$99+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Sep 3 — Sep 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Virginia Beach to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Virginia Beach to Chicago are usually found in September or December, booked 2 days in advance, depart on a Thursday or Wednesday and return on a Saturday
Cheap flight deals from Virginia Beach to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Virginia Beach to ChicagoExplore the most affordable flight options available from Virginia Beach to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 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 August 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Mon 9/217:00 am
ORF
- MDW
2 stops17h 44m
Multiple Airlines
Thu 9/246:25 am
MDW
- ORF
1 stop5h 04m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$316
This Justfly.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
ORF
- ORD
1 stop8h 39m
JetBlue
Mon 8/2411:01 am
ORD
- ORF
1 stop5h 09m
JetBlue
Deal found 7/31![JetBlue logo]()
$316
This Southwest deal was found by Cheapflights users on 8/1. 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.
Sat 9/54:00 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Fri 9/119:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 8/1![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 9/511:30 am
ORF
- ORD
Nonstop2h 34m
United Airlines
Tue 9/86:59 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 7/30![United Airlines logo]()
$317
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Mon 9/76:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/31![Frontier logo]()
$318
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Sun 11/19:26 am
ORD
- ORF
1 stop6h 49m
Frontier
Deal found 7/31![Frontier logo]()
$318
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:37 pm
ORF
- ORD
Nonstop2h 29m
American Airlines
Sun 9/68:45 am
ORD
- ORF
Nonstop2h 19m
American Airlines
Deal found 8/1![American Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 11/112:57 pm
ORF
- MDW
1 stop9h 56m
Multiple Airlines
Mon 11/27:25 am
MDW
- ORF
2 stops14h 18m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Sat 9/127:00 am
ORF
- MDW
2 stops11h 51m
Multiple Airlines
Sat 9/196:25 am
MDW
- ORF
1 stop8h 25m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/201:20 pm
ORF
- ORD
1 stop7h 39m
Frontier
Fri 8/218:11 pm
ORD
- ORF
2 stops15h 14m
Frontier
Deal found 7/31![Frontier logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Thu 8/201:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Sun 8/237:05 am
ORD
- ORF
1 stop28h 20m
Frontier
Deal found 8/3![Frontier logo]()
$323
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/169:34 pm
ORF
- ORD
1 stop12h 37m
Frontier
Thu 8/207:44 pm
ORD
- ORF
1 stop19h 27m
Frontier
Deal found 7/30![Frontier logo]()
$325
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 August 4, 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 August 4, 2026.
This JetBlue deal was found by Cheapflights users on 8/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/227:25 am
ORF
- ORD
1 stop7h 20m
JetBlue
Wed 9/233:00 pm
ORD
- ORF
1 stop6h 41m
JetBlue
Deal found 8/3![JetBlue logo]()
$325
This Southwest deal was found by Cheapflights users on 7/30. 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.
Mon 9/213:45 pm
ORF
- MDW
1 stop6h 15m
Southwest
Thu 9/246:50 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/30![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/1. 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 8/2911:30 am
ORF
- ORD
Nonstop2h 34m
United Airlines
Sun 9/611:59 am
ORD
- ORF
Nonstop2h 18m
United Airlines
Deal found 8/1![United Airlines logo]()
$331
This KAYAK deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:13 pm
ORF
- ORD
Nonstop2h 36m
American Airlines
Fri 9/252:22 pm
ORD
- ORF
Nonstop2h 25m
American Airlines
Deal found 7/31![American Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 7/30. 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.
Fri 9/113:16 pm
ORF
- ORD
1 stop6h 40m
Delta
Tue 9/159:30 am
ORD
- ORF
1 stop7h 10m
Delta
Deal found 7/30![Delta logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 10/27:00 am
ORF
- RFD
1 stop13h 12m
Multiple Airlines
Sun 10/411:12 am
RFD
- ORF
2 stops22h 30m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$456
This Southwest deal was found by Cheapflights users on 7/30. 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.
Thu 8/2710:10 am
ORF
- MDW
1 stop4h 55m
Southwest
Thu 9/36:50 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/30![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Tue 9/156:10 am
ORF
- ORD
Nonstop2h 29m
United Airlines
Mon 9/216:59 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 8/1![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 8/3. 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.
Tue 9/156:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Tue 9/228:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 8/3![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:02 pm
ORF
- ORD
Nonstop2h 28m
United Airlines
Tue 9/226:15 pm
ORD
- ORF
Nonstop2h 26m
United Airlines
Deal found 8/3![United Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am
ORF
- ORD
Nonstop2h 34m
United Airlines
Mon 9/77:30 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 8/3![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 8/1. 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.
Tue 9/16:15 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Fri 9/46:50 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 8/1![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sun 11/18:00 am
MDW
- ORF
1 stop5h 50m
Southwest
Deal found 7/31![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 8/296:00 am
ORF
- ORD
1 stop5h 58m
United Airlines
Sun 8/3011:59 am
ORD
- ORF
Nonstop2h 18m
United Airlines
Deal found 7/30![United Airlines logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Mon 9/217:00 am
ORF
- RFD
1 stop10h 30m
Multiple Airlines
Thu 9/249:29 pm
RFD
- ORF
1 stop22h 13m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$499
This Southwest deal was found by Cheapflights users on 8/2. 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.
Wed 9/164:35 pm
ORF
- MDW
1 stop7h 20m
Southwest
Wed 9/238:50 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 8/2![Southwest logo]()
$355
This KAYAK deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:05 am
ORF
- ORD
Nonstop2h 29m
United Airlines
Fri 9/254:00 pm
ORD
- ORF
1 stop6h 44m
United Airlines
Deal found 7/31![United Airlines logo]()
$362
This Southwest deal was found by Cheapflights users on 8/1. 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 9/310:10 am
ORF
- MDW
1 stop7h 05m
Southwest
Mon 9/79:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 8/1![Southwest logo]()
$361
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Sun 8/306:00 am
ORF
- ORD
Nonstop2h 34m
United Airlines
Sun 9/66:15 pm
ORD
- ORF
Nonstop2h 33m
United Airlines
Deal found 7/30![United Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Thu 8/205:06 pm
ORF
- RFD
1 stop26h 00m
Multiple Airlines
Sun 8/239:35 pm
RFD
- ORF
1 stop20h 51m
Multiple Airlines
Deal found 8/3![Multiple Airlines logo]()
$579
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 8/276:15 am
ORF
- ORD
1 stop6h 38m
United Airlines
Thu 9/37:30 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 7/30![United Airlines logo]()
$407
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated August 4, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/169:34 pm
ORF
- ORD
1 stop12h 37m
Frontier
Thu 8/207:44 pm
ORD
- ORF
1 stop19h 27m
Frontier
Deal found 7/30![Frontier logo]()
$325
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:24 am
ORF
- ORD
Nonstop2h 36m
American Airlines
Mon 8/247:21 pm
ORD
- ORF
Nonstop2h 21m
American Airlines
Deal found 7/30![American Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/201:20 pm
ORF
- ORD
1 stop7h 39m
Frontier
Fri 8/218:11 pm
ORD
- ORF
2 stops15h 14m
Frontier
Deal found 7/31![Frontier logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Thu 8/201:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Sun 8/237:05 am
ORD
- ORF
1 stop28h 20m
Frontier
Deal found 8/3![Frontier logo]()
$323
This Justfly.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
ORF
- ORD
1 stop8h 39m
JetBlue
Mon 8/2411:01 am
ORD
- ORF
1 stop5h 09m
JetBlue
Deal found 7/31![JetBlue logo]()
$316
This Southwest deal was found by Cheapflights users on 7/30. 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.
Thu 8/2710:10 am
ORF
- MDW
1 stop4h 55m
Southwest
Thu 9/36:50 pm
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 7/30![Southwest logo]()
$327
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Mon 9/76:05 am
MDW
- ORF
1 stop5h 20m
Frontier
Deal found 7/31![Frontier logo]()
$318
This Southwest deal was found by Cheapflights users on 8/1. 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.
Sat 9/54:00 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Fri 9/119:00 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 8/1![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 9/511:30 am
ORF
- ORD
Nonstop2h 34m
United Airlines
Tue 9/86:59 am
ORD
- ORF
Nonstop2h 30m
United Airlines
Deal found 7/30![United Airlines logo]()
$317
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:37 pm
ORF
- ORD
Nonstop2h 29m
American Airlines
Sun 9/68:45 am
ORD
- ORF
Nonstop2h 19m
American Airlines
Deal found 8/1![American Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Sat 9/127:00 am
ORF
- MDW
2 stops11h 51m
Multiple Airlines
Sat 9/196:25 am
MDW
- ORF
1 stop8h 25m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Mon 9/217:00 am
ORF
- MDW
2 stops17h 44m
Multiple Airlines
Thu 9/246:25 am
MDW
- ORF
1 stop5h 04m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$316
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 August 4, 2026.
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Trip.com deal was found by Cheapflights users on 7/30. 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.
Tue 8/251:20 pm
ORF
- ORD
1 stop7h 39m
Frontier
Deal found 7/30![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Deal found 7/31![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/231:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Deal found 7/31![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 11/1612:57 pm
ORF
- MDW
1 stop23h 01m
Frontier
Deal found 7/31![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Sat 8/291:20 pm
ORF
- ORD
1 stop19h 33m
Frontier
Deal found 8/1![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 11/1712:57 pm
ORF
- MDW
1 stop9h 56m
Frontier
Deal found 7/31![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:20 pm
ORF
- ORD
1 stop7h 39m
Frontier
Deal found 7/31![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/291:18 pm
ORF
- ORD
1 stop23h 33m
Frontier
Deal found 7/31![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 10/1512:57 pm
ORF
- ORD
1 stop20h 18m
Frontier
Deal found 8/2![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 10/2912:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Deal found 8/1![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:20 pm
ORF
- ORD
1 stop7h 48m
Frontier
Deal found 7/31![Frontier logo]()
$114
This Trip.com deal was found by Cheapflights users on 7/30. 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.
Tue 8/251:20 pm
ORF
- MDW
1 stop10h 27m
Frontier
Deal found 7/30![Frontier logo]()
$116
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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $316 (Kiwi.com) |
One-way from | $99 (Trip.com) |
Popular in | July |
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 August 4, 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
Tue 9/22
7:25 am-1:45 pm
1 stop7h 20m
Chicago O'Hare Intl
Wed 9/23
3:00 pm-10:41 pm
1 stop6h 41m
$325
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Mon 9/21
3:45 pm-9:00 pm
1 stop6h 15m
Chicago Midway
Thu 9/24
6:50 pm-10:00 pm
Nonstop2h 10m
$327
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 8/27
10:10 am-2:05 pm
1 stop4h 55m
Chicago Midway
Thu 9/3
6:50 pm-10:00 pm
Nonstop2h 10m
$327
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Sat 8/29
11:30 am-1:04 pm
Nonstop2h 34m
Chicago O'Hare Intl
Sun 9/6
11:59 am-3:17 pm
Nonstop2h 18m
$331
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Tue 9/15
6:10 am-7:39 am
Nonstop2h 29m
Chicago O'Hare Intl
Mon 9/21
6:59 am-10:29 am
Nonstop2h 30m
$345
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Tue 9/15
6:15 pm-7:20 pm
Nonstop2h 05m
Chicago Midway
Tue 9/22
8:50 am-12:05 pm
Nonstop2h 15m
$345
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Tue 9/15
5:02 pm-6:30 pm
Nonstop2h 28m
Chicago O'Hare Intl
Tue 9/22
6:15 pm-9:41 pm
Nonstop2h 26m
$345
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 9/3
6:00 am-7:34 am
Nonstop2h 34m
Chicago O'Hare Intl
Mon 9/7
7:30 am-11:00 am
Nonstop2h 30m
$345
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Mon 9/21
12:13 pm-1:49 pm
Nonstop2h 36m
Chicago O'Hare Intl
Fri 9/25
2:22 pm-5:47 pm
Nonstop2h 25m
$352
Quickest round-trip
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Tue 9/1
6:15 pm-7:20 pm
Nonstop2h 05m
Chicago Midway
Fri 9/4
6:50 pm-10:00 pm
Nonstop2h 10m
$352
Showing 1-10 of 46 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-ORD
ORF-MDW
ORF-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Virginia Beach to Chicago
V1B-CHI
ORF-ORD
ORF-MDW
ORF-RFD
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 August 4, 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.
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 August 4, 2026.
The most flights from V1B to CHI are scheduled on a Friday (28 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (15 on average).
How much does it cost to fly round-trip from Virginia Beach to Chicago?
Airfare is below average for this route at the moment.
Virginia Beach to Chicago flights typically cost between $327 and $460 in September.The cheapest round-trip price found within the last 5 days was $316 on Multiple Airlines (Sep 21-Sep 24).
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 August 1, 2026.
Travelers seeking maximum savings on their Virginia Beach to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 4, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican Airlines from Virginia Beach to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Virginia Beach to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Virginia Beach to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 4, 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 August 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Virginia Beach to Chicago flights
Consider these flights traveling from Virginia Beach to Chicago.
Top 6 airlines flying from Virginia Beach to Chicago
Discover the top 6 airlines that operate flights from Virginia Beach to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$369 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$352 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$397 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$390 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$243 | Average$437 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$260 | Average$260 | FlexibilityNo cancel fee | On-timeN/A |