CHS - CHI

$102 Find Cheap Flights from Charleston to Chicago - Compare and Save

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 10/27. 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.
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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$278
Typical prices: $286-$467
Multiple Airlines
Sun 8/30Tue 9/1
CHS - ORD • 2 stops
Cheapest non-stop
$288
Typical prices: $286-$432
United Airlines
Fri 8/21Mon 8/24
CHS - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Basic Economy is carry-on only; Main Cabin Extra adds early boarding.
United Economy Plus adds up to 6 inches more legroom; Southwest offers Cash + Points.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $282 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 28m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 8% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $210 (round-trip)
Shortest trip • 4h 17m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 49% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 8% price drop
Most popular
Good to know
Good to know
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+1
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Flight Deals

Cheap Flights from Charleston to Chicago (CHS-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

Sun, Aug 30 - Tue, Sep 1
Multiple Airlines Logo
6:45 am - 7:53 am
CHS
-
ORD
26h 08m
2 stops
Multiple Airlines Logo
8:05 am - 6:14 pm
ORD
-
CHS
9h 09m
1 stop
$278Multiple Airlines
Wed, Sep 16 - Fri, Sep 18
American Airlines Logo
2:05 pm - 3:42 pm
CHS
-
ORD
2h 37mnonstop
American Airlines Logo
5:20 am - 1:38 pm
ORD
-
CHS
7h 18m
1 stop
$281American Airlines
Sun, Aug 30 - Tue, Sep 1
Multiple Airlines Logo
2:53 pm - 1:20 pm
CHS
-
ORD
23h 27m
1 stop
Multiple Airlines Logo
7:44 pm - 9:08 am
ORD
-
CHS
12h 24m
1 stop
$281Multiple Airlines
Fri, Sep 4 - Tue, Sep 8
American Airlines Logo
2:06 pm - 5:42 pm
CHS
-
ORD
4h 36m
1 stop
American Airlines Logo
8:13 am - 11:33 am
ORD
-
CHS
2h 20mnonstop
$281American Airlines
Thu, Aug 20 - Tue, Aug 25
Multiple Airlines Logo
7:47 pm - 12:50 pm
CHS
-
ORD
18h 03m
1 stop
Multiple Airlines Logo
8:05 am - 6:14 pm
ORD
-
CHS
9h 09m
1 stop
$281Multiple Airlines
Wed, Dec 30 - Fri, Jan 1
American Airlines Logo
3:53 pm - 5:37 pm
CHS
-
ORD
2h 44mnonstop
American Airlines Logo
9:02 am - 2:15 pm
ORD
-
CHS
4h 13m
1 stop
$281American Airlines
Wed, Dec 16 - Tue, Dec 29
Southwest Logo
7:55 am - 9:15 am
CHS
-
MDW
2h 20mnonstop
Southwest Logo
10:05 am - 7:20 pm
MDW
-
CHS
8h 15m
2 stops
$282Southwest
Wed, Sep 30 - Thu, Oct 1
Southwest Logo
7:35 am - 8:45 am
CHS
-
MDW
2h 10mnonstop
Southwest Logo
11:50 am - 12:15 am
MDW
-
CHS
11h 25m
1 stop
$287Southwest
Fri, Aug 21 - Mon, Aug 24
United Airlines Logo
11:40 am - 1:13 pm
CHS
-
ORD
2h 33mnonstop
United Airlines Logo
10:33 am - 1:58 pm
ORD
-
CHS
2h 25mnonstop
$288United Airlines
Fri, Nov 6 - Mon, Nov 9
United Airlines Logo
6:47 pm - 8:28 pm
CHS
-
ORD
2h 41mnonstop
United Airlines Logo
2:15 pm - 5:49 pm
ORD
-
CHS
2h 34mnonstop
$288United 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 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 to Chicago departing in August.

Flight prices are typical for this route right now.

Flights to Chicago from Charleston usually cost between $270 and $426 in August.
The lowest price found in the past 5 days was $278 on Multiple Airlines (Aug 30-Sep 1).

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 $237 on the route between Charleston (CHS) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 8% cheaper than other Charleston-Chicago routes. The most popular route is between Charleston (CHS) and Chicago O'Hare Intl Airport (ORD).

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 Tuesdays and the most expensive ones on Sundays.

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 September, where tickets cost $341 (return) on average. On the other hand, the most expensive months are July and May, where the average cost of round-trip tickets is $410 and $399 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 $354 on average.

How far in advance should I book a flight from Charleston to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Charleston to Chicago, you should book around 5 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Expert advice

Expert advice for your flight from Charleston to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Brandon Schultz

Brandon Schultz

Expert on CHS

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Good to know

Low season

January

Cheapest flight

$102
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Charleston to Chicago Midway 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

  • Where can you stay for a short stay near Chicago O'Hare International Airport (ORD)?

    If you are looking for a place to stay for a short stay near Chicago O'Hare international, you can consider Hilton Chicago O’Hare Airport Hotel. The hotel is located inside the airport and offers free shuttle services. Additionally, you can consider nearby hotels with complimentary shuttle services, such as Aloft Chicago O’Hare and DoubleTree by Hilton Hotel Chicago O’Hare Airport Rosemont.

  • Which services are available at the USO lounge in Chicago Midway International Airport?

    The USO lounge at Chicago Midway international airport offers various services to military officers and their families. These services include a kitchenette with food and drinks, a cyber canteen with printers, computers, and Wi-Fi access, a gaming station, a library with reading materials, restrooms, fax machines, and travel and ground transportation assistance. The lounge is located airside of Concourse C.

  • Where can you eat at the departure airport?

    If you are hungry at Charleston International Airport, you will find many food concessions operating on the airside and landside. In Concourse A there is a Charleston Beer Works. Concourse B has Cinnabon, Dunkin Donuts, Desano Pizza Bakery, and Samuel Adams Brewhouse. Those at the central marketplace will find Caviar, Burger King, Bananas, Grounds and Jack Nicklaus Golden Bear, Grill, and Harvest. Additionally, there are vending machines in the baggage claim area.

  • Where can you relax and unwind at the departure airport?

    If you arrive early at CHS, you can relax at the Club CHS Lounge before departure. Take advantage of lounge facilities such as alcoholic and non-alcoholic beverages, computer workstations, flight information monitors, newspapers, magazines, and television. You can purchase a lounge pass or pay at the door when space is available to access the lounge. The lounge is located on the airside of Concourse B.

  • What is the cheapest flight from Charleston to Chicago?

    In the last 5 days, the lowest price for a flight from Charleston to Chicago was $102 for a one-way ticket and $278 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?

    Charleston is served by only 1 airport and there are 2 airports in Chicago. You will leave Charleston from Charleston and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

    American Airlines, Delta, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Charleston to Chicago flight route.

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

    The Boeing 737-800 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, and oneworld are the airline alliances operating flights between Charleston and Chicago, with Star Alliance being the most commonly used for this route.

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

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

  • Which is the best airline for flights from Charleston to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Charleston to Chicago are Southwest and United Airlines. With an average price for the route of $386 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $384 and an overall rating of 7.4.

  • 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 $213 or less one-way and $385 or less round-trip.
  • If you need assistance at Charleston International Airport (CHS), visit the information desks. Information desks are available at the landside between arrivals and baggage claim areas. Additionally, airport ambassadors roam throughout the airport.
  • If you have an early morning flight at CHS, you can consider spending the night at a nearby hotel. Hotels near the airport that offer free shuttle services include Hilton Garden Inn Charleston Airport, Embassy Suites North Charleston Airport Hotel & Convention Center, and DoubleTree by Hilton North Charleston.
  • Those planning to explore Chicago can consider renting a car at Chicago Midway Airport (MDW). There are various car providers, including Alamo, Avis, Budget, Corporate Rent a Cart, Dollar, Enterprise, Hertz, National, and Thrifty. In addition, complimentary shuttles pick up passengers outside the arrivals lower level front curb near door 2 and drop them at the car rental facility.
  • If you arrive at Chicago Midway international airport during rush hour, you can consider using the CTA Orange Line train. This train operates between downtown Chicago and the Midway Airport Orange Line station.
  • CHS offers various parking options for passengers who want to leave their vehicles at the airport. These options include hourly parking with covered and uncovered parking, economy lot, valet parking, and daily parking.

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 to Chicago.
Find which airlines fly direct from Charleston Airport to Chicago, which days they fly and book direct flights.

Direct departures

Charleston to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Charleston

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Reviews of the top 3 airlines serving 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.
8.0
SouthwestOverall score based on 4228 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

I think Southwest can offer a whole can of beverage instead of such a small cup

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

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.

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

The attendant were friendly. I suggest you have a medical attendant on board every flight so that in case someone is sick , he/she will help them.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

Flight was fine, but not having WiFi was a major negative

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

Would have thought that they would gas up plane before everyone got on board

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

American switched my flight to a 5 hour layover then cancelled my whole reservation with no notice and refused refund. Won’t fly with them again.

We sat on runway for an 1 hour because they were short handed at key west airport was not fun

The WiFi and app don’t work as easily as other airlines

Late. Then next flight was an hour late due to mx.

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

Information on your arrival and departure airports