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Cheap flights from Charleston, West Virginia to Chicago from $158

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 10/25. 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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Find the cheapest flights from Charleston, West Virginia to Chicago

Cheap round-trip flights

American Airlines Logo
4:03 pm - 9:29 pmCRW-ORD
6h 26m1 stop
American Airlines Logo
8:15 am - 3:33 pmORD-CRW
6h 18m1 stop
$158American Airlines
Find Deal
Sat, Oct 25 - Sat, Nov 1
American Airlines Logo
1:09 pm - 7:42 pmCRW-ORD
7h 33m1 stop
American Airlines Logo
4:08 pm - 9:45 pmORD-CRW
4h 37m1 stop
$160American Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Delta Logo
6:00 am - 10:37 amCRW-ORD
5h 37m1 stop
Delta Logo
5:23 am - 10:38 amORD-CRW
4h 15m1 stop
$168Delta
Find Deal
Wed, Nov 12 - Thu, Nov 13
American Airlines Logo
7:11 pm - 10:54 pmCRW-ORD
4h 43m1 stop
American Airlines Logo
3:11 pm - 9:34 pmORD-CRW
5h 23m1 stop
$178American Airlines
Find Deal
Tue, Oct 21 - Wed, Oct 22
American Airlines Logo
12:21 pm - 3:56 pmCRW-ORD
4h 35m1 stop
American Airlines Logo
3:50 pm - 9:56 pmORD-CRW
5h 06m1 stop
$198American Airlines
Find Deal
Wed, Nov 5 - Fri, Nov 7
Delta Logo
11:23 am - 5:00 pmCRW-ORD
6h 37m1 stop
Delta Logo
5:20 am - 10:43 amORD-CRW
4h 23m1 stop
$212Delta
Find Deal
Sat, Nov 1 - Sun, Nov 2
United Airlines Logo
5:35 pm - 6:34 pmCRW-ORD
1h 59mnonstop
United Airlines Logo
10:43 am - 1:24 pmORD-CRW
1h 41mnonstop
$229United Airlines
Find Deal
Fri, Oct 24 - Sun, Oct 26
United Airlines Logo
5:35 pm - 6:34 pmCRW-ORD
1h 59mnonstop
United Airlines Logo
10:43 am - 1:24 pmORD-CRW
1h 41mnonstop
$236United Airlines
Find Deal
Fri, Oct 24 - Sun, Oct 26
Multiple Airlines Logo
7:36 pm - 10:14 amCRW-ORD
15h 38m1 stop
Multiple Airlines Logo
1:14 pm - 6:56 pmORD-CRW
28h 42m2 stops
$277Multiple Airlines
Find Deal
Fri, Oct 24 - Sun, Oct 26
Multiple Airlines Logo
2:43 pm - 7:34 amCRW-ORD
17h 51m1 stop
Multiple Airlines Logo
1:14 pm - 6:56 pmORD-CRW
28h 42m2 stops
$279Multiple Airlines
Find Deal
Thu, Oct 23 - Sun, Oct 26

United Airlines flights from Charleston, West Virginia to Chicago

Our best United Airlines deals on Charleston, West Virginia to Chicago flight tickets
United Airlines
Oct 24
CRW5:35 pmCharleston Yeager
1h 59m
ORD6:34 pmChicago O'Hare Intl
Oct 26
ORD10:43 amChicago O'Hare Intl
1h 41m
CRW1:24 pmCharleston Yeager
$229
Find similar
United Airlines
Oct 24
CRW5:35 pmCharleston Yeager
1h 59m
ORD6:34 pmChicago O'Hare Intl
Oct 26
ORD10:43 amChicago O'Hare Intl
1h 41m
CRW1:24 pmCharleston Yeager
$236
Find similar
United Airlines
Nov 8
CRW5:45 pmCharleston Yeager
1h 56m
ORD6:41 pmChicago O'Hare Intl
Nov 15
ORD10:43 amChicago O'Hare Intl
1h 41m
CRW1:24 pmCharleston Yeager
$238
Find similar

American Airlines flights from Charleston, West Virginia to Chicago

Our best American Airlines deals on Charleston, West Virginia to Chicago flight tickets
American Airlines
Oct 25
CRW4:03 pmCharleston Yeager
6h 26m
1 stop
ORD9:29 pmChicago O'Hare Intl
Nov 1
ORD8:15 amChicago O'Hare Intl
6h 18m
1 stop
CRW3:33 pmCharleston Yeager
$158
Find similar
American Airlines
Nov 8
CRW1:09 pmCharleston Yeager
7h 33m
1 stop
ORD7:42 pmChicago O'Hare Intl
Nov 15
ORD4:08 pmChicago O'Hare Intl
4h 37m
1 stop
CRW9:45 pmCharleston Yeager
$160
Find similar
American Airlines
Oct 21
CRW7:11 pmCharleston Yeager
4h 43m
1 stop
ORD10:54 pmChicago O'Hare Intl
Oct 22
ORD3:11 pmChicago O'Hare Intl
5h 23m
1 stop
CRW9:34 pmCharleston Yeager
$178
Find similar

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 September 25, 2025.
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

Sat 10/25

4:03 pm-9:29 pm

1 stop6h 26m

Chicago O'Hare Intl

Sat 11/1

8:15 am-3:33 pm

1 stop6h 18m

$158

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sat 11/8

1:09 pm-7:42 pm

1 stop7h 33m

Chicago O'Hare Intl

Sat 11/15

4:08 pm-9:45 pm

1 stop4h 37m

$160

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 11/12

6:00 am-10:37 am

1 stop5h 37m

Chicago O'Hare Intl

Thu 11/13

5:23 am-10:38 am

1 stop4h 15m

$168

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Tue 10/21

7:11 pm-10:54 pm

1 stop4h 43m

Chicago O'Hare Intl

Wed 10/22

3:11 pm-9:34 pm

1 stop5h 23m

$178

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 11/5

12:21 pm-3:56 pm

1 stop4h 35m

Chicago O'Hare Intl

Fri 11/7

3:50 pm-9:56 pm

1 stop5h 06m

$198

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sat 11/1

11:23 am-5:00 pm

1 stop6h 37m

Chicago O'Hare Intl

Sun 11/2

5:20 am-10:43 am

1 stop4h 23m

$212

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 10/24

5:35 pm-6:34 pm

Nonstop1h 59m

Chicago O'Hare Intl

Sun 10/26

10:43 am-1:24 pm

Nonstop1h 41m

$229

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 10/24

5:35 pm-6:34 pm

Nonstop1h 59m

Chicago O'Hare Intl

Sun 10/26

10:43 am-1:24 pm

Nonstop1h 41m

$236

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 10/24

7:36 pm-10:14 am

1 stop15h 38m

Chicago O'Hare Intl

Sun 10/26

1:14 pm-6:56 pm

2 stops28h 42m

$277

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 10/23

2:43 pm-7:34 am

1 stop17h 51m

Chicago O'Hare Intl

Sun 10/26

1:14 pm-6:56 pm

2 stops28h 42m

$279

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 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 cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Charleston, West Virginia, with most prices found around $239. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Charleston, West Virginia to Chicago during April average around $239.

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 Friday when prices can be found for as low as $522. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Charleston, West Virginia to Chicago for around $737.

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 afternoon. Flights from Charleston, West Virginia to Chicago during this time can be as low as $521. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $632.

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.

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

$268

Fastest flight time

1h 48m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Charleston, West Virginia in the past 72 hours is $268. The best round-trip flight deal from Charleston, West Virginia to Chicago found on momondo in the last 72 hours is $297.
The fastest flight from Charleston, West Virginia to Chicago takes 1h 48m
Direct flights go from Charleston, West Virginia to Chicago every day.
There is 1 airport near Chicago: 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 $184Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
American AirlinesPriceFrom $198Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • United Airlines Flights From Charleston, West Virginia to Chicago

    United Airlines flies from Charleston, West Virginia to Chicago around 15 times per week, with 8,928 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 $184 (round-trip), much lower than the average airfare cost of $312 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
Crown Point
Munster
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