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$116+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Roanoke to Chicago are usually found in January or September, booked 83 days in advance, depart on a Friday or Wednesday 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 julio 3, 2025.

Round-trip from

$209
(United Airlines)

One-way from

$116
(American Airlines)

Popular in

May

Cheapest in

January

Average price

$369

Good round-trip deal

$357 or less

Good one-way deal

$299 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. 10% potential increase in price ($45 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 July 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 julio 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/3. 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.
jue. 9/187:45 amROA - ORD
Nonstop2h 09mAmerican Airlines
sáb. 9/208:30 pmORD - ROA
Nonstop2h 02mAmerican Airlines
Deal found 7/3$209
This United Airlines deal was found by Cheapflights users on 7/1. 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.
jue. 8/217:35 pmROA - ORD
1 stop4h 40mUnited Airlines
dom. 8/247:10 amORD - ROA
Nonstop1h 56mUnited Airlines
Deal found 7/1$219
This Delta deal was found by Cheapflights users on 7/3. 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.
mar. 7/298:12 pmROA - ORD
1 stop4h 57mDelta
sáb. 8/26:32 pmORD - ROA
1 stop5h 00mDelta
Deal found 7/3$229
This Delta deal was found by Cheapflights users on 7/3. 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.
sáb. 8/98:40 amROA - MDW
1 stop4h 08mDelta
mar. 8/126:42 pmMDW - ROA
1 stop4h 50mDelta
Deal found 7/3$229

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 julio 3, 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

jue. 9/18

7:45 am-8:54 am

Nonstop2h 09m

Chicago O'Hare Intl

sáb. 9/20

8:30 pm-11:32 pm

Nonstop2h 02m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

jue. 8/21

7:35 pm-11:15 pm

1 stop4h 40m

Chicago O'Hare Intl

dom. 8/24

7:10 am-10:06 am

Nonstop1h 56m

$219

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

mar. 7/29

8:12 pm-12:09 am

1 stop4h 57m

Chicago O'Hare Intl

sáb. 8/2

6:32 pm-12:32 am

1 stop5h 00m

$229

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

sáb. 8/9

8:40 am-11:48 am

1 stop4h 08m

Chicago Midway

mar. 8/12

6:42 pm-12:32 am

1 stop4h 50m

$229

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

sáb. 8/23

7:43 am-8:50 am

Nonstop2h 07m

$116

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

sáb. 8/23

3:32 pm-9:12 pm

1 stop6h 40m

$126

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

dom. 7/13

10:12 am-9:41 am

2 stops24h 29m

$160

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

dom. 8/3

8:13 pm-8:55 am

3 stops37h 42m

$223

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

sáb. 7/26

7:00 am-8:05 am

Nonstop2h 05m

$287

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

jue. 7/10

7:05 am-1:10 pm

1 stop7h 05m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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 June 27, 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 julio 3, 2025.

It’s optimal to fly from Roanoke to Chicago in the evening. By choosing this option you can save up to 55% 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. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 julio 3, 2025.
See what other customers who have flown with Delta, United Airlines, and Allegiant Air 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.
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Allegiant Air
7.3
Good
708 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 6 outbound flights to Chicago per day from 2 airlines. Roanoke is conveniently located just 4.2 mi from Roanoke’s city center.

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

    United Airlines, at $209, was found to be the cheapest airline from Roanoke to Chicago.Alternate airlines to your destination round-trip include Delta and American Airlines. United 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 American Airlines. According to our data, you can fly for as low as $116. Users have also found prices from $126 and $151 on Delta and United Airlines, 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 (90%), SkyWest Airlines (78%), Air New Zealand (76%).

  • What are the cheapest flights from Roanoke to Chicago?

    The cheapest flight price from Roanoke to Chicago is $236. On average you can expect to pay $1,074. 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 Roanoke?

Book flights to Roanoke if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 2 airlines flying from Roanoke to Chicago

Discover the top 2 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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$218Average$320FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$370FlexibilityNo cancel feeOn-time69%

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