CRW - CHI

$169 Find Cheap Flights from Charleston to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Charleston to Chicago departing on 3/14. 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
$169
Typical prices: $291-$412
United Airlines
Sat 3/14Tue 3/17
CRW - ORD • Non-stop
Cheapest one-way
$202
Multiple Airlines
Sun 5/31
CRW - ORD • 1 stop
Top airlines
United Airlines
Cheapest • from $169 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
CRW
-
ORD
Cheapest
CRW
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 23% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Sat, Mar 14 - Tue, Mar 17
United Airlines Logo
5:53 pm - 6:55 pm
CRW
-
ORD
2h 02mnonstop
United Airlines Logo
5:50 pm - 8:32 pm
ORD
-
CRW
1h 42mnonstop
$169United Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
6:45 am - 7:50 am
CRW
-
ORD
2h 05mnonstop
United Airlines Logo
5:56 pm - 8:38 pm
ORD
-
CRW
1h 42mnonstop
$179United Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
11:48 am - 5:57 pm
CRW
-
ORD
7h 09m
1 stop
American Airlines Logo
5:00 am - 11:15 am
ORD
-
CRW
5h 15m
1 stop
$188American Airlines
Thu, Apr 23 - Sun, Apr 26
United Airlines Logo
7:10 pm - 8:11 pm
CRW
-
ORD
2h 01mnonstop
United Airlines Logo
6:10 pm - 8:55 pm
ORD
-
CRW
1h 45mnonstop
$189United Airlines
Tue, Mar 10 - Tue, Mar 17
Delta Logo
6:59 pm - 10:31 pm
CRW
-
MDW
4h 32m
1 stop
Delta Logo
6:00 am - 1:57 pm
MDW
-
CRW
6h 57m
1 stop
$198Delta
Thu, Apr 23 - Sat, Apr 25
Delta Logo
3:12 pm - 8:16 pm
CRW
-
ORD
6h 04m
1 stop
Delta Logo
5:10 am - 10:20 am
ORD
-
CRW
4h 10m
1 stop
$198Delta
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
5:35 pm - 6:37 pm
CRW
-
ORD
2h 02mnonstop
United Airlines Logo
5:56 pm - 8:38 pm
ORD
-
CRW
1h 42mnonstop
$199United Airlines
Tue, Feb 24 - Sat, Feb 28
American Airlines Logo
11:48 am - 5:58 pm
CRW
-
ORD
7h 10m
1 stop
American Airlines Logo
4:04 pm - 9:18 pm
ORD
-
CRW
4h 14m
1 stop
$218American Airlines
Thu, Apr 23 - Sat, Apr 25
Multiple Airlines Logo
2:43 pm - 8:04 am
CRW
-
MDW
18h 21m
1 stop
Multiple Airlines Logo
9:14 am - 9:19 am
MDW
-
CRW
23h 05m
1 stop
$320Multiple Airlines
Thu, Apr 23 - Sun, Apr 26
Multiple Airlines Logo
9:59 am - 1:00 pm
CRW
-
MDW
28h 01m
1 stop
Multiple Airlines Logo
7:30 am - 2:03 pm
MDW
-
CRW
5h 33m
1 stop
$322Multiple 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.

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 $244 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 April, where tickets cost $243 (return) on average. On the other hand, the most expensive months are July and November, 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.

No, with an average price for the route of $292, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$169
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 3% 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 $204 for a one-way ticket and $169 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 aircraft models fly most regularly from Charleston to Chicago?

    The Canadair (Bombardier) Regional Jet CRJ-550 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 $363 or less one-way and $322 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 9269 reviews
7.7Boarding
6.6Food
7.3Comfort
8.1Crew
7.1Entertainment
Airline reviews

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.

10.0 ExcellentYesica, Feb 2026
CHS - ORD
Read more United Airlines reviews

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 was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

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

Information on your arrival and departure airports

Charleston (CRW)