$107+ Cheap flights from Virginia to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Oct 27 — Nov 31
Round-trip
1 adult, Economy
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Find cheap flights from Virginia 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.Cheap flight deals from Virginia to Chicago
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Cheapest flights from Virginia to ChicagoExplore the most affordable flight options available from Virginia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 27, 2026.
Explore the most affordable flight options available from Virginia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 27, 2026.
This American Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:46 pm -
Nonstop2h 14m
Mon 11/26:20 pm -
Nonstop1h 59m
Deal found 9/27![American Airlines logo]()
$234
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/226:35 am -
1 stop4h 03m
Thu 10/225:58 pm -
Nonstop2h 12m
Deal found 9/22![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 9/24. 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.
Thu 10/224:20 pm -
1 stop9h 00m
Sat 10/248:20 am -
Nonstop1h 55m
Deal found 9/24![Southwest logo]()
$307
This American Airlines deal was found by Cheapflights users on 9/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
1 stop7h 05m
Mon 11/25:19 am -
1 stop5h 26m
Deal found 9/25![American Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:20 am -
Nonstop2h 22m
Mon 10/192:00 pm -
Nonstop2h 21m
Deal found 9/23![United Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 9/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:35 pm -
Nonstop2h 00m
Mon 10/1912:45 pm -
Nonstop1h 55m
Deal found 9/25![Southwest logo]()
$308
This American Airlines deal was found by Cheapflights users on 9/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:46 pm -
Nonstop2h 14m
Sun 10/186:20 pm -
Nonstop2h 06m
Deal found 9/25![American Airlines logo]()
$309
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:25 am -
Nonstop2h 26m
Mon 11/165:19 am -
1 stop4h 32m
Deal found 9/24![American Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 9/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:05 am -
2 stops9h 40m
Mon 10/1912:45 pm -
Nonstop1h 55m
Deal found 9/25![Southwest logo]()
$312
This American Airlines deal was found by Cheapflights users on 9/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:26 pm -
Nonstop2h 34m
Tue 12/294:40 pm -
Nonstop2h 16m
Deal found 9/23![American Airlines logo]()
$313
This Cheapflightsfares deal was found by Cheapflights users on 9/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/303:21 pm -
1 stop10h 21m
Tue 12/15:24 pm -
1 stop18h 36m
Deal found 9/22![Frontier logo]()
$314
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/203:21 pm -
1 stop10h 21m
Sun 11/225:12 pm -
1 stop20h 14m
Deal found 9/23![Frontier logo]()
$316
Best flights from Virginia to ChicagoDiscover carefully curated flight deals from Virginia to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 27, 2026.
Discover carefully curated flight deals from Virginia to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 27, 2026.
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:46 pm -
Nonstop2h 14m
Sun 10/186:20 pm -
Nonstop2h 06m
Deal found 9/24![American Airlines logo]()
$234
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 11/610:02 am -
Nonstop2h 17m
Mon 11/99:20 pm -
Nonstop1h 58m
Deal found 9/22![United Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 9/23. 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.
Mon 11/28:25 pm -
1 stop3h 40m
Tue 11/31:15 pm -
Nonstop1h 45m
Deal found 9/23![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:58 pm -
1 stop5h 45m
Wed 11/115:30 am -
1 stop5h 10m
Deal found 9/27![Delta logo]()
$317
This American Airlines deal was found by Cheapflights users on 9/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:46 pm -
Nonstop2h 14m
Sat 10/316:20 pm -
Nonstop2h 06m
Deal found 9/22![American Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:46 pm -
Nonstop2h 14m
Tue 11/36:50 pm -
Nonstop1h 59m
Deal found 9/27![American Airlines logo]()
$234
This United Airlines deal was found by Cheapflights users on 9/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
Nonstop2h 32m
Sat 12/123:35 pm -
1 stop6h 41m
Deal found 9/23![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/138:10 am -
Nonstop2h 05m
Mon 11/161:15 pm -
Nonstop1h 45m
Deal found 9/26![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:59 pm -
1 stop6h 01m
Wed 11/116:00 am -
1 stop4h 40m
Deal found 9/27![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/24. 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.
Thu 11/266:10 am -
Nonstop2h 40m
Fri 11/276:20 pm -
Nonstop2h 29m
Deal found 9/24![United Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 9/24. 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.
Wed 12/164:40 pm -
2 stops7h 00m
Wed 12/237:10 pm -
Nonstop1h 50m
Deal found 9/24![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 9/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
1 stop5h 37m
Mon 11/96:44 pm -
1 stop3h 49m
Deal found 9/22![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:35 pm -
Nonstop2h 00m
Mon 10/196:25 pm -
1 stop4h 30m
Deal found 9/25![Southwest logo]()
$318
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 10/1610:53 am -
Nonstop2h 06m
Tue 10/206:55 am -
Nonstop2h 02m
Deal found 9/22![United Airlines logo]()
$319
This KAYAK deal was found by Cheapflights users on 9/25. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:43 pm -
Nonstop2h 17m
Wed 11/116:20 pm -
Nonstop1h 59m
Deal found 9/25![American Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 9/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/65:50 am -
1 stop3h 55m
Mon 1/1110:35 am -
1 stop5h 24m
Deal found 9/22![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:58 pm -
Nonstop2h 07m
Mon 12/76:25 am -
Nonstop2h 02m
Deal found 9/27![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/1410:10 am -
2 stops8h 15m
Mon 11/161:20 pm -
2 stops7h 00m
Deal found 9/26![Southwest logo]()
$327
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:46 pm -
Nonstop2h 14m
Sat 10/106:20 pm -
Nonstop2h 06m
Deal found 9/24![American Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 12/107:00 am -
1 stop7h 09m
Mon 12/149:59 am -
1 stop6h 00m
Deal found 9/26![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/2910:02 am -
Nonstop2h 17m
Sat 10/319:20 pm -
Nonstop1h 58m
Deal found 9/22![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 9/24. 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 12/74:40 pm -
1 stop5h 45m
Fri 12/1112:45 pm -
2 stops6h 05m
Deal found 9/24![Southwest logo]()
$333
This American Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/141:46 pm -
Nonstop2h 14m
Sat 10/176:20 pm -
Nonstop2h 06m
Deal found 9/27![American Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:10 am -
1 stop6h 58m
Sat 10/243:15 pm -
1 stop5h 42m
Deal found 9/22![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:20 am -
Nonstop2h 33m
Wed 10/284:40 pm -
1 stop4h 54m
Deal found 9/23![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:05 am -
1 stop7h 04m
Mon 12/78:04 am -
1 stop5h 54m
Deal found 9/27![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 9/23. 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.
Mon 2/2212:15 pm -
1 stop5h 10m
Wed 2/2410:05 am -
2 stops8h 25m
Deal found 9/23![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 9/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/228:00 pm -
1 stop4h 15m
Wed 2/2411:00 am -
Nonstop2h 16m
Deal found 9/23![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 9/24. 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.
Thu 10/223:32 pm -
1 stop6h 06m
Tue 10/271:55 pm -
2 stops9h 32m
Deal found 9/24![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 9/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:30 am -
Nonstop2h 15m
Mon 11/97:05 pm -
Nonstop2h 05m
Deal found 9/25![Southwest logo]()
$351
Last-minute flights from Virginia to ChicagoDiscover last-minute flight deals from Virginia to Chicago. Data last updated September 27, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Chicago. Data last updated September 27, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:46 pm -
Nonstop2h 14m
Sun 10/186:20 pm -
Nonstop2h 06m
Deal found 9/25![American Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Thu 10/151:23 pm -
1 stop5h 22m
Mon 10/196:15 am -
2 stops17h 03m
Deal found 9/24![Multiple Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:20 am -
Nonstop2h 33m
Mon 10/1911:57 am -
Nonstop2h 19m
Deal found 9/23![United Airlines logo]()
$317
This Super.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:23 pm -
1 stop5h 22m
Tue 10/206:21 am -
1 stop5h 13m
Deal found 9/26![Frontier logo]()
$318
This Southwest deal was found by Cheapflights users on 9/23. 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.
Fri 10/167:35 pm -
Nonstop2h 00m
Mon 10/1912:45 pm -
Nonstop1h 55m
Deal found 9/23![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 9/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:05 am -
2 stops9h 40m
Mon 10/1912:45 pm -
Nonstop1h 55m
Deal found 9/25![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 9/24. 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.
Wed 10/216:00 am -
1 stop4h 32m
Mon 10/266:44 pm -
1 stop3h 42m
Deal found 9/24![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/23. 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 10/227:35 pm -
Nonstop2h 00m
Thu 10/298:35 am -
1 stop4h 50m
Deal found 9/23![Southwest logo]()
$307
This Mytrip deal was found by Cheapflights users on 9/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:23 pm -
1 stop6h 08m
Sun 10/257:44 pm -
2 stops18h 09m
Deal found 9/25![Frontier logo]()
$318
This American Airlines deal was found by Cheapflights users on 9/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
1 stop7h 05m
Mon 11/25:19 am -
1 stop5h 26m
Deal found 9/25![American Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:46 pm -
Nonstop2h 14m
Tue 11/36:50 pm -
Nonstop1h 59m
Deal found 9/27![American Airlines logo]()
$234
This United Airlines deal was found by Cheapflights users on 9/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:03 pm -
Nonstop2h 16m
Tue 11/36:55 am -
Nonstop2h 07m
Deal found 9/25![United Airlines logo]()
$319
One-way flights from Virginia to ChicagoSearch for one-way flight options from Virginia to Chicago. Find affordable one-way fares based on user searches. Data last updated September 27, 2026.
Search for one-way flight options from Virginia to Chicago. Find affordable one-way fares based on user searches. Data last updated September 27, 2026.
This Super.com deal was found by Cheapflights users on 9/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:23 pm -
1 stop6h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 9/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:23 pm -
1 stop5h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:54 pm -
1 stop8h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:19 pm -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 9/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/234:54 pm -
1 stop27h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$123
This Super.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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.
Mon 11/163:44 pm -
1 stop26h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$123
This Expedia deal was found by Cheapflights users on 9/24. 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 10/173:50 pm -
1 stop8h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/243:50 pm -
1 stop8h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$125
This Frontier deal was found by Cheapflights users on 9/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:41 pm -
1 stop12h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$125
This Frontier deal was found by Cheapflights users on 9/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:21 pm -
1 stop10h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Fri 11/207:34 pm -
1 stop28h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 9/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/217:19 pm -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$129
Find flight deals from Virginia to Chicago
Keep the following information in mind while searching for Virginia to Chicago flight deals. Data was last updated September 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $234 (American Airlines) |
One-way from | $107 (Super.com) |
Popular in | July |
Cheapest in | January |
Average price | $381 |
Good round-trip deal | $233 or less |
Good one-way deal | $227 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Virginia 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 7,457,451 searches. Data last updated September 27, 2026.
Use the filters below to find and compare flights from Virginia to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
RichmondChicago
RIC Richmond Byrd Intl - ORD Chicago O'Hare Intl
RICORD
Richmond Byrd Intl
Wed 12/23
6:26 am-8:00 am
Nonstop2h 34m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Quickest round-trip
RichmondChicago
RIC Richmond Byrd Intl - MDW Chicago Midway
RICMDW
Richmond Byrd Intl
Sat 10/24
8:35 am-9:35 am
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
RichmondChicago
RIC Richmond Byrd Intl - ORD Chicago O'Hare Intl
RICORD
Richmond Byrd Intl
Mon 11/23
6:10 am-7:42 am
Nonstop2h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
RichmondChicago
RIC Richmond Byrd Intl - MDW Chicago Midway
RICMDW
Richmond Byrd Intl
Mon 10/26
7:35 pm-8:35 pm
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
RichmondChicago
RIC Richmond Byrd Intl - ORD Chicago O'Hare Intl
RICORD
Richmond Byrd Intl
Thu 11/26
6:10 am-7:50 am
Nonstop2h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
RichmondChicago
RIC Richmond Byrd Intl - ORD Chicago O'Hare Intl
RICORD
Richmond Byrd Intl
Thu 12/24
5:59 pm-11:03 pm
1 stop6h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
RichmondChicago
RIC Richmond Byrd Intl - ORD Chicago O'Hare Intl
RICORD
Richmond Byrd Intl
Wed 10/21
1:00 pm-7:11 pm
1 stop7h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
RichmondChicago
RIC Richmond Byrd Intl - ORD Chicago O'Hare Intl
RICORD
Richmond Byrd Intl
Tue 10/20
1:00 pm-7:11 pm
1 stop7h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
RichmondChicago
RIC Richmond Byrd Intl - MDW Chicago Midway
RICMDW
Richmond Byrd Intl
Tue 12/22
6:10 am-12:15 pm
1 stop7h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
RichmondChicago
RIC Richmond Byrd Intl - MDW Chicago Midway
RICMDW
Richmond Byrd Intl
Sat 10/24
6:00 am-10:37 am
1 stop5h 37m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Virginia to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Virginia with our price prediction graph.
SHD-ORD
LYH-ORD
RIC-MDW
RIC-ORD
ROA-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 to Chicago
USVA-CHI
SHD-ORD
LYH-ORD
RIC-MDW
RIC-ORD
What is the cheapest month to book a flight from Virginia to Chicago?
Currently, January is the cheapest month in which you can book a flight from Virginia to Chicago (average of $351). Flying from Virginia to Chicago in July is currently the most expensive (average of $430). 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 VA to CHI?
Find hourly flight availability from Virginia 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 September 27, 2026.
When flying from Virginia to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 4% versus a flight in the morning.
Weekly flight availability from Virginia to Chicago
Explore weekly flight availability from Virginia 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 September 27, 2026.
The most flights from USVA to CHI are scheduled on a Monday (29 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (26 on average).
How much does it cost to fly round-trip from Virginia to Chicago?
Airfare is below average for this route at the moment.
Virginia to Chicago flights typically cost between $365 and $495 in October.The cheapest round-trip price found within the last 5 days was $307 on United Airlines (Oct 22-Oct 22).
How far ahead should I book a flight from Virginia to Chicago?
Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Virginia 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 day to fly from Virginia to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Virginia to Chicago. Price data was last updated on September 26, 2026.
Travelers seeking maximum savings on their Virginia to Chicago flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Virginia 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.
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Alternative routes for Virginia 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 September 27, 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 to Chicago by cabin class
Find flights from Virginia to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Virginia and Chicago flights
Browse other Virginia and Chicago flight options. Last updated on September 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Virginia to Chicago flights
Consider these flights traveling from Virginia to Chicago.
Top 6 airlines flying from Virginia to Chicago
Discover the top 6 airlines that operate flights from Virginia 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 7,457,451 searches. Data last updated September 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$154 | Average$369 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$209 | Average$409 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$220 | Average$352 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$229 | Average$345 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$260 | Average$260 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$290 | Average$418 | FlexibilityNo cancel fee | On-time63% |