CRW - CHI

$168 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 5/5. 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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Everything you should know

Cheapest round-trip
$239
Typical prices: $352-$269
United Airlines
Tue 5/5Tue 5/12
CRW - ORD • Non-stop
Cheapest one-way
$168
American Airlines
Tue 5/5
CRW - ORD • 1 stop
Top airlines
Cheapest • from $239 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 2h 00m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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, May 5 - Tue, May 12
United Airlines Logo
6:45 am - 7:47 am
CRW
-
ORD
2h 02mnonstop
United Airlines Logo
8:00 pm - 10:49 pm
ORD
-
CRW
1h 49mnonstop
$239United Airlines
Fri, Apr 24 - Mon, May 4
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
Wed, May 20 - Wed, May 27
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, Aug 26 - Sat, Aug 29
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
Fri, May 1 - Tue, May 5
United Airlines Logo
3:21 pm - 4:20 pm
CRW
-
ORD
1h 59mnonstop
United Airlines Logo
8:00 pm - 10:49 pm
ORD
-
CRW
1h 49mnonstop
$259United Airlines
Wed, May 20 - Wed, May 27
United Airlines Logo
10:28 am - 11:27 am
CRW
-
ORD
1h 59mnonstop
United Airlines Logo
2:20 pm - 5:12 pm
ORD
-
CRW
1h 52mnonstop
$270United Airlines
Wed, Apr 22 - Sun, Apr 26
Delta Logo
7:20 pm - 11:59 pm
CRW
-
ORD
5h 39m
1 stop
Delta Logo
5:15 am - 10:20 am
ORD
-
CRW
4h 05m
1 stop
$273Delta
Fri, May 1 - Tue, May 5
Delta Logo
3:22 pm - 9:25 pm
CRW
-
ORD
7h 03m
1 stop
Delta Logo
7:10 am - 2:42 pm
ORD
-
CRW
6h 32m
1 stop
$278Delta
Fri, Apr 24 - Mon, May 4
Delta Logo
7:10 pm - 10:28 pm
CRW
-
MDW
4h 18m
1 stop
Delta Logo
10:41 am - 6:24 pm
MDW
-
CRW
6h 43m
1 stop
$288Delta
Wed, Apr 22 - Sun, Apr 26
Delta Logo
7:20 pm - 11:59 pm
CRW
-
ORD
5h 39m
1 stop
Delta Logo
5:15 am - 10:20 am
ORD
-
CRW
4h 05m
1 stop
$288Delta
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 May.

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 $294 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.

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 $347, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$168
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 4% 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 3 days, the lowest price for a flight from Charleston to Chicago was $168 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 $346 or less one-way and $386 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 9554 reviews
7.3Comfort
8.1Crew
7.1Entertainment
6.6Food
7.7Boarding
Airline reviews

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

10.0 ExcellentMargaret, Apr 2026
DEN - ORD
Read more United Airlines reviews

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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

Information on your arrival and departure airports