CHS - CHI

$103 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 12/8. 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
$277
Typical prices: $295-$246
Delta
Sat 7/25Tue 7/28
CHS - MDW • 1 stop
Cheapest non-stop
$279
Southwest
Tue 7/14Wed 7/15
CHS - MDW • 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 $277 (round-trip)
Best reviews • 7.9 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 • 1% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $210 (round-trip)
Shortest trip • 4h 20m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 46% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 37% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
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Expert advice
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

Sat, Jul 25 - Tue, Jul 28
Delta Logo
5:00 pm - 10:15 pm
CHS
-
MDW
6h 15m
1 stop
Delta Logo
6:00 am - 1:42 pm
MDW
-
CHS
6h 42m
1 stop
$277Delta
Wed, Jul 8 - Wed, Jul 15
Delta Logo
7:06 am - 1:03 pm
CHS
-
ORD
6h 57m
1 stop
Delta Logo
6:35 am - 1:42 pm
ORD
-
CHS
6h 07m
1 stop
$277Delta
Sat, Sep 5 - Wed, Sep 9
Southwest Logo
8:05 am - 1:05 pm
CHS
-
MDW
6h 00m
2 stops
Southwest Logo
12:45 pm - 7:15 pm
MDW
-
CHS
5h 30m
1 stop
$278Southwest
Thu, Aug 27 - Mon, Aug 31
American Airlines Logo
12:23 pm - 1:59 pm
CHS
-
ORD
2h 36mnonstop
American Airlines Logo
7:03 am - 1:28 pm
ORD
-
CHS
5h 25m
1 stop
$279American Airlines
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
6:30 pm - 7:40 pm
CHS
-
MDW
2h 10mnonstop
Southwest Logo
11:00 am - 4:40 pm
MDW
-
CHS
4h 40m
1 stop
$279Southwest
Thu, Aug 6 - Mon, Aug 10
Multiple Airlines Logo
8:20 pm - 7:49 am
CHS
-
RFD
12h 29m
1 stop
Multiple Airlines Logo
6:26 pm - 8:38 am
RFD
-
CHS
13h 12m
1 stop
$279Multiple Airlines
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
10:20 am - 2:22 pm
CHS
-
ORD
5h 02m
1 stop
American Airlines Logo
8:13 am - 11:33 am
ORD
-
CHS
2h 20mnonstop
$280American Airlines
Wed, Jul 8 - Wed, Jul 15
Southwest Logo
3:00 pm - 8:10 pm
CHS
-
MDW
6h 10m
2 stops
Southwest Logo
7:25 am - 1:30 pm
MDW
-
CHS
5h 05m
1 stop
$282Southwest
Thu, Jul 9 - Mon, Jul 13
Multiple Airlines Logo
2:53 pm - 7:00 pm
CHS
-
RFD
29h 07m
1 stop
Multiple Airlines Logo
7:50 pm - 8:38 am
RFD
-
CHS
11h 48m
1 stop
$285Multiple Airlines
Thu, Jul 30 - Tue, Aug 4
United Airlines Logo
11:31 am - 1:10 pm
CHS
-
ORD
2h 39mnonstop
United Airlines Logo
6:25 pm - 9:48 pm
ORD
-
CHS
2h 23mnonstop
$297United 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 July.

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 $280 on the route between Charleston (CHS) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 1% 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 Mondays 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 $104 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $237 and $225 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 4 weeks before departure, which saves you about 46% 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 seasonJanuary
Cheapest flight$103
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 4% 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 $103 for a one-way ticket and $277 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, Alaska Airlines, and JetBlue 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Charleston and Chicago, with SkyTeam 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 $370 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $371 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 $195 or less one-way and $360 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.
7.9
SouthwestOverall score based on 4235 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

10.0 ExcellentAnonymous, Jun 2026
DEN - ORF
Read more Southwest reviews

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

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

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

Information on your arrival and departure airports