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 3/31. 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
Travelers love KAYAK
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: $314-$216
United Airlines
Fri 4/17Sun 4/19
CRW - ORD • Non-stop
Cheapest one-way
$168
American Airlines
Tue 3/31
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 1h 59m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $198 (round-trip)
Shortest trip • 4h 44m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 38% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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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

Fri, Apr 17 - Sun, Apr 19
United Airlines Logo
7:39 pm - 8:40 pm
CRW
-
ORD
2h 01mnonstop
United Airlines Logo
6:55 am - 9:31 am
ORD
-
CRW
1h 36mnonstop
$239United Airlines
Thu, May 14 - Sun, May 17
United Airlines Logo
6:45 am - 7:47 am
CRW
-
ORD
2h 02mnonstop
United Airlines Logo
6:55 am - 9:31 am
ORD
-
CRW
1h 36mnonstop
$253United Airlines
Fri, Jul 3 - Wed, Jul 8
Delta Logo
6:55 pm - 10:17 pm
CRW
-
MDW
4h 22m
1 stop
Delta Logo
6:05 am - 2:02 pm
MDW
-
CRW
6h 57m
1 stop
$258Delta
Thu, May 28 - Mon, Jun 1
Delta Logo
6:59 pm - 11:59 pm
CRW
-
ORD
6h 00m
1 stop
Delta Logo
7:07 am - 2:50 pm
ORD
-
CRW
6h 43m
1 stop
$258Delta
Wed, Apr 8 - Sun, Apr 12
United Airlines Logo
10:30 am - 11:27 am
CRW
-
ORD
1h 57mnonstop
United Airlines Logo
6:55 am - 9:31 am
ORD
-
CRW
1h 36mnonstop
$269United 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
Sun, May 10 - Wed, May 13
Multiple Airlines Logo
9:56 am - 6:38 pm
CRW
-
ORD
9h 42m
1 stop
Multiple Airlines Logo
1:49 pm - 2:05 pm
ORD
-
CRW
23h 16m
1 stop
$281Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
American Airlines Logo
11:04 am - 4:21 pm
CRW
-
ORD
6h 17m
1 stop
American Airlines Logo
5:00 am - 10:34 am
ORD
-
CRW
4h 34m
1 stop
$288American Airlines
Thu, Apr 2 - Mon, Apr 6
American Airlines Logo
6:10 am - 10:57 am
CRW
-
ORD
5h 47m
1 stop
American Airlines Logo
5:00 am - 10:55 am
ORD
-
CRW
4h 55m
1 stop
$312American Airlines
Thu, Apr 30 - Sun, May 3
Multiple Airlines Logo
2:43 pm - 10:28 am
CRW
-
MDW
20h 45m
1 stop
Multiple Airlines Logo
7:30 am - 2:03 pm
MDW
-
CRW
5h 33m
1 stop
$331Multiple Airlines
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 April.

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 $271 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 Saturday 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 $192 (return) on average. On the other hand, the most expensive months are July and March, where the average cost of round-trip tickets is $411 and $379 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 $404 on average.

Good to know

Low seasonJanuary
Cheapest flight$168
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 2% 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 $228 or less one-way and $349 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 9499 reviews
6.6Food
7.1Entertainment
7.3Comfort
8.1Crew
7.7Boarding
Airline reviews

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.

2.0 MediocreJill, Mar 2026
LGA - ORD
Read more United Airlines reviews

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.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

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

Information on your arrival and departure airports