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$90+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Roanoke to Chicago are usually found in January or February, booked 22 days in advance, depart on a Wednesday or Friday 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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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 3/37:33 am
ROA
-
ORD
Nonstop2h 18m
American Airlines
Tue 3/39:03 pm
ORD
-
ROA
Nonstop1h 54m
American Airlines
Deal found 1/27$159
This Delta deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
ROA
-
ORD
1 stop5h 14m
Delta
Wed 3/45:53 pm
ORD
-
ROA
1 stop5h 13m
Delta
Deal found 1/29$179
This Delta deal was found by Cheapflights users on 1/26. 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 2/186:00 am
ROA
-
MDW
1 stop4h 54m
Delta
Tue 2/246:40 pm
MDW
-
ROA
1 stop4h 26m
Delta
Deal found 1/26$179
This Delta deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
ROA
-
ORD
1 stop5h 14m
Delta
Mon 3/95:59 pm
ORD
-
ROA
1 stop5h 05m
Delta
Deal found 1/29$204
This Delta deal was found by Cheapflights users on 1/26. 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 2/196:00 am
ROA
-
MDW
1 stop4h 54m
Delta
Wed 2/256:40 pm
MDW
-
ROA
1 stop4h 26m
Delta
Deal found 1/26$204
This United Airlines deal was found by Cheapflights users on 1/26. 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 2/206:40 am
ROA
-
ORD
Nonstop2h 17m
United Airlines
Sun 2/227:10 am
ORD
-
ROA
Nonstop1h 58m
United Airlines
Deal found 1/26$209
This United Airlines deal was found by Cheapflights users on 1/27. 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 2/136:40 am
ROA
-
ORD
Nonstop2h 17m
United Airlines
Tue 2/178:50 am
ORD
-
ROA
1 stop4h 22m
United Airlines
Deal found 1/27$214
This Delta deal was found by Cheapflights users on 1/27. 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 2/1311:20 am
ROA
-
ORD
1 stop6h 29m
Delta
Tue 2/175:59 pm
ORD
-
ROA
1 stop5h 07m
Delta
Deal found 1/27$224
This Delta deal was found by Cheapflights users on 1/26. 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 2/176:00 am
ROA
-
MDW
1 stop4h 54m
Delta
Tue 2/246:40 pm
MDW
-
ROA
1 stop4h 26m
Delta
Deal found 1/26$224
This United Airlines deal was found by Cheapflights users on 1/26. 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 2/1810:43 am
ROA
-
ORD
Nonstop2h 17m
United Airlines
Sat 2/217:10 am
ORD
-
ROA
Nonstop1h 58m
United Airlines
Deal found 1/26$229
This Delta deal was found by Cheapflights users on 1/26. 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 2/196:00 am
ROA
-
MDW
1 stop6h 59m
Delta
Mon 2/236:40 pm
MDW
-
ROA
1 stop4h 26m
Delta
Deal found 1/26$229
This United Airlines deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:45 am
ROA
-
ORD
Nonstop2h 09m
United Airlines
Sun 4/267:07 am
ORD
-
ROA
Nonstop2h 06m
United Airlines
Deal found 1/28$230

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$159
(American Airlines)

One-way from

$90
(Delta)

Popular in

March

Cheapest in

January

Average price

$256

Good round-trip deal

$315 or less

Good one-way deal

$340 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. 8% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
Use the filters below to find and compare flights from Roanoke to Chicago that are best for you.

Fly from

Roanoke

Fly to

Chicago

Route

Depart

Return

Price

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Tue 3/3

7:33 am-8:51 am

Nonstop2h 18m

Chicago O'Hare Intl

Tue 3/3

9:03 pm-11:57 pm

Nonstop1h 54m

$159

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Tue 3/3

6:00 am-10:14 am

1 stop5h 14m

Chicago O'Hare Intl

Tue 3/3

5:53 pm-12:06 am

1 stop5h 13m

$179

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Wed 2/18

6:00 am-10:14 am

1 stop5h 14m

Chicago O'Hare Intl

Tue 2/24

2:30 pm-10:52 pm

1 stop7h 22m

$179

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 3/3

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Tue 3/3

6:40 pm-12:06 am

1 stop4h 26m

$179

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 2/20

7:59 pm-11:56 pm

1 stop4h 57m

Chicago O'Hare Intl

Tue 2/24

2:30 pm-10:52 pm

1 stop7h 22m

$204

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 2/21

7:59 pm-11:56 pm

1 stop4h 57m

Chicago O'Hare Intl

Mon 2/23

5:53 pm-12:06 am

1 stop5h 13m

$204

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 2/18

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Mon 2/23

6:40 pm-12:06 am

1 stop4h 26m

$204

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 2/20

6:40 am-7:57 am

Nonstop2h 17m

Chicago O'Hare Intl

Sun 2/22

7:10 am-10:08 am

Nonstop1h 58m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 6/20

6:47 am-8:00 am

Nonstop2h 13m

Chicago O'Hare Intl

Tue 6/23

3:47 pm-11:38 pm

1 stop6h 51m

$219

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Tue 2/17

7:59 pm-11:56 pm

1 stop4h 57m

Chicago O'Hare Intl

Wed 2/25

2:30 pm-10:52 pm

1 stop7h 22m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 36 results
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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 January.
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

How far ahead should I book a flight from Roanoke to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Roanoke to Chicago. Price data was last updated on January 23, 2026.

To ensure you get the cheapest price possible for a flight from Roanoke to Chicago, you should look to book at least 22 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.

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

Currently, October is the cheapest month in which you can book a flight from Roanoke to Chicago (average of $129). Flying from Roanoke to Chicago in April is currently the most expensive (average of $217). 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 January 29, 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 January 29, 2026.

The most flights from ROA to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

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

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 January 29, 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
9,215 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,205 reviews
United Airlines
7.4
Good
9,215 reviews

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 9 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 $159, American Airlines can have you in Chicago from Roanoke in 2h 18m. 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 38% 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: ANA (79%), SkyWest Airlines (75%), Emirates (70%).

  • What are the cheapest flights from Roanoke to Chicago?

    The cheapest flight price from Roanoke to Chicago is $239. On average you can expect to pay $861. The most popular route, (Roanoke - Chicago O'Hare Intl), can usually be booked for $209.

  • 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, October is the cheapest month in which you can book a flight from Roanoke to Chicago (average of $129). Flying from Roanoke to Chicago in April is currently the most expensive (average of $217). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Roanoke to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$276FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$340FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$228FlexibilityNo cancel feeOn-timeN/A

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