$231+ Cheap flights from Roanoke (ROA) 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
Jul 10 — Jul 171
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 January or September, 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
Last-minute
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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 June 10, 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 June 10, 2026.
This United Airlines deal was found by Cheapflights users on 6/5. 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 7/86:40 am
ROA
- ORD
Nonstop2h 13m
United Airlines
Sat 7/116:45 am
ORD
- ROA
Nonstop2h 01m
United Airlines
Deal found 6/5![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 6/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Tue 7/288:28 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/6![American Airlines logo]()
$277
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Mon 7/138:19 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/9![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 6/5. 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.
Fri 7/176:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Tue 7/218:28 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/5![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Sat 8/19:12 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/9![American Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 6/9. 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 9/186:40 pm
ROA
- MDW
1 stop4h 45m
Delta
Wed 9/235:10 pm
MDW
- ROA
1 stop4h 34m
Delta
Deal found 6/9![Delta logo]()
$289
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:53 pm
ROA
- ORD
1 stop5h 08m
American Airlines
Tue 7/218:28 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/9![American Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 10/86:49 am
ROA
- ORD
Nonstop2h 11m
United Airlines
Sun 10/116:55 am
ORD
- ROA
Nonstop2h 07m
United Airlines
Deal found 6/9![United Airlines logo]()
$294
This Delta deal was found by Cheapflights users on 6/6. 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.
Tue 7/2111:12 am
ROA
- MDW
1 stop6h 03m
Delta
Tue 7/285:10 pm
MDW
- ROA
1 stop6h 15m
Delta
Deal found 6/6![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 10/286:00 am
ROA
- MDW
1 stop4h 52m
Delta
Sat 10/311:05 pm
MDW
- ROA
1 stop5h 08m
Delta
Deal found 6/8![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 6/5. 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.
Sat 6/275:10 pm
ROA
- MDW
1 stop6h 07m
Delta
Wed 7/19:17 am
MDW
- ROA
2 stops13h 02m
Delta
Deal found 6/5![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 7/115:00 pm
ROA
- MDW
1 stop6h 15m
Delta
Tue 7/145:10 pm
MDW
- ROA
1 stop5h 40m
Delta
Deal found 6/8![Delta logo]()
$399
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 June 10, 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 June 10, 2026.
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Sun 7/128:19 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/9![American Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 6/6. 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.
Tue 7/2111:12 am
ROA
- MDW
1 stop6h 03m
Delta
Tue 7/285:10 pm
MDW
- ROA
1 stop6h 15m
Delta
Deal found 6/6![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 6/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:40 am
ROA
- ORD
Nonstop2h 13m
United Airlines
Mon 8/36:45 am
ORD
- ROA
Nonstop2h 01m
United Airlines
Deal found 6/6![United Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/264:03 pm
ROA
- RFD
1 stop18h 14m
Allegiant Air
Wed 7/14:47 pm
RFD
- ROA
1 stop20h 19m
Allegiant Air
Deal found 6/5![Allegiant Air logo]()
$559
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:00 am
ROA
- ORD
Nonstop2h 22m
American Airlines
Fri 6/267:50 pm
ORD
- ROA
Nonstop2h 04m
American Airlines
Deal found 6/9![American Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 8/298:05 pm
ROA
- ORD
1 stop4h 35m
United Airlines
Tue 9/112:56 pm
ORD
- ROA
1 stop5h 10m
United Airlines
Deal found 6/9![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 7/1411:12 am
ROA
- MDW
1 stop6h 03m
Delta
Sat 7/186:00 am
MDW
- ROA
1 stop14h 43m
Delta
Deal found 6/8![Delta logo]()
$414
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Sat 6/205:56 pm
ROA
- ORD
Nonstop2h 09m
United Airlines
Sun 6/215:55 pm
ORD
- ROA
Nonstop2h 06m
United Airlines
Deal found 6/8![United Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 6/8. 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.
Thu 6/257:59 pm
ROA
- ORD
1 stop5h 00m
Delta
Tue 6/3012:27 pm
ORD
- ROA
2 stops9h 52m
Delta
Deal found 6/8![Delta logo]()
$529
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Wed 6/2410:39 am
ROA
- ORD
1 stop4h 50m
United Airlines
Sun 7/54:42 pm
ORD
- ROA
2 stops20h 13m
United Airlines
Deal found 6/9![United Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 6/5. 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.
Thu 7/306:00 am
ROA
- MDW
1 stop5h 05m
Delta
Mon 8/35:10 pm
MDW
- ROA
1 stop6h 17m
Delta
Deal found 6/5![Delta logo]()
$529
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/253:48 pm
ROA
- RFD
1 stop16h 57m
Allegiant Air
Wed 7/14:47 pm
RFD
- ROA
1 stop20h 19m
Allegiant Air
Deal found 6/5![Allegiant Air logo]()
$647
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Sat 8/16:40 am
ROA
- ORD
Nonstop2h 13m
United Airlines
Sat 8/111:00 am
ORD
- ROA
2 stops21h 42m
United Airlines
Deal found 6/9![United Airlines logo]()
$493
This Delta deal was found by Cheapflights users on 6/6. 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.
Sat 8/15:00 pm
ROA
- MDW
1 stop6h 15m
Delta
Mon 8/35:10 pm
MDW
- ROA
1 stop6h 17m
Delta
Deal found 6/6![Delta logo]()
$544
This United Airlines deal was found by Cheapflights users on 6/9. 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 7/1010:30 am
ROA
- ORD
1 stop7h 32m
United Airlines
Mon 7/134:42 pm
ORD
- ROA
2 stops20h 13m
United Airlines
Deal found 6/9![United Airlines logo]()
$522
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/281:48 pm
ROA
- RFD
1 stop18h 57m
Allegiant Air
Wed 7/14:47 pm
RFD
- ROA
1 stop20h 19m
Allegiant Air
Deal found 6/5![Allegiant Air logo]()
$734
This Delta deal was found by Cheapflights users on 6/7. 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 8/206:00 am
ROA
- MDW
1 stop4h 59m
Delta
Sat 8/2210:56 am
MDW
- ROA
1 stop4h 16m
Delta
Deal found 6/7![Delta logo]()
$604
This Delta deal was found by Cheapflights users on 6/5. 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.
Wed 7/86:00 am
ROA
- MDW
2 stops7h 38m
Delta
Sat 7/114:22 pm
MDW
- ROA
1 stop4h 21m
Delta
Deal found 6/5![Delta logo]()
$634
This Delta deal was found by Cheapflights users on 6/9. 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.
Thu 6/186:00 am
ROA
- MDW
1 stop5h 09m
Delta
Fri 6/265:11 pm
MDW
- ROA
1 stop6h 21m
Delta
Deal found 6/9![Delta logo]()
$649
This Delta deal was found by Cheapflights users on 6/6. 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 6/2511:13 am
ROA
- MDW
1 stop6h 03m
Delta
Tue 6/301:26 pm
MDW
- ROA
2 stops8h 53m
Delta
Deal found 6/6![Delta logo]()
$649
Last-minute flights from Roanoke to ChicagoDiscover last-minute flight deals from Roanoke to Chicago. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Roanoke to Chicago. Data last updated June 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/5. 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.
Sat 6/275:10 pm
ROA
- MDW
1 stop6h 07m
Delta
Wed 7/19:17 am
MDW
- ROA
2 stops13h 02m
Delta
Deal found 6/5![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 6/5. 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.
Sat 6/275:10 pm
ROA
- MDW
1 stop6h 07m
Delta
Tue 6/304:25 pm
MDW
- ROA
1 stop7h 07m
Delta
Deal found 6/5![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 6/5. 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 7/86:40 am
ROA
- ORD
Nonstop2h 13m
United Airlines
Sat 7/116:45 am
ORD
- ROA
Nonstop2h 01m
United Airlines
Deal found 6/5![United Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Mon 7/138:19 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/9![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 7/115:00 pm
ROA
- MDW
1 stop6h 15m
Delta
Tue 7/145:10 pm
MDW
- ROA
1 stop5h 40m
Delta
Deal found 6/8![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 7/115:00 pm
ROA
- MDW
1 stop6h 15m
Delta
Thu 7/165:10 pm
MDW
- ROA
1 stop6h 15m
Delta
Deal found 6/8![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 7/1411:12 am
ROA
- MDW
1 stop6h 03m
Delta
Sat 7/186:00 am
MDW
- ROA
1 stop14h 43m
Delta
Deal found 6/8![Delta logo]()
$414
This American Airlines deal was found by Cheapflights users on 6/5. 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.
Fri 7/176:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Tue 7/218:28 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/5![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:53 pm
ROA
- ORD
1 stop5h 08m
American Airlines
Tue 7/218:28 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/9![American Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 6/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Tue 7/288:28 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/6![American Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 6/6. 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.
Tue 7/2111:12 am
ROA
- MDW
1 stop6h 03m
Delta
Tue 7/285:10 pm
MDW
- ROA
1 stop6h 15m
Delta
Deal found 6/6![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Sat 8/19:12 pm
ORD
- ROA
Nonstop1h 59m
American Airlines
Deal found 6/9![American Airlines logo]()
$281
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 June 10, 2026.
Search for one-way flight options from Roanoke to Chicago. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/103:27 pm
ROA
- ORD
3 stops30h 25m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/87:00 am
ROA
- ORD
2 stops14h 24m
Delta
Deal found 6/10![Delta logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:51 am
ROA
- ORD
3 stops50h 34m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/314:40 pm
ROA
- ORD
3 stops43h 50m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Mon 6/294:03 pm
ROA
- MDW
2 stops20h 09m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Thu 8/62:46 pm
ROA
- ORD
3 stops46h 29m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$251
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:00 am
ROA
- ORD
Nonstop2h 14m
American Airlines
Deal found 6/9![American Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Thu 9/310:46 am
ROA
- ORD
3 stops46h 17m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 6/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
ROA
- ORD
Nonstop2h 22m
American Airlines
Deal found 6/8![American Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
ROA
- ORD
1 stop4h 23m
Delta
Deal found 6/10![Delta logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Fri 6/264:03 pm
ROA
- RFD
1 stop18h 14m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$267
This Delta deal was found by Cheapflights users on 6/5. 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.
Tue 7/2111:12 am
ROA
- MDW
1 stop6h 03m
Delta
Deal found 6/5![Delta logo]()
$269
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 June 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (American Airlines) |
One-way from | $231 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $289 |
Good round-trip deal | $368 or less |
Good one-way deal | $313 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 2,558,603 searches. Data last updated June 10, 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 - ORD
ROAORD
Roanoke
Wed 7/8
6:00 am-7:14 am
Nonstop2h 14m
Chicago O'Hare Intl
Sun 7/12
8:19 pm-11:18 pm
Nonstop1h 59m
$269
RoanokeChicago
ROA - MDW
ROAMDW
Roanoke
Tue 7/21
11:12 am-4:15 pm
1 stop6h 03m
Chicago Midway
Tue 7/28
5:10 pm-12:25 am
1 stop6h 15m
$319
RoanokeChicago
ROA - ORD
ROAORD
Roanoke
Sat 8/1
6:40 am-7:53 am
Nonstop2h 13m
Chicago O'Hare Intl
Mon 8/3
6:45 am-9:46 am
Nonstop2h 01m
$324
RoanokeChicago
ROA - ORD
ROAORD
Roanoke
Thu 6/18
6:00 am-7:22 am
Nonstop2h 22m
Chicago O'Hare Intl
Fri 6/26
7:50 pm-10:54 pm
Nonstop2h 04m
$344
RoanokeChicago
ROA - ORD
ROAORD
Roanoke
Sat 8/29
8:05 pm-11:40 pm
1 stop4h 35m
Chicago O'Hare Intl
Tue 9/1
12:56 pm-7:06 pm
1 stop5h 10m
$369
RoanokeChicago
ROA - ORD
ROAORD
Roanoke
Sat 6/20
5:56 pm-7:05 pm
Nonstop2h 09m
Chicago O'Hare Intl
Sun 6/21
5:55 pm-9:01 pm
Nonstop2h 06m
$389
RoanokeChicago
ROA - MDW
ROAMDW
Roanoke
Tue 7/14
11:12 am-4:15 pm
1 stop6h 03m
Chicago Midway
Sat 7/18
6:00 am-9:43 pm
1 stop14h 43m
$414
RoanokeChicago
ROA - ORD
ROAORD
Roanoke
Wed 6/24
10:39 am-2:29 pm
1 stop4h 50m
Chicago O'Hare Intl
Sun 7/5
4:42 pm-1:55 pm
2 stops20h 13m
$488
RoanokeChicago
ROA - ORD
ROAORD
Roanoke
Sat 8/1
6:40 am-7:53 am
Nonstop2h 13m
Chicago O'Hare Intl
Sat 8/1
11:00 am-9:42 am
2 stops21h 42m
$493
RoanokeChicago
ROA - ORD
ROAORD
Roanoke
Fri 7/10
10:30 am-5:02 pm
1 stop7h 32m
Chicago O'Hare Intl
Mon 7/13
4:42 pm-1:55 pm
2 stops20h 13m
$522
Showing 1-10 of 44 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 June.
| 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, December is the cheapest month in which you can book a flight from Roanoke to Chicago (average of $145). Flying from Roanoke to Chicago in July is currently the most expensive (average of $214). 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 June 10, 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 June 10, 2026.
The most flights from ROA to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Roanoke to Chicago?
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 61 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 June 10, 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.
Crew
8.1
Food
6.6
Overall
7.4
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Food
6.6
Overall
7.4
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Food
6.6
Overall
7.4
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
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
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 10, 2026.
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Roanoke and Chicago flights
Browse other Roanoke and Chicago flight options. Last updated on June 10, 2026.
Other flights from Roanoke
Browse through other flights departing from Roanoke. Flights are based on user searches made on Cheapflights and were last updated on June 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Roanoke to Chicago
Discover the top 3 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 2,558,603 searches. Data last updated June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$287 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$209 | Average$345 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$228 | Average$228 | FlexibilityNo cancel fee | On-timeN/A |