CRW - CHI

$164 Find Cheap Flights from Charleston to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Charleston to Chicago departing on 6/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charleston to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Charleston to Chicago, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$239
Typical prices: $390-$269
United Airlines
Tue 6/16Tue 6/23
CRW - ORD • Non-stop
Cheapest one-way
$164
Typical prices: $242-$278
United Airlines
Mon 6/15
CRW - ORD • Non-stop
Top airlines
United Airlines
Cheapest • from $239 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with United Airlines. Average duration is 1h 59m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
CRW
-
ORD
Cheapest
CRW
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 16% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Charleston to Chicago (CRW-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Charleston to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Charleston to Chicago

Tue, Jun 16 - Tue, Jun 23
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
$239United Airlines
Fri, Jul 3 - Fri, Jul 10
Delta Logo
6:55 pm - 10:17 pm
CRW
-
MDW
4h 22m
1 stop
Delta Logo
6:00 am - 2:02 pm
MDW
-
CRW
7h 02m
1 stop
$258Delta
Wed, Aug 26 - Sat, Aug 29
Delta Logo
2:52 pm - 6:49 pm
CRW
-
ORD
4h 57m
1 stop
Delta Logo
8:02 am - 3:54 pm
ORD
-
CRW
6h 52m
1 stop
$258Delta
Wed, Jul 8 - Wed, Jul 15
American Airlines Logo
7:26 pm - 11:30 pm
CRW
-
ORD
5h 04m
1 stop
American Airlines Logo
5:07 am - 10:30 am
ORD
-
CRW
4h 23m
1 stop
$259American Airlines
Wed, Aug 26 - Sat, Aug 29
Delta Logo
6:50 pm - 12:02 am
CRW
-
ORD
6h 12m
1 stop
Delta Logo
6:51 am - 3:54 pm
ORD
-
CRW
8h 03m
2 stops
$264Delta
Fri, Jun 12 - Mon, Jun 15
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
Sat, Jun 6 - Mon, Jun 8
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
Thu, Jun 25 - Sat, Jun 27
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
Wed, Jul 8 - Wed, Jul 15
Delta Logo
11:05 am - 4:15 pm
CRW
-
MDW
6h 10m
1 stop
Delta Logo
6:00 am - 2:02 pm
MDW
-
CRW
7h 02m
1 stop
$273Delta
Wed, Jul 8 - Wed, Jul 15
Delta Logo
6:00 am - 12:38 pm
CRW
-
MDW
7h 38m
2 stops
Delta Logo
6:00 am - 2:02 pm
MDW
-
CRW
7h 02m
1 stop
$279Delta
Booking Insights

KAYAK's insights & trends for Charleston to Chicago flights

Get data-powered insights and trends into flights from Charleston to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Charleston, West Virginia to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Charleston, West Virginia to Chicago departing in June.

What is the cheapest Charleston to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Charleston to Chicago costs $279 on the route between Charleston (CRW) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Charleston to Chicago?

The average price of all round-trip flights from Charleston to Chicago clicked on KAYAK for each day over the last 12 months.

When flying from Charleston to Chicago, you should consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to Charleston, you’ll find the best rates on Saturdays and the most expensive ones on Mondays.

What is the cheapest month to fly from Charleston to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Charleston to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Charleston to Chicago is February, where tickets cost $178 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $278 and $268 respectively.

Can I save money by flying with a layover from Charleston to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $308, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$164
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Charleston to Chicago O'Hare Airport

When to book flights from Charleston to Chicago

Are your dates flexible? Find out the best times to travel from Charleston to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Charleston to Chicago

  • What is the cheapest flight from Charleston to Chicago?

    In the last 7 days, the lowest price for a flight from Charleston to Chicago was $164 for a one-way ticket and $239 for a round-trip.

  • Do I need a passport to fly between Charleston and Chicago?

    No

  • Which airports will I be using when flying from Charleston to Chicago?

    On your way to Chicago, you’ll fly out from Charleston Yeager. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Charleston to Chicago?

    Only American Airlines offers inflight Wi-Fi service on the Charleston to Chicago flight route.

  • Which aircraft models fly most regularly from Charleston to Chicago?

    The Canadair (Bombardier) Regional Jet is the aircraft model that flies most regularly on the Charleston to Chicago flight route.

  • Which airline alliances offer flights from Charleston to Chicago?

    Star Alliance is the only airline alliance operating flights between Charleston and Chicago.

  • On which days can I fly direct from Charleston to Chicago?

    There are nonstop flights from Charleston to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Charleston to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Charleston to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Charleston to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Charleston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Charleston to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Charleston with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Charleston to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Charleston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Charleston to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $389 or less one-way and $436 or less round-trip.

Prefer to fly direct from Charleston to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Charleston Yeager to Chicago.
Find which airlines fly direct from Charleston Yeager Airport to Chicago, which days they fly and book direct flights.

Direct departures

Charleston Yeager to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Charleston Yeager

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top airline flying from Charleston to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Charleston to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Charleston to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9747 reviews
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

This flight is a quick way to get to Chicago, but a bit expensive.

8.0 ExcellentAnonymous, May 2026
DTW - ORD
Read more United Airlines reviews

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

Everything you need to know for your flight from Charleston to Chicago

Information on your arrival and departure airports

Charleston (CRW)