$179+ Cheap flights from Roanoke (ROA) 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
Oct 9 — Oct 161
Round-trip
1 adult, Economy
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Find cheap flights from Roanoke 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 Roanoke to Chicago are usually found in December or January, booked 22 days in advance, depart on a Friday or Wednesday and return on a Saturday
Cheap flight deals from Roanoke to Chicago
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Best
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One-way
Cheapest flights from Roanoke to ChicagoExplore the most affordable flight options available from Roanoke to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
Explore the most affordable flight options available from Roanoke to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/306:49 am -
Nonstop2h 11m
Sun 10/47:45 pm -
Nonstop2h 14m
Deal found 9/8![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/236:15 am -
1 stop6h 33m
Sun 10/256:30 am -
Nonstop1h 57m
Deal found 9/9![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/2311:13 am -
1 stop6h 01m
Mon 10/265:09 pm -
1 stop6h 18m
Deal found 9/9![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/236:38 pm -
1 stop6h 19m
Mon 10/261:45 pm -
2 stops9h 42m
Deal found 9/9![Delta logo]()
$324
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/247:20 am -
1 stop5h 56m
Mon 9/282:13 pm -
Nonstop2h 04m
Deal found 9/5![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/86:49 am -
Nonstop2h 11m
Sun 10/116:55 am -
Nonstop2h 02m
Deal found 9/7![United Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:32 pm -
1 stop6h 27m
Wed 9/302:29 pm -
1 stop7h 19m
Deal found 9/9![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/76:15 am -
1 stop4h 23m
Sun 10/116:55 am -
Nonstop2h 02m
Deal found 9/5![United Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/306:40 pm -
1 stop6h 19m
Sat 10/1011:09 am -
2 stops9h 48m
Deal found 9/7![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/296:38 pm -
1 stop4h 55m
Sat 10/319:29 am -
2 stops11h 28m
Deal found 9/6![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/237:20 am -
2 stops12h 13m
Wed 9/301:19 pm -
2 stops8h 29m
Deal found 9/9![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/236:40 pm -
1 stop5h 04m
Tue 9/2910:48 am -
1 stop6h 04m
Deal found 9/9![Delta logo]()
$359
Best flights from Roanoke to ChicagoDiscover carefully curated flight deals from Roanoke to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
Discover carefully curated flight deals from Roanoke to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/136:00 am -
1 stop4h 45m
Sun 11/156:29 am -
Nonstop1h 57m
Deal found 9/4![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/236:38 pm -
1 stop4h 55m
Mon 10/265:09 pm -
1 stop6h 18m
Deal found 9/5![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/84:41 pm -
1 stop27h 31m
Wed 10/1411:04 am -
1 stop27h 47m
Deal found 9/6![Allegiant Air logo]()
$618
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/236:49 am -
Nonstop2h 11m
Mon 11/26:29 am -
Nonstop1h 57m
Deal found 9/5![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 12/136:55 pm -
1 stop5h 00m
Wed 1/65:25 pm -
1 stop4h 14m
Deal found 9/4![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/66:38 pm -
1 stop6h 19m
Tue 11/102:44 pm -
2 stops8h 35m
Deal found 9/4![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/296:38 pm -
1 stop6h 19m
Sat 10/3110:55 am -
2 stops10h 02m
Deal found 9/4![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/166:49 am -
Nonstop2h 11m
Mon 10/197:45 pm -
Nonstop2h 14m
Deal found 9/8![United Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/155:51 pm -
Nonstop2h 09m
Mon 10/197:45 pm -
Nonstop2h 14m
Deal found 9/8![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/157:10 am -
1 stop6h 58m
Mon 10/191:25 pm -
2 stops10h 02m
Deal found 9/7![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/226:40 pm -
1 stop6h 19m
Sat 9/267:05 am -
2 stops9h 07m
Deal found 9/7![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/2211:12 am -
1 stop6h 03m
Sat 9/269:29 am -
2 stops6h 43m
Deal found 9/7![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/66:38 pm -
1 stop4h 55m
Tue 11/1011:27 am -
1 stop5h 47m
Deal found 9/4![Delta logo]()
$429
Last-minute flights from Roanoke to ChicagoDiscover last-minute flight deals from Roanoke to Chicago. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from Roanoke to Chicago. Data last updated September 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/237:20 am -
2 stops12h 13m
Wed 9/301:19 pm -
2 stops8h 29m
Deal found 9/9![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/236:40 pm -
1 stop5h 04m
Tue 9/2910:48 am -
1 stop6h 04m
Deal found 9/9![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/245:47 pm -
Nonstop2h 27m
Sat 9/261:19 pm -
1 stop6h 40m
Deal found 9/5![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/256:49 am -
Nonstop2h 11m
Sun 9/277:45 pm -
Nonstop2h 14m
Deal found 9/9![United Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/306:49 am -
Nonstop2h 11m
Sun 10/47:45 pm -
Nonstop2h 14m
Deal found 9/8![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/306:40 pm -
1 stop6h 19m
Sat 10/1011:09 am -
2 stops9h 48m
Deal found 9/6![Delta logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/76:15 am -
1 stop4h 23m
Sun 10/116:55 am -
Nonstop2h 02m
Deal found 9/5![United Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/86:49 am -
Nonstop2h 11m
Sun 10/116:55 am -
Nonstop2h 02m
Deal found 9/7![United Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/236:15 am -
1 stop6h 33m
Sun 10/256:30 am -
Nonstop1h 57m
Deal found 9/9![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/2311:13 am -
1 stop6h 01m
Mon 10/265:09 pm -
1 stop6h 18m
Deal found 9/9![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/236:38 pm -
1 stop6h 19m
Mon 10/261:45 pm -
2 stops9h 42m
Deal found 9/9![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/296:38 pm -
1 stop4h 55m
Sat 10/319:29 am -
2 stops11h 28m
Deal found 9/6![Delta logo]()
$344
One-way flights from Roanoke to ChicagoSearch for one-way flight options from Roanoke to Chicago. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
Search for one-way flight options from Roanoke to Chicago. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/1911:08 am -
2 stops25h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Tue 10/134:49 pm -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/46:20 am -
1 stop5h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/53:12 pm -
2 stops32h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:55 pm -
1 stop16h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/114:42 pm -
2 stops30h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 12/1111:17 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 11/206:00 am -
1 stop5h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$370
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/86:00 am -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Delta logo]()
$440
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/206:00 am -
1 stop4h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$454
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/46:00 am -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$470
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2010:51 am -
3 stops32h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$534
Find flight deals from Roanoke to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Roanoke (ROA) 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 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (United Airlines) |
One-way from | $179 (Kiwi.com) |
Popular in | March |
Cheapest in | December |
Average price | $299 |
Good round-trip deal | $358 or less |
Good one-way deal | $378 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Roanoke 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 9, 2026.
Use the filters below to find and compare flights from Roanoke to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Sun 10/4
6:49 am-8:00 am
Nonstop2h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$269
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Sat 12/5
6:00 am-12:19 pm
1 stop7h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Fri 12/11
6:55 pm-11:52 pm
1 stop5h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Sat 9/19
6:40 am-7:51 am
Nonstop2h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
RoanokeChicago
ROA Roanoke - MDW Chicago Midway
ROAMDW
Roanoke
Fri 12/11
11:17 am-4:17 pm
1 stop6h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$279
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Sun 3/7
7:50 pm-11:50 pm
1 stop5h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
RoanokeChicago
ROA Roanoke - MDW Chicago Midway
ROAMDW
Roanoke
Wed 9/30
6:00 am-9:49 am
1 stop4h 49m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
RoanokeChicago
ROA Roanoke - MDW Chicago Midway
ROAMDW
Roanoke
Tue 10/13
11:13 am-4:14 pm
1 stop6h 01m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
RoanokeChicago
ROA Roanoke - MDW Chicago Midway
ROAMDW
Roanoke
Mon 10/12
6:00 am-11:54 am
1 stop6h 54m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Tue 12/1
11:17 am-6:26 pm
2 stops8h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$294
Showing 1-10 of 28 resultsSorted by cheapest first
Compare providers for flights from Roanoke to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Roanoke to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Roanoke-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Roanoke-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Roanoke-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Roanoke-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 Roanoke-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 Roanoke to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Roanoke with our price prediction graph.
ROA-CHI
ROA-ORD
ROA-MDW
ROA-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 Roanoke to Chicago
ROA-CHI
ROA-ORD
ROA-MDW
ROA-RFD
What is the cheapest month to book a flight from Roanoke to Chicago?
Currently, January is the cheapest month in which you can book a flight from Roanoke to Chicago (average of $294). Flying from Roanoke to Chicago in March is currently the most expensive (average of $366). 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 ROA to CHI?
Find hourly flight availability from Roanoke 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 9, 2026.
When flying from Roanoke to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Roanoke to Chicago
Explore weekly flight availability from Roanoke 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 9, 2026.
The most flights from ROA to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Roanoke to Chicago?
Airfare is typical for this route at the moment.
Roanoke to Chicago flights typically cost between $269 and $379 in September.The cheapest round-trip price found within the last 5 days was $299 on United Airlines (Sep 30-Oct 4).
How far ahead should I book a flight from Roanoke to Chicago?
To ensure you get the cheapest price possible for a flight from Roanoke to Chicago, you should look to book at least 57 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 9, 2026.
See what other customers who have flown with United Airlines and American Airlines from Roanoke to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Overall
7.4
Comfort
7.3
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Roanoke 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Roanoke and Chicago flights
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Top 2 airlines flying from Roanoke to Chicago
Discover the top 2 airlines that operate flights from Roanoke 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$358 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$296 | FlexibilityNo cancel fee | On-time71% |