ROA - CHI

$90 Find Cheap Flights from Roanoke to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Roanoke to Chicago departing on 2/25. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Roanoke to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Roanoke to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$159
Overall average: $499
American Airlines
Tue 3/3Tue 3/3
ROA - ORD • Non-stop
Cheapest one-way
$90
Typical prices: $223-$468
Delta
Wed 2/25
ROA - ORD • 1 stop
Top airlines
American Airlines
Cheapest • from $159 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ROA
-
ORD
Cheapest
ROA
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 36% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 24% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Roanoke to Chicago (ROA-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Roanoke to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Roanoke to Chicago

Tue, Mar 3 - Tue, Mar 3
American Airlines Logo
7:33 am - 8:51 am
ROA
-
ORD
2h 18mnonstop
American Airlines Logo
9:03 pm - 11:57 pm
ORD
-
ROA
1h 54mnonstop
$159American Airlines
Tue, Mar 3 - Tue, Mar 3
Delta Logo
6:00 am - 10:14 am
ROA
-
ORD
5h 14m
1 stop
Delta Logo
2:30 pm - 10:52 pm
ORD
-
ROA
7h 22m
1 stop
$179Delta
Tue, Mar 3 - Tue, Mar 3
Delta Logo
6:00 am - 11:59 am
ROA
-
MDW
6h 59m
1 stop
Delta Logo
6:40 pm - 12:06 am
MDW
-
ROA
4h 26m
1 stop
$179Delta
Tue, Mar 3 - Tue, Mar 10
Delta Logo
7:59 pm - 11:56 pm
ROA
-
ORD
4h 57m
1 stop
Delta Logo
2:40 pm - 10:59 pm
ORD
-
ROA
7h 19m
1 stop
$204Delta
Thu, Feb 19 - Mon, Feb 23
American Airlines Logo
7:33 am - 8:51 am
ROA
-
ORD
2h 18mnonstop
American Airlines Logo
9:03 pm - 11:57 pm
ORD
-
ROA
1h 54mnonstop
$209American Airlines
Thu, Feb 19 - Mon, Feb 23
United Airlines Logo
10:15 am - 2:20 pm
ROA
-
ORD
5h 05m
1 stop
United Airlines Logo
7:10 am - 10:08 am
ORD
-
ROA
1h 58mnonstop
$219United Airlines
Wed, Mar 4 - Sun, Mar 8
American Airlines Logo
7:33 am - 8:51 am
ROA
-
ORD
2h 18mnonstop
American Airlines Logo
9:05 pm - 11:59 pm
ORD
-
ROA
1h 54mnonstop
$224American Airlines
Fri, Apr 24 - Wed, Apr 29
Delta Logo
7:43 pm - 11:59 pm
ROA
-
ORD
5h 16m
1 stop
Delta Logo
5:10 am - 10:28 am
ORD
-
ROA
4h 18m
1 stop
$229Delta
Thu, Apr 23 - Sun, Apr 26
United Airlines Logo
6:45 am - 7:54 am
ROA
-
ORD
2h 09mnonstop
United Airlines Logo
7:07 am - 10:13 am
ORD
-
ROA
2h 06mnonstop
$230United Airlines
Mon, Mar 16 - Fri, Mar 20
Multiple Airlines Logo
9:50 pm - 6:13 pm
ROA
-
MDW
21h 23m
1 stop
Multiple Airlines Logo
6:15 am - 7:51 pm
MDW
-
ROA
12h 36m
1 stop
$484Multiple Airlines
Booking Insights

KAYAK's insights & trends for Roanoke to Chicago flights

Get data-powered insights and trends into flights from Roanoke to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Roanoke to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Roanoke to Chicago departing in March.

What is the cheapest Roanoke to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Roanoke to Chicago costs $239 on the route between Roanoke (ROA) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Roanoke to Chicago?

The average price of all round-trip flights from Roanoke to Chicago clicked on KAYAK for each day over the last 12 months.

For Roanoke to Chicago, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to Roanoke, the best deals are generally found on Saturday, with Sunday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Roanoke to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Roanoke to Chicago is January, where tickets cost $256 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $424 and $423 respectively.

Can I save money by flying with a layover from Roanoke to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $254 on average.

How far in advance should I book a flight from Roanoke to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Roanoke to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Roanoke to Chicago, you should book around 3 weeks before departure, which saves you about 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$90
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Roanoke to Chicago O'Hare Airport

When to book flights from Roanoke to Chicago

Are your dates flexible? Find out the best times to travel from Roanoke to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Roanoke to Chicago

  • What is the cheapest flight from Roanoke to Chicago?

    In the last 3 days, the lowest price for a flight from Roanoke to Chicago was $90 for a one-way ticket and $159 for a round-trip.

  • Do I need a passport to fly between Roanoke and Chicago?

    No

  • Which airports will I be using when flying from Roanoke to Chicago?

    On your way to Chicago, you’ll fly out from Roanoke. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Roanoke to Chicago?

    American Airlines, and Delta offer inflight Wi-Fi service on the Roanoke to Chicago flight route.

  • Which aircraft models fly most regularly from Roanoke to Chicago?

    The Canadair (Bombardier) Regional Jet CRJ-550 is the aircraft model that flies most regularly on the Roanoke to Chicago flight route.

  • Which airline alliances offer flights from Roanoke to Chicago?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Roanoke and Chicago, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Roanoke to Chicago?

    There are nonstop flights from Roanoke to Chicago on a daily basis.

  • Which is the best airline for flights from Roanoke to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Roanoke to Chicago are United Airlines and American Airlines. With an average price for the route of $351 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $289 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Roanoke to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Roanoke to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Roanoke to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Roanoke is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Roanoke to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Roanoke with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Roanoke to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Roanoke up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Roanoke to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $340 or less one-way and $315 or less round-trip.

Prefer to fly direct from Roanoke to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Roanoke to Chicago.
Find which airlines fly direct from Roanoke Airport to Chicago, which days they fly and book direct flights.

Direct departures

Roanoke to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Chicago to Roanoke

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top airlines flying from Roanoke to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Roanoke to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Roanoke to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9215 reviews
6.6Food
7.3Comfort
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

4.0 OkaySean, Jan 2026
BOS - ORD
Read more United Airlines reviews

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Everything you need to know for your flight from Roanoke to Chicago

Information on your arrival and departure airports