CHS - CHI

$118 Find Cheap Flights from Charleston to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$250
Typical prices: $313-$445
Multiple Airlines
Mon 10/15Fri 10/19
CHS - ORD • 1 stop
Cheapest non-stop
$321
Typical prices: $316-$449
Southwest
Wed 10/31Sat 11/3
CHS - MDW • Non-stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and Southwest. Average duration is 2h 36m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 25 weeks in advance save around 52% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 8% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $225 (round-trip)
Shortest trip • 4h 36m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Charleston to Chicago (CHS-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Charleston to Chicago

Thu, Oct 15 - Mon, Oct 19
Multiple Airlines Logo
2:13 pm - 7:31 amCHS  Charleston-ORD Chicago O'Hare Intl
18h 18m1 stop Orlando
Multiple Airlines Logo
8:11 pm - 2:38 pmORD  Chicago O'Hare Intl-CHS Charleston
17h 27m1 stop Orlando
$250Multiple Airlines
Thu, Oct 15 - Mon, Oct 26
Multiple Airlines Logo
2:13 pm - 7:31 amCHS  Charleston-ORD Chicago O'Hare Intl
18h 18m1 stop Orlando
Multiple Airlines Logo
8:11 pm - 8:38 amORD  Chicago O'Hare Intl-CHS Charleston
11h 27m1 stop Orlando
$252Multiple Airlines
Thu, Oct 15 - Mon, Oct 19
Multiple Airlines Logo
2:13 pm - 7:31 amCHS  Charleston-ORD Chicago O'Hare Intl
18h 18m1 stop Orlando
Multiple Airlines Logo
8:11 pm - 2:38 pmORD  Chicago O'Hare Intl-CHS Charleston
17h 27m1 stop Orlando
$263Multiple Airlines
Wed, Dec 23 - Thu, Dec 24
United Airlines Logo
6:39 pm - 8:19 pmCHS  Charleston-ORD Chicago O'Hare Intl
2h 40mnonstop
United Airlines Logo
6:25 pm - 9:57 pmORD  Chicago O'Hare Intl-CHS Charleston
2h 32mnonstop
$321United Airlines
Tue, Nov 10 - Sat, Nov 14
United Airlines Logo
7:00 pm - 8:40 pmCHS  Charleston-ORD Chicago O'Hare Intl
2h 40mnonstop
United Airlines Logo
7:47 am - 11:21 amORD  Chicago O'Hare Intl-CHS Charleston
2h 34mnonstop
$321United Airlines
Wed, Oct 14 - Wed, Oct 21
American Airlines Logo
7:16 am - 8:59 amCHS  Charleston-ORD Chicago O'Hare Intl
2h 43mnonstop
American Airlines Logo
8:40 pm - 11:59 pmORD  Chicago O'Hare Intl-CHS Charleston
2h 19mnonstop
$321American Airlines
Wed, Oct 14 - Thu, Oct 22
American Airlines Logo
7:16 am - 8:59 amCHS  Charleston-ORD Chicago O'Hare Intl
2h 43mnonstop
American Airlines Logo
8:40 pm - 11:59 pmORD  Chicago O'Hare Intl-CHS Charleston
2h 19mnonstop
$321American Airlines
Sat, Oct 31 - Tue, Nov 3
Southwest Logo
8:20 am - 9:30 amCHS  Charleston-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
1:25 pm - 4:30 pmMDW  Chicago Midway-CHS Charleston
2h 05mnonstop
$321Southwest
Tue, Oct 27 - Thu, Oct 29
Southwest Logo
7:15 am - 8:25 amCHS  Charleston-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
12:55 pm - 4:05 pmMDW  Chicago Midway-CHS Charleston
2h 10mnonstop
$321Southwest
Sat, Oct 31 - Wed, Nov 4
Southwest Logo
8:20 am - 9:30 amCHS  Charleston-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
1:25 pm - 4:30 pmMDW  Chicago Midway-CHS Charleston
2h 05mnonstop
$321Southwest
Booking Insights

Price, demand and travel trends for Charleston to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Charleston to Chicago with more confidence.

What is the cheapest Charleston to Chicago flight route?

There's little price difference between Charleston to Chicago routes. They average around $374 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Charleston to Chicago?

Wednesday is the cheapest day of the week to fly from Charleston to Chicago, it is 11% cheaper than the average day. Monday is the most expensive day with flight prices 16% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Charleston to Chicago?

  • September is the cheapest month to fly from Charleston to Chicago at $344 round-trip.
  • May ($404) and July ($389) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 17% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Charleston to Chicago the cheapest?

Flights from Charleston to Chicago are cheapest 25 weeks before departure. Booking in this window typically costs about 52% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Charleston to Chicago

 
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.

Key details for Charleston to Chicago flights

Low season

February

Cheapest flight

$118
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 4% increase in price.
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

Your Charleston to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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.

  • Which airlines offer extra legroom and free seat selection on Charleston to Chicago flights?

    Among airlines operating Charleston to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Charleston to Chicago?

    3 airlines operate flights between Charleston and Chicago. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Southwest

  • Which airports can I use when flying from Charleston to Chicago?

    Flights from Charleston to Chicago usually depart from Charleston (CHS) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airlines include bags at no extra cost on Charleston to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Business Class
    • Southwest: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Charleston to Chicago?

    Three cabin classes are available on flights from Charleston to Chicago:

    • Economy Class
    • Business Class
    • First Class

  • How much can I save by taking a layover when flying from Charleston to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $225 round-trip via Fort Lauderdale (FLL), compared to $376 for nonstop.

  • What is the standard checked-bag allowance on flights from Charleston to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Charleston to Chicago pass through?

    One-stop flights from Charleston to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 46% of one-stop connections
    • Fort Lauderdale (FLL) - 21% of one-stop connections
    • New York John F Kennedy Intl (JFK) - 13% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 13% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Charleston to Chicago?

    Yes. Being flexible with your travel dates can save you up to 24% on the Charleston to Chicago route. Wednesday is the cheapest departure day at $333 round-trip on average, while Monday is the most expensive at $434, a difference of $101. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How are flight departures from Charleston to Chicago spread across the day?

    Morning is the busiest departure period on Charleston to Chicago flights, with 38% of flights leaving in that window. Afternoon departures account for 37%, evening flights for 25%, and night flights for 0%.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

  • What are the earliest and latest flights from Charleston to Chicago?

    These are the earliest and latest flight times available from Charleston to Chicago:

    • Earliest: departs at 5:35 am and lands at 8:11 am
    • Latest: departs at 7:46 pm and lands at 10:22 pm.

    The flight takes about 2h 36m.

  • How expensive are last-minute Charleston to Chicago flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 48% above the route average of $373. Book 25 weeks before departure for the lowest fares.

  • How long is a flight from Charleston to Chicago?

    A nonstop flight from Charleston to Chicago takes 2h 36m, covering 746 miles.

  • Do I need a passport to fly from Charleston to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Charleston to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $243 to $1,574. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Charleston to Chicago looking right now?

    One-way fares from Charleston to Chicago are currently lower than usual. Average one-way flight prices are about $142, which is 38% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Charleston to Chicago?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 4h 36m, compared with 5h 21m via Detroit Metropolitan Wayne County (DTW) and 6h 20m via Chicago O'Hare Intl (ORD).

  • What is the time difference between Charleston and Chicago?

    Chicago is 1 hour behind Charleston (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Dollar
    • Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • How much should I expect to pay for a Charleston to Chicago flight?

    Round-trip flights from Charleston to Chicago range from $313 to $445, with an average of $373 over the past 12 months. Anything below $313 counts as a good deal.

  • Which airlines offer Wi-Fi on Charleston to Chicago flights?

    American Airlines is the only airline on the Charleston to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.

Your guide to booking Charleston to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Monday. On this route, Wednesday flights average $333 - about $101 less than Monday (23% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 25 weeks before you fly. On this route, that window historically saves about 52% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Charleston to Chicago trip for September. Fares historically average $344 round-trip in that month - typically $60 less than the most expensive month, which is May (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Fort Lauderdale Airport (FLL) can be cheaper than flying direct. The cheapest layover option averages $225 round-trip on this route - about $152 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel
  • 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?

 
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

More options for your flight from Charleston to Chicago

Complete your trip to Chicago with a hotel stay or car rental