HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$124+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Roanoke to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Roanoke to Chicago are usually found in January or May, booked 1 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 May 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$199
(American Airlines)

One-way from

$124
(Delta)

Popular in

February

Cheapest in

January

Average price

$279

Good round-trip deal

$376 or less

Good one-way deal

$258 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. 3% potential increase in price ($12 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 May 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

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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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 5/97:30 amROA - ORD
1 stop6h 11mAmerican Airlines
Mon 5/126:35 pmORD - ROA
1 stop4h 13mAmerican Airlines
Deal found 4/30$199
This Delta deal was found by Cheapflights users on 4/30. 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 6/67:49 pmROA - ORD
1 stop5h 09mDelta
Fri 6/135:59 pmORD - ROA
1 stop5h 24mDelta
Deal found 4/30$229
This Delta deal was found by Cheapflights users on 4/30. 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 6/63:38 pmROA - MDW
1 stop6h 49mDelta
Fri 6/136:47 pmMDW - ROA
1 stop4h 36mDelta
Deal found 4/30$229
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 5/277:40 pmROA - ORD
1 stop4h 50mUnited Airlines
Tue 6/36:00 pmORD - ROA
Nonstop2h 05mUnited Airlines
Deal found 4/30$289
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/184:04 pmROA - ORD
2 stops25h 21mMultiple Airlines
Thu 5/224:35 pmORD - ROA
1 stop21h 51mMultiple Airlines
Deal found 4/30$438

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 May 1, 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 5/9

7:30 am-12:41 pm

1 stop6h 11m

Chicago O'Hare Intl

Mon 5/12

6:35 pm-11:48 pm

1 stop4h 13m

$199

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 6/6

7:49 pm-11:58 pm

1 stop5h 09m

Chicago O'Hare Intl

Fri 6/13

5:59 pm-12:23 am

1 stop5h 24m

$229

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Fri 6/6

3:38 pm-9:27 pm

1 stop6h 49m

Chicago Midway

Fri 6/13

6:47 pm-12:23 am

1 stop4h 36m

$229

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Tue 5/27

7:40 pm-11:30 pm

1 stop4h 50m

Chicago O'Hare Intl

Tue 6/3

6:00 pm-9:05 pm

Nonstop2h 05m

$289

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sun 5/18

4:04 pm-4:25 pm

2 stops25h 21m

Chicago O'Hare Intl

Thu 5/22

4:35 pm-3:26 pm

1 stop21h 51m

$438

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sun 5/25

7:05 am-1:43 pm

1 stop7h 38m

$124

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Sun 5/25

6:00 am-9:40 am

1 stop4h 40m

$124

RoanokeChicago

ROA - RFD

ROARFD

Roanoke

Sun 6/15

9:43 pm-7:55 am

1 stop11h 12m

$125

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Sun 6/15

8:13 pm-2:03 pm

2 stops18h 50m

$159

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sun 6/15

8:13 pm-3:33 pm

2 stops20h 20m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 12 results
1
2

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 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 April 25, 2025.

To ensure you get the cheapest price possible for a flight from Roanoke to Chicago, you should look to book at least 1 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 May 1, 2025.

It’s optimal to fly from Roanoke to Chicago in the evening. By choosing this option you can save up to 58% 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. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Allegiant Air
7.3
Good
734 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 4 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?

    American Airlines, at $199, was found to be the cheapest airline from Roanoke to Chicago.Alternate airlines to your destination round-trip include Delta and United Airlines. American Airlines is currently priced 47% 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 $124. Users have also found prices from $125 and $224 on Allegiant Air 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 (84%), GoJet (79%), United Airlines (69%).

  • What are the cheapest flights from Roanoke to Chicago?

    The cheapest flight price from Roanoke to Chicago is $185. On average you can expect to pay $891. The most popular route, (Roanoke - Chicago O'Hare Intl), can usually be booked for $229.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Roanoke to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Dulles Intl to Midway flights
Reagan-National to Midway flights
Richmond to O'Hare Intl flights
Dulles Intl to St. Louis flights
Raleigh to Midway flights
Greensboro to O'Hare Intl flights
Norfolk to O'Hare Intl flights
Richmond to Midway flights
Reagan-National to St. Louis flights
Charlottesville to O'Hare Intl flights
Raleigh to St. Louis flights
Greensboro to Midway flights
Roanoke to O'Hare Intl flights
Richmond to St. Louis flights
Norfolk to Midway flights
Raleigh to Moline flights
Charlottesville to Midway flights
Dulles Intl to Moline flights
Norfolk to St. Louis flights
Greensboro to Peoria flights
Raleigh to Peoria flights
Roanoke to Midway flights
Raleigh to Bloomington flights
Greensboro to St. Louis flights
Dulles Intl to Peoria flights
Blountville to O'Hare Intl flights
Reagan-National to Peoria flights
Dulles Intl to Evansville flights
Reagan-National to Moline flights
Blountville to Midway flights
Reagan-National to Evansville flights
Staunton to O'Hare Intl flights
Raleigh to Rockford flights
Reagan-National to Champaign flights
Richmond to Moline flights
Charlottesville to Evansville flights
Richmond to Peoria flights
Norfolk to Moline flights
Charlottesville to St. Louis flights
Blountville to St. Louis flights
Newport News to O'Hare Intl flights
Raleigh to Evansville flights
Reagan-National to Bloomington flights
Dulles Intl to Bloomington flights
Lynchburg to O'Hare Intl flights
Roanoke to St. Louis flights

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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$148Average$301FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$210Average$367FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.