$70+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jun 2 — Jun 91
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 May 3, 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 3, 2026.
This CheapOair deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2410:50 am
ORF
- ORD
1 stop22h 10m
Multiple Airlines
Sun 5/315:05 am
ORD
- ORF
1 stop11h 34m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$310
This CheapOair deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Sat 5/237:44 pm
ORF
- ORD
1 stop27h 30m
Spirit Airlines
Sun 5/315:05 am
ORD
- ORF
1 stop11h 34m
Spirit Airlines
Deal found 4/27![Spirit Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 7/299:35 pm
ORF
- MDW
2 stops25h 33m
Frontier
Tue 8/1112:11 pm
MDW
- ORF
1 stop22h 10m
Frontier
Deal found 4/29![Frontier logo]()
$312
This eDestinos deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2412:06 pm
ORF
- ORD
2 stops12h 07m
Frontier
Sat 5/301:50 pm
ORD
- ORF
2 stops29h 27m
Frontier
Deal found 4/30![Frontier logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2012:06 pm
ORF
- MDW
1 stop10h 56m
Multiple Airlines
Fri 5/224:28 pm
MDW
- ORF
2 stops25h 21m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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
- ORD
1 stop8h 32m
Frontier
Sat 7/119:57 pm
ORD
- ORF
2 stops36h 24m
Frontier
Deal found 4/27![Frontier logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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
- MDW
1 stop10h 47m
Frontier
Sun 7/1912:11 pm
MDW
- ORF
1 stop22h 10m
Frontier
Deal found 4/29![Frontier logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 stop6h 41m
Multiple Airlines
Sun 7/197:07 pm
ORD
- ORF
2 stops39h 14m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$315
This CheapOair deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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.
Wed 5/612:06 pm
ORF
- ORD
1 stop8h 45m
Frontier
Sat 5/95:30 pm
ORD
- ORF
1 stop25h 24m
Frontier
Deal found 4/30![Frontier logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 8/2612:21 pm
ORF
- MDW
1 stop10h 50m
Multiple Airlines
Fri 8/286:00 am
MDW
- ORF
2 stops14h 41m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/276:19 pm
ORF
- ORD
Nonstop2h 38m
American Airlines
Wed 6/32:30 pm
ORD
- ORF
Nonstop2h 19m
American Airlines
Deal found 4/29![American Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 8/912:21 pm
ORF
- MDW
1 stop10h 47m
Frontier
Fri 8/1412:11 pm
MDW
- ORF
1 stop22h 03m
Frontier
Deal found 4/28![Frontier logo]()
$318
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 3, 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 3, 2026.
This CheapOair deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/127:52 pm
ORF
- ORD
1 stop27h 22m
Spirit Airlines
Sun 6/145:05 am
ORD
- ORF
1 stop11h 34m
Spirit Airlines
Deal found 4/27![Spirit Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/28:00 am
ORF
- ORD
Nonstop2h 32m
United Airlines
Thu 6/49:19 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 4/28![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/35:20 am
ORF
- ORD
1 stop5h 56m
Delta
Wed 6/35:19 pm
ORD
- ORF
1 stop4h 56m
Delta
Deal found 4/28![Delta logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/87:00 am
ORF
- RFD
1 stop9h 57m
Multiple Airlines
Sat 7/1110:05 am
RFD
- ORF
1 stop9h 34m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/36:50 am
ORF
- MDW
1 stop4h 50m
Southwest
Sat 6/66:30 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 4/29![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/57:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 6/87:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 4/28![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/236:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Sun 5/317:00 am
ORD
- ORF
Nonstop2h 31m
United Airlines
Deal found 4/27![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/265:01 pm
ORF
- ORD
1 stop4h 30m
Delta
Tue 6/305:22 pm
ORD
- ORF
1 stop5h 07m
Delta
Deal found 4/28![Delta logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 7/96:08 pm
ORF
- RFD
1 stop25h 52m
Multiple Airlines
Mon 7/137:50 pm
RFD
- ORF
2 stops14h 31m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/276:25 am
ORF
- MDW
1 stop6h 45m
Southwest
Sat 5/307:50 am
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 4/29![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/128:00 am
ORF
- ORD
Nonstop2h 32m
United Airlines
Sun 6/149:19 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 4/27![United Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/299:12 pm
ORF
- RFD
1 stop13h 09m
Multiple Airlines
Sun 5/3111:27 am
RFD
- ORF
2 stops22h 13m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/253:30 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Mon 6/297:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 4/28![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/236:05 am
ORF
- ORD
1 stop6h 49m
United Airlines
Sat 5/236:12 pm
ORD
- ORF
1 stop4h 32m
United Airlines
Deal found 5/1![United Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/224:58 pm
ORF
- ORD
1 stop4h 16m
Delta
Mon 5/257:00 am
ORD
- ORF
1 stop4h 17m
Delta
Deal found 4/28![Delta logo]()
$416
This Mytrip deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:44 pm
ORF
- ORD
3 stops25h 27m
Spirit Airlines
Sun 5/317:33 pm
ORD
- ORF
3 stops22h 16m
Spirit Airlines
Deal found 4/27![Spirit Airlines logo]()
$475
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/128:20 am
ORF
- RFD
1 stop27h 59m
Multiple Airlines
Sun 5/1710:37 am
RFD
- ORF
2 stops32h 40m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$395
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sun 7/197:45 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 4/29![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:05 am
ORF
- MDW
Nonstop2h 05m
Southwest
Sun 8/27:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/2![Southwest logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/219:12 pm
ORF
- RFD
1 stop23h 01m
Multiple Airlines
Mon 5/258:03 pm
RFD
- ORF
2 stops38h 08m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/226:05 am
ORF
- ORD
1 stop4h 31m
United Airlines
Fri 5/2211:53 am
ORD
- ORF
Nonstop2h 21m
United Airlines
Deal found 4/30![United Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/1511:25 am
ORF
- MDW
2 stops6h 15m
Southwest
Tue 6/301:00 pm
MDW
- ORF
2 stops8h 35m
Southwest
Deal found 4/29![Southwest logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:23 pm
ORF
- RFD
1 stop15h 29m
Multiple Airlines
Sun 9/203:53 pm
RFD
- ORF
2 stops22h 11m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 9/178:00 am
ORF
- MDW
Nonstop2h 00m
Southwest
Sun 9/207:30 am
MDW
- ORF
1 stop6h 00m
Southwest
Deal found 5/1![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:45 pm
ORF
- MDW
1 stop6h 15m
Southwest
Mon 9/79:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 4/29![Southwest logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 9/47:00 am
ORF
- RFD
1 stop13h 07m
Multiple Airlines
Mon 9/76:02 pm
RFD
- ORF
1 stop18h 28m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/239:35 pm
ORF
- RFD
1 stop12h 42m
Multiple Airlines
Sat 6/2710:07 am
RFD
- ORF
1 stop9h 33m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$484
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/295:25 pm
ORF
- MDW
1 stop5h 55m
Southwest
Sun 5/314:45 pm
MDW
- ORF
1 stop5h 35m
Southwest
Deal found 4/30![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/236:10 am
ORF
- ORD
2 stops10h 20m
Southwest
Sun 5/312:40 pm
ORD
- ORF
2 stops8h 00m
Southwest
Deal found 4/27![Southwest logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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
Mon 9/214:50 pm
RFD
- ORF
1 stop23h 53m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$794
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated May 3, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated May 3, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/712:06 pm
ORF
- ORD
1 stop8h 45m
Frontier
Sat 5/95:30 pm
ORD
- ORF
1 stop25h 24m
Frontier
Deal found 5/1![Frontier logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/89:12 pm
ORF
- ORD
1 stop26h 02m
Multiple Airlines
Sun 5/173:44 pm
ORD
- ORF
2 stops18h 27m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/97:44 pm
ORF
- ORD
2 stops19h 55m
Multiple Airlines
Sun 5/171:59 pm
ORD
- ORF
1 stop20h 12m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$325
This CheapOair deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
Mon 5/1112:06 pm
ORF
- ORD
1 stop8h 45m
Frontier
Wed 5/133:55 pm
ORD
- ORF
1 stop26h 44m
Frontier
Deal found 5/1![Frontier logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/119:12 pm
ORF
- ORD
2 stops23h 39m
Multiple Airlines
Wed 5/138:30 am
ORD
- ORF
1 stop13h 12m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/128:20 am
ORF
- ORD
2 stops13h 12m
Multiple Airlines
Thu 5/145:05 am
ORD
- ORF
1 stop11h 34m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2012:06 pm
ORF
- MDW
1 stop10h 56m
Multiple Airlines
Fri 5/224:28 pm
MDW
- ORF
2 stops25h 21m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/2112:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Sat 5/2311:59 am
MDW
- ORF
1 stop22h 12m
Frontier
Deal found 4/30![Frontier logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/2112:06 pm
ORF
- MDW
1 stop10h 56m
Multiple Airlines
Sat 5/236:00 am
MDW
- ORF
2 stops11h 49m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/266:20 am
ORF
- MDW
1 stop4h 40m
Delta
Tue 6/210:59 am
MDW
- ORF
1 stop5h 22m
Delta
Deal found 4/30![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/266:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Fri 5/297:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/2![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/316:55 am
ORF
- MDW
Nonstop2h 10m
Southwest
Tue 6/26:05 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 4/30![Southwest logo]()
$340
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 3, 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 3, 2026.
This Trip.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 5/1![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/2712:06 pm
ORF
- ORD
1 stop8h 35m
Frontier
Deal found 4/29![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/2612:06 pm
ORF
- ORD
1 stop20h 49m
Frontier
Deal found 4/30![Frontier logo]()
$76
This Trip.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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
- MDW
1 stop11h 02m
Frontier
Deal found 4/30![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/189:12 pm
ORF
- ORD
1 stop27h 01m
Frontier
Deal found 4/28![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/412:06 pm
ORF
- ORD
1 stop8h 23m
Frontier
Deal found 5/2![Frontier logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/2312:00 pm
ORF
- ORD
1 stop8h 41m
Frontier
Deal found 4/30![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/2412:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Deal found 4/29![Frontier logo]()
$88
This Trip.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/2312:00 pm
ORF
- MDW
1 stop11h 02m
Frontier
Deal found 5/1![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:06 pm
ORF
- ORD
1 stop8h 45m
Frontier
Deal found 4/29![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/2812:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 4/29![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 5/2812:06 pm
ORF
- ORD
1 stop8h 35m
Frontier
Deal found 4/30![Frontier logo]()
$96
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 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $310 (CheapOair) |
One-way from | $70 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $357 |
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 3, 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 - ORD
ORFORD
Norfolk
Fri 6/12
7:52 pm-10:14 pm
1 stop27h 22m
Chicago O'Hare Intl
Sun 6/14
5:05 am-5:39 pm
1 stop11h 34m
$334
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Tue 6/2
8:00 am-9:32 am
Nonstop2h 32m
Chicago O'Hare Intl
Thu 6/4
9:19 pm-12:41 am
Nonstop2h 22m
$336
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Wed 6/3
5:20 am-10:16 am
1 stop5h 56m
Chicago O'Hare Intl
Wed 6/3
5:19 pm-11:15 pm
1 stop4h 56m
$337
NorfolkChicago
ORF - RFD
ORFRFD
Norfolk
Wed 7/8
7:00 am-3:57 pm
1 stop9h 57m
Chicago Greater Rockford
Sat 7/11
10:05 am-8:39 pm
1 stop9h 34m
$339
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 6/3
6:50 am-10:40 am
1 stop4h 50m
Chicago Midway
Sat 6/6
6:30 pm-9:30 pm
Nonstop2h 00m
$346
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 6/5
7:15 pm-8:20 pm
Nonstop2h 05m
Chicago Midway
Mon 6/8
7:40 am-10:45 am
Nonstop2h 05m
$359
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Sat 5/23
6:00 am-7:28 am
Nonstop2h 28m
Chicago O'Hare Intl
Sun 5/31
7:00 am-10:31 am
Nonstop2h 31m
$359
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 5/27
6:25 am-12:10 pm
1 stop6h 45m
Chicago Midway
Sat 5/30
7:50 am-10:50 am
Nonstop2h 00m
$359
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Fri 6/26
5:01 pm-8:31 pm
1 stop4h 30m
Chicago O'Hare Intl
Tue 6/30
5:22 pm-11:29 pm
1 stop5h 07m
$360
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Fri 6/12
8:00 am-9:32 am
Nonstop2h 32m
Chicago O'Hare Intl
Sun 6/14
9:19 pm-12:41 am
Nonstop2h 22m
$363
Showing 1-10 of 54 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 3, 2026.
A simple way to save on the total cost of your ticket is to fly from Virginia Beach to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 10% on your trip compared to booking a flight in the morning.
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 April 25, 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 3, 2026.
The most flights from V1B to CHI are scheduled on a Friday (33 on average). You will have fewer flight options on Thursday, 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 3, 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.
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
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.
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 May 3, 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 3, 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 3, 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$362 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$211 | Average$399 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$217 | Average$371 | FlexibilityNo cancel fee | On-time71% |