Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Charleston, West Virginia to Chicago from $168

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 4/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
5:50 pm - 6:52 pm
CRW
-
ORD
2h 02mnonstop
United Airlines Logo
8:00 pm - 10:49 pm
ORD
-
CRW
1h 49mnonstop
$239United Airlines
Fri, May 8 - Sat, May 16
United Airlines Logo
5:59 pm - 6:47 pm
CRW
-
ORD
1h 48mnonstop
United Airlines Logo
6:45 am - 9:26 am
ORD
-
CRW
1h 41mnonstop
$247United Airlines
Sat, Aug 15 - Tue, Aug 18
United Airlines Logo
5:47 pm - 6:51 pm
CRW
-
ORD
2h 04mnonstop
United Airlines Logo
8:00 pm - 10:53 pm
ORD
-
CRW
1h 53mnonstop
$251United Airlines
Fri, May 29 - Sun, May 31
United Airlines Logo
6:45 am - 7:46 am
CRW
-
ORD
2h 01mnonstop
United Airlines Logo
2:16 pm - 5:09 pm
ORD
-
CRW
1h 53mnonstop
$254United Airlines
Fri, Apr 24 - Mon, May 4
Delta Logo
3:30 pm - 9:09 pm
CRW
-
MDW
6h 39m
1 stop
Delta Logo
5:12 pm - 11:07 pm
MDW
-
CRW
4h 55m
1 stop
$258Delta
Wed, May 20 - Wed, May 27
Delta Logo
6:40 pm - 11:57 pm
CRW
-
ORD
6h 17m
1 stop
Delta Logo
7:10 am - 2:43 pm
ORD
-
CRW
6h 33m
1 stop
$258Delta
Wed, Aug 26 - Sat, Aug 29
American Airlines Logo
6:11 pm - 11:54 pm
CRW
-
ORD
6h 43m
1 stop
American Airlines Logo
4:00 pm - 10:20 pm
ORD
-
CRW
5h 20m
1 stop
$261American Airlines
Sat, May 2 - Sat, May 9
United Airlines Logo
7:39 pm - 8:40 pm
CRW
-
ORD
2h 01mnonstop
United Airlines Logo
6:10 pm - 8:55 pm
ORD
-
CRW
1h 45mnonstop
$269United Airlines
Fri, Apr 17 - Sun, Apr 19
Multiple Airlines Logo
2:45 pm - 2:53 pm
CRW
-
RFD
25h 08m
1 stop
Multiple Airlines Logo
7:57 pm - 1:42 pm
RFD
-
CRW
16h 45m
2 stops
$341Multiple Airlines
Thu, Aug 27 - Fri, Sep 4
Multiple Airlines Logo
2:43 pm - 7:59 am
CRW
-
RFD
18h 16m
1 stop
Multiple Airlines Logo
9:34 am - 9:19 am
RFD
-
CRW
22h 45m
1 stop
$441Multiple Airlines
Thu, Oct 1 - Wed, Oct 7

United Airlines flights from Charleston, West Virginia to Chicago

Our best United Airlines deals on Charleston, West Virginia to Chicago flight tickets
United Airlines
May 8
CRW5:50 pmCharleston Yeager
2h 02m
ORD6:52 pmChicago O'Hare Intl
May 16
ORD8:00 pmChicago O'Hare Intl
1h 49m
CRW10:49 pmCharleston Yeager
$239
United Airlines
Aug 15
CRW5:59 pmCharleston Yeager
1h 48m
ORD6:47 pmChicago O'Hare Intl
Aug 18
ORD6:45 amChicago O'Hare Intl
1h 41m
CRW9:26 amCharleston Yeager
$247
United Airlines
May 29
CRW5:47 pmCharleston Yeager
2h 04m
ORD6:51 pmChicago O'Hare Intl
May 31
ORD8:00 pmChicago O'Hare Intl
1h 53m
CRW10:53 pmCharleston Yeager
$251

American Airlines flights from Charleston, West Virginia to Chicago

Our best American Airlines deals on Charleston, West Virginia to Chicago flight tickets
American Airlines
May 2
CRW6:11 pmCharleston Yeager
6h 43m
1 stop
ORD11:54 pmChicago O'Hare Intl
May 9
ORD4:00 pmChicago O'Hare Intl
5h 20m
1 stop
CRW10:20 pmCharleston Yeager
$261
American Airlines
May 28
CRW8:06 pmCharleston Yeager
4h 53m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jun 1
ORD5:34 pmChicago O'Hare Intl
5h 22m
1 stop
CRW11:56 pmCharleston Yeager
$316
American Airlines
May 1
CRW5:00 amCharleston Yeager
4h 30m
1 stop
ORD8:30 amChicago O'Hare Intl
May 8
ORD5:00 amChicago O'Hare Intl
4h 34m
1 stop
CRW10:34 amCharleston Yeager
$320

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 April 6, 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

Fri 5/8

5:50 pm-6:52 pm

Nonstop2h 02m

Chicago O'Hare Intl

Sat 5/16

8:00 pm-10:49 pm

Nonstop1h 49m

$239
Quickest round-trip

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sat 8/15

5:59 pm-6:47 pm

Nonstop1h 48m

Chicago O'Hare Intl

Tue 8/18

6:45 am-9:26 am

Nonstop1h 41m

$247

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 5/29

5:47 pm-6:51 pm

Nonstop2h 04m

Chicago O'Hare Intl

Sun 5/31

8:00 pm-10:53 pm

Nonstop1h 53m

$251

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 4/24

6:45 am-7:46 am

Nonstop2h 01m

Chicago O'Hare Intl

Mon 5/4

2:16 pm-5:09 pm

Nonstop1h 53m

$254

CharlestonChicago

CRW - MDW

CRWMDW

Charleston Yeager

Wed 5/20

3:30 pm-9:09 pm

1 stop6h 39m

Chicago Midway

Wed 5/27

5:12 pm-11:07 pm

1 stop4h 55m

$258

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Wed 8/26

6:40 pm-11:57 pm

1 stop6h 17m

Chicago O'Hare Intl

Sat 8/29

7:10 am-2:43 pm

1 stop6h 33m

$258

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Sat 5/2

6:11 pm-11:54 pm

1 stop6h 43m

Chicago O'Hare Intl

Sat 5/9

4:00 pm-10:20 pm

1 stop5h 20m

$261

CharlestonChicago

CRW - ORD

CRWORD

Charleston Yeager

Fri 4/17

7:39 pm-8:40 pm

Nonstop2h 01m

Chicago O'Hare Intl

Sun 4/19

6:10 pm-8:55 pm

Nonstop1h 45m

$269

CharlestonChicago

CRW - RFD

CRWRFD

Charleston Yeager

Thu 8/27

2:45 pm-2:53 pm

1 stop25h 08m

Chicago Greater Rockford

Fri 9/4

7:57 pm-1:42 pm

2 stops16h 45m

$341

CharlestonChicago

CRW - RFD

CRWRFD

Charleston Yeager

Thu 10/1

2:43 pm-7:59 am

1 stop18h 16m

Chicago Greater Rockford

Wed 10/7

9:34 am-9:19 am

1 stop22h 45m

$441

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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 $455. 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 $703.

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 $477. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $572.

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?

You could potentially save up to 12% 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

$346

Fastest flight time

1h 48m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Charleston, West Virginia in the past 72 hours is $346. The best round-trip flight deal from Charleston, West Virginia to Chicago found on momondo in the last 72 hours is $386.
The fastest flight from Charleston, West Virginia to Chicago takes 1h 48m
Direct flights go from Charleston, West Virginia to Chicago on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. 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

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 $179Free CancellationRating
7.4
9,545 reviews
Search United Airlines flights

  • United Airlines Flights From Charleston, West Virginia to Chicago

    United Airlines flies from Charleston, West Virginia to Chicago around 21 times per week, with 9,545 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 5/6
Wed 5/13
By creating a price alert you accept our terms of use and privacy policy.

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