$104+ 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jul 24 — Jul 311
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 Saturday
Cheap flight deals from Virginia Beach to Chicago
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Best
Last-minute
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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 June 24, 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 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:06 pm
ORF
- RFD
2 stops16h 31m
Multiple Airlines
Fri 7/247:50 pm
RFD
- ORF
1 stop23h 49m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$341
This CheapOair deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/59:34 pm
ORF
- ORD
1 stop12h 37m
Frontier
Tue 7/145:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 6/21![Frontier logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/2212:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Thu 7/236:05 am
MDW
- ORF
2 stops13h 34m
Frontier
Deal found 6/23![Frontier logo]()
$342
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 8/88:10 am
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 8/106:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/23![Southwest logo]()
$343
This CheapOair deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:06 pm
ORF
- ORD
1 stop7h 02m
Frontier
Mon 9/79:10 pm
ORD
- ORF
1 stop18h 01m
Frontier
Deal found 6/21![Frontier logo]()
$343
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:05 pm
ORF
- MDW
1 stop6h 10m
Southwest
Fri 8/149:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 6/21![Southwest logo]()
$344
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:24 am
ORF
- ORD
Nonstop2h 36m
American Airlines
Sun 8/167:30 am
ORD
- ORF
1 stop5h 44m
American Airlines
Deal found 6/23![American Airlines logo]()
$344
This Trip.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com 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
Frontier
Fri 7/175:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 6/20![Frontier logo]()
$345
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:20 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sat 7/256:30 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/19![Southwest logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop8h 43m
Frontier
Thu 7/169:57 pm
ORD
- ORF
2 stops36h 24m
Frontier
Deal found 6/21![Frontier logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/1612:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Sun 7/197:05 am
ORD
- ORF
1 stop27h 10m
Frontier
Deal found 6/22![Frontier logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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
ORF
- RFD
1 stop13h 12m
Multiple Airlines
Mon 10/56:31 pm
RFD
- ORF
2 stops16h 31m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$350
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 24, 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 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:06 pm
ORF
- RFD
2 stops16h 31m
Multiple Airlines
Fri 7/247:50 pm
RFD
- ORF
1 stop23h 49m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:10 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 10/59:00 am
MDW
- ORF
1 stop5h 20m
Southwest
Deal found 6/23![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/45:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Sun 9/611:59 am
ORD
- ORF
Nonstop2h 18m
United Airlines
Deal found 6/23![United Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/255:02 pm
ORF
- MDW
1 stop6h 43m
Delta
Mon 9/2810:48 am
MDW
- ORF
1 stop4h 06m
Delta
Deal found 6/24![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:19 pm
ORF
- ORD
1 stop6h 11m
American Airlines
Sun 8/166:45 am
ORD
- ORF
1 stop5h 09m
American Airlines
Deal found 6/19![American Airlines logo]()
$354
This CheapOair deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 pm
ORF
- ORD
2 stops28h 55m
Multiple Airlines
Sun 8/165:13 pm
ORD
- ORF
1 stop26h 45m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/193:20 pm
ORF
- MDW
2 stops8h 00m
Southwest
Fri 8/212:35 pm
MDW
- ORF
2 stops6h 00m
Southwest
Deal found 6/22![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:05 am
ORF
- ORD
Nonstop2h 29m
United Airlines
Tue 9/157:00 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 6/19![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 9/42:42 pm
ORF
- ORD
1 stop7h 07m
Delta
Sun 9/69:30 am
ORD
- ORF
1 stop7h 59m
Delta
Deal found 6/22![Delta logo]()
$370
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:13 pm
ORF
- ORD
Nonstop2h 36m
American Airlines
Sun 9/136:45 am
ORD
- ORF
1 stop5h 07m
American Airlines
Deal found 6/19![American Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/224:30 pm
ORF
- MDW
2 stops7h 45m
Southwest
Sat 7/2510:20 am
MDW
- ORF
2 stops6h 40m
Southwest
Deal found 6/23![Southwest logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:00 am
ORF
- RFD
1 stop11h 12m
Multiple Airlines
Mon 9/145:20 pm
RFD
- ORF
2 stops17h 42m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:10 pm
ORF
- ORD
1 stop6h 12m
United Airlines
Wed 8/1210:55 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/20![United Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sun 7/265:00 am
MDW
- ORF
1 stop10h 30m
Southwest
Deal found 6/19![Southwest logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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
Mon 8/245:13 pm
RFD
- ORF
2 stops18h 12m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$373
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 stop4h 31m
United Airlines
Wed 8/56:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/22![United Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:45 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Fri 9/255:00 am
MDW
- ORF
1 stop7h 20m
Southwest
Deal found 6/19![Southwest logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/117:06 pm
ORF
- RFD
2 stops16h 31m
Multiple Airlines
Mon 7/137:50 pm
RFD
- ORF
1 stop23h 49m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/268:05 pm
ORF
- MDW
1 stop5h 20m
Southwest
Sun 8/27:45 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 6/23![Southwest logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:10 pm
ORF
- RFD
1 stop15h 42m
Multiple Airlines
Fri 9/255:05 pm
RFD
- ORF
2 stops17h 57m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$376
This United Airlines deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 7/316:05 am
ORF
- ORD
1 stop6h 48m
United Airlines
Sun 8/26:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/24![United Airlines logo]()
$453
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/307:10 am
MDW
- ORF
1 stop4h 25m
Southwest
Deal found 6/22![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:05 am
ORF
- ORD
1 stop4h 31m
United Airlines
Tue 7/216:30 am
ORD
- ORF
1 stop6h 47m
United Airlines
Deal found 6/20![United Airlines logo]()
$457
This CheapOair deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:05 pm
ORF
- ORD
2 stops28h 01m
Multiple Airlines
Sun 9/134:49 pm
ORD
- ORF
1 stop23h 26m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$416
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/133:30 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 7/207:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/19![Southwest logo]()
$400
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 7/208:55 am
MDW
- ORF
1 stop5h 10m
Southwest
Deal found 6/20![Southwest logo]()
$410
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/206:30 am
ORF
- MDW
1 stop5h 25m
Southwest
Fri 7/247:00 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/23![Southwest logo]()
$410
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:15 am
ORF
- MDW
Nonstop2h 10m
Southwest
Sat 7/256:30 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/20![Southwest logo]()
$422
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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
Wed 7/810:03 am
RFD
- ORF
1 stop9h 36m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$562
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/239:35 pm
RFD
- ORF
1 stop20h 51m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$564
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated June 24, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com 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
Frontier
Fri 7/175:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 6/20![Frontier logo]()
$345
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/111:56 am
ORF
- ORD
Nonstop2h 37m
American Airlines
Wed 7/292:52 pm
ORD
- ORF
Nonstop2h 24m
American Airlines
Deal found 6/23![American Airlines logo]()
$351
This CheapOair deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/59:34 pm
ORF
- ORD
1 stop12h 37m
Frontier
Tue 7/145:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 6/21![Frontier logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Mon 7/136:05 am
MDW
- ORF
1 stop28h 10m
Frontier
Deal found 6/21![Frontier logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:16 pm
ORF
- ORD
1 stop20h 37m
Frontier
Mon 7/139:57 pm
ORD
- ORF
2 stops36h 18m
Frontier
Deal found 6/21![Frontier logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop8h 43m
Frontier
Thu 7/169:57 pm
ORD
- ORF
2 stops36h 24m
Frontier
Deal found 6/21![Frontier logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/1612:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Sun 7/197:05 am
ORD
- ORF
1 stop27h 10m
Frontier
Deal found 6/22![Frontier logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:06 pm
ORF
- RFD
2 stops16h 31m
Multiple Airlines
Fri 7/247:50 pm
RFD
- ORF
1 stop23h 49m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:20 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sat 7/256:30 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/19![Southwest logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/2212:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Thu 7/236:05 am
MDW
- ORF
2 stops13h 34m
Frontier
Deal found 6/23![Frontier logo]()
$342
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 7/224:30 pm
ORF
- MDW
2 stops7h 45m
Southwest
Sat 7/254:50 pm
MDW
- ORF
1 stop5h 20m
Southwest
Deal found 6/23![Southwest logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2212:10 pm
ORF
- MDW
1 stop10h 53m
Multiple Airlines
Sun 7/266:05 am
MDW
- ORF
2 stops28h 14m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$352
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 24, 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 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/512:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Deal found 6/21![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:57 pm
ORF
- MDW
1 stop10h 01m
Frontier
Deal found 6/21![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Deal found 6/21![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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 9/2112:57 pm
ORF
- MDW
1 stop23h 01m
Frontier
Deal found 6/23![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:57 pm
ORF
- ORD
1 stop24h 05m
Frontier
Deal found 6/21![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/286:12 pm
ORF
- ORD
2 stops19h 03m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:12 pm
ORF
- ORD
2 stops19h 48m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$114
This Trip.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:57 pm
ORF
- MDW
1 stop10h 01m
Frontier
Deal found 6/21![Frontier logo]()
$116
This Super.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/181:20 pm
ORF
- ORD
1 stop7h 48m
Frontier
Deal found 6/21![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/191:20 pm
ORF
- ORD
1 stop7h 48m
Frontier
Deal found 6/24![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 9/1812:57 pm
ORF
- ORD
1 stop24h 05m
Frontier
Deal found 6/24![Frontier logo]()
$121
This Frontier deal was found by Cheapflights users on 6/24. Clicking the “Pick Dates” 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 8/201:20 pm
ORF
- ORD
1 stop7h 39m
Frontier
Deal found 6/24![Frontier logo]()
$122
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 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $341 (CheapOair) |
One-way from | $104 (Kiwi.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 24, 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
Sat 7/18
7:06 pm-10:37 am
2 stops16h 31m
Chicago Greater Rockford
Fri 7/24
7:50 pm-8:39 pm
1 stop23h 49m
$341
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 10/2
7:10 pm-8:15 pm
Nonstop2h 05m
Chicago Midway
Mon 10/5
9:00 am-3:20 pm
1 stop5h 20m
$344
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 8/13
6:00 pm-9:55 pm
2 stops28h 55m
Chicago O'Hare Intl
Sun 8/16
5:13 pm-8:58 pm
1 stop26h 45m
$344
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Fri 9/4
5:02 pm-6:30 pm
Nonstop2h 28m
Chicago O'Hare Intl
Sun 9/6
11:59 am-3:17 pm
Nonstop2h 18m
$350
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 8/19
3:20 pm-10:20 pm
2 stops8h 00m
Chicago Midway
Fri 8/21
2:35 pm-9:35 pm
2 stops6h 00m
$350
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 7/22
4:30 pm-11:15 pm
2 stops7h 45m
Chicago Midway
Sat 7/25
10:20 am-6:00 pm
2 stops6h 40m
$350
NorfolkChicago
ORF - RFD
ORFRFD
Norfolk
Mon 9/7
7:00 am-5:12 pm
1 stop11h 12m
Chicago Greater Rockford
Mon 9/14
5:20 pm-12:02 pm
2 stops17h 42m
$351
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 9/25
5:02 pm-10:45 pm
1 stop6h 43m
Chicago Midway
Mon 9/28
10:48 am-3:54 pm
1 stop4h 06m
$354
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 8/13
5:19 pm-10:30 pm
1 stop6h 11m
Chicago O'Hare Intl
Sun 8/16
6:45 am-12:54 pm
1 stop5h 09m
$354
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Wed 9/9
6:05 am-7:34 am
Nonstop2h 29m
Chicago O'Hare Intl
Tue 9/15
7:00 am-10:30 am
Nonstop2h 30m
$357
Showing 1-10 of 59 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-RFD
ORF-MDW
ORF-ORD
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-RFD
ORF-MDW
ORF-ORD
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 24, 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 June 24, 2026.
The most flights from V1B to CHI are scheduled on a Monday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 20, 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 24, 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
Boarding
8.1
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
7.9
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
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 24, 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 24, 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 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$354 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$314 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$385 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$200 | Average$260 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$387 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$425 | FlexibilityNo cancel fee | On-time69% |