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$97+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Roanoke to Chicago are usually found in January or September, booked 45 days in advance, depart on a Friday or Tuesday and return on a Thursday

Cheap flight deals from Roanoke to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Roanoke (ROA) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$209
(American Airlines)

One-way from

$97
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$308

Good round-trip deal

$288 or less

Good one-way deal

$223 or less
From Roanoke to Chicago (CHI)
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One-way flight from Roanoke to Chicago (CHI)
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Highest demand for flights based on searches. 14% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Roanoke to Chicago (CHI).
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Price to beat on a one-way flight from Roanoke to Chicago (CHI).
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Find 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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/11. 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 12/127:04 amROA - ORD
Nonstop2h 21mAmerican Airlines
Mon 12/159:04 pmORD - ROA
Nonstop1h 55mAmerican Airlines
Deal found 9/11$209
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Wed 10/159:49 pmROA - ORD
1 stop20h 08mMultiple Airlines
Mon 10/206:18 pmORD - ROA
1 stop13h 05mMultiple Airlines
Deal found 9/10$210
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:12 pmROA - ORD
1 stop25h 46mMultiple Airlines
Wed 10/88:00 amORD - ROA
1 stop11h 59mMultiple Airlines
Deal found 9/11$213
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:38 pmROA - ORD
Nonstop2h 10mUnited Airlines
Tue 11/116:20 pmORD - ROA
1 stop4h 10mUnited Airlines
Deal found 9/10$219
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:55 amROA - ORD
Nonstop2h 14mAmerican Airlines
Tue 10/148:35 pmORD - ROA
Nonstop2h 02mAmerican Airlines
Deal found 9/11$220
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Tue 10/79:13 amROA - ORD
1 stop25h 55mMultiple Airlines
Sat 10/116:00 pmORD - ROA
1 stop25h 30mMultiple Airlines
Deal found 9/11$222
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Fri 9/268:26 pmROA - ORD
1 stop19h 51mMultiple Airlines
Sun 10/265:50 amORD - ROA
1 stop13h 40mMultiple Airlines
Deal found 9/10$223
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:12 pmROA - ORD
1 stop25h 46mMultiple Airlines
Sat 10/116:00 pmORD - ROA
1 stop25h 30mMultiple Airlines
Deal found 9/11$224
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Tue 10/79:13 amROA - ORD
1 stop25h 55mMultiple Airlines
Sun 10/125:50 amORD - ROA
1 stop13h 40mMultiple Airlines
Deal found 9/11$225
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/89:49 pmROA - ORD
1 stop11h 25mMultiple Airlines
Sun 10/125:50 amORD - ROA
1 stop13h 40mMultiple Airlines
Deal found 9/11$226
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Sun 9/2810:54 amROA - RFD
1 stop22h 46mAllegiant Air
Wed 10/18:50 amRFD - ROA
1 stop6h 08mAllegiant Air
Deal found 9/10$226
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:12 pmROA - ORD
1 stop25h 46mMultiple Airlines
Sun 10/125:50 amORD - ROA
1 stop13h 40mMultiple Airlines
Deal found 9/11$227

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 September 11, 2025.
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

Fri 10/24

7:30 pm-11:15 pm

1 stop4h 45m

Chicago O'Hare Intl

Tue 10/28

9:00 am-11:59 am

Nonstop1h 59m

$219

RoanokeChicago

ROA - RFD

ROARFD

Roanoke

Sun 9/28

10:54 am-8:40 am

1 stop22h 46m

Chicago Greater Rockford

Wed 10/1

8:50 am-3:58 pm

1 stop6h 08m

$226

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 12/6

6:00 am-12:05 pm

1 stop7h 05m

Chicago O'Hare Intl

Mon 12/8

2:30 pm-11:19 pm

1 stop7h 49m

$229

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Thu 11/13

7:50 pm-11:43 pm

1 stop4h 53m

Chicago O'Hare Intl

Sun 11/16

8:50 am-2:12 pm

1 stop4h 22m

$229

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Sat 11/8

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Mon 11/10

5:34 pm-12:21 am

1 stop5h 47m

$229

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Wed 11/12

6:20 am-9:46 am

1 stop4h 26m

Chicago O'Hare Intl

Tue 11/18

8:50 am-2:12 pm

1 stop4h 22m

$229

RoanokeChicago

ROA - RFD

ROARFD

Roanoke

Thu 10/2

9:20 pm-8:14 am

1 stop11h 54m

Chicago Greater Rockford

Wed 10/8

8:50 am-8:59 pm

1 stop11h 09m

$234

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 10/1

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Sat 10/4

4:25 pm-11:57 pm

1 stop6h 32m

$239

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 9/26

7:30 pm-11:15 pm

1 stop4h 45m

Chicago O'Hare Intl

Sun 9/28

7:21 am-10:17 am

Nonstop1h 56m

$239

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 11/12

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

Tue 11/18

5:34 pm-12:21 am

1 stop5h 47m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 43 results
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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 August 29, 2025.

To ensure you get the cheapest price possible for a flight from Roanoke to Chicago, you should look to book at least 45 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, August is the cheapest month in which you can book a flight from Roanoke to Chicago (average of $245). Flying from Roanoke to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ROA to CHI?

Find hourly flight availability from Roanoke to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

It’s optimal to fly from Roanoke to Chicago in the afternoon. By choosing this option you can save up to 51% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Roanoke to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Roanoke to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Roanoke to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Roanoke to Chicago

Explore weekly flight availability from Roanoke to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

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 September 11, 2025.
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
8,937 reviews

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

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
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

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
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

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 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 $219, United Airlines can have you in Chicago from Roanoke in 4h 45m. 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 48% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Roanoke to Chicago one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $224. Users have also found prices from $309 and $354 on Delta and Allegiant Air, respectively.

  • 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 (84%), American Airlines (73%), Republic Airways (73%).

  • What are the cheapest flights from Roanoke to Chicago?

    The cheapest flight price from Roanoke to Chicago is $139. On average you can expect to pay $999. 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, August is the cheapest month in which you can book a flight from Roanoke to Chicago (average of $245). Flying from Roanoke to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$279FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$363FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$228FlexibilityNo cancel feeOn-timeN/A

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