$60+ 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Mar 27 — Apr 31
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 78 days in advance, depart on a Thursday or Friday and return on a Wednesday
Cheap flight deals from Virginia Beach to Chicago
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Best
Last-minute
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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 February 25, 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 February 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/143:26 pm
ORF
- MDW
1 stop7h 19m
Multiple Airlines
Tue 3/1711:19 am
MDW
- ORF
1 stop9h 28m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/117:31 pm
ORF
- ORD
1 stop16h 46m
Multiple Airlines
Thu 3/124:18 pm
ORD
- ORF
1 stop18h 29m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$273
This CheapOair deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/83:20 pm
ORF
- ORD
1 stop9h 16m
Multiple Airlines
Fri 4/108:58 am
ORD
- ORF
1 stop7h 07m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$274
This Expedia deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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.
Sat 3/73:26 pm
ORF
- MDW
1 stop7h 19m
Frontier
Thu 3/129:10 am
MDW
- ORF
1 stop25h 37m
Frontier
Deal found 2/24![Frontier logo]()
$275
This Priceline deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/73:26 pm
ORF
- ORD
1 stop9h 12m
Frontier
Thu 3/128:05 am
ORD
- ORF
1 stop8h 43m
Frontier
Deal found 2/24![Frontier logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 6/36:05 am
ORF
- ORD
2 stops13h 49m
Spirit Airlines
Mon 6/87:06 am
ORD
- ORF
1 stop11h 26m
Spirit Airlines
Deal found 2/24![Spirit Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/195:50 am
ORF
- ORD
1 stop5h 10m
Delta
Sun 3/227:14 pm
ORD
- ORF
1 stop4h 10m
Delta
Deal found 2/23![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/132:30 pm
ORF
- MDW
1 stop6h 50m
Southwest
Fri 4/177:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 2/24![Southwest logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/2611:50 am
ORF
- ORD
2 stops13h 26m
Multiple Airlines
Tue 3/3112:45 pm
ORD
- ORF
1 stop8h 02m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/16:30 pm
ORF
- MDW
Nonstop2h 20m
Southwest
Sat 4/187:25 am
MDW
- ORF
1 stop8h 15m
Southwest
Deal found 2/23![Southwest logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 3/2711:33 am
ORF
- MDW
1 stop11h 46m
Multiple Airlines
Mon 3/309:51 pm
MDW
- ORF
1 stop22h 56m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 4/188:27 pm
ORF
- RFD
1 stop14h 20m
Multiple Airlines
Mon 4/207:09 pm
RFD
- ORF
1 stop17h 22m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$282
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 February 25, 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 February 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 4/188:27 pm
ORF
- RFD
1 stop14h 20m
Multiple Airlines
Mon 4/207:09 pm
RFD
- ORF
1 stop17h 22m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/26:00 am
ORF
- ORD
Nonstop2h 31m
United Airlines
Mon 4/66:01 pm
ORD
- ORF
1 stop4h 39m
United Airlines
Deal found 2/22![United Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 3/215:55 pm
ORF
- MDW
1 stop6h 05m
Southwest
Sat 3/2812:10 pm
MDW
- ORF
1 stop4h 05m
Southwest
Deal found 2/21![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 6/294:27 pm
ORF
- ORD
1 stop4h 51m
Delta
Fri 7/31:15 pm
ORD
- ORF
1 stop4h 39m
Delta
Deal found 2/21![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/267:20 pm
ORF
- MDW
Nonstop2h 15m
Southwest
Tue 3/318:55 am
MDW
- ORF
1 stop7h 55m
Southwest
Deal found 2/22![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/79:45 am
ORF
- ORD
Nonstop2h 42m
United Airlines
Fri 4/105:00 am
ORD
- ORF
1 stop5h 54m
United Airlines
Deal found 2/22![United Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/132:30 pm
ORF
- MDW
1 stop6h 50m
Southwest
Thu 4/1612:50 pm
MDW
- ORF
2 stops9h 05m
Southwest
Deal found 2/24![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/266:00 am
ORF
- ORD
Nonstop2h 31m
United Airlines
Fri 5/15:45 pm
ORD
- ORF
Nonstop2h 20m
United Airlines
Deal found 2/24![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/267:20 pm
ORF
- MDW
Nonstop2h 15m
Southwest
Mon 3/305:00 pm
MDW
- ORF
1 stop5h 35m
Southwest
Deal found 2/23![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 7/135:44 pm
ORF
- ORD
1 stop6h 46m
United Airlines
Mon 7/2011:53 am
ORD
- ORF
Nonstop2h 21m
United Airlines
Deal found 2/21![United Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/287:20 pm
ORF
- MDW
Nonstop2h 15m
Southwest
Sun 3/2912:55 pm
MDW
- ORF
2 stops9h 10m
Southwest
Deal found 2/22![Southwest logo]()
$319
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:00 am
ORF
- ORD
Nonstop2h 28m
United Airlines
Wed 6/106:12 pm
ORD
- ORF
1 stop4h 32m
United Airlines
Deal found 2/21![United Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 7/227:50 am
ORF
- MDW
Nonstop2h 00m
Southwest
Wed 7/2912:00 pm
MDW
- ORF
Nonstop2h 00m
Southwest
Deal found 2/21![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 7/246:05 am
ORF
- ORD
1 stop6h 48m
United Airlines
Mon 7/276:15 pm
ORD
- ORF
Nonstop2h 22m
United Airlines
Deal found 2/24![United Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/88:41 pm
ORF
- RFD
1 stop14h 06m
Multiple Airlines
Sun 4/1210:37 am
RFD
- ORF
1 stop8h 09m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$534
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:05 am
ORF
- MDW
Nonstop2h 05m
Southwest
Wed 6/107:40 am
MDW
- ORF
Nonstop2h 05m
Southwest
Deal found 2/21![Southwest logo]()
$334
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 8/126:00 am
ORF
- ORD
1 stop7h 06m
United Airlines
Fri 8/146:04 pm
ORD
- ORF
1 stop4h 32m
United Airlines
Deal found 2/24![United Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/207:20 pm
ORF
- MDW
Nonstop2h 15m
Southwest
Mon 3/231:30 pm
MDW
- ORF
Nonstop1h 55m
Southwest
Deal found 2/24![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 7/226:05 am
ORF
- ORD
2 stops8h 10m
Southwest
Wed 7/292:40 pm
ORD
- ORF
2 stops6h 55m
Southwest
Deal found 2/21![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 6/56:30 am
ORF
- ORD
2 stops8h 00m
Southwest
Wed 6/102:40 pm
ORD
- ORF
2 stops6h 55m
Southwest
Deal found 2/21![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 7/612:15 pm
ORF
- MDW
2 stops6h 40m
Southwest
Fri 7/108:05 am
MDW
- ORF
2 stops6h 00m
Southwest
Deal found 2/22![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:30 pm
ORF
- MDW
2 stops6h 35m
Southwest
Sun 5/106:15 pm
MDW
- ORF
1 stop4h 25m
Southwest
Deal found 2/21![Southwest logo]()
$395
Last-minute flights from Virginia Beach to ChicagoDiscover last-minute flight deals from Virginia Beach to Chicago. Data last updated February 25, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Chicago. Data last updated February 25, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 2/267:13 pm
ORF
- ORD
1 stop28h 34m
Frontier
Mon 3/23:50 pm
ORD
- ORF
1 stop19h 15m
Frontier
Deal found 2/21![Frontier logo]()
$282
This Expedia deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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.
Sat 3/73:26 pm
ORF
- MDW
1 stop7h 19m
Frontier
Thu 3/129:10 am
MDW
- ORF
1 stop25h 37m
Frontier
Deal found 2/24![Frontier logo]()
$275
This Priceline deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/73:26 pm
ORF
- ORD
1 stop9h 12m
Frontier
Thu 3/128:05 am
ORD
- ORF
1 stop8h 43m
Frontier
Deal found 2/24![Frontier logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/107:31 pm
ORF
- ORD
1 stop16h 05m
Multiple Airlines
Thu 3/127:31 pm
ORD
- ORF
2 stops20h 35m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/117:31 pm
ORF
- ORD
1 stop16h 46m
Multiple Airlines
Thu 3/124:18 pm
ORD
- ORF
1 stop18h 29m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/143:26 pm
ORF
- MDW
1 stop7h 19m
Multiple Airlines
Tue 3/1711:19 am
MDW
- ORF
1 stop9h 28m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:50 am
ORF
- MDW
1 stop7h 12m
Delta
Tue 3/176:07 pm
MDW
- ORF
1 stop5h 16m
Delta
Deal found 2/24![Delta logo]()
$283
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/195:50 am
ORF
- ORD
1 stop5h 10m
Delta
Sun 3/227:14 pm
ORD
- ORF
1 stop4h 10m
Delta
Deal found 2/23![Delta logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/2611:50 am
ORF
- ORD
1 stop11h 49m
Multiple Airlines
Mon 3/3011:25 am
ORD
- ORF
1 stop10h 26m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/2611:50 am
ORF
- ORD
2 stops13h 26m
Multiple Airlines
Tue 3/3112:45 pm
ORD
- ORF
1 stop8h 02m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 3/2711:33 am
ORF
- MDW
1 stop11h 46m
Multiple Airlines
Mon 3/309:51 pm
MDW
- ORF
1 stop22h 56m
Multiple Airlines
Deal found 2/21![Multiple Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/316:08 am
ORF
- ORD
1 stop4h 30m
United Airlines
Tue 3/314:30 pm
ORD
- ORF
1 stop6h 02m
United Airlines
Deal found 2/24![United Airlines logo]()
$283
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 February 25, 2026.
Search for one-way flight options from Virginia Beach to Chicago. Find affordable one-way fares based on user searches. Data last updated February 25, 2026.
This Trip.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:33 am
ORF
- MDW
1 stop11h 46m
Frontier
Deal found 2/25![Frontier logo]()
$60
This Trip.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:33 am
ORF
- ORD
1 stop12h 06m
Frontier
Deal found 2/25![Frontier logo]()
$60
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/2511:27 am
ORF
- MDW
1 stop8h 10m
Frontier
Deal found 2/25![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/2311:27 am
ORF
- MDW
1 stop9h 04m
Frontier
Deal found 2/25![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/2711:27 am
ORF
- MDW
1 stop9h 04m
Frontier
Deal found 2/25![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/2411:27 am
ORF
- ORD
1 stop25h 06m
Frontier
Deal found 2/25![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/911:31 am
ORF
- MDW
1 stop11h 50m
Frontier
Deal found 2/25![Frontier logo]()
$66
This Trip.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/1811:27 am
ORF
- ORD
1 stop8h 27m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:32 am
ORF
- MDW
1 stop11h 47m
Frontier
Deal found 2/25![Frontier logo]()
$70
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” 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 3/216:15 am
ORF
- ORD
Nonstop2h 35m
United Airlines
Deal found 2/21![United Airlines logo]()
$71
This Trip.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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.
Mon 4/2011:27 am
ORF
- MDW
1 stop9h 04m
Frontier
Deal found 2/25![Frontier logo]()
$72
This Trip.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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.
Mon 4/2711:27 am
ORF
- ORD
1 stop12h 12m
Frontier
Deal found 2/25![Frontier logo]()
$72
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 February 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (Kiwi.com) |
One-way from | $60 (Trip.com) |
Popular in | June |
Cheapest in | September |
Average price | $348 |
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 February 25, 2026.
Use the filters below to find and compare flights from Virginia Beach to Chicago that are best for you.
Fly from
Virginia Beach
Fly to
Chicago
Route
Depart
Return
Price
NorfolkChicago
ORF - RFD
ORFRFD
Norfolk
Sat 4/18
8:27 pm-9:47 am
1 stop14h 20m
Chicago Greater Rockford
Mon 4/20
7:09 pm-1:31 pm
1 stop17h 22m
$282
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Thu 4/2
6:00 am-7:31 am
Nonstop2h 31m
Chicago O'Hare Intl
Mon 4/6
6:01 pm-11:40 pm
1 stop4h 39m
$282
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 3/21
5:55 pm-11:00 pm
1 stop6h 05m
Chicago Midway
Sat 3/28
12:10 pm-5:15 pm
1 stop4h 05m
$296
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 3/26
7:20 pm-8:35 pm
Nonstop2h 15m
Chicago Midway
Tue 3/31
8:55 am-5:50 pm
1 stop7h 55m
$302
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Mon 4/13
2:30 pm-8:20 pm
1 stop6h 50m
Chicago Midway
Thu 4/16
12:50 pm-10:55 pm
2 stops9h 05m
$307
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Thu 3/26
7:20 pm-8:35 pm
Nonstop2h 15m
Chicago Midway
Mon 3/30
5:00 pm-11:35 pm
1 stop5h 35m
$307
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Tue 4/7
9:45 am-11:27 am
Nonstop2h 42m
Chicago O'Hare Intl
Fri 4/10
5:00 am-11:54 am
1 stop5h 54m
$310
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Sat 3/28
7:20 pm-8:35 pm
Nonstop2h 15m
Chicago Midway
Sun 3/29
12:55 pm-11:05 pm
2 stops9h 10m
$319
NorfolkChicago
ORF - MDW
ORFMDW
Norfolk
Wed 7/22
7:50 am-8:50 am
Nonstop2h 00m
Chicago Midway
Wed 7/29
12:00 pm-3:00 pm
Nonstop2h 00m
$323
NorfolkChicago
ORF - ORD
ORFORD
Norfolk
Sun 4/26
6:00 am-7:31 am
Nonstop2h 31m
Chicago O'Hare Intl
Fri 5/1
5:45 pm-9:05 pm
Nonstop2h 20m
$325
Showing 1-10 of 52 results
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-ORD
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-MDW
ORF-ORD
ORF-RFD
How far ahead should I book a flight from Virginia Beach to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Virginia Beach to Chicago. Price data was last updated on February 20, 2026.
Booking 78 days in advance of your planned departure date is, on average, the best time to get cheap flights from Virginia Beach to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Virginia Beach to Chicago?
Currently, May is the cheapest month in which you can book a flight from Virginia Beach to Chicago (average of $108). Flying from Virginia Beach to Chicago in July is currently the most expensive (average of $266). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 February 25, 2026.
A simple way to save on the total cost of your ticket is to fly from Virginia Beach to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 9% on your trip compared to booking a flight in the morning.
What is the cheapest day to fly from Virginia Beach to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Virginia Beach to Chicago. Price data was last updated on February 21, 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.
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 February 25, 2026.
The most flights from V1B to CHI are scheduled on a Wednesday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).
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 February 25, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American 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.
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different 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 February 25, 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 February 25, 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 February 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$92 | Average$303 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$260 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$172 | Average$208 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$363 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$208 | Average$361 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$211 | Average$389 | FlexibilityNo cancel fee | On-time69% |