$65+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Apr 15 — Apr 221
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 September or October, booked 60 days in advance, depart on a Thursday or Friday 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 March 16, 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 March 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mon 3/233:26 pm
ORF
- ORD
1 stop29h 37m
Multiple Airlines
Mon 3/306:10 pm
ORD
- ORF
1 stop24h 36m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mon 4/1311:33 am
ORF
- ORD
1 stop12h 06m
Multiple Airlines
Mon 4/206:40 am
ORD
- ORF
1 stop9h 24m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:41 pm
ORF
- ORD
1 stop25h 36m
Multiple Airlines
Mon 4/205:50 am
ORD
- ORF
2 stops13h 12m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$279
This Frontier deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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.
Sun 4/128:15 pm
ORF
- ORD
1 stop13h 02m
Frontier
Thu 4/167:38 am
ORD
- ORF
1 stop11h 08m
Frontier
Deal found 3/14![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/157:05 am
ORF
- MDW
2 stops13h 26m
Multiple Airlines
Sat 4/187:34 pm
MDW
- ORF
1 stop13h 58m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$281
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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 6/113:15 pm
ORF
- ORD
1 stop9h 26m
Frontier
Mon 6/155:14 pm
ORD
- ORF
1 stop17h 07m
Frontier
Deal found 3/13![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/146:45 am
ORF
- MDW
2 stops16h 29m
Multiple Airlines
Fri 4/179:14 am
MDW
- ORF
1 stop7h 13m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$282
This CheapOair deal was found by Cheapflights users on 3/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:41 pm
ORF
- ORD
1 stop21h 34m
Spirit Airlines
Tue 4/147:17 am
ORD
- ORF
1 stop11h 29m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mon 3/238:41 pm
ORF
- ORD
2 stops22h 45m
Spirit Airlines
Mon 3/306:10 pm
ORD
- ORF
1 stop24h 36m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/1512:06 pm
ORF
- ORD
2 stops12h 01m
Multiple Airlines
Mon 5/1810:50 am
ORD
- ORF
1 stop8h 27m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Fri 4/176:12 pm
ORF
- ORD
1 stop15h 53m
Multiple Airlines
Thu 4/2310:31 am
ORD
- ORF
1 stop8h 15m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$285
This CheapOair deal was found by Cheapflights users on 3/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:33 am
ORF
- ORD
1 stop12h 06m
Multiple Airlines
Wed 4/158:31 am
ORD
- ORF
2 stops23h 41m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$286
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 March 16, 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 March 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/118:41 pm
ORF
- RFD
1 stop14h 06m
Multiple Airlines
Thu 4/1610:37 am
RFD
- ORF
1 stop8h 25m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Sat 4/186:11 am
ORF
- ORD
1 stop6h 16m
United Airlines
Wed 4/225:48 pm
ORD
- ORF
Nonstop2h 20m
United Airlines
Deal found 3/11![United Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1610:05 am
ORF
- MDW
1 stop6h 00m
Southwest
Sat 4/187:50 am
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 3/11![Southwest logo]()
$329
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 4/1510:34 am
ORF
- ORD
Nonstop2h 36m
American Airlines
Sun 4/197:16 pm
ORD
- ORF
Nonstop2h 16m
American Airlines
Deal found 3/15![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/145:50 am
ORF
- MDW
1 stop5h 06m
Delta
Thu 4/166:00 am
MDW
- ORF
1 stop5h 57m
Delta
Deal found 3/14![Delta logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 4/157:00 am
ORF
- ORD
1 stop12h 47m
Multiple Airlines
Sun 4/195:59 am
ORD
- ORF
1 stop27h 33m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$314
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:30 am
ORF
- ORD
Nonstop2h 39m
United Airlines
Mon 6/89:19 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 3/12![United Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/411:25 am
ORF
- MDW
2 stops6h 25m
Southwest
Mon 6/812:45 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 3/11![Southwest logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Wed 7/297:00 am
ORF
- RFD
2 stops28h 37m
Multiple Airlines
Fri 8/76:26 pm
RFD
- ORF
1 stop16h 58m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Thu 4/166:11 am
ORF
- ORD
1 stop6h 16m
United Airlines
Sat 4/185:48 pm
ORD
- ORF
Nonstop2h 20m
United Airlines
Deal found 3/11![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 6/57:05 am
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 6/87:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 3/15![Southwest logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:00 am
ORF
- RFD
2 stops28h 37m
Multiple Airlines
Mon 8/108:39 am
RFD
- ORF
1 stop13h 09m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 3/11. 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 6/114:27 pm
ORF
- MDW
1 stop6h 18m
Delta
Mon 6/155:59 pm
MDW
- ORF
1 stop4h 34m
Delta
Deal found 3/11![Delta logo]()
$409
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:15 pm
ORF
- MDW
2 stops7h 50m
Southwest
Mon 4/203:50 pm
MDW
- ORF
2 stops6h 05m
Southwest
Deal found 3/12![Southwest logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:16 pm
ORF
- RFD
1 stop21h 57m
Multiple Airlines
Fri 8/76:26 pm
RFD
- ORF
1 stop16h 58m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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 7/38:00 am
ORF
- ORD
Nonstop2h 32m
United Airlines
Mon 7/66:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 3/13![United Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 5/58:40 am
ORF
- ORD
2 stops10h 45m
Southwest
Fri 5/82:40 pm
ORD
- ORF
2 stops7h 15m
Southwest
Deal found 3/15![Southwest logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:32 pm
ORF
- RFD
1 stop19h 41m
Multiple Airlines
Mon 8/108:39 am
RFD
- ORF
1 stop13h 09m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$352
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
ORF
- ORD
Nonstop2h 31m
United Airlines
Mon 4/203:35 pm
ORD
- ORF
Nonstop2h 25m
United Airlines
Deal found 3/12![United Airlines logo]()
$389
This Southwest deal was found by Cheapflights users on 3/10. 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.
Tue 5/56:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sun 5/107:05 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 3/10![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/159:45 am
ORF
- ORD
Nonstop2h 42m
United Airlines
Wed 4/153:35 pm
ORD
- ORF
Nonstop2h 25m
United Airlines
Deal found 3/14![United Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/1310:05 am
ORF
- MDW
2 stops11h 00m
Southwest
Thu 4/165:50 pm
MDW
- ORF
1 stop4h 05m
Southwest
Deal found 3/14![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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 4/126:55 am
ORF
- MDW
Nonstop2h 10m
Southwest
Sun 4/197:05 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 3/13![Southwest logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Wed 4/88:41 pm
ORF
- RFD
1 stop14h 06m
Multiple Airlines
Sun 4/1210:37 am
RFD
- ORF
1 stop8h 09m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$571
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated March 16, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated March 16, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mon 3/233:26 pm
ORF
- ORD
1 stop29h 37m
Multiple Airlines
Mon 3/306:10 pm
ORD
- ORF
1 stop24h 36m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mon 3/238:41 pm
ORF
- ORD
2 stops22h 45m
Spirit Airlines
Mon 3/306:10 pm
ORD
- ORF
1 stop24h 36m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$283
This CheapOair deal was found by Cheapflights users on 3/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:41 pm
ORF
- ORD
1 stop21h 34m
Spirit Airlines
Tue 4/147:17 am
ORD
- ORF
1 stop11h 29m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$282
This CheapOair deal was found by Cheapflights users on 3/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:33 am
ORF
- ORD
1 stop12h 06m
Multiple Airlines
Wed 4/158:31 am
ORD
- ORF
2 stops23h 41m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/118:41 pm
ORF
- RFD
1 stop14h 06m
Multiple Airlines
Thu 4/1610:37 am
RFD
- ORF
1 stop8h 25m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$287
This Frontier deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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.
Sun 4/128:15 pm
ORF
- ORD
1 stop13h 02m
Frontier
Thu 4/167:38 am
ORD
- ORF
1 stop11h 08m
Frontier
Deal found 3/14![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/128:15 pm
ORF
- ORD
1 stop13h 02m
Frontier
Fri 4/174:28 pm
ORD
- ORF
1 stop17h 04m
Frontier
Deal found 3/14![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mon 4/1311:33 am
ORF
- ORD
1 stop12h 06m
Multiple Airlines
Mon 4/206:40 am
ORD
- ORF
1 stop9h 24m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:41 pm
ORF
- ORD
1 stop25h 36m
Multiple Airlines
Mon 4/205:50 am
ORD
- ORF
2 stops13h 12m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/146:45 am
ORF
- MDW
2 stops16h 29m
Multiple Airlines
Fri 4/179:14 am
MDW
- ORF
1 stop7h 13m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 4/157:05 am
ORF
- MDW
2 stops13h 26m
Multiple Airlines
Sat 4/187:34 pm
MDW
- ORF
1 stop13h 58m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Fri 4/176:12 pm
ORF
- ORD
1 stop15h 53m
Multiple Airlines
Thu 4/2310:31 am
ORD
- ORF
1 stop8h 15m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$285
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 March 16, 2026.
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated March 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:00 pm
ORF
- MDW
1 stop11h 02m
Frontier
Deal found 3/10![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mon 5/1112:06 pm
ORF
- ORD
1 stop20h 49m
Frontier
Deal found 3/11![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/1312:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 3/14![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 5/912:00 pm
ORF
- ORD
1 stop10h 12m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 5/1212:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 3/15![Frontier logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 5/1212:06 pm
ORF
- ORD
1 stop20h 49m
Frontier
Deal found 3/15![Frontier logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Thu 5/712:06 pm
ORF
- ORD
1 stop23h 40m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Thu 5/1412:06 pm
ORF
- ORD
1 stop8h 45m
Frontier
Deal found 3/11![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/812:06 pm
ORF
- MDW
1 stop23h 58m
Frontier
Deal found 3/10![Frontier logo]()
$92
This Frontier deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:33 am
ORF
- MDW
1 stop11h 46m
Frontier
Deal found 3/12![Frontier logo]()
$96
This Expedia deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” 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.
Mon 4/1311:33 am
ORF
- ORD
1 stop12h 06m
Frontier
Deal found 3/13![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/1112:06 pm
ORF
- MDW
1 stop24h 06m
Frontier
Deal found 3/14![Frontier logo]()
$97
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 March 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $278 (Kiwi.com) |
One-way from | $65 (Kiwi.com) |
Popular in | June |
Cheapest in | September |
Average price | $373 |
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 March 16, 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 4/11
8:41 pm-9:47 am
1 stop14h 06m
Chicago Greater Rockford
Thu 4/16
10:37 am-8:02 pm
1 stop8h 25m
$287
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Sat 4/18
6:11 am-11:27 am
1 stop6h 16m
Chicago O'Hare Intl
Wed 4/22
5:48 pm-9:08 pm
Nonstop2h 20m
$313
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Wed 4/15
7:00 am-6:47 pm
1 stop12h 47m
Chicago O'Hare Intl
Sun 4/19
5:59 am-10:32 am
1 stop27h 33m
$314
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Wed 6/3
11:30 am-1:09 pm
Nonstop2h 39m
Chicago O'Hare Intl
Mon 6/8
9:19 pm-12:41 am
Nonstop2h 22m
$326
NorfolkChicago
ORF - RFD
ORFRFD
Norfolk
Wed 7/29
7:00 am-10:37 am
2 stops28h 37m
Chicago Greater Rockford
Fri 8/7
6:26 pm-12:24 pm
1 stop16h 58m
$327
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 4/16
10:05 am-3:05 pm
1 stop6h 00m
Chicago Midway
Sat 4/18
7:50 am-10:50 am
Nonstop2h 00m
$329
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 4/16
6:11 am-11:27 am
1 stop6h 16m
Chicago O'Hare Intl
Sat 4/18
5:48 pm-9:08 pm
Nonstop2h 20m
$329
NorfolkChicago
ORF - RFD
ORFRFD
Norfolk
Wed 7/29
7:00 am-10:37 am
2 stops28h 37m
Chicago Greater Rockford
Mon 8/10
8:39 am-10:48 pm
1 stop13h 09m
$335
NorfolkChicago
ORF - RFD
ORFRFD
Norfolk
Tue 7/28
12:16 pm-9:13 am
1 stop21h 57m
Chicago Greater Rockford
Fri 8/7
6:26 pm-12:24 pm
1 stop16h 58m
$342
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 6/4
11:25 am-4:50 pm
2 stops6h 25m
Chicago Midway
Mon 6/8
12:45 pm-3:50 pm
Nonstop2h 05m
$350
Showing 1-10 of 50 resultsSorted by cheapest first
Best time to book a flight from Virginia Beach to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Virginia Beach with our price prediction graph.
ORF-MDW
ORF-ORD
ORF-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Virginia Beach to Chicago
V1B-CHI
ORF-MDW
ORF-ORD
ORF-RFD
How far ahead should I book a flight from Virginia Beach to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Virginia Beach to Chicago. Price data was last updated on March 13, 2026.
Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Virginia Beach to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Virginia Beach to Chicago?
Currently, May is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $108). Flying from Virginia Beach to Chicago in July is currently the most expensive (average of $266). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 March 16, 2026.
A simple way to save on the total cost of your ticket is to fly from Virginia Beach to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 9% on your trip compared to booking a flight in the morning.
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 March 12, 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.
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 March 16, 2026.
The most flights from V1B to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Virginia Beach to Chicago?
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 March 16, 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
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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 March 16, 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 March 16, 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 March 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$92 | Average$303 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$260 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$172 | Average$208 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$362 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$211 | Average$389 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$215 | Average$364 | FlexibilityNo cancel fee | On-time71% |