CHS - CHI

$44 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 2/25. 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
$123
Overall average: $454
Spirit Airlines
Mon 3/2Mon 3/9
CHS - ORD • 1 stop
Cheapest non-stop
$279
Southwest
Sat 2/21Mon 2/23
CHS - MDW • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest offers two free checked bags for savings.
Use the CTA Orange Line from MDW for a quick downtown trip.
Expert advice
Expert advice
Expert advice
Expert advice
Top routes
CHS
-
MDW
Cheapest • 9% average savings
CHS
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 48% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 22% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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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

Mon, Mar 2 - Mon, Mar 9
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
7:00 am - 5:40 pm
ORD
-
CHS
9h 40m
1 stop
$123Spirit Airlines
Tue, Feb 24 - Tue, Mar 3
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
6:51 pm - 4:05 pm
ORD
-
CHS
20h 14m
1 stop
$126Spirit Airlines
Mon, Mar 2 - Mon, Mar 9
Multiple Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Multiple Airlines Logo
12:05 pm - 4:05 pm
ORD
-
CHS
27h 00m
1 stop
$135Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Multiple Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Multiple Airlines Logo
3:40 pm - 5:40 pm
ORD
-
CHS
25h 00m
1 stop
$138Multiple Airlines
Thu, Feb 12 - Sun, Feb 15
Spirit Airlines Logo
6:35 pm - 11:47 pm
CHS
-
ORD
6h 12m
1 stop
Spirit Airlines Logo
7:00 am - 5:40 pm
ORD
-
CHS
9h 40m
1 stop
$142Spirit Airlines
Tue, Mar 3 - Wed, Mar 4
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
8:16 pm - 5:40 pm
ORD
-
CHS
20h 24m
1 stop
$144Spirit Airlines
Tue, Feb 24 - Tue, Mar 3
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
8:16 pm - 4:05 pm
ORD
-
CHS
18h 49m
2 stops
$150Spirit Airlines
Sat, Mar 14 - Mon, Mar 16
Multiple Airlines Logo
8:07 am - 7:46 pm
CHS
-
ORD
12h 39m
1 stop
Multiple Airlines Logo
12:20 pm - 8:03 pm
ORD
-
CHS
6h 43m
1 stop
$151Multiple Airlines
Sat, Feb 21 - Mon, Feb 23
Spirit Airlines Logo
5:00 pm - 12:40 am
CHS
-
ORD
8h 40m
1 stop
Spirit Airlines Logo
6:51 pm - 4:05 pm
ORD
-
CHS
20h 14m
1 stop
$153Spirit Airlines
Sat, Feb 21 - Mon, Feb 23
Southwest Logo
6:00 am - 7:15 am
CHS
-
MDW
2h 15mnonstop
Southwest Logo
2:45 pm - 5:45 pm
MDW
-
CHS
2h 00mnonstop
$279Southwest
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 $220 on the route between Charleston (CHS) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 9% 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 Fridays.

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 August, where tickets cost $284 (return) on average. On the other hand, the most expensive months are January and November, where the average cost of round-trip tickets is $498 and $381 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 $371, prices are generally cheapest when you fly direct.

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 48% 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$44
Best time to beat the crowds but there is an average 36% increase in price.
Most popular time to fly and prices are also 5% 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

  • 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 3 days, the lowest price for a flight from Charleston to Chicago was $44 for a one-way ticket and $123 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?

    All the following airlines offer inflight Wi-Fi service on the Charleston to Chicago flight route: American Airlines, JetBlue, Delta, Alaska Airlines, Air France, and KLM.

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

    The Embraer 175 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, oneworld, and Star Alliance 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 $324 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 $378 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 $183 or less one-way and $355 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, United Airlines, Southwest

American Airlines, United Airlines, +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, United Airlines, Southwest

American Airlines, United Airlines, +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 4268 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

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

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

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

Information on your arrival and departure airports