ROA - CHI

$136 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 4/14. 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

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$249
Typical prices: $249-$453
United Airlines
Fri 4/24Sun 4/26
ROA - ORD • Non-stop
Cheapest one-way
$136
Typical prices: $225-$310
American Airlines
Tue 4/14
ROA - ORD • Non-stop
Top airlines
Cheapest • from $249 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 2h 13m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $228 (round-trip)
Shortest trip • 4h 26m (one-way)
Insights
Insights
Insights
Insights
When to book
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
Cheapest • 13% price drop
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

Fri, Apr 24 - Sun, Apr 26
United Airlines Logo
2:04 pm - 3:13 pm
ROA
-
ORD
2h 09mnonstop
United Airlines Logo
6:50 am - 9:44 am
ORD
-
ROA
1h 54mnonstop
$249United Airlines
Fri, Apr 24 - Sun, Apr 26
United Airlines Logo
7:59 pm - 11:43 pm
ROA
-
ORD
4h 44m
1 stop
United Airlines Logo
6:50 am - 9:44 am
ORD
-
ROA
1h 54mnonstop
$259United Airlines
Fri, Apr 3 - Sun, Apr 5
American Airlines Logo
7:50 am - 9:08 am
ROA
-
ORD
2h 18mnonstop
American Airlines Logo
9:07 pm - 11:59 pm
ORD
-
ROA
1h 52mnonstop
$268American Airlines
Fri, Apr 24 - Sun, Apr 26
American Airlines Logo
6:03 pm - 10:47 pm
ROA
-
ORD
5h 44m
1 stop
American Airlines Logo
5:00 am - 12:33 pm
ORD
-
ROA
6h 33m
1 stop
$269American Airlines
Fri, May 8 - Wed, May 13
American Airlines Logo
7:28 am - 8:58 am
ROA
-
ORD
2h 30mnonstop
American Airlines Logo
9:15 pm - 12:14 am
ORD
-
ROA
1h 59mnonstop
$270American Airlines
Wed, Apr 15 - Mon, Apr 20
Delta Logo
7:50 pm - 11:59 pm
ROA
-
ORD
5h 09m
1 stop
Delta Logo
2:30 pm - 11:13 pm
ORD
-
ROA
7h 43m
1 stop
$289Delta
Tue, Apr 21 - Tue, Apr 28
Delta Logo
6:00 am - 9:56 am
ROA
-
MDW
4h 56m
1 stop
Delta Logo
5:21 pm - 12:25 am
MDW
-
ROA
6h 04m
1 stop
$289Delta
Thu, Apr 16 - Thu, Apr 23
Allegiant Air Logo
3:48 pm - 6:19 pm
ROA
-
RFD
27h 31m
1 stop
Allegiant Air Logo
11:50 am - 5:53 pm
RFD
-
ROA
29h 03m
1 stop
$445Allegiant Air
Thu, Apr 23 - Wed, Apr 29
Allegiant Air Logo
3:43 pm - 6:19 pm
ROA
-
RFD
27h 36m
1 stop
Allegiant Air Logo
12:09 pm - 3:03 pm
RFD
-
ROA
25h 54m
1 stop
$457Allegiant Air
Thu, Jul 2 - Sun, Jul 5
Multiple Airlines Logo
2:56 pm - 7:49 am
ROA
-
RFD
17h 53m
1 stop
Multiple Airlines Logo
9:19 am - 3:50 pm
RFD
-
ROA
29h 31m
2 stops
$520Multiple 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 April.

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 $229 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, Friday 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 Tuesday 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 $270 (return) on average. On the other hand, the most expensive months are March and July, where the average cost of round-trip tickets is $408 and $369 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 5 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$136
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 10% 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 $136 for a one-way ticket and $249 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 $328 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 $288 and an overall rating of 7.1.

  • 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 $280 or less one-way and $337 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 9435 reviews
7.3Comfort
6.6Food
7.7Boarding
7.1Entertainment
8.1Crew
Airline reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

10.0 ExcellentDr. Joseph, Feb 2026
DCA - ORD
Read more United Airlines reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

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

Information on your arrival and departure airports