$146+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
Nov 24 — Dec 11
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 February, booked 58 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Roanoke to Chicago
Cheapest
Best
Last-minute
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 October 25, 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 October 25, 2026.
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:30 am -
Nonstop2h 14m
Mon 11/1610:25 am -
Nonstop2h 01m
Deal found 10/22![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:52 pm -
Nonstop2h 28m
Mon 11/161:22 pm -
1 stop5h 34m
Deal found 10/22![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:15 am -
1 stop7h 11m
Wed 11/256:29 am -
1 stop6h 24m
Deal found 10/21![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:51 pm -
Nonstop2h 09m
Fri 11/278:50 am -
1 stop4h 25m
Deal found 10/22![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/37:05 am -
2 stops10h 38m
Sun 12/66:49 am -
1 stop7h 09m
Deal found 10/20![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals ”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:40 am -
Nonstop2h 14m
Sun 11/158:50 am -
1 stop4h 25m
Deal found 10/24![United Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:00 am -
1 stop4h 45m
Fri 11/278:50 am -
1 stop4h 25m
Deal found 10/24![United Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:15 am -
1 stop5h 45m
Mon 11/308:00 am -
1 stop6h 42m
Deal found 10/20![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:00 am -
2 stops11h 18m
Mon 11/306:15 pm -
1 stop5h 04m
Deal found 10/21![Delta logo]()
$375
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:01 pm -
Nonstop2h 09m
Sun 11/86:29 am -
Nonstop1h 57m
Deal found 10/21![United Airlines logo]()
$379
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 October 25, 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 October 25, 2026.
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
2 stops8h 59m
Mon 11/163:47 pm -
2 stops7h 32m
Deal found 10/24![Delta logo]()
$389
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/83:05 pm -
2 stops17h 45m
Sat 1/910:25 am -
Nonstop2h 05m
Deal found 10/22![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:05 am -
2 stops10h 36m
Sat 11/217:25 am -
2 stops10h 53m
Deal found 10/23![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/46:00 am -
2 stops8h 56m
Sun 12/62:41 pm -
2 stops8h 45m
Deal found 10/20![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/232:01 pm -
Nonstop2h 09m
Fri 11/2710:25 am -
Nonstop2h 01m
Deal found 10/20![United Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:38 pm -
1 stop6h 19m
Wed 1/209:30 am -
1 stop4h 10m
Deal found 10/22![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:26 am -
1 stop5h 12m
Tue 11/176:29 am -
Nonstop1h 57m
Deal found 10/21![United Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:00 am -
2 stops11h 26m
Fri 11/1312:38 pm -
2 stops9h 38m
Deal found 10/23![Delta logo]()
$410
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:00 am -
1 stop6h 38m
Fri 1/229:38 pm -
Nonstop2h 07m
Deal found 10/22![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
2 stops8h 59m
Sun 11/156:49 am -
1 stop6h 59m
Deal found 10/22![Delta logo]()
$464
Last-minute flights from Roanoke to ChicagoDiscover last-minute flight deals from Roanoke to Chicago. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Roanoke to Chicago. Data last updated October 25, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:01 pm -
Nonstop2h 09m
Sun 11/86:29 am -
Nonstop1h 57m
Deal found 10/21![United Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:40 am -
Nonstop2h 14m
Sun 11/158:50 am -
1 stop4h 25m
Deal found 10/24![United Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:30 am -
Nonstop2h 14m
Mon 11/1610:25 am -
Nonstop2h 01m
Deal found 10/22![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/144:52 pm -
Nonstop2h 28m
Mon 11/161:22 pm -
1 stop5h 34m
Deal found 10/22![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/148:30 am -
1 stop6h 15m
Mon 11/163:47 pm -
2 stops7h 32m
Deal found 10/24![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:55 am -
1 stop4h 38m
Fri 11/275:19 am -
1 stop6h 25m
Deal found 10/21![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:08 am -
1 stop7h 25m
Wed 11/251:36 pm -
Nonstop1h 52m
Deal found 10/21![American Airlines logo]()
$360
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:00 am -
1 stop4h 45m
Fri 11/278:50 am -
1 stop4h 25m
Deal found 10/24![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:00 am -
2 stops11h 18m
Mon 11/306:15 pm -
1 stop5h 04m
Deal found 10/21![Delta logo]()
$375
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:51 pm -
Nonstop2h 09m
Fri 11/278:50 am -
1 stop4h 25m
Deal found 10/22![United Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:15 am -
1 stop5h 45m
Mon 11/308:00 am -
1 stop6h 42m
Deal found 10/20![American Airlines logo]()
$374
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 October 25, 2026.
Search for one-way flight options from Roanoke to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/1611:52 am -
2 stops31h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:13 pm -
2 stops31h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/192:37 pm -
2 stops26h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/234:13 pm -
1 stop9h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:13 pm -
2 stops29h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/243:57 pm -
2 stops24h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$255
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:00 am -
2 stops9h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$266
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:30 am -
Nonstop2h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![United Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/203:57 pm -
2 stops31h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$297
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (American Airlines) |
One-way from | $146 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $404 |
Good round-trip deal | $416 or less |
Good one-way deal | $360 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 October 25, 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
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Tue 12/15
5:03 pm-6:24 pm
Nonstop2h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
Quickest round-trip
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Sat 11/21
5:51 pm-7:00 pm
Nonstop2h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Thu 11/19
4:58 pm-6:29 pm
Nonstop2h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Thu 11/19
6:30 am-7:44 am
Nonstop2h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Tue 12/15
11:18 am-5:06 pm
1 stop6h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Fri 12/11
6:00 am-10:25 am
1 stop5h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Sun 11/29
6:30 am-7:44 am
Nonstop2h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$323
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Thu 11/19
11:18 am-6:30 pm
2 stops8h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$324
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Thu 11/12
6:00 am-1:59 pm
2 stops8h 59m
Chicago O'Hare Intl
Mon 11/16
3:47 pm-12:19 am
2 stops7h 32m
$389
RoanokeChicago
ROA Roanoke - ORD Chicago O'Hare Intl
ROAORD
Roanoke
Wed 11/18
7:05 am-4:41 pm
2 stops10h 36m
Chicago O'Hare Intl
Sat 11/21
7:25 am-7:18 pm
2 stops10h 53m
$389
Showing 1-10 of 18 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 October.
| 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
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
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 $296). Flying from Roanoke to Chicago in November is currently the most expensive (average of $424). 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 October 25, 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.
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 $309 and $562 in January.The cheapest round-trip price found within the last 5 days was $339 on American Airlines (Jan 20-Jan 23).
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 October 25, 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.
Boarding
7.7
Food
6.7
Overall
7.3
Crew
8.1
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Food
6.7
Overall
7.3
Crew
8.1
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Food
6.7
Overall
7.3
Crew
8.1
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Roanoke to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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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 October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$219 | Average$372 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$249 | Average$329 | FlexibilityNo cancel fee | On-time71% |