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$151+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
Aug 24 — Aug 311
Mon 8/24
Mon 8/31
1 adult, Economy
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Cheapflights Tip: The best prices from Roanoke to Chicago are usually found in September or December, booked 22 days in advance, depart on a Friday or Wednesday and return on a Saturday

Cheap flight deals from Roanoke to Chicago

Cheapest flights from Roanoke to Chicago
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 July 25, 2026.

This United Airlines deal was found by Cheapflights users on 7/21. 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.
Sat 8/1510:44 am
ROA
-
ORD
Nonstop2h 11m
United Airlines
Sat 8/225:45 pm
ORD
-
ROA
Nonstop2h 09m
United Airlines
Deal found 7/21$269
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:40 am
ROA
-
ORD
Nonstop2h 11m
United Airlines
Sat 9/196:57 am
ORD
-
ROA
Nonstop2h 12m
United Airlines
Deal found 7/23$279
This American Airlines deal was found by Cheapflights users on 7/20. 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.
Fri 9/45:35 pm
ROA
-
ORD
Nonstop2h 23m
American Airlines
Tue 9/82:09 pm
ORD
-
ROA
Nonstop1h 56m
American Airlines
Deal found 7/20$280
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Fri 9/188:05 pm
ROA
-
ORD
1 stop4h 35m
United Airlines
Wed 9/236:30 am
ORD
-
ROA
1 stop6h 24m
United Airlines
Deal found 7/21$289
This Delta deal was found by Cheapflights users on 7/20. 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 10/236:00 am
ROA
-
MDW
1 stop7h 05m
Delta
Mon 10/265:15 pm
MDW
-
ROA
1 stop6h 13m
Delta
Deal found 7/20$289
This United Airlines deal was found by Cheapflights users on 7/20. 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.
Thu 12/316:00 am
ROA
-
ORD
Nonstop2h 11m
United Airlines
Sun 1/37:25 am
ORD
-
ROA
Nonstop1h 46m
United Airlines
Deal found 7/20$294
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Fri 9/185:47 pm
ROA
-
ORD
Nonstop2h 27m
American Airlines
Mon 9/212:13 pm
ORD
-
ROA
Nonstop2h 04m
American Airlines
Deal found 7/22$299
This Delta deal was found by Cheapflights users on 7/23. 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 12/211:20 am
ROA
-
MDW
1 stop6h 05m
Delta
Thu 12/101:05 pm
MDW
-
ROA
1 stop5h 08m
Delta
Deal found 7/23$299
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:47 pm
ROA
-
ORD
Nonstop2h 27m
American Airlines
Sat 9/122:13 pm
ORD
-
ROA
Nonstop2h 04m
American Airlines
Deal found 7/23$301
This American Airlines deal was found by Cheapflights users on 7/22. 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 8/812:33 pm
ROA
-
ORD
1 stop4h 24m
American Airlines
Sat 8/158:19 am
ORD
-
ROA
1 stop4h 41m
American Airlines
Deal found 7/22$309
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:35 pm
ROA
-
ORD
Nonstop2h 23m
American Airlines
Sat 8/291:59 pm
ORD
-
ROA
Nonstop1h 56m
American Airlines
Deal found 7/23$310
This United Airlines deal was found by Cheapflights users on 7/22. 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 8/85:52 pm
ROA
-
ORD
Nonstop2h 13m
United Airlines
Sun 8/92:05 pm
ORD
-
ROA
Nonstop2h 06m
United Airlines
Deal found 7/22$319

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 July 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(United Airlines)

One-way from

$151
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$349

Good round-trip deal

$357 or less

Good one-way deal

$368 or less
Provider with most accurate pricing for Roanoke-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Roanoke-Chicago (CHI) flights.
Search Deals
From Roanoke to Chicago (CHI)
Search Deals
One-way flight from Roanoke to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Roanoke to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Roanoke to Chicago (CHI).
Search Deals

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 July 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

Price

Cheapest round-trip
Quickest round-trip

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 9/18

6:40 am-7:51 am

Nonstop2h 11m

Chicago O'Hare Intl

Mon 9/21

6:57 am-10:09 am

Nonstop2h 12m

$269

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Thu 9/17

5:47 pm-7:14 pm

Nonstop2h 27m

Chicago O'Hare Intl

Mon 9/21

5:20 am-1:26 pm

1 stop7h 06m

$289

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Thu 12/3

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

Mon 12/7

1:05 pm-7:13 pm

1 stop5h 08m

$289

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 8/15

11:18 am-2:48 pm

1 stop4h 30m

Chicago O'Hare Intl

Sat 8/29

10:50 am-4:12 pm

1 stop4h 22m

$299

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Thu 10/15

11:13 am-4:57 pm

1 stop6h 44m

Chicago O'Hare Intl

Mon 10/19

8:05 am-2:52 pm

1 stop5h 47m

$299

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 8/8

6:15 am-9:36 am

1 stop4h 21m

Chicago O'Hare Intl

Sun 8/9

2:05 pm-5:11 pm

Nonstop2h 06m

$329

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Thu 9/17

6:32 pm-10:45 pm

1 stop5h 13m

Chicago Midway

Mon 9/21

5:10 pm-11:59 pm

1 stop5h 49m

$339

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 8/7

7:59 pm-11:57 pm

1 stop4h 58m

Chicago O'Hare Intl

Sun 8/9

6:40 am-2:51 pm

1 stop7h 11m

$379

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 8/1

10:47 am-11:57 am

Nonstop2h 10m

Chicago O'Hare Intl

Sat 8/1

1:57 pm-9:42 am

2 stops18h 45m

$409

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Thu 7/30

7:57 pm-11:53 pm

1 stop4h 56m

Chicago O'Hare Intl

Tue 8/4

6:40 am-2:51 pm

1 stop7h 11m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 38 resultsSorted by cheapest first
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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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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

What is the cheapest month to book a flight from Roanoke to Chicago?

Currently, September is the cheapest month in which you can book a flight from Roanoke to Chicago (average of $285). 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 July 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.

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 July 25, 2026.

The most flights from ROA to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip from Roanoke to Chicago?

Airfare is below average for this route at the moment.
Roanoke to Chicago flights typically cost between $290 and $395 in August.
The cheapest round-trip price found within the last 5 days was $269 on United Airlines (Aug 15-Aug 22).

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 75 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 July 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.
United Airlines
7.4
Good
10,034 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
10,034 reviews
United Airlines
7.4
Good
10,034 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.1
Good
11,848 reviews
United Airlines
7.4
Good
10,034 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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.

  • What airport do you fly from for flights from Roanoke to Chicago?

    Most people fly from Roanoke (ROA) if they book a flight from Roanoke to Chicago. On average, Roanoke has 10 outbound flights to Chicago per day from 3 airlines. Roanoke is conveniently located just 4.2 mi from Roanoke’s city center.

  • How long is the flight from Roanoke to Chicago?

    For as low as $269, United Airlines can have you in Chicago from Roanoke in 2h 11m. Airlines will cover a distance of 530 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Roanoke to Chicago round-trip?

    American Airlines, at $209, was found to be the cheapest airline from Roanoke to Chicago.Alternate airlines to your destination round-trip include United Airlines and Delta. American Airlines is currently priced 34% below the average price you’ll pay for this route.

  • What are the most popular routes from Roanoke to Chicago?

    While some choose either Roanoke - Chicago Midway or Roanoke - Chicago Greater Rockford, Roanoke - Chicago O'Hare Intl is the most popular route from Roanoke to Chicago.

  • What are the most reliable airlines from Roanoke to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Roanoke to Chicago on time: Qatar Airways (94%), American Airlines (85%), Republic Airways (85%).

  • What are the cheapest flights from Roanoke to Chicago?

    The cheapest flight price from Roanoke to Chicago is $268. On average you can expect to pay $1,531. The most popular route, (Roanoke - Chicago O'Hare Intl), can usually be booked for $279.

  • Can I find deals for flights from Roanoke to Chicago that include hotel bookings?

    Yes. In addition to deals on Roanoke to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Roanoke to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Roanoke to Chicago.

  • Can I find deals for business class flights from Roanoke to Chicago?

    Yes. Cheapflights offers flight deals from Roanoke to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Roanoke to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Roanoke to Chicago (average of $285). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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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 July 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$287FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$347FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$228FlexibilityNo cancel feeOn-timeN/A

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