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Cheap flights from Charleston, West Virginia to Chicago from $169

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Charleston, West Virginia to Chicago departing on 4/23. 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 Charleston, West Virginia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:10 pm - 8:11 pm
CRW
-
ORD
2h 01mnonstop
United Airlines Logo
6:10 pm - 8:55 pm
ORD
-
CRW
1h 45mnonstop
$169United Airlines
Thu, Apr 23 - Sat, Apr 25
United Airlines Logo
6:45 am - 7:50 am
CRW
-
ORD
2h 05mnonstop
United Airlines Logo
5:56 pm - 8:38 pm
ORD
-
CRW
1h 42mnonstop
$179United Airlines
Tue, Feb 24 - Sat, Feb 28
American Airlines Logo
11:48 am - 5:57 pm
CRW
-
ORD
7h 09m
1 stop
American Airlines Logo
5:00 am - 11:15 am
ORD
-
CRW
5h 15m
1 stop
$188American Airlines
Tue, Mar 10 - Tue, Mar 17
United Airlines Logo
7:10 pm - 8:11 pm
CRW
-
ORD
2h 01mnonstop
United Airlines Logo
6:10 pm - 8:55 pm
ORD
-
CRW
1h 45mnonstop
$189United Airlines
Thu, Apr 23 - Sun, Apr 26
Delta Logo
6:59 pm - 10:31 pm
CRW
-
MDW
4h 32m
1 stop
Delta Logo
6:00 am - 1:57 pm
MDW
-
CRW
6h 57m
1 stop
$198Delta
Tue, Mar 10 - Tue, Mar 17
Delta Logo
3:12 pm - 8:16 pm
CRW
-
ORD
6h 04m
1 stop
Delta Logo
5:10 am - 10:20 am
ORD
-
CRW
4h 10m
1 stop
$198Delta
Thu, Apr 23 - Sat, Apr 25
United Airlines Logo
5:35 pm - 6:37 pm
CRW
-
ORD
2h 02mnonstop
United Airlines Logo
5:56 pm - 8:38 pm
ORD
-
CRW
1h 42mnonstop
$199United Airlines
Tue, Feb 24 - Sat, Feb 28
American Airlines Logo
11:48 am - 5:58 pm
CRW
-
ORD
7h 10m
1 stop
American Airlines Logo
4:04 pm - 9:18 pm
ORD
-
CRW
4h 14m
1 stop
$218American Airlines
Tue, Feb 24 - Sat, Feb 28
Multiple Airlines Logo
9:59 am - 1:00 pm
CRW
-
MDW
28h 01m
1 stop
Multiple Airlines Logo
7:30 am - 2:03 pm
MDW
-
CRW
5h 33m
1 stop
$296Multiple Airlines
Thu, Apr 23 - Sun, Apr 26
Multiple Airlines Logo
2:43 pm - 8:04 am
CRW
-
MDW
18h 21m
1 stop
Multiple Airlines Logo
9:14 am - 9:19 am
MDW
-
CRW
23h 05m
1 stop
$320Multiple Airlines
Thu, Apr 23 - Sat, Apr 25

United Airlines flights from Charleston, West Virginia to Chicago

Our best United Airlines deals on Charleston, West Virginia to Chicago flight tickets
United Airlines
Apr 23
CRW7:10 pmCharleston Yeager
2h 01m
ORD8:11 pmChicago O'Hare Intl
Apr 25
ORD6:10 pmChicago O'Hare Intl
1h 45m
CRW8:55 pmCharleston Yeager
$169
United Airlines
Feb 24
CRW6:45 amCharleston Yeager
2h 05m
ORD7:50 amChicago O'Hare Intl
Feb 28
ORD5:56 pmChicago O'Hare Intl
1h 42m
CRW8:38 pmCharleston Yeager
$179
United Airlines
Apr 23
CRW7:10 pmCharleston Yeager
2h 01m
ORD8:11 pmChicago O'Hare Intl
Apr 26
ORD6:10 pmChicago O'Hare Intl
1h 45m
CRW8:55 pmCharleston Yeager
$189

Delta flights from Charleston, West Virginia to Chicago

Our best Delta deals on Charleston, West Virginia to Chicago flight tickets
Delta
Apr 23
CRW3:12 pmCharleston Yeager
6h 04m
1 stop
ORD8:16 pmChicago O'Hare Intl
Apr 25
ORD5:10 amChicago O'Hare Intl
4h 10m
1 stop
CRW10:20 amCharleston Yeager
$198
Delta
Feb 27
CRW6:44 pmCharleston Yeager
6h 12m
1 stop
ORD11:56 pmChicago O'Hare Intl
Mar 3
ORD9:52 amChicago O'Hare Intl
7h 07m
1 stop
CRW5:59 pmCharleston Yeager
$208
Delta
Feb 27
CRW6:44 pmCharleston Yeager
4h 47m
1 stop
MDW10:31 pmChicago Midway
Mar 3
MDW10:49 amChicago Midway
6h 10m
1 stop
CRW5:59 pmCharleston Yeager
$223

momondo Fare Finder

 
Customize your flight search to find flights from Charleston, West Virginia 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 February 12, 2026.
Use the filters below to find and compare flights from Charleston, West Virginia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 4/23

7:10 pm-8:11 pm

Nonstop2h 01m

Chicago O'Hare Intl

Sat 4/25

6:10 pm-8:55 pm

Nonstop1h 45m

$169

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 2/24

6:45 am-7:50 am

Nonstop2h 05m

Chicago O'Hare Intl

Sat 2/28

5:56 pm-8:38 pm

Nonstop1h 42m

$179

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 3/10

11:48 am-5:57 pm

1 stop7h 09m

Chicago O'Hare Intl

Tue 3/17

5:00 am-11:15 am

1 stop5h 15m

$188

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 4/23

7:10 pm-8:11 pm

Nonstop2h 01m

Chicago O'Hare Intl

Sun 4/26

6:10 pm-8:55 pm

Nonstop1h 45m

$189

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Tue 3/10

6:59 pm-10:31 pm

1 stop4h 32m

Chicago Midway

Tue 3/17

6:00 am-1:57 pm

1 stop6h 57m

$198

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 4/23

3:12 pm-8:16 pm

1 stop6h 04m

Chicago O'Hare Intl

Sat 4/25

5:10 am-10:20 am

1 stop4h 10m

$198

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 2/24

5:35 pm-6:37 pm

Nonstop2h 02m

Chicago O'Hare Intl

Sat 2/28

5:56 pm-8:38 pm

Nonstop1h 42m

$199

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 2/24

11:48 am-5:58 pm

1 stop7h 10m

Chicago O'Hare Intl

Sat 2/28

4:04 pm-9:18 pm

1 stop4h 14m

$218

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 4/23

9:59 am-1:00 pm

1 stop28h 01m

Chicago Midway

Sun 4/26

7:30 am-2:03 pm

1 stop5h 33m

$296

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Thu 4/23

2:43 pm-8:04 am

1 stop18h 21m

Chicago Midway

Sat 4/25

9:14 am-9:19 am

1 stop23h 05m

$320

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Charleston, West Virginia 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 typical price of a round-trip flight between Charleston, West Virginia and Chicago?

What is the cheapest month to fly to Chicago?

The month of April is, on average, the cheapest month to fly to Chicago from Charleston, West Virginia, with most prices found around $243. If you’re not able to fly to Chicago in April, then January is your next best option. Flight prices from Charleston, West Virginia to Chicago during January average around $267.

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 Saturday 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 Charleston, West Virginia to Chicago for around $759.

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 Charleston, West Virginia to Chicago during this time can be as low as $428. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $600.

What is the cheapest Charleston Yeager to Chicago flight route?

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

What cabin class options are available on Charleston Yeager to Chicago flights?

There are 4 cabin classes available to choose from on Charleston Yeager 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 Charleston, West Virginia to Chicago flights?

No. A direct flight is the cheapest option for a flight between Charleston, West Virginia to Chicago.

When to book flights from Charleston, West Virginia to Chicago

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

Cheap Charleston, West Virginia to Chicago (CRW to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Charleston, West Virginia to Chicago

Best Price Found

$363

Fastest flight time

1h 48m

Direct flights

Mon, Tue, Wed, Thu, Fri and Sat

Airports in Chicago

3 airports
The best one-way flight to Chicago from Charleston, West Virginia in the past 72 hours is $363. The best round-trip flight deal from Charleston, West Virginia to Chicago found on momondo in the last 72 hours is $322.
The fastest flight from Charleston, West Virginia to Chicago takes 1h 48m
Direct flights go from Charleston, West Virginia to Chicago on Monday, Tuesday, Wednesday, Thursday, Friday and Saturday. The only airline offering direct flights is United Airlines.
There are 3 airports in Chicago. From Charleston, West Virginia there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is Charleston Yeager to Chicago by plane?

    Charleston Yeager and Chicago are 399.2 mi apart from one another. A reasonable flight in good conditions will take 1h 48m.

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

    Prices for flights from Charleston Yeager Airport to Chicago are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Charleston Yeager Airport to Chicago.

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

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Charleston, West Virginia to Chicago?

  • What is the most popular airline from Charleston, West Virginia to Chicago?

Best airlines flying from Charleston, West Virginia to Chicago

Compare and see reviews for airlines that fly from Charleston, West Virginia to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $179Free CancellationRating
7.4
9,281 reviews
Search United Airlines flights

  • United Airlines Flights From Charleston, West Virginia to Chicago

    United Airlines flies from Charleston, West Virginia to Chicago around 12 times per week, with 9,281 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Charleston, West Virginia to Chicago in the last 72 hours was $179 (round-trip), much lower than the average airfare cost of $299 for United Airlines flights on this route.

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
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Charleston to Chicago for you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Charleston with this policy.

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

Once you have performed a search for Charleston to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Charleston to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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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