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$134+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 Wednesday or Friday and return on a Thursday

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 October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:04 amROA - ORD
Nonstop2h 21mAmerican Airlines
Mon 12/89:04 pmORD - ROA
Nonstop1h 55mAmerican Airlines
Deal found 10/26$209
This Delta deal was found by Cheapflights users on 10/26. 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 11/196:00 amROA - ORD
1 stop7h 19mDelta
Wed 12/39:49 amORD - ROA
1 stop4h 19mDelta
Deal found 10/26$229
This Delta deal was found by Cheapflights users on 10/27. 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.
Tue 12/307:03 pmROA - MDW
1 stop4h 19mDelta
Mon 1/126:45 amMDW - ROA
1 stop5h 55mDelta
Deal found 10/27$229
This United Airlines deal was found by Cheapflights users on 10/26. 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.
Sun 12/286:40 amROA - ORD
Nonstop2h 14mUnited Airlines
Tue 1/68:52 amORD - ROA
1 stop4h 17mUnited Airlines
Deal found 10/26$235
This United Airlines deal was found by Cheapflights users on 10/26. 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.
Sun 12/286:40 amROA - ORD
Nonstop2h 14mUnited Airlines
Sun 1/45:50 pmORD - ROA
Nonstop2h 08mUnited Airlines
Deal found 10/26$237
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 12/127:04 amROA - ORD
Nonstop2h 21mAmerican Airlines
Mon 12/159:04 pmORD - ROA
Nonstop1h 55mAmerican Airlines
Deal found 10/27$238
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:02 amROA - ORD
Nonstop2h 18mAmerican Airlines
Wed 5/137:05 pmORD - ROA
Nonstop2h 32mAmerican Airlines
Deal found 10/26$244
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Wed 12/1010:20 amROA - ORD
1 stop5h 05mUnited Airlines
Sun 1/119:03 amORD - ROA
Nonstop2h 06mUnited Airlines
Deal found 10/27$247
This Delta deal was found by Cheapflights users on 10/27. 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.
Sat 11/153:50 pmROA - ORD
1 stop7h 40mDelta
Sun 11/165:23 amORD - ROA
1 stop4h 17mDelta
Deal found 10/27$249
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Sun 11/235:38 pmROA - ORD
Nonstop2h 10mUnited Airlines
Fri 11/286:20 pmORD - ROA
1 stop4h 10mUnited Airlines
Deal found 10/27$250
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:07 pmROA - ORD
1 stop5h 35mAmerican Airlines
Tue 1/68:12 amORD - ROA
1 stop5h 53mAmerican Airlines
Deal found 10/26$251
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:00 amROA - ORD
Nonstop2h 18mAmerican Airlines
Tue 12/28:55 pmORD - ROA
Nonstop1h 58mAmerican Airlines
Deal found 10/28$254

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$134
(American Airlines)

Popular in

May

Cheapest in

January

Average price

$324

Good round-trip deal

$300 or less

Good one-way deal

$347 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. 17% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 28, 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 3/3

10:48 am-12:05 pm

Nonstop2h 17m

Chicago O'Hare Intl

Tue 3/10

7:14 am-10:12 am

Nonstop1h 58m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Thu 1/22

2:55 pm-6:37 pm

1 stop4h 42m

Chicago O'Hare Intl

Sun 1/25

9:03 am-12:09 pm

Nonstop2h 06m

$219

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Thu 1/1

6:40 am-7:54 am

Nonstop2h 14m

Chicago O'Hare Intl

Sat 1/10

9:03 am-12:09 pm

Nonstop2h 06m

$226

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 12/6

6:00 am-12:06 pm

1 stop7h 06m

Chicago O'Hare Intl

Mon 12/8

5:59 pm-12:11 am

1 stop5h 12m

$229

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 2/21

7:50 pm-11:54 pm

1 stop5h 04m

Chicago O'Hare Intl

Tue 2/24

5:55 pm-11:49 pm

1 stop4h 54m

$229

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Wed 11/19

6:00 am-12:19 pm

1 stop7h 19m

Chicago O'Hare Intl

Wed 12/3

9:49 am-3:08 pm

1 stop4h 19m

$229

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 1/21

6:00 am-10:01 am

1 stop5h 01m

Chicago Midway

Sat 1/24

4:30 pm-12:06 am

1 stop6h 36m

$229

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Tue 12/30

7:03 pm-10:22 pm

1 stop4h 19m

Chicago Midway

Wed 1/7

5:31 pm-12:06 am

1 stop5h 35m

$229

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 11/19

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

Wed 12/3

5:29 pm-12:11 am

1 stop5h 42m

$229

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Sat 12/6

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Sun 12/14

5:13 pm-12:11 am

1 stop5h 58m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 48 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Roanoke-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 24, 2025.

To ensure you get the cheapest price possible for a flight from Roanoke to Chicago, you should look to book at least 26 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 $157). 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 October 28, 2025.

It’s optimal to fly from Roanoke to Chicago in the evening. By choosing this option you can save up to 37% 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 Wednesday at noon when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 28, 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
9,001 reviews

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,001 reviews
United Airlines
7.4
Good
9,001 reviews

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,032 reviews
United Airlines
7.4
Good
9,001 reviews

Comfort

7.3

Boarding

7.7

Crew

8.1

Food

6.6

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 8 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, United Airlines can have you in Chicago from Roanoke in 2h 17m. 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 45% 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 Delta. According to our data, you can fly for as low as $190. Users have also found prices from $224 and $315 on United Airlines 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 (82%), SkyWest Airlines (77%), Air New Zealand (77%).

  • What are the cheapest flights from Roanoke to Chicago?

    The cheapest flight price from Roanoke to Chicago is $223. On average you can expect to pay $510. 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 $157). 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
Merrillville
Lansing
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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$279FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$210Average$354FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$228FlexibilityNo cancel feeOn-timeN/A

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