$77+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Aug 21 — Aug 281
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 September 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
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 July 22, 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 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/412:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Thu 8/66:05 am
MDW
- ORF
1 stop28h 10m
Frontier
Deal found 7/20![Frontier logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/281:20 pm
ORF
- ORD
1 stop7h 39m
Multiple Airlines
Sun 8/307:05 am
ORD
- ORF
2 stops27h 14m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$312
This Frontier deal was found by Cheapflights users on 7/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Sun 9/66:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/22![Frontier logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/1212:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Thu 8/139:34 pm
ORD
- ORF
2 stops36h 47m
Frontier
Deal found 7/19![Frontier logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Wed 8/512:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Sat 8/811:06 am
MDW
- ORF
1 stop23h 09m
Frontier
Deal found 7/21![Frontier logo]()
$316
This Southwest deal was found by Cheapflights users on 7/22. 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.
Sat 9/58:10 am
ORF
- MDW
Nonstop2h 05m
Southwest
Tue 9/88:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 7/22![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:20 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Sat 9/2611:57 am
ORD
- ORF
Nonstop2h 19m
United Airlines
Deal found 7/21![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 7/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:37 pm
ORF
- ORD
Nonstop2h 29m
American Airlines
Sun 9/62:29 pm
ORD
- ORF
Nonstop2h 17m
American Airlines
Deal found 7/20![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 7/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:37 pm
ORF
- ORD
Nonstop2h 29m
American Airlines
Sat 9/122:22 pm
ORD
- ORF
Nonstop2h 25m
American Airlines
Deal found 7/22![American Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/1112:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Sat 8/156:41 pm
MDW
- ORF
2 stops39h 34m
Frontier
Deal found 7/20![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Fri 8/1412:10 pm
ORF
- ORD
1 stop20h 52m
Frontier
Sun 8/168:05 am
ORD
- ORF
2 stops26h 10m
Frontier
Deal found 7/19![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/812:16 pm
ORF
- ORD
1 stop8h 37m
Frontier
Sat 8/151:50 pm
ORD
- ORF
1 stop20h 25m
Frontier
Deal found 7/21![Frontier logo]()
$322
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 22, 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 22, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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.
Tue 9/86:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Thu 9/106:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/21![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:20 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Sat 9/2611:57 am
ORD
- ORF
Nonstop2h 19m
United Airlines
Deal found 7/21![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 7/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:00 pm
ORF
- ORD
1 stop4h 55m
Delta
Sun 9/62:50 pm
ORD
- ORF
1 stop6h 52m
Delta
Deal found 7/20![Delta logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/246:10 pm
ORF
- RFD
1 stop15h 42m
Multiple Airlines
Sun 9/273:53 pm
RFD
- ORF
2 stops17h 49m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 7/21. 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.
Tue 8/256:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Tue 9/19:25 am
MDW
- ORF
1 stop5h 30m
Southwest
Deal found 7/21![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/21. 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 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
Tue 8/256:15 pm
ORD
- ORF
Nonstop2h 33m
United Airlines
Deal found 7/21![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 7/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:02 pm
ORF
- MDW
1 stop6h 42m
Delta
Tue 9/156:05 am
MDW
- ORF
1 stop7h 01m
Delta
Deal found 7/20![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 9/108:00 am
ORF
- MDW
Nonstop2h 00m
Southwest
Fri 9/119:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/18![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 1/1412:15 pm
ORF
- ORD
Nonstop2h 44m
United Airlines
Tue 1/197:15 am
ORD
- ORF
Nonstop2h 31m
United Airlines
Deal found 7/18![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 9/112:24 pm
ORF
- ORD
1 stop7h 07m
Delta
Tue 9/155:30 am
ORD
- ORF
1 stop5h 32m
Delta
Deal found 7/18![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 7/20. 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.
Wed 8/266:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sat 8/293:15 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 7/20![Southwest logo]()
$337
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:41 am
ORF
- ORD
1 stop7h 18m
United Airlines
Mon 9/77:30 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 7/17![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 7/21. 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.
Fri 10/97:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Mon 10/126:45 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 7/21![Southwest logo]()
$340
This United Airlines deal was found by Cheapflights users on 7/20. 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 8/271:00 pm
ORF
- ORD
Nonstop2h 34m
United Airlines
Sun 8/307:15 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 7/20![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:55 pm
ORF
- ORD
1 stop6h 44m
Delta
Sun 11/85:24 pm
ORD
- ORF
1 stop5h 02m
Delta
Deal found 7/18![Delta logo]()
$383
This United Airlines deal was found by Cheapflights users on 7/20. 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.
Sun 8/235:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Sat 8/296:15 pm
ORD
- ORF
Nonstop2h 33m
United Airlines
Deal found 7/20![United Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 7/20. 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 9/59:55 am
ORF
- MDW
2 stops8h 15m
Southwest
Sun 9/61:45 pm
MDW
- ORF
2 stops7h 45m
Southwest
Deal found 7/20![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 7/20. 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.
Fri 9/45:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Sun 9/611:59 am
ORD
- ORF
Nonstop2h 18m
United Airlines
Deal found 7/20![United Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 7/19. 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.
Sat 8/156:25 am
ORF
- MDW
1 stop5h 15m
Southwest
Mon 8/179:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/19![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/87:06 pm
ORF
- RFD
2 stops16h 41m
Multiple Airlines
Mon 8/108:39 am
RFD
- ORF
1 stop13h 29m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$586
This Southwest deal was found by Cheapflights users on 7/22. 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.
Thu 8/206:00 am
ORF
- MDW
2 stops7h 20m
Southwest
Mon 8/249:20 am
MDW
- ORF
2 stops7h 35m
Southwest
Deal found 7/22![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Wed 10/1412:57 pm
ORF
- RFD
2 stops20h 53m
Multiple Airlines
Sun 10/189:33 pm
RFD
- ORF
1 stop22h 09m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$620
This Southwest deal was found by Cheapflights users on 7/19. 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 10/255:45 pm
ORF
- MDW
1 stop6h 50m
Southwest
Thu 10/296:45 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 7/19![Southwest logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Wed 8/57:06 pm
ORF
- RFD
2 stops16h 41m
Multiple Airlines
Sun 8/91:24 pm
RFD
- ORF
1 stop29h 02m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$654
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated July 22, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated July 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/412:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Thu 8/66:05 am
MDW
- ORF
1 stop28h 10m
Frontier
Deal found 7/20![Frontier logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Wed 8/512:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Sat 8/811:06 am
MDW
- ORF
1 stop23h 09m
Frontier
Deal found 7/21![Frontier logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Fri 8/712:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Tue 8/111:50 pm
ORD
- ORF
1 stop20h 25m
Frontier
Deal found 7/21![Frontier logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/812:16 pm
ORF
- ORD
1 stop8h 37m
Frontier
Sat 8/151:50 pm
ORD
- ORF
1 stop20h 25m
Frontier
Deal found 7/21![Frontier logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Sun 8/912:10 pm
ORF
- ORD
1 stop20h 52m
Frontier
Mon 8/171:50 pm
ORD
- ORF
1 stop21h 35m
Frontier
Deal found 7/21![Frontier logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 7/21. 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.
Sun 8/912:10 pm
ORF
- ORD
1 stop20h 52m
Frontier
Tue 8/111:50 pm
ORD
- ORF
1 stop20h 25m
Frontier
Deal found 7/21![Frontier logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/1112:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Sat 8/156:41 pm
MDW
- ORF
2 stops39h 34m
Frontier
Deal found 7/20![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/1212:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Thu 8/139:34 pm
ORD
- ORF
2 stops36h 47m
Frontier
Deal found 7/19![Frontier logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Fri 8/1412:10 pm
ORF
- ORD
1 stop20h 52m
Frontier
Sun 8/168:05 am
ORD
- ORF
2 stops26h 10m
Frontier
Deal found 7/19![Frontier logo]()
$321
This Southwest deal was found by Cheapflights users on 7/22. 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 8/198:05 am
ORF
- MDW
Nonstop2h 00m
Southwest
Wed 8/266:25 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 7/22![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/20. 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.
Wed 8/261:00 pm
ORF
- ORD
Nonstop2h 34m
United Airlines
Sat 8/296:15 pm
ORD
- ORF
Nonstop2h 33m
United Airlines
Deal found 7/20![United Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/281:20 pm
ORF
- ORD
1 stop7h 39m
Multiple Airlines
Sun 8/307:05 am
ORD
- ORF
2 stops27h 14m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$312
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 22, 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 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 10/1912:57 pm
ORF
- ORD
1 stop20h 18m
Frontier
Deal found 7/17![Frontier logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Fri 8/211:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Deal found 7/20![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sat 8/221:20 pm
ORF
- ORD
1 stop7h 48m
Frontier
Deal found 7/20![Frontier logo]()
$79
This Trip.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Deal found 7/18![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 9/1612:57 pm
ORF
- ORD
1 stop24h 05m
Frontier
Deal found 7/19![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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
- ORD
1 stop19h 33m
Frontier
Deal found 7/18![Frontier logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 10/2112:57 pm
ORF
- ORD
1 stop20h 18m
Frontier
Deal found 7/19![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 10/1412:57 pm
ORF
- ORD
1 stop20h 18m
Frontier
Deal found 7/17![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:57 pm
ORF
- ORD
2 stops24h 35m
Frontier
Deal found 7/18![Frontier logo]()
$112
This Trip.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 10/1712:57 pm
ORF
- ORD
1 stop8h 31m
Frontier
Deal found 7/18![Frontier logo]()
$113
This Trip.com deal was found by Cheapflights users on 7/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 7/19![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/1712:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 7/18![Frontier logo]()
$126
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 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $312 (Kiwi.com) |
One-way from | $77 (Kiwi.com) |
Popular in | July |
Cheapest in | September |
Average price | $463 |
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 22, 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
Tue 9/8
6:15 pm-7:20 pm
Nonstop2h 05m
Chicago Midway
Thu 9/10
6:50 pm-9:55 pm
Nonstop2h 05m
$317
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 9/24
6:20 am-7:48 am
Nonstop2h 28m
Chicago O'Hare Intl
Sat 9/26
11:57 am-3:16 pm
Nonstop2h 19m
$317
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Tue 8/25
6:15 pm-7:20 pm
Nonstop2h 05m
Chicago Midway
Tue 9/1
9:25 am-3:55 pm
1 stop5h 30m
$327
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Tue 8/18
6:15 am-11:53 am
1 stop6h 38m
Chicago O'Hare Intl
Tue 8/25
6:15 pm-9:48 pm
Nonstop2h 33m
$327
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 9/10
8:00 am-9:00 am
Nonstop2h 00m
Chicago Midway
Fri 9/11
9:00 am-12:10 pm
Nonstop2h 10m
$327
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Sat 9/5
5:00 pm-8:55 pm
1 stop4h 55m
Chicago O'Hare Intl
Sun 9/6
2:50 pm-10:42 pm
1 stop6h 52m
$337
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 1/14
12:15 pm-1:59 pm
Nonstop2h 44m
Chicago O'Hare Intl
Tue 1/19
7:15 am-10:46 am
Nonstop2h 31m
$337
Quickest round-trip
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 8/26
6:15 pm-7:20 pm
Nonstop2h 05m
Chicago Midway
Sat 8/29
3:15 pm-6:15 pm
Nonstop2h 00m
$337
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Sat 9/5
10:41 am-4:59 pm
1 stop7h 18m
Chicago O'Hare Intl
Mon 9/7
7:30 am-11:00 am
Nonstop2h 30m
$337
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 10/9
7:00 pm-8:10 pm
Nonstop2h 10m
Chicago Midway
Mon 10/12
6:45 pm-9:45 pm
Nonstop2h 00m
$340
Showing 1-10 of 51 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 July 22, 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 22, 2026.
The most flights from V1B to CHI are scheduled on a Monday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 18, 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 22, 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.
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Virginia Beach to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 22, 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 22, 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$369 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$352 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$397 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$388 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$432 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$260 | Average$260 | FlexibilityNo cancel fee | On-timeN/A |