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Cheap flights from Roanoke to Chicago from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Roanoke to Chicago departing on 11/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Roanoke to Chicago (ROA-CHI)

Cheap round-trip flights

United Airlines Logo
5:40 pm - 6:50 pmROA-ORD
2h 10mnonstop
United Airlines Logo
7:21 am - 10:17 amORD-ROA
1h 56mnonstop
$209United Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
Delta Logo
6:00 am - 9:40 amROA-MDW
4h 40m1 stop
Delta Logo
4:25 pm - 11:57 pmMDW-ROA
6h 32m1 stop
$209Delta
Find Deal
Wed, Oct 1 - Sat, Oct 4
United Airlines Logo
5:40 pm - 6:50 pmROA-ORD
2h 10mnonstop
United Airlines Logo
4:00 pm - 11:24 pmORD-ROA
6h 24m1 stop
$219United Airlines
Find Deal
Fri, Sep 26 - Mon, Sep 29
American Airlines Logo
7:55 am - 9:09 amROA-ORD
2h 14mnonstop
American Airlines Logo
8:37 pm - 11:39 pmORD-ROA
2h 02mnonstop
$220American Airlines
Find Deal
Wed, Oct 8 - Sat, Oct 11
Delta Logo
7:10 am - 1:09 pmROA-ORD
6h 59m1 stop
Delta Logo
7:05 am - 2:52 pmORD-ROA
6h 47m1 stop
$229Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
6:00 am - 9:40 amROA-MDW
4h 40m1 stop
Delta Logo
4:25 pm - 11:57 pmMDW-ROA
6h 32m1 stop
$229Delta
Find Deal
Wed, Oct 1 - Sat, Oct 4
American Airlines Logo
4:49 pm - 9:14 pmROA-ORD
5h 25m1 stop
American Airlines Logo
7:05 pm - 10:37 pmORD-ROA
2h 32mnonstop
$230American Airlines
Find Deal
Sat, Dec 6 - Mon, Dec 8
Logo
8:26 pm - 3:17 pmROA-ORD
19h 51m1 stop
Logo
6:30 am - 5:43 pmORD-ROA
10h 13m1 stop
$233
Find Deal
Fri, Sep 26 - Mon, Sep 29
Logo
8:26 pm - 10:52 amROA-ORD
15h 26m2 stops
Logo
8:49 pm - 5:43 pmORD-ROA
19h 54m1 stop
$235
Find Deal
Fri, Sep 19 - Sun, Sep 28
Logo
8:26 pm - 3:17 pmROA-ORD
19h 51m1 stop
Logo
6:30 am - 5:43 pmORD-ROA
10h 13m1 stop
$236
Find Deal
Fri, Sep 19 - Mon, Sep 29

United Airlines flights from Roanoke to Chicago

Our best United Airlines deals on Roanoke to Chicago flight tickets
United Airlines
Sep 26
ROA5:40 pmRoanoke
2h 10m
ORD6:50 pmChicago O'Hare Intl
Sep 29
ORD7:21 amChicago O'Hare Intl
1h 56m
ROA10:17 amRoanoke
$209
Find similar
United Airlines
Sep 26
ROA5:40 pmRoanoke
2h 10m
ORD6:50 pmChicago O'Hare Intl
Sep 29
ORD4:00 pmChicago O'Hare Intl
6h 24m
1 stop
ROA11:24 pmRoanoke
$219
Find similar
United Airlines
Oct 17
ROA7:30 pmRoanoke
4h 45m
1 stop
ORD11:15 pmChicago O'Hare Intl
Oct 21
ORD6:30 pmChicago O'Hare Intl
2h 11m
ROA9:41 pmRoanoke
$237
Find similar

American Airlines flights from Roanoke to Chicago

Our best American Airlines deals on Roanoke to Chicago flight tickets
American Airlines
Oct 8
ROA7:55 amRoanoke
2h 14m
ORD9:09 amChicago O'Hare Intl
Oct 11
ORD8:37 pmChicago O'Hare Intl
2h 02m
ROA11:39 pmRoanoke
$220
Find similar
American Airlines
Dec 6
ROA4:49 pmRoanoke
5h 25m
1 stop
ORD9:14 pmChicago O'Hare Intl
Dec 8
ORD7:05 pmChicago O'Hare Intl
2h 32m
ROA10:37 pmRoanoke
$230
Find similar
American Airlines
Nov 14
ROA7:15 amRoanoke
2h 18m
ORD8:33 amChicago O'Hare Intl
Nov 16
ORD9:02 pmChicago O'Hare Intl
1h 57m
ROA11:59 pmRoanoke
$244
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Roanoke to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 9/26

5:40 pm-6:50 pm

Nonstop2h 10m

Chicago O'Hare Intl

Mon 9/29

7:21 am-10:17 am

Nonstop1h 56m

$209

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 10/1

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Sat 10/4

4:25 pm-11:57 pm

1 stop6h 32m

$209

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 9/26

5:40 pm-6:50 pm

Nonstop2h 10m

Chicago O'Hare Intl

Mon 9/29

4:00 pm-11:24 pm

1 stop6h 24m

$219

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Wed 10/8

7:55 am-9:09 am

Nonstop2h 14m

Chicago O'Hare Intl

Sat 10/11

8:37 pm-11:39 pm

Nonstop2h 02m

$220

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Wed 9/3

7:10 am-1:09 pm

1 stop6h 59m

Chicago O'Hare Intl

Sat 9/6

7:05 am-2:52 pm

1 stop6h 47m

$229

RoanokeChicago

ROA - MDW

ROAMDW

Roanoke

Wed 10/1

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Sat 10/4

4:25 pm-11:57 pm

1 stop6h 32m

$229

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Sat 12/6

4:49 pm-9:14 pm

1 stop5h 25m

Chicago O'Hare Intl

Mon 12/8

7:05 pm-10:37 pm

Nonstop2h 32m

$230

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 9/26

8:26 pm-3:17 pm

1 stop19h 51m

Chicago O'Hare Intl

Mon 9/29

6:30 am-5:43 pm

1 stop10h 13m

$233

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 9/19

8:26 pm-10:52 am

2 stops15h 26m

Chicago O'Hare Intl

Sun 9/28

8:49 pm-5:43 pm

1 stop19h 54m

$235

RoanokeChicago

ROA - ORD

ROAORD

Roanoke

Fri 9/19

8:26 pm-3:17 pm

1 stop19h 51m

Chicago O'Hare Intl

Mon 9/29

6:30 am-5:43 pm

1 stop10h 13m

$236

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Roanoke to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Roanoke, with most prices found around $279. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from Roanoke to Chicago during September average around $356.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $464. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Roanoke to Chicago for around $723.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Roanoke to Chicago during this time can be as low as $253. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $532.

What is the cheapest Roanoke to Chicago flight route?

Fly from Roanoke to Chicago O'Hare Intl for the best Roanoke - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Roanoke when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $383 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Roanoke for as low as $218 on momondo.

What cabin class options are available on Roanoke to Chicago flights?

There are 4 cabin classes available to choose from on Roanoke to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Roanoke to Chicago flights?

You could potentially save up to 6% on your flight if you consider stops on a Roanoke to Chicago flight.

How have Roanoke to Chicago flight prices changed over time?

When to book flights from Roanoke to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Roanoke to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Roanoke to Chicago (ROA to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Roanoke to Chicago

Best Price Found

$100

Fastest flight time

2h 07m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Roanoke in the past 72 hours is $100. The best round-trip flight deal from Roanoke to Chicago found on momondo in the last 72 hours is $209.
The fastest flight from Roanoke to Chicago takes 2h 07m
Direct flights go from Roanoke to Chicago every day.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)
Search flight deals

  • How far is Roanoke to Chicago by plane?

    Chicago is 517.7 mi away from Roanoke. By plane, this route typically takes 2h 07m.

  • When did momondo last update prices for flights from Roanoke Airport to Chicago?

    Prices for flights from Roanoke Airport to Chicago are updated daily.

  • How many operators does momondo search for flights from Roanoke Airport to Chicago?

  • How old do you have to be to fly from Roanoke Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Roanoke Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Roanoke to Chicago?

  • What is the most popular airline from Roanoke to Chicago?

Best airlines flying from Roanoke to Chicago

Compare and see reviews for airlines that fly from Roanoke to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $209Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $216Free CancellationRating
7.4
8,916 reviews
Search United Airlines flights
DeltaPriceFrom $228Free CancellationRating
8.0
7,980 reviews
Search Delta flights

  • United Airlines Flights From Roanoke to Chicago

    United Airlines flight deals from Roanoke to Chicago start from $216 round-trip. Over the 14 United Airlines flights for this route in a normal week, average airfare is usually $373 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Roanoke to Chicago

    American Airlines is also a popular choice for this route. American Airlines flight deals for Roanoke to Chicago start from as low as $209 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around $295. American Airlines operates 7 flights to Chicago from Roanoke in an average week. Users have rated it 7.2/10 across 10,000 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Roanoke to Chicago?

Finding the right flight to Chicago from Roanoke is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Roanoke to Chicago with flexible booking policies on momondo?

All flight searches from Roanoke to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Roanoke to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Roanoke. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Roanoke to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Roanoke are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport