CRW - CHI

$152 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 7/27. 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

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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Flights 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

Sat, Aug 30 - Wed, Sep 3
United Airlines Logo
5:45 pm - 6:39 pmCRW-ORD
1h 54mnonstop
United Airlines Logo
6:20 pm - 9:15 pmORD-CRW
1h 55mnonstop
$179United Airlines
Find Deal
Fri, Sep 5 - Sun, Sep 7
American Airlines Logo
5:35 am - 11:06 amCRW-ORD
6h 31m1 stop
American Airlines Logo
5:00 am - 10:25 amORD-CRW
4h 25m1 stop
$198American Airlines
Find Deal
Wed, Sep 3 - Sun, Sep 7
United Airlines Logo
5:45 pm - 6:39 pmCRW-ORD
1h 54mnonstop
United Airlines Logo
6:20 pm - 9:15 pmORD-CRW
1h 55mnonstop
$200United Airlines
Find Deal
Wed, Aug 6 - Wed, Aug 13
American Airlines Logo
6:00 am - 12:09 pmCRW-ORD
7h 09m1 stop
American Airlines Logo
3:32 pm - 9:41 pmORD-CRW
5h 09m1 stop
$208American Airlines
Find Deal
Fri, Aug 15 - Sun, Aug 17
American Airlines Logo
7:11 pm - 10:59 pmCRW-ORD
4h 48m1 stop
American Airlines Logo
5:20 am - 10:33 amORD-CRW
4h 13m1 stop
$228American Airlines
Find Deal
Sat, Aug 30 - Wed, Sep 3
Delta Logo
11:15 am - 4:13 pmCRW-ORD
5h 58m2 stops
Delta Logo
7:05 am - 2:45 pmORD-CRW
6h 40m1 stop
$234Delta
Find Deal
Wed, Aug 6 - Wed, Aug 13
United Airlines Logo
1:55 pm - 2:45 pmCRW-ORD
1h 50mnonstop
United Airlines Logo
10:35 am - 1:16 pmORD-CRW
1h 41mnonstop
$239United Airlines
Find Deal
Tue, Jul 29 - Sat, Aug 2
United Airlines Logo
1:55 pm - 2:49 pmCRW-ORD
1h 54mnonstop
United Airlines Logo
6:20 pm - 9:04 pmORD-CRW
1h 44mnonstop
$249United Airlines
Find Deal
Fri, Sep 12 - Wed, Sep 17
Delta Logo
3:25 pm - 9:36 pmCRW-MDW
7h 11m1 stop
Delta Logo
10:35 am - 6:08 pmMDW-CRW
6h 33m1 stop
$263Delta
Find Deal
Tue, Aug 26 - Tue, Sep 2
United Airlines Logo
5:45 pm - 6:39 pmCRW-ORD
1h 54mnonstop
United Airlines Logo
10:40 am - 1:25 pmORD-CRW
1h 45mnonstop
$269United Airlines
Find Deal
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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?

What is the cheapest Charleston to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Charleston to Chicago.

Our data shows that the cheapest route for a return flight from Charleston to Chicago cost $278 and was between Charleston (CRW) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $278.

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 Thursday and avoid Sundays 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 $239 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $510 and $479 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $274 on average.

Good to know

Low seasonDecember
High seasonSeptember
Cheapest flight$152
Best time to beat the crowds but there is an average 33% increase in price.
Most popular time to fly with an average 23% increase in price.
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 3 days, the lowest price for a flight from Charleston to Chicago was $152 for a one-way ticket and $179 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?

    American Airlines, and Delta offer 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 $246 or less one-way and $393 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 8856 reviews
6.6Food
7.0Entertainment
8.1Crew
7.3Comfort
7.7Boarding
Airline reviews

Overall it was good. I missed my connection but I was put on another flight.

8.0 ExcellentJohanna, Jul 2025IAH - ORD
Read more United Airlines reviews

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

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

Information on your arrival and departure airports

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