$62+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jun 13 — Jun 201
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 2 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from Virginia Beach to Chicago
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Best
Last-minute
One-way
Cheapest flights from Virginia Beach to ChicagoExplore the most affordable flight options available from Virginia Beach to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 14, 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 May 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 5/3012:00 pm
ORF
- ORD
1 stop8h 41m
Frontier
Mon 6/19:37 pm
ORD
- ORF
2 stops36h 34m
Frontier
Deal found 5/10![Frontier logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:00 pm
ORF
- ORD
1 stop8h 29m
Frontier
Sun 6/76:55 am
ORD
- ORF
1 stop27h 16m
Frontier
Deal found 5/12![Frontier logo]()
$321
This CheapOair deal was found by Cheapflights users on 5/11. 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.
Thu 6/412:06 pm
ORF
- ORD
1 stop8h 23m
Multiple Airlines
Tue 6/98:30 pm
ORD
- ORF
1 stop12h 29m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:21 pm
ORF
- ORD
1 stop20h 42m
Frontier
Sun 6/146:55 am
ORD
- ORF
1 stop27h 31m
Frontier
Deal found 5/13![Frontier logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:04 pm
ORF
- MDW
2 stops11h 07m
Multiple Airlines
Tue 9/112:27 pm
MDW
- ORF
1 stop21h 59m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$324
This CheapOair deal was found by Cheapflights users on 5/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:21 pm
ORF
- ORD
1 stop8h 32m
Frontier
Sun 7/125:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 5/12![Frontier logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/119:35 pm
ORF
- MDW
2 stops42h 03m
Multiple Airlines
Sat 7/2512:11 pm
MDW
- ORF
1 stop22h 10m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 6/612:00 pm
ORF
- ORD
1 stop8h 29m
Frontier
Tue 6/99:48 pm
ORD
- ORF
2 stops36h 38m
Frontier
Deal found 5/14![Frontier logo]()
$327
This Frontier deal was found by Cheapflights users on 5/14. 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.
Thu 7/169:35 pm
ORF
- ORD
1 stop12h 36m
Frontier
Mon 7/2010:16 am
ORD
- ORF
1 stop9h 23m
Frontier
Deal found 5/14![Frontier logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 7/1612:21 pm
ORF
- ORD
1 stop8h 32m
Frontier
Sun 7/197:05 am
ORD
- ORF
1 stop27h 16m
Frontier
Deal found 5/11![Frontier logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1912:21 pm
ORF
- MDW
1 stop23h 43m
Frontier
Tue 6/2312:27 pm
MDW
- ORF
1 stop21h 59m
Frontier
Deal found 5/13![Frontier logo]()
$330
This Trip.com deal was found by Cheapflights users on 5/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:06 pm
ORF
- ORD
1 stop8h 35m
Frontier
Wed 6/244:59 pm
ORD
- ORF
1 stop26h 41m
Frontier
Deal found 5/11![Frontier logo]()
$330
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 May 14, 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 May 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:35 pm
ORF
- RFD
1 stop12h 42m
Multiple Airlines
Mon 6/157:53 pm
RFD
- ORF
1 stop21h 47m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 5/13. 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.
Wed 6/108:00 am
ORF
- ORD
Nonstop2h 32m
United Airlines
Wed 6/176:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 5/13![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 5/11. 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.
Wed 7/1511:40 am
ORF
- MDW
Nonstop2h 05m
Southwest
Wed 7/154:10 pm
MDW
- ORF
1 stop5h 25m
Southwest
Deal found 5/11![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 5/11. 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.
Wed 6/106:20 am
ORF
- ORD
1 stop4h 53m
Delta
Sat 6/136:10 pm
ORD
- ORF
1 stop5h 37m
Delta
Deal found 5/11![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 5/14. 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.
Sat 6/66:35 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Tue 6/96:50 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/14![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 5/14. 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.
Sat 6/66:00 am
ORF
- ORD
Nonstop2h 29m
United Airlines
Tue 6/96:15 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 5/14![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/261:57 pm
ORF
- ORD
1 stop7h 35m
Delta
Tue 6/301:46 pm
ORD
- ORF
1 stop6h 56m
Delta
Deal found 5/10![Delta logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 10/37:00 am
ORF
- RFD
2 stops27h 18m
Multiple Airlines
Wed 10/711:04 am
RFD
- ORF
1 stop10h 25m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:50 am
ORF
- MDW
Nonstop2h 00m
Southwest
Mon 7/67:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 5/12![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 5/11. 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.
Fri 8/75:00 pm
ORF
- ORD
Nonstop2h 32m
United Airlines
Sun 8/96:15 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 5/11![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/115:20 am
ORF
- MDW
1 stop5h 49m
Delta
Mon 6/156:00 am
MDW
- ORF
1 stop4h 29m
Delta
Deal found 5/10![Delta logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Thu 9/106:10 pm
ORF
- RFD
1 stop15h 42m
Multiple Airlines
Mon 9/144:50 pm
RFD
- ORF
2 stops18h 12m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 5/13. 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.
Wed 6/1012:40 pm
ORF
- MDW
2 stops8h 10m
Southwest
Wed 6/175:10 am
MDW
- ORF
2 stops8h 15m
Southwest
Deal found 5/13![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:23 am
ORF
- MDW
1 stop7h 28m
Delta
Sun 8/166:42 pm
MDW
- ORF
1 stop4h 00m
Delta
Deal found 5/9![Delta logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 6/49:12 pm
ORF
- RFD
1 stop22h 51m
Multiple Airlines
Mon 6/87:53 pm
RFD
- ORF
1 stop23h 47m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$394
This Southwest deal was found by Cheapflights users on 5/10. 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.
Wed 7/16:05 am
ORF
- MDW
2 stops5h 55m
Southwest
Wed 7/87:50 am
MDW
- ORF
2 stops5h 35m
Southwest
Deal found 5/10![Southwest logo]()
$367
This United Airlines deal was found by Cheapflights users on 5/14. 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 6/310:48 am
ORF
- ORD
Nonstop2h 39m
United Airlines
Sat 6/69:29 pm
ORD
- ORF
Nonstop2h 28m
United Airlines
Deal found 5/14![United Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 5/11. 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.
Mon 6/86:10 pm
ORF
- MDW
1 stop4h 50m
Southwest
Wed 6/107:45 am
MDW
- ORF
2 stops7h 05m
Southwest
Deal found 5/11![Southwest logo]()
$372
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:02 am
ORF
- ORD
1 stop8h 14m
Delta
Sun 5/315:30 am
ORD
- ORF
1 stop4h 52m
Delta
Deal found 5/9![Delta logo]()
$421
This United Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1710:48 am
ORF
- ORD
Nonstop2h 39m
United Airlines
Sun 6/216:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 5/9![United Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 6/119:35 pm
ORF
- RFD
1 stop22h 28m
Multiple Airlines
Mon 6/157:53 pm
RFD
- ORF
1 stop21h 47m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$440
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/212:45 pm
ORF
- MDW
2 stops8h 00m
Southwest
Thu 6/42:40 pm
MDW
- ORF
2 stops7h 45m
Southwest
Deal found 5/12![Southwest logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:35 pm
ORF
- RFD
1 stop12h 42m
Multiple Airlines
Mon 6/297:48 pm
RFD
- ORF
2 stops14h 38m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 5/13. 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.
Thu 5/288:05 am
ORF
- MDW
Nonstop2h 10m
Southwest
Wed 6/36:05 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 5/13![Southwest logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 6/129:35 pm
ORF
- RFD
1 stop12h 42m
Multiple Airlines
Mon 6/157:53 pm
RFD
- ORF
2 stops14h 33m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$476
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 am
ORF
- RFD
1 stop9h 45m
Multiple Airlines
Sun 9/133:53 pm
RFD
- ORF
2 stops17h 49m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$629
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated May 14, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated May 14, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 5/2912:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Wed 6/2412:04 pm
MDW
- ORF
1 stop22h 22m
Frontier
Deal found 5/11![Frontier logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 5/3012:00 pm
ORF
- MDW
1 stop11h 02m
Frontier
Mon 6/16:00 am
MDW
- ORF
2 stops13h 17m
Frontier
Deal found 5/10![Frontier logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Sun 5/319:12 pm
ORF
- MDW
2 stops39h 00m
Frontier
Sat 6/611:59 am
MDW
- ORF
1 stop22h 12m
Frontier
Deal found 5/11![Frontier logo]()
$331
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Thu 6/47:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/12![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Thu 6/49:12 pm
ORF
- MDW
2 stops18h 36m
Multiple Airlines
Tue 6/96:00 am
MDW
- ORF
1 stop28h 26m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Sun 6/76:00 am
MDW
- ORF
1 stop28h 11m
Frontier
Deal found 5/12![Frontier logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:00 pm
ORF
- MDW
1 stop11h 02m
Multiple Airlines
Sun 6/76:00 am
MDW
- ORF
2 stops12h 55m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:35 pm
ORF
- RFD
1 stop12h 42m
Multiple Airlines
Mon 6/157:53 pm
RFD
- ORF
1 stop21h 47m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 5/13. 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.
Wed 6/107:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Wed 6/1712:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/13![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Thu 6/1112:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Mon 6/1512:04 pm
MDW
- ORF
1 stop22h 22m
Frontier
Deal found 5/12![Frontier logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1312:06 pm
ORF
- MDW
1 stop11h 05m
Frontier
Mon 6/1512:04 pm
MDW
- ORF
1 stop22h 22m
Frontier
Deal found 5/12![Frontier logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1912:21 pm
ORF
- MDW
1 stop23h 43m
Frontier
Tue 6/2312:27 pm
MDW
- ORF
1 stop21h 59m
Frontier
Deal found 5/13![Frontier logo]()
$330
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 May 14, 2026.
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated May 14, 2026.
This Trip.com deal was found by Cheapflights users on 5/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:21 pm
ORF
- ORD
1 stop8h 32m
Frontier
Deal found 5/14![Frontier logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 6/2312:21 pm
ORF
- ORD
1 stop20h 42m
Frontier
Deal found 5/11![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 5/14. 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 6/912:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Deal found 5/14![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Mon 6/812:06 pm
ORF
- MDW
1 stop24h 06m
Frontier
Deal found 5/12![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:06 pm
ORF
- ORD
1 stop20h 57m
Frontier
Deal found 5/13![Frontier logo]()
$70
This Trip.com deal was found by Cheapflights users on 5/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:00 pm
ORF
- ORD
1 stop8h 29m
Frontier
Deal found 5/11![Frontier logo]()
$77
This Trip.com deal was found by Cheapflights users on 5/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:21 pm
ORF
- ORD
1 stop8h 32m
Frontier
Deal found 5/14![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Deal found 5/13![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:00 pm
ORF
- MDW
1 stop11h 02m
Frontier
Deal found 5/13![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:21 pm
ORF
- ORD
1 stop8h 32m
Frontier
Deal found 5/13![Frontier logo]()
$84
This Trip.com deal was found by Cheapflights users on 5/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2312:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Deal found 5/13![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 7/812:21 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 5/12![Frontier logo]()
$88
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 May 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (Kiwi.com) |
One-way from | $62 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $363 |
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 May 14, 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
Tue 6/9
9:35 pm-9:17 am
1 stop12h 42m
Chicago Greater Rockford
Mon 6/15
7:53 pm-6:40 pm
1 stop21h 47m
$331
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Wed 6/10
8:00 am-9:32 am
Nonstop2h 32m
Chicago O'Hare Intl
Wed 6/17
6:45 am-10:07 am
Nonstop2h 22m
$337
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 7/15
11:40 am-12:45 pm
Nonstop2h 05m
Chicago Midway
Wed 7/15
4:10 pm-10:35 pm
1 stop5h 25m
$347
Quickest round-trip
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 6/6
6:35 pm-7:40 pm
Nonstop2h 05m
Chicago Midway
Tue 6/9
6:50 pm-9:50 pm
Nonstop2h 00m
$347
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Sat 6/6
6:00 am-7:29 am
Nonstop2h 29m
Chicago O'Hare Intl
Tue 6/9
6:15 pm-9:37 pm
Nonstop2h 22m
$347
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 6/24
7:50 am-8:50 am
Nonstop2h 00m
Chicago Midway
Mon 7/6
7:40 am-10:45 am
Nonstop2h 05m
$350
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Fri 8/7
5:00 pm-6:32 pm
Nonstop2h 32m
Chicago O'Hare Intl
Sun 8/9
6:15 pm-9:37 pm
Nonstop2h 22m
$363
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Wed 6/10
6:20 am-10:13 am
1 stop4h 53m
Chicago O'Hare Intl
Sat 6/13
6:10 pm-12:47 am
1 stop5h 37m
$367
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 6/10
12:40 pm-7:50 pm
2 stops8h 10m
Chicago Midway
Wed 6/17
5:10 am-2:25 pm
2 stops8h 15m
$367
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 7/1
6:05 am-11:00 am
2 stops5h 55m
Chicago Midway
Wed 7/8
7:50 am-2:25 pm
2 stops5h 35m
$367
Showing 1-10 of 56 resultsSorted by cheapest first
Best time to book a flight from Virginia Beach to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Virginia Beach with our price prediction graph.
ORF-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 May 14, 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 May 9, 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.
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 May 14, 2026.
The most flights from V1B to CHI are scheduled on a Wednesday (30 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (21 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 May 14, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Virginia Beach to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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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 May 14, 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 May 14, 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 7 airlines flying from Virginia Beach to Chicago
Discover the top 7 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 May 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$354 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$303 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$260 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$126 | Average$352 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$375 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$374 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$217 | Average$402 | FlexibilityNo cancel fee | On-time69% |