-10:20 pm
2 stops7h 35m
Chicago Midway
Sun 9/13
6:55 pm-10:00 pm
Nonstop2h 05m
$362
Quickest round-trip
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 8/22
4:00 pm-5:05 pm
Nonstop2h 05m
Chicago Midway
Tue 8/25
6:25 pm-9:30 pm
Nonstop2h 05m
$363
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Mon 8/3
5:00 pm-6:41 pm
Nonstop2h 41m
Chicago O'Hare Intl
Sat 8/8
6:45 am-10:07 am
Nonstop2h 22m
$363
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Tue 9/15
8:05 am-9:05 am
Nonstop2h 00m
Chicago Midway
Tue 9/22
8:50 am-12:05 pm
Nonstop2h 15m
$363
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 8/6
10:48 am-12:27 pm
Nonstop2h 39m
Chicago O'Hare Intl
Sun 8/9
6:45 am-10:07 am
Nonstop2h 22m
$363
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 7/4
10:00 am-2:35 pm
2 stops5h 35m
Chicago Midway
Tue 7/7
7:50 am-2:25 pm
2 stops5h 35m
$367
Showing 1-10 of 56 resultsSorted by cheapest first
Best time to book a flight from Virginia Beach to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Virginia Beach with our price prediction graph.
ORF-ORD
ORF-MDW
ORF-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Virginia Beach to Chicago
V1B-CHI
ORF-ORD
ORF-MDW
ORF-RFD
What is the cheapest time of day to fly from V1B to CHI?
Find hourly flight availability from Virginia Beach to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 11, 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 10% 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 June 11, 2026.
The most flights from V1B to CHI are scheduled on a Thursday (32 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 June 8, 2026.
Travelers seeking maximum savings on their Virginia Beach to Chicago flight should consider departing on Sunday afternoons 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 June 11, 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
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from 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
Hammond
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 June 11, 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 June 11, 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 June 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$354 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$260 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$126 | Average$314 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$380 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$216 | Average$384 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$422 | FlexibilityNo cancel fee | On-time69% |