CHS - CHI

$79 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 4/14. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$274
Overall average: $571
Southwest
Mon 5/18Tue 5/19
CHS - MDW • 1 stop
Cheapest non-stop
$276
Southwest
Wed 4/22Fri 4/24
CHS - MDW • Non-stop
Advice from real travelers
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 airlines
Cheapest • from $274 (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 36m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 2% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $196 (round-trip)
Shortest trip • 4h 12m (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 52% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 17% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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
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, May 18 - Tue, May 19
Southwest Logo
5:45 pm - 11:55 pm
CHS
-
MDW
7h 10m
1 stop
Southwest Logo
8:15 am - 3:00 pm
MDW
-
CHS
5h 45m
1 stop
$274Southwest
Tue, May 5 - Sat, May 9
United Airlines Logo
10:15 am - 2:28 pm
CHS
-
ORD
5h 13m
1 stop
United Airlines Logo
4:20 pm - 7:39 pm
ORD
-
CHS
2h 19mnonstop
$274United Airlines
Tue, May 5 - Sat, May 9
American Airlines Logo
4:41 pm - 10:00 pm
CHS
-
ORD
6h 19m
1 stop
American Airlines Logo
2:36 pm - 6:02 pm
ORD
-
CHS
2h 26mnonstop
$275American Airlines
Wed, Apr 22 - Fri, Apr 24
American Airlines Logo
6:38 pm - 8:31 pm
CHS
-
ORD
2h 53mnonstop
American Airlines Logo
7:51 pm - 11:08 pm
ORD
-
CHS
2h 17mnonstop
$276American Airlines
Tue, May 5 - Sat, May 9
Southwest Logo
3:40 pm - 9:50 pm
CHS
-
MDW
7h 10m
1 stop
Southwest Logo
9:10 am - 8:15 pm
MDW
-
CHS
10h 05m
2 stops
$276Southwest
Mon, May 4 - Fri, May 8
Southwest Logo
2:15 pm - 5:50 pm
CHS
-
MDW
4h 35m
1 stop
Southwest Logo
3:50 pm - 8:50 pm
MDW
-
CHS
4h 00m
1 stop
$277Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
6:40 am - 12:50 pm
CHS
-
ORD
7h 10m
1 stop
Southwest Logo
2:40 pm - 8:00 pm
ORD
-
CHS
4h 20m
1 stop
$277Southwest
Fri, Apr 10 - Fri, Apr 17
Multiple Airlines Logo
8:07 am - 4:00 pm
CHS
-
ORD
8h 53m
1 stop
Multiple Airlines Logo
12:47 pm - 11:08 am
ORD
-
CHS
21h 21m
1 stop
$278Multiple Airlines
Wed, Apr 15 - Mon, Apr 20
Southwest Logo
3:40 pm - 10:15 pm
CHS
-
MDW
7h 35m
2 stops
Southwest Logo
12:00 pm - 6:20 pm
MDW
-
CHS
5h 20m
1 stop
$279Southwest
Tue, Apr 21 - Tue, Apr 28
Multiple Airlines Logo
3:01 pm - 1:00 pm
CHS
-
ORD
22h 59m
1 stop
Multiple Airlines Logo
1:27 pm - 11:08 am
ORD
-
CHS
20h 41m
2 stops
$279Multiple 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 May.

What is the cheapest Charleston to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The absolute cheapest return flight from Charleston to Chicago costs $259 on the route between Charleston (CHS) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Charleston (CHS) and Chicago Midway Airport (MDW) were, on average, 2% 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 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 November and March, where the average cost of round-trip tickets is $381 and $369 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 $369, 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 52% 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$79
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 5% 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 3 days, the lowest price for a flight from Charleston to Chicago was $79 for a one-way ticket and $274 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, Air France, and KLM offer inflight Wi-Fi service on the Charleston to Chicago flight route.

  • 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 $318 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 $368 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 $192 or less one-way and $359 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 4318 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

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

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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 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

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

Information on your arrival and departure airports