$64+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jun 7 — Jun 141
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 8, 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 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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
2 stops18h 07m
Frontier
Sat 7/111:50 pm
ORD
- ORF
1 stop20h 31m
Frontier
Deal found 5/4![Frontier logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/1212:21 pm
ORF
- MDW
1 stop23h 43m
Frontier
Tue 6/1612:27 pm
MDW
- ORF
1 stop21h 59m
Frontier
Deal found 5/4![Frontier logo]()
$314
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Thu 6/1112:21 pm
ORF
- ORD
1 stop8h 29m
Frontier
Mon 6/154:59 pm
ORD
- ORF
1 stop24h 41m
Frontier
Deal found 5/4![Frontier logo]()
$315
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/36:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Tue 6/97:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 5/5![Southwest logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/36:45 am
ORF
- ORD
Nonstop2h 42m
American Airlines
Tue 6/92:39 pm
ORD
- ORF
Nonstop2h 20m
American Airlines
Deal found 5/5![American Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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
- MDW
1 stop10h 56m
Frontier
Sun 5/3112:27 pm
MDW
- ORF
1 stop21h 44m
Frontier
Deal found 5/7![Frontier logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/297:06 pm
ORF
- ORD
2 stops18h 19m
Multiple Airlines
Thu 8/61:50 pm
ORD
- ORF
1 stop20h 31m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$318
This CheapOair deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/1412:06 pm
ORF
- ORD
1 stop8h 45m
Multiple Airlines
Tue 5/199:49 am
ORD
- ORF
1 stop24h 09m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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
Multiple Airlines
Wed 6/312:04 pm
MDW
- ORF
2 stops9h 38m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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
- ORD
1 stop8h 44m
Frontier
Wed 6/179:48 pm
ORD
- ORF
2 stops36h 38m
Frontier
Deal found 5/4![Frontier logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/1712:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Sun 6/216:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 5/3![Frontier logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/306:00 am
ORF
- ORD
2 stops11h 08m
Multiple Airlines
Wed 8/51:50 pm
ORD
- ORF
1 stop20h 31m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$321
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 8, 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 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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
Fri 6/128:35 am
RFD
- ORF
1 stop13h 13m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/36:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sat 6/66:30 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/7![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/46:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Tue 6/98:40 am
ORD
- ORF
1 stop4h 37m
United Airlines
Deal found 5/4![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Mon 5/256:20 am
ORF
- MDW
1 stop4h 40m
Delta
Sat 5/306:36 pm
MDW
- ORF
1 stop3h 44m
Delta
Deal found 5/4![Delta logo]()
$375
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/7![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Wed 6/179:29 pm
ORD
- ORF
Nonstop2h 28m
United Airlines
Deal found 5/6![United Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 8/712:44 pm
ORF
- ORD
1 stop7h 02m
Delta
Sun 8/95:28 am
ORD
- ORF
1 stop5h 11m
Delta
Deal found 5/3![Delta logo]()
$383
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 10/96:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Tue 10/137:15 am
ORD
- ORF
Nonstop2h 31m
United Airlines
Deal found 5/6![United Airlines logo]()
$350
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/148:05 pm
ORF
- MDW
1 stop5h 15m
Southwest
Wed 6/176:50 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/6![Southwest logo]()
$360
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/2412:40 pm
ORF
- MDW
1 stop6h 35m
Southwest
Sun 6/287:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/6![Southwest logo]()
$360
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/118:00 am
ORF
- ORD
Nonstop2h 32m
United Airlines
Wed 10/144:00 pm
ORD
- ORF
1 stop6h 43m
United Airlines
Deal found 5/6![United Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/199:35 pm
ORF
- RFD
1 stop12h 42m
Multiple Airlines
Mon 6/227:53 pm
RFD
- ORF
2 stops14h 33m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/289:12 pm
ORF
- RFD
1 stop23h 01m
Multiple Airlines
Mon 6/18:35 am
RFD
- ORF
1 stop13h 13m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 8/27:20 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Thu 8/66:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 5/7![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:30 am
ORF
- ORD
Nonstop2h 26m
United Airlines
Sun 8/162:00 pm
ORD
- ORF
Nonstop2h 18m
United Airlines
Deal found 5/4![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/257:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sun 6/287:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/5![Southwest logo]()
$363
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:20 am
ORF
- ORD
1 stop6h 07m
United Airlines
Sun 8/236:45 am
ORD
- ORF
Nonstop2h 25m
United Airlines
Deal found 5/5![United Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/39:35 pm
ORF
- RFD
1 stop12h 40m
Multiple Airlines
Mon 7/67:50 pm
RFD
- ORF
1 stop23h 49m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$458
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/194:30 pm
ORF
- MDW
1 stop4h 35m
Southwest
Fri 6/267:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/5![Southwest logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/237:25 pm
ORF
- RFD
1 stop14h 52m
Multiple Airlines
Fri 6/268:35 am
RFD
- ORF
1 stop13h 13m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$458
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/256:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Sun 7/2612:22 pm
ORD
- ORF
Nonstop2h 21m
United Airlines
Deal found 5/7![United Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/247:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Sun 7/268:50 am
MDW
- ORF
1 stop4h 20m
Southwest
Deal found 5/6![Southwest logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/229:12 pm
ORF
- RFD
1 stop13h 09m
Multiple Airlines
Mon 5/258:03 pm
RFD
- ORF
2 stops35h 23m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/56:00 am
ORF
- MDW
1 stop5h 35m
Southwest
Sun 6/77:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 5/3![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/276:05 am
ORF
- ORD
1 stop4h 31m
United Airlines
Sat 5/3011:53 am
ORD
- ORF
Nonstop2h 21m
United Airlines
Deal found 5/4![United Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/261:59 pm
ORF
- RFD
2 stops26h 56m
Multiple Airlines
Sat 5/3010:11 am
RFD
- ORF
1 stop10h 34m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$497
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/295:00 pm
ORF
- ORD
Nonstop2h 32m
United Airlines
Sat 8/112:26 pm
ORD
- ORF
Nonstop2h 21m
United Airlines
Deal found 5/6![United Airlines logo]()
$430
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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
Fri 5/157:09 pm
RFD
- ORF
1 stop26h 33m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Mon 8/310:48 am
ORF
- ORD
Nonstop2h 39m
United Airlines
Wed 8/56:12 pm
ORD
- ORF
1 stop4h 32m
United Airlines
Deal found 5/5![United Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/237:25 pm
ORF
- RFD
1 stop14h 52m
Multiple Airlines
Thu 6/259:19 am
RFD
- ORF
2 stops13h 19m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$505
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated May 8, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/1412:06 pm
ORF
- ORD
1 stop8h 45m
Multiple Airlines
Tue 5/199:49 am
ORD
- ORF
1 stop24h 09m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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
- MDW
1 stop10h 56m
Frontier
Sun 5/3112:27 pm
MDW
- ORF
1 stop21h 44m
Frontier
Deal found 5/7![Frontier logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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
Multiple Airlines
Wed 6/312:04 pm
MDW
- ORF
2 stops9h 38m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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
Mon 6/112:04 pm
MDW
- ORF
1 stop22h 07m
Frontier
Deal found 5/6![Frontier logo]()
$322
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/36:25 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Tue 6/97:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 5/5![Southwest logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/36:45 am
ORF
- ORD
Nonstop2h 42m
American Airlines
Tue 6/92:39 pm
ORD
- ORF
Nonstop2h 20m
American Airlines
Deal found 5/5![American Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/312:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Fri 6/56:00 am
MDW
- ORF
2 stops13h 17m
Frontier
Deal found 5/6![Frontier logo]()
$323
This CheapOair deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/3![Multiple Airlines logo]()
$322
This Expedia deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Thu 6/1112:21 pm
ORF
- ORD
1 stop8h 29m
Frontier
Mon 6/154:59 pm
ORD
- ORF
1 stop24h 41m
Frontier
Deal found 5/4![Frontier logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/1212:21 pm
ORF
- MDW
1 stop23h 43m
Frontier
Tue 6/1612:27 pm
MDW
- ORF
1 stop21h 59m
Frontier
Deal found 5/4![Frontier logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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
- ORD
1 stop8h 44m
Frontier
Wed 6/179:48 pm
ORD
- ORF
2 stops36h 38m
Frontier
Deal found 5/4![Frontier logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/1712:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Sun 6/216:00 am
MDW
- ORF
1 stop28h 26m
Frontier
Deal found 5/3![Frontier logo]()
$321
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 8, 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 8, 2026.
This Trip.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/312:06 pm
ORF
- MDW
1 stop10h 56m
Frontier
Deal found 5/7![Frontier logo]()
$64
This Trip.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/2412:21 pm
ORF
- MDW
1 stop10h 50m
Frontier
Deal found 5/5![Frontier logo]()
$65
This Trip.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2212:21 pm
ORF
- ORD
1 stop8h 32m
Frontier
Deal found 5/7![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/3012:21 pm
ORF
- MDW
1 stop23h 48m
Frontier
Deal found 5/7![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/2812:06 pm
ORF
- ORD
1 stop20h 49m
Frontier
Deal found 5/6![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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
Deal found 5/5![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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
- ORD
1 stop8h 35m
Frontier
Deal found 5/4![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/112:06 pm
ORF
- MDW
1 stop24h 06m
Frontier
Deal found 5/6![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/4![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/3![Frontier logo]()
$76
This Trip.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/6![Frontier logo]()
$78
This Trip.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2212:21 pm
ORF
- MDW
1 stop10h 47m
Frontier
Deal found 5/7![Frontier logo]()
$81
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 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $312 (Kiwi.com) |
One-way from | $64 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $367 |
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 8, 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
Fri 6/12
8:35 am-10:48 pm
1 stop13h 13m
$334
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 6/3
6:25 pm-7:35 pm
Nonstop2h 10m
Chicago Midway
Sat 6/6
6:30 pm-9:30 pm
Nonstop2h 00m
$346
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 6/4
6:00 am-7:28 am
Nonstop2h 28m
Chicago O'Hare Intl
Tue 6/9
8:40 am-2:17 pm
1 stop4h 37m
$346
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Tue 6/2
6:25 pm-7:35 pm
Nonstop2h 10m
Chicago Midway
Thu 6/4
7:00 pm-10:00 pm
Nonstop2h 00m
$346
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Sun 6/14
6:00 am-7:28 am
Nonstop2h 28m
Chicago O'Hare Intl
Wed 6/17
9:29 pm-12:57 am
Nonstop2h 28m
$350
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Fri 10/9
6:00 am-7:28 am
Nonstop2h 28m
Chicago O'Hare Intl
Tue 10/13
7:15 am-10:46 am
Nonstop2h 31m
$350
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sun 6/14
8:05 pm-12:20 am
1 stop5h 15m
Chicago Midway
Wed 6/17
6:50 pm-9:50 pm
Nonstop2h 00m
$360
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 6/24
12:40 pm-6:15 pm
1 stop6h 35m
Chicago Midway
Sun 6/28
7:00 pm-10:00 pm
Nonstop2h 00m
$360
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Sun 10/11
8:00 am-9:32 am
Nonstop2h 32m
Chicago O'Hare Intl
Wed 10/14
4:00 pm-11:43 pm
1 stop6h 43m
$360
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sun 8/2
7:20 pm-8:25 pm
Nonstop2h 05m
Chicago Midway
Thu 8/6
6:50 pm-9:55 pm
Nonstop2h 05m
$363
Showing 1-10 of 60 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-RFD
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-MDW
ORF-RFD
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 8, 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 May 2, 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 8, 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 (17 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 8, 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
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 8, 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 8, 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 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$376 | 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$372 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$213 | Average$401 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$217 | Average$372 | FlexibilityNo cancel fee | On-time71% |