$100+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Jul 18 — Jul 251
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 October 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 June 18, 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 June 18, 2026.
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:30 pm
ORF
- MDW
2 stops7h 30m
Southwest
Tue 7/77:50 am
MDW
- ORF
2 stops5h 35m
Southwest
Deal found 6/15![Southwest logo]()
$337
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Sun 7/125:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 6/16![Frontier logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1812:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Thu 7/2312:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Deal found 6/14![Frontier logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Mon 7/205:46 pm
ORD
- ORF
2 stops40h 29m
Frontier
Deal found 6/15![Frontier logo]()
$338
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/126:14 pm
ORF
- MDW
1 stop5h 22m
Delta
Sun 8/166:42 pm
MDW
- ORF
1 stop4h 00m
Delta
Deal found 6/18![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/215:08 pm
ORF
- ORD
1 stop4h 22m
Delta
Tue 8/256:40 am
ORD
- ORF
1 stop5h 05m
Delta
Deal found 6/18![Delta logo]()
$340
This CheapOair deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:00 pm
ORF
- ORD
2 stops15h 48m
Multiple Airlines
Mon 8/175:13 pm
ORD
- ORF
1 stop26h 48m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Sat 7/119:57 pm
ORD
- ORF
2 stops36h 18m
Frontier
Deal found 6/15![Frontier logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Thu 8/66:05 am
MDW
- ORF
2 stops13h 34m
Frontier
Deal found 6/15![Frontier logo]()
$343
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/89:34 pm
ORF
- ORD
1 stop26h 36m
Multiple Airlines
Tue 7/149:40 am
ORD
- ORF
2 stops30h 30m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:10 pm
ORF
- MDW
1 stop4h 50m
Southwest
Thu 8/66:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/15![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/206:10 pm
ORF
- ORD
1 stop6h 12m
United Airlines
Sun 8/2311:59 am
ORD
- ORF
Nonstop2h 18m
United Airlines
Deal found 6/17![United Airlines logo]()
$344
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 June 18, 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 June 18, 2026.
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/198:05 pm
ORF
- MDW
1 stop5h 20m
Southwest
Tue 7/217:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 6/17![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:50 pm
ORF
- MDW
1 stop6h 43m
Delta
Mon 10/56:05 am
MDW
- ORF
1 stop6h 49m
Delta
Deal found 6/13![Delta logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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
Fri 9/255:05 pm
RFD
- ORF
2 stops17h 57m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/186:00 am
ORF
- ORD
1 stop7h 06m
United Airlines
Thu 7/236:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/17![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:30 pm
ORF
- MDW
2 stops7h 45m
Southwest
Sat 8/11:15 pm
MDW
- ORF
2 stops8h 55m
Southwest
Deal found 6/17![Southwest logo]()
$350
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/42:42 pm
ORF
- ORD
1 stop5h 30m
Delta
Sun 9/67:05 am
ORD
- ORF
1 stop5h 56m
Delta
Deal found 6/16![Delta logo]()
$370
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/93:30 pm
ORF
- MDW
Nonstop2h 05m
Southwest
Tue 7/147:55 am
MDW
- ORF
Nonstop2h 10m
Southwest
Deal found 6/14![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 6/305:00 pm
ORF
- ORD
Nonstop2h 32m
United Airlines
Thu 7/96:30 am
ORD
- ORF
1 stop6h 47m
United Airlines
Deal found 6/17![United Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/129:34 pm
ORF
- RFD
1 stop22h 26m
Multiple Airlines
Fri 7/247:50 pm
RFD
- ORF
1 stop23h 49m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:00 pm
ORF
- MDW
Nonstop2h 10m
Southwest
Sat 7/118:00 am
MDW
- ORF
Nonstop2h 15m
Southwest
Deal found 6/15![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/16:05 am
ORF
- ORD
1 stop4h 31m
United Airlines
Wed 8/512:22 pm
ORD
- ORF
Nonstop2h 28m
United Airlines
Deal found 6/18![United Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/146:00 am
ORF
- MDW
2 stops7h 20m
Southwest
Sat 8/155:55 am
MDW
- ORF
1 stop4h 50m
Southwest
Deal found 6/16![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/224:30 pm
ORF
- MDW
1 stop4h 05m
Southwest
Sun 7/268:05 am
MDW
- ORF
2 stops9h 40m
Southwest
Deal found 6/16![Southwest logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 6/17![Multiple Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:00 pm
ORF
- ORD
Nonstop2h 41m
United Airlines
Mon 7/136:12 pm
ORD
- ORF
1 stop4h 32m
United Airlines
Deal found 6/18![United Airlines logo]()
$461
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3011:25 am
ORF
- MDW
2 stops6h 15m
Southwest
Thu 8/61:20 pm
MDW
- ORF
2 stops7h 15m
Southwest
Deal found 6/15![Southwest logo]()
$364
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:05 am
ORF
- ORD
1 stop4h 31m
United Airlines
Mon 7/276:45 am
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 6/13![United Airlines logo]()
$490
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 am
ORF
- RFD
1 stop10h 15m
Multiple Airlines
Sun 9/133:53 pm
RFD
- ORF
2 stops17h 49m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$556
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/17:00 am
ORF
- RFD
1 stop9h 57m
Multiple Airlines
Sun 7/511:27 am
RFD
- ORF
2 stops34h 41m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$626
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/287:20 am
ORF
- RFD
1 stop10h 03m
Multiple Airlines
Sun 8/309:35 pm
RFD
- ORF
1 stop20h 51m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$638
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/39:56 pm
ORF
- RFD
1 stop11h 06m
Multiple Airlines
Sun 9/69:29 pm
RFD
- ORF
1 stop20h 57m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$873
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:00 am
ORF
- RFD
1 stop13h 07m
Multiple Airlines
Sun 9/69:29 pm
RFD
- ORF
1 stop20h 57m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$974
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/157:06 pm
ORF
- RFD
2 stops16h 31m
Multiple Airlines
Sun 7/191:14 pm
RFD
- ORF
1 stop29h 12m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$983
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated June 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:30 pm
ORF
- MDW
2 stops7h 30m
Southwest
Tue 7/77:50 am
MDW
- ORF
2 stops5h 35m
Southwest
Deal found 6/15![Southwest logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Sat 7/119:57 pm
ORD
- ORF
2 stops36h 18m
Frontier
Deal found 6/15![Frontier logo]()
$342
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/89:34 pm
ORF
- ORD
1 stop26h 36m
Multiple Airlines
Tue 7/149:40 am
ORD
- ORF
2 stops30h 30m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$343
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Sun 7/125:13 pm
ORD
- ORF
1 stop26h 26m
Frontier
Deal found 6/16![Frontier logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/1212:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Fri 7/248:58 pm
ORD
- ORF
2 stops37h 17m
Frontier
Deal found 6/16![Frontier logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:10 pm
ORF
- ORD
1 stop20h 43m
Frontier
Mon 7/205:46 pm
ORD
- ORF
2 stops40h 29m
Frontier
Deal found 6/15![Frontier logo]()
$338
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:40 pm
ORF
- MDW
2 stops8h 10m
Southwest
Fri 7/175:20 pm
MDW
- ORF
1 stop5h 20m
Southwest
Deal found 6/14![Southwest logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1812:16 pm
ORF
- MDW
1 stop10h 47m
Frontier
Thu 7/2312:11 pm
MDW
- ORF
1 stop22h 04m
Frontier
Deal found 6/14![Frontier logo]()
$338
This CheapOair deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/309:34 pm
ORF
- ORD
1 stop12h 37m
Multiple Airlines
Wed 8/56:00 am
ORD
- ORF
2 stops10h 10m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Thu 8/66:05 am
MDW
- ORF
2 stops13h 34m
Frontier
Deal found 6/15![Frontier logo]()
$343
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:10 pm
ORF
- MDW
1 stop4h 50m
Southwest
Thu 8/66:50 pm
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 6/15![Southwest logo]()
$344
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:40 am
ORF
- ORD
Nonstop2h 40m
American Airlines
Thu 8/65:00 am
ORD
- ORF
1 stop4h 22m
American Airlines
Deal found 6/15![American Airlines logo]()
$344
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 June 18, 2026.
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This Trip.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/1512:57 pm
ORF
- MDW
1 stop10h 01m
Frontier
Deal found 6/18![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/1412:57 pm
ORF
- MDW
1 stop10h 01m
Frontier
Deal found 6/18![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 9/1412:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Deal found 6/17![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 9/1312:57 pm
ORF
- ORD
1 stop24h 05m
Frontier
Deal found 6/17![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Wed 9/1612:57 pm
ORF
- ORD
1 stop7h 47m
Frontier
Deal found 6/17![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/1212:57 pm
ORF
- MDW
1 stop10h 01m
Frontier
Deal found 6/18![Frontier logo]()
$121
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Sat 9/126:10 pm
ORF
- ORD
1 stop6h 45m
Frontier
Deal found 6/17![Frontier logo]()
$122
This Trip.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/1412:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/18![Frontier logo]()
$123
This Trip.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/1512:16 pm
ORF
- ORD
1 stop8h 37m
Frontier
Deal found 6/18![Frontier logo]()
$123
This Super.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Wed 7/1512:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/18![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Wed 8/1212:10 pm
ORF
- MDW
1 stop10h 53m
Frontier
Deal found 6/18![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Wed 8/1212:10 pm
ORF
- ORD
1 stop8h 43m
Frontier
Deal found 6/18![Frontier logo]()
$126
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 June 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $337 (Southwest) |
One-way from | $100 (Trip.com) |
Popular in | May |
Cheapest in | October |
Average price | $391 |
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 June 18, 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 - MDW
ORFMDW
Norfolk
Sun 7/19
8:05 pm-12:25 am
1 stop5h 20m
Chicago Midway
Tue 7/21
7:55 am-11:05 am
Nonstop2h 10m
$347
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 7/29
4:30 pm-11:15 pm
2 stops7h 45m
Chicago Midway
Sat 8/1
1:15 pm-11:10 pm
2 stops8h 55m
$350
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 10/2
12:50 pm-6:33 pm
1 stop6h 43m
Chicago Midway
Mon 10/5
6:05 am-1:54 pm
1 stop6h 49m
$354
NorfolkChicago
ORF - RFD
ORFRFD
Norfolk
Mon 9/21
7:00 am-4:30 pm
1 stop10h 30m
Chicago Greater Rockford
Fri 9/25
5:05 pm-12:02 pm
2 stops17h 57m
$354
Quickest round-trip
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 7/9
3:30 pm-4:35 pm
Nonstop2h 05m
Chicago Midway
Tue 7/14
7:55 am-11:05 am
Nonstop2h 10m
$357
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 7/8
7:00 pm-8:10 pm
Nonstop2h 10m
Chicago Midway
Sat 7/11
8:00 am-11:15 am
Nonstop2h 15m
$357
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Fri 8/14
6:00 am-12:20 pm
2 stops7h 20m
Chicago Midway
Sat 8/15
5:55 am-11:45 am
1 stop4h 50m
$359
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 7/22
4:30 pm-7:35 pm
1 stop4h 05m
Chicago Midway
Sun 7/26
8:05 am-6:45 pm
2 stops9h 40m
$360
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 7/30
11:25 am-4:40 pm
2 stops6h 15m
Chicago Midway
Thu 8/6
1:20 pm-9:35 pm
2 stops7h 15m
$364
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Fri 9/4
2:42 pm-7:12 pm
1 stop5h 30m
Chicago O'Hare Intl
Sun 9/6
7:05 am-2:01 pm
1 stop5h 56m
$370
Showing 1-10 of 49 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 June 18, 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 June 18, 2026.
The most flights from V1B to CHI are scheduled on a Thursday (32 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).
How much does it cost to fly round-trip from Virginia Beach to Chicago?
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 June 13, 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.
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 June 18, 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.
Boarding
8.1
Overall
7.9
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Overall
7.9
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Overall
7.9
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Overall
7.9
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Overall
7.9
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 18, 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 June 18, 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 June 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$354 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$314 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$380 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$200 | Average$260 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$386 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$235 | Average$423 | FlexibilityNo cancel fee | On-time69% |