$189+ Cheap flights from Charlottesville (CHO) 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — CHI
Oct 2 — Oct 91
Round-trip
1 adult, Economy
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Find cheap flights from Charlottesville 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 Charlottesville Albemarle to Chicago are usually found in January or October, booked 80 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
Cheap flight deals from Charlottesville to Chicago
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Cheapest flights from Charlottesville to ChicagoExplore the most affordable flight options available from Charlottesville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 2, 2026.
Explore the most affordable flight options available from Charlottesville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 2, 2026.
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:42 pm -
Nonstop2h 10m
Mon 12/143:02 pm -
Nonstop2h 10m
Deal found 9/2![American Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/106:23 pm -
Nonstop2h 07m
Sun 10/118:45 am -
Nonstop2h 12m
Deal found 8/29![United Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am -
1 stop6h 54m
Tue 10/135:09 pm -
1 stop5h 35m
Deal found 8/31![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:37 pm -
1 stop7h 01m
Sat 10/1010:35 am -
1 stop5h 18m
Deal found 8/31![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:25 am -
1 stop6h 23m
Sun 10/188:45 am -
Nonstop2h 12m
Deal found 8/31![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:11 pm -
1 stop5h 48m
Tue 10/66:29 am -
1 stop4h 38m
Deal found 9/1![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:25 am -
1 stop4h 13m
Sun 9/206:30 am -
1 stop6h 23m
Deal found 8/29![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:00 am -
1 stop6h 54m
Sun 11/16:04 am -
1 stop4h 10m
Deal found 9/1![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:30 pm -
1 stop5h 50m
Thu 10/295:27 am -
1 stop7h 23m
Deal found 8/31![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/113:14 pm -
2 stops21h 28m
Sat 9/122:10 pm -
Nonstop2h 14m
Deal found 8/29![United Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/186:45 am -
Nonstop2h 05m
Sun 9/206:55 am -
Nonstop2h 03m
Deal found 8/28![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:59 pm -
1 stop4h 33m
Mon 10/195:50 pm -
Nonstop2h 09m
Deal found 8/31![United Airlines logo]()
$356
Best flights from Charlottesville to ChicagoDiscover carefully curated flight deals from Charlottesville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 2, 2026.
Discover carefully curated flight deals from Charlottesville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 2, 2026.
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop5h 24m
Sun 11/226:00 am -
1 stop4h 15m
Deal found 8/30![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/106:25 am -
1 stop6h 23m
Sun 10/118:45 am -
Nonstop2h 12m
Deal found 8/29![United Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/165:32 pm -
1 stop6h 01m
Tue 10/206:04 am -
1 stop6h 46m
Deal found 8/28![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop5h 03m
Wed 10/286:04 am -
1 stop4h 10m
Deal found 8/31![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/105:33 pm -
1 stop6h 00m
Sun 10/116:04 am -
1 stop4h 10m
Deal found 8/29![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:59 pm -
1 stop4h 33m
Tue 10/68:45 am -
Nonstop2h 12m
Deal found 8/30![United Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/145:38 pm -
1 stop6h 16m
Mon 11/1611:27 am -
1 stop4h 31m
Deal found 8/28![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:59 pm -
1 stop4h 33m
Mon 9/288:45 am -
Nonstop2h 12m
Deal found 8/31![United Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
1 stop5h 03m
Thu 10/296:04 am -
1 stop4h 10m
Deal found 8/31![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:53 pm -
Nonstop2h 07m
Sun 10/118:45 am -
Nonstop2h 12m
Deal found 8/31![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:30 pm -
1 stop5h 50m
Thu 11/56:00 am -
1 stop6h 50m
Deal found 9/2![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1712:40 pm -
Nonstop2h 07m
Sun 9/206:55 am -
Nonstop2h 03m
Deal found 8/28![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/162:30 pm -
1 stop5h 50m
Tue 10/206:08 pm -
1 stop4h 36m
Deal found 8/28![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop5h 25m
Sun 11/225:30 am -
1 stop7h 21m
Deal found 8/30![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:59 pm -
1 stop4h 33m
Sun 10/118:45 am -
Nonstop2h 12m
Deal found 8/31![United Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:00 am -
1 stop7h 20m
Mon 12/145:30 am -
1 stop7h 21m
Deal found 8/31![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/166:45 am -
Nonstop2h 07m
Tue 10/208:45 am -
Nonstop2h 12m
Deal found 8/28![United Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:38 pm -
1 stop6h 06m
Tue 10/66:04 am -
1 stop4h 10m
Deal found 9/1![Delta logo]()
$559
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:02 am -
2 stops6h 45m
Sun 10/116:04 am -
1 stop4h 10m
Deal found 8/31![Delta logo]()
$564
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:38 pm -
1 stop6h 06m
Mon 9/281:19 pm -
2 stops8h 35m
Deal found 8/31![Delta logo]()
$564
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 11/1410:35 am -
2 stops8h 29m
Tue 11/176:00 am -
1 stop6h 51m
Deal found 8/29![Delta logo]()
$564
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:02 am -
2 stops10h 45m
Sun 10/256:04 am -
1 stop4h 10m
Deal found 8/31![Delta logo]()
$594
Last-minute flights from Charlottesville to ChicagoDiscover last-minute flight deals from Charlottesville to Chicago. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from Charlottesville to Chicago. Data last updated September 2, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/113:14 pm -
2 stops21h 28m
Sat 9/122:10 pm -
Nonstop2h 14m
Deal found 8/29![United Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:25 am -
1 stop4h 13m
Sun 9/206:30 am -
1 stop6h 23m
Deal found 8/29![United Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:11 pm -
1 stop5h 48m
Tue 10/66:29 am -
1 stop4h 38m
Deal found 9/1![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/186:45 am -
Nonstop2h 05m
Sun 9/206:55 am -
Nonstop2h 03m
Deal found 8/28![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:00 am -
1 stop6h 54m
Tue 10/135:09 pm -
1 stop5h 35m
Deal found 8/31![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:37 pm -
1 stop7h 01m
Sat 10/1010:35 am -
1 stop5h 18m
Deal found 8/31![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/106:23 pm -
Nonstop2h 07m
Sun 10/118:45 am -
Nonstop2h 12m
Deal found 8/29![United Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:25 am -
1 stop6h 23m
Sun 10/188:45 am -
Nonstop2h 12m
Deal found 8/31![United Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:59 pm -
1 stop4h 33m
Mon 10/195:50 pm -
Nonstop2h 09m
Deal found 8/31![United Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:30 pm -
1 stop5h 50m
Sun 10/255:27 am -
1 stop4h 47m
Deal found 8/31![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:03 pm -
Nonstop2h 16m
Thu 11/56:55 am -
Nonstop2h 07m
Deal found 9/2![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:31 pm -
1 stop6h 02m
Tue 11/36:04 am -
1 stop4h 10m
Deal found 8/31![Delta logo]()
$349
One-way flights from Charlottesville to ChicagoSearch for one-way flight options from Charlottesville to Chicago. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
Search for one-way flight options from Charlottesville to Chicago. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:53 pm -
Nonstop2h 07m
Deal found 9/1![United Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:00 am -
1 stop5h 10m
Deal found 9/2![American Airlines logo]()
$199
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:41 pm -
Nonstop2h 07m
Deal found 9/2![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/264:20 pm -
1 stop7h 24m
Deal found 8/29![Delta logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:05 pm -
1 stop4h 56m
Deal found 8/30![United Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/302:03 pm -
Nonstop2h 16m
Deal found 9/2![United Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/288:05 pm -
1 stop4h 56m
Deal found 9/2![United Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:59 am -
2 stops10h 31m
Deal found 8/31![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/276:00 am -
2 stops16h 37m
Deal found 9/1![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/268:00 pm -
1 stop4h 59m
Deal found 9/2![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:25 am -
2 stops11h 37m
Deal found 9/1![United Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:00 am -
1 stop5h 10m
Deal found 9/2![American Airlines logo]()
$337
Find flight deals from Charlottesville to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Charlottesville (CHO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (United Airlines) |
One-way from | $189 (United Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $467 |
Good round-trip deal | $436 or less |
Good one-way deal | $338 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Charlottesville 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 2, 2026.
Use the filters below to find and compare flights from Charlottesville to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Sun 11/15
6:00 am-10:24 am
1 stop5h 24m
Chicago Midway
Sun 11/22
6:00 am-11:15 am
1 stop4h 15m
$319
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Fri 10/16
5:32 pm-10:33 pm
1 stop6h 01m
Chicago Midway
Tue 10/20
6:04 am-1:50 pm
1 stop6h 46m
$319
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Wed 10/21
6:00 am-10:03 am
1 stop5h 03m
Chicago Midway
Wed 10/28
6:04 am-11:14 am
1 stop4h 10m
$319
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Sat 10/10
5:33 pm-10:33 pm
1 stop6h 00m
Chicago Midway
Sun 10/11
6:04 am-11:14 am
1 stop4h 10m
$319
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Sat 11/14
5:38 pm-10:54 pm
1 stop6h 16m
Chicago Midway
Mon 11/16
11:27 am-4:58 pm
1 stop4h 31m
$319
CharlottesvilleChicago
CHO Charlottesville Albemarle - MDW Chicago Midway
CHOMDW
Charlottesville Albemarle
Tue 10/20
6:00 am-10:03 am
1 stop5h 03m
Chicago Midway
Thu 10/29
6:04 am-11:14 am
1 stop4h 10m
$319
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Thu 10/29
2:30 pm-7:20 pm
1 stop5h 50m
Chicago O'Hare Intl
Thu 11/5
6:00 am-1:50 pm
1 stop6h 50m
$319
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Fri 10/16
2:30 pm-7:20 pm
1 stop5h 50m
Chicago O'Hare Intl
Tue 10/20
6:08 pm-11:44 pm
1 stop4h 36m
$319
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Sun 11/15
6:00 am-10:25 am
1 stop5h 25m
Chicago O'Hare Intl
Sun 11/22
5:30 am-1:51 pm
1 stop7h 21m
$319
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Thu 12/10
6:00 am-12:20 pm
1 stop7h 20m
Chicago O'Hare Intl
Mon 12/14
5:30 am-1:51 pm
1 stop7h 21m
$319
Showing 1-10 of 38 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Charlottesville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charlottesville-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charlottesville-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Charlottesville-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Charlottesville-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Charlottesville to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Charlottesville with our price prediction graph.
CHO-CHI
CHO-ORD
CHO-MDW
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 Charlottesville to Chicago
CHO-CHI
CHO-ORD
CHO-MDW
What is the cheapest month to book a flight from Charlottesville to Chicago?
Currently, November is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $308). Flying from Charlottesville to Chicago in September is currently the most expensive (average of $500). 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 CHO to CHI?
Find hourly flight availability from Charlottesville 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 2, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 16% on flights from Charlottesville to Chicago by exploring options for tickets at noon.
Weekly flight availability from Charlottesville to Chicago
Explore weekly flight availability from Charlottesville 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 2, 2026.
The most flights from CHO to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Charlottesville to Chicago?
Airfare is below average for this route at the moment.
Charlottesville to Chicago flights typically cost between $343 and $633 in December.The cheapest round-trip price found within the last 5 days was $299 on American Airlines (Dec 10-Dec 14).
How far ahead should I book a flight from Charlottesville to Chicago?
To ensure you get the cheapest price possible for a flight from Charlottesville to Chicago, you should look to book at least 28 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 September 2, 2026.
Peruse reviews from past customers who have flown with United Airlines from Charlottesville 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
7.7
Overall
7.4
Food
6.6
Entertainment
7.1
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Overall
7.4
Food
6.6
Entertainment
7.1
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Charlottesville 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
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Charlottesville and Chicago flights
Browse other Charlottesville and Chicago flight options. Last updated on September 2, 2026.
Other flights from Charlottesville
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Top 2 airlines flying from Charlottesville to Chicago
Discover the top 2 airlines that operate flights from Charlottesville 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$413 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$293 | Average$423 | FlexibilityNo cancel fee | On-time71% |