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$135+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Roanoke to Chicago are usually found in January or September, booked 82 days in advance, depart on a Tuesday or Friday and return on a Saturday

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 August 20, 2025.

Round-trip from

$209
(Delta)

One-way from

$135
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$364

Good round-trip deal

$332 or less

Good one-way deal

$229 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. 13% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 20, 2025.

This Delta deal was found by Cheapflights users on 8/19. 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 9/166:00 amROA - ORD
1 stop5h 10mDelta
Tue 9/232:45 pmORD - ROA
1 stop7h 07mDelta
Deal found 8/19$209
This Delta deal was found by Cheapflights users on 8/19. 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 9/166:00 amROA - MDW
1 stop6h 48mDelta
Tue 9/236:30 pmMDW - ROA
1 stop4h 55mDelta
Deal found 8/19$209
This Kiwi.com deal was found by Cheapflights users on 8/19. 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
Thu 10/28:49 pmORD - ROA
1 stop22h 33mMultiple Airlines
Deal found 8/19$211
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/198:26 pmROA - MDW
1 stop14h 25mMultiple Airlines
Sun 9/216:21 amMDW - ROA
1 stop13h 13mMultiple Airlines
Deal found 8/19$213
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/186:45 amROA - ORD
Nonstop2h 10mUnited Airlines
Sun 9/218:50 amORD - ROA
1 stop4h 13mUnited Airlines
Deal found 8/19$219
This Delta deal was found by Cheapflights users on 8/19. 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 9/166:00 amROA - MDW
1 stop4h 40mDelta
Mon 9/226:30 pmMDW - ROA
1 stop4h 55mDelta
Deal found 8/19$219
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/257:45 amROA - ORD
Nonstop2h 09mAmerican Airlines
Wed 10/18:30 pmORD - ROA
Nonstop2h 02mAmerican Airlines
Deal found 8/19$220
This Kiwi.com deal was found by Cheapflights users on 8/19. 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
Fri 10/36:30 amORD - ROA
1 stop12h 52mMultiple Airlines
Deal found 8/19$225
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/198:26 pmROA - ORD
1 stop19h 51mMultiple Airlines
Sun 9/218:05 amORD - ROA
1 stop11h 29mMultiple Airlines
Deal found 8/19$227
This Delta deal was found by Cheapflights users on 8/18. 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 10/257:59 pmROA - ORD
1 stop4h 58mDelta
Sat 11/14:09 pmORD - ROA
1 stop7h 00mDelta
Deal found 8/18$229
This American Airlines deal was found by Cheapflights users on 8/18. 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 12/64:08 pmROA - ORD
1 stop6h 34mAmerican Airlines
Mon 12/87:05 pmORD - ROA
Nonstop2h 32mAmerican Airlines
Deal found 8/18$230
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 - ORD
1 stop24h 24mMultiple Airlines
Thu 10/28:49 pmORD - ROA
1 stop22h 33mMultiple Airlines
Deal found 8/19$231

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 August 20, 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

Tue 11/11

7:00 am-1:14 pm

1 stop7h 14m

Chicago O'Hare Intl

Sat 11/15

1:16 pm-7:13 pm

1 stop4h 57m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 12/12

7:00 am-8:05 am

Nonstop2h 05m

Chicago O'Hare Intl

Mon 12/15

7:05 pm-10:37 pm

Nonstop2h 32m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Thu 9/18

5:40 pm-6:50 pm

Nonstop2h 10m

Chicago O'Hare Intl

Sun 9/21

7:10 am-10:06 am

Nonstop1h 56m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Tue 11/11

7:00 am-1:14 pm

1 stop7h 14m

Chicago O'Hare Intl

Tue 11/18

11:19 am-7:13 pm

1 stop6h 54m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 12/6

7:00 am-8:05 am

Nonstop2h 05m

Chicago O'Hare Intl

Mon 12/8

7:05 pm-10:37 pm

Nonstop2h 32m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 11/8

7:15 am-8:33 am

Nonstop2h 18m

Chicago O'Hare Intl

Mon 11/10

9:02 pm-11:59 pm

Nonstop1h 57m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Tue 9/16

6:00 am-10:10 am

1 stop5h 10m

Chicago O'Hare Intl

Wed 9/24

6:00 pm-12:25 am

1 stop5h 25m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Wed 11/12

7:00 am-1:14 pm

1 stop7h 14m

Chicago O'Hare Intl

Tue 11/18

7:10 am-2:40 pm

1 stop6h 30m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Thu 9/18

7:45 am-8:54 am

Nonstop2h 09m

Chicago O'Hare Intl

Sat 9/20

8:30 pm-11:32 pm

Nonstop2h 02m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Wed 11/12

7:00 am-1:14 pm

1 stop7h 14m

Chicago O'Hare Intl

Sat 11/15

11:19 am-7:13 pm

1 stop6h 54m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 41 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 8, 2025.

To ensure you get the cheapest price possible for a flight from Roanoke to Chicago, you should look to book at least 81 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 August 20, 2025.

It’s optimal to fly from Roanoke to Chicago in the evening. By choosing this option you can save up to 52% 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 August 20, 2025.

The most flights from ROA to CHI are scheduled on a Tuesday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 August 20, 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
8,928 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

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
8,928 reviews
United Airlines
7.4
Good
8,928 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

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
8,928 reviews

Boarding

7.7

Food

6.6

Overall

7.4

Crew

8.1

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 7 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 $209, Delta can have you in Chicago from Roanoke in 2h 05m. 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 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: American Airlines (89%), Republic Airways (89%), ANA (87%).

  • What are the cheapest flights from Roanoke to Chicago?

    The cheapest flight price from Roanoke to Chicago is $175. On average you can expect to pay $762. 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$292FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$372FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$228FlexibilityNo cancel feeOn-timeN/A

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