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Cheap flights from Charleston, West Virginia to Chicago from $164

This is the cheapest one-way 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 6/15. 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
7:00 am - 8:00 am
CRW
-
ORD
2h 00mnonstop
United Airlines Logo
7:35 am - 10:25 am
ORD
-
CRW
1h 50mnonstop
$239United Airlines
Thu, Jun 25 - Sat, Jun 27
American Airlines Logo
6:55 pm - 11:37 pm
CRW
-
ORD
5h 42m
1 stop
American Airlines Logo
1:22 pm - 6:25 pm
ORD
-
CRW
4h 03m
1 stop
$258American Airlines
Wed, Aug 26 - Sat, Aug 29
Delta Logo
4:44 pm - 8:46 pm
CRW
-
ORD
5h 02m
1 stop
Delta Logo
12:29 pm - 11:39 pm
ORD
-
CRW
10h 10m
2 stops
$264Delta
Sat, Aug 22 - Wed, Aug 26
United Airlines Logo
7:00 am - 7:59 am
CRW
-
ORD
1h 59mnonstop
United Airlines Logo
7:35 am - 10:25 am
ORD
-
CRW
1h 50mnonstop
$266United Airlines
Fri, Jun 12 - Mon, Jun 15
United Airlines Logo
5:57 pm - 7:01 pm
CRW
-
ORD
2h 04mnonstop
United Airlines Logo
7:35 am - 10:25 am
ORD
-
CRW
1h 50mnonstop
$269United Airlines
Sat, Jun 6 - Mon, Jun 8
United Airlines Logo
7:00 am - 7:59 am
CRW
-
ORD
1h 59mnonstop
United Airlines Logo
7:35 am - 10:25 am
ORD
-
CRW
1h 50mnonstop
$270United Airlines
Mon, Jun 15 - Mon, Jun 22
American Airlines Logo
8:05 pm - 11:58 pm
CRW
-
ORD
4h 53m
1 stop
American Airlines Logo
2:57 pm - 10:06 pm
ORD
-
CRW
6h 09m
1 stop
$273American Airlines
Thu, Jun 25 - Sat, Jun 27
Delta Logo
4:45 pm - 8:46 pm
CRW
-
ORD
5h 01m
1 stop
Delta Logo
1:40 pm - 11:31 pm
ORD
-
CRW
8h 51m
2 stops
$279Delta
Sat, Jun 27 - Wed, Jul 1
United Airlines Logo
11:00 am - 11:58 am
CRW
-
ORD
1h 58mnonstop
United Airlines Logo
7:35 am - 10:25 am
ORD
-
CRW
1h 50mnonstop
$285United Airlines
Thu, Jul 23 - Sat, Jul 25
Delta Logo
6:50 pm - 10:36 pm
CRW
-
MDW
4h 46m
1 stop
Delta Logo
10:54 am - 6:10 pm
MDW
-
CRW
6h 16m
1 stop
$333Delta
Wed, Aug 5 - Wed, Aug 12

Delta flights from Charleston, West Virginia to Chicago

Our best Delta deals on Charleston, West Virginia to Chicago flight tickets
Delta
Aug 26
CRW6:50 pmCharleston Yeager
6h 12m
1 stop
ORD12:02 amChicago O'Hare Intl
Aug 29
ORD8:02 amChicago O'Hare Intl
6h 52m
1 stop
CRW3:54 pmCharleston Yeager
$258
Delta
Aug 22
CRW4:44 pmCharleston Yeager
5h 02m
1 stop
ORD8:46 pmChicago O'Hare Intl
Aug 26
ORD12:29 pmChicago O'Hare Intl
10h 10m
2 stops
CRW11:39 pmCharleston Yeager
$264
Delta
Jun 27
CRW4:45 pmCharleston Yeager
5h 01m
1 stop
ORD8:46 pmChicago O'Hare Intl
Jul 1
ORD1:40 pmChicago O'Hare Intl
8h 51m
2 stops
CRW11:31 pmCharleston Yeager
$279

American Airlines flights from Charleston, West Virginia to Chicago

Our best American Airlines deals on Charleston, West Virginia to Chicago flight tickets
American Airlines
Jun 25
CRW8:05 pmCharleston Yeager
4h 53m
1 stop
ORD11:58 pmChicago O'Hare Intl
Jun 27
ORD2:57 pmChicago O'Hare Intl
6h 09m
1 stop
CRW10:06 pmCharleston Yeager
$273
American Airlines
Jun 4
CRW8:05 pmCharleston Yeager
4h 53m
1 stop
ORD11:58 pmChicago O'Hare Intl
Jun 6
ORD4:49 pmChicago O'Hare Intl
6h 07m
1 stop
CRW11:56 pmCharleston Yeager
$288
American Airlines
Jun 25
CRW8:05 pmCharleston Yeager
4h 53m
1 stop
ORD11:58 pmChicago O'Hare Intl
Jun 27
ORD2:57 pmChicago O'Hare Intl
6h 09m
1 stop
CRW10:06 pmCharleston Yeager
$338

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 May 23, 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

Cheapest round-trip

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 6/25

7:00 am-8:00 am

Nonstop2h 00m

Chicago O'Hare Intl

Sat 6/27

7:35 am-10:25 am

Nonstop1h 50m

$239

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 8/26

6:55 pm-11:37 pm

1 stop5h 42m

Chicago O'Hare Intl

Sat 8/29

1:22 pm-6:25 pm

1 stop4h 03m

$258

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sat 8/22

4:44 pm-8:46 pm

1 stop5h 02m

Chicago O'Hare Intl

Wed 8/26

12:29 pm-11:39 pm

2 stops10h 10m

$264

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 6/12

7:00 am-7:59 am

Nonstop1h 59m

Chicago O'Hare Intl

Mon 6/15

7:35 am-10:25 am

Nonstop1h 50m

$266

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sat 6/6

5:57 pm-7:01 pm

Nonstop2h 04m

Chicago O'Hare Intl

Mon 6/8

7:35 am-10:25 am

Nonstop1h 50m

$269

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Mon 6/15

7:00 am-7:59 am

Nonstop1h 59m

Chicago O'Hare Intl

Mon 6/22

7:35 am-10:25 am

Nonstop1h 50m

$270

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 6/25

8:05 pm-11:58 pm

1 stop4h 53m

Chicago O'Hare Intl

Sat 6/27

2:57 pm-10:06 pm

1 stop6h 09m

$273

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sat 6/27

4:45 pm-8:46 pm

1 stop5h 01m

Chicago O'Hare Intl

Wed 7/1

1:40 pm-11:31 pm

2 stops8h 51m

$279
Quickest round-trip

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Thu 7/23

11:00 am-11:58 am

Nonstop1h 58m

Chicago O'Hare Intl

Sat 7/25

7:35 am-10:25 am

Nonstop1h 50m

$285

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 8/5

6:50 pm-10:36 pm

1 stop4h 46m

Chicago Midway

Wed 8/12

10:54 am-6:10 pm

1 stop6h 16m

$333

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 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 February is, on average, the cheapest month to fly to Chicago from Charleston, West Virginia, with most prices found around $178. If you’re not able to fly to Chicago in February, then October is your next best option. Flight prices from Charleston, West Virginia to Chicago during October average around $179.

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 $444. 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 $683.

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 $468. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $561.

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, West Virginia to Chicago flights?

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

You could potentially save up to 51% on your flight if you consider stops on a Charleston, West Virginia to Chicago flight.

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

$389

Fastest flight time

1h 48m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Charleston, West Virginia in the past 72 hours is $389. The best round-trip flight deal from Charleston, West Virginia to Chicago found on momondo in the last 72 hours is $420.
The fastest flight from Charleston, West Virginia to Chicago takes 1h 48m
Direct flights go from Charleston, West Virginia to Chicago every day.
There are 3 airports in Chicago. From Charleston, West Virginia there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Charleston, West Virginia to Chicago

  • 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 $190Free CancellationRating
7.4
9,751 reviews
Search United Airlines flights

  • United Airlines Flights From Charleston, West Virginia to Chicago

    United Airlines flies from Charleston, West Virginia to Chicago around 20 times per week, with 9,751 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 $190 (round-trip), much lower than the average airfare cost of $328 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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