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Charleston to Chicago flight ticket price

Compare live prices for CHS to MDW. Use the search panel to change origin, destination, passengers, cabin and trip type instantly.
CHS → MDW Approx. 1199.41 km 11 May 2026 Live inventory
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Showing 25 of 151 live flights
Delta Air Lines
DL-3179
19:59
05/11/2026
CHS
Charleston Air Force Base-International Airport
4h 0m
1 Stop
⏱ ATL · 1h 21mATL Airport
23:59
05/11/2026
ORD
Chicago Midway International Airport
₹13,639
per person
✕ Non-refundable
Delta Air Lines
DL-1381
16:55
05/11/2026
CHS
Charleston Air Force Base-International Airport
4h 58m
1 Stop
⏱ ATL · 2h 37mATL Airport
21:53
05/11/2026
ORD
Chicago Midway International Airport
₹13,639
per person
✕ Non-refundable
Southwest Airlines
WN-1291
19:55
05/11/2026
CHS
Charleston Air Force Base-International Airport
3h 35m
1 Stop
⏱ BNA · 1h 25mBNA Airport
23:30
05/11/2026
MDW
Chicago Midway International Airport
₹14,315
per person
✕ Non-refundable10 fare options
Southwest Airlines
WN-3165
07:40
05/11/2026
CHS
Charleston Air Force Base-International Airport
1h 15m
Non-stop
08:55
05/11/2026
MDW
Chicago Midway International Airport
₹17,067
per person
✕ Non-refundable10 fare options
Southwest Airlines
WN-1086
14:15
05/11/2026
CHS
Charleston Air Force Base-International Airport
3h 35m
1 Stop
⏱ STL · 1h 10mSTL Airport
17:50
05/11/2026
MDW
Chicago Midway International Airport
₹18,170
per person
✕ Non-refundable10 fare options
Southwest Airlines
WN-1364
15:00
05/11/2026
CHS
Charleston Air Force Base-International Airport
6h 55m
1 Stop
⏱ HOU · 2h 45mHOU Airport
21:55
05/11/2026
MDW
Chicago Midway International Airport
₹18,170
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-1364
15:00
05/11/2026
CHS
Charleston Air Force Base-International Airport
8h 30m
2 Stops
⏱ HOU · 2h 35mHOU Airport⏱ BNA · 0h 40mBNA Airport
23:30
05/11/2026
MDW
Chicago Midway International Airport
₹18,848
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-1364
15:00
05/11/2026
CHS
Charleston Air Force Base-International Airport
8h 55m
2 Stops
⏱ HOU · 0h 45mHOU Airport⏱ DAL · 3h 5mDAL Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹18,848
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-1364
15:00
05/11/2026
CHS
Charleston Air Force Base-International Airport
8h 55m
2 Stops
⏱ HOU · 1h 45mHOU Airport⏱ DAL · 1h 55mDAL Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹18,848
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-1441
06:00
05/11/2026
CHS
Charleston Air Force Base-International Airport
8h 55m
2 Stops
⏱ BNA · 3h 0mBNA Airport⏱ SDF · 3h 0mSDF Airport
14:55
05/11/2026
MDW
Chicago Midway International Airport
₹18,848
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-1364
15:00
05/11/2026
CHS
Charleston Air Force Base-International Airport
8h 30m
2 Stops
⏱ HOU · 0h 45mHOU Airport⏱ BNA · 0h 50mBNA Airport
23:30
05/11/2026
MDW
Chicago Midway International Airport
₹19,349
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-1291
19:55
05/11/2026
CHS
Charleston Air Force Base-International Airport
10h 55m
2 Stops
⏱ BNA · 1h 35mBNA Airport⏱ MSP · 5h 0mMSP Airport
06:50
05/12/2026
+1
MDW
Chicago Midway International Airport
₹19,377
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-1441
06:00
05/11/2026
CHS
Charleston Air Force Base-International Airport
6h 50m
1 Stop
⏱ BNA · 4h 25mBNA Airport
12:50
05/11/2026
ORD
Chicago Midway International Airport
₹19,909
per person
✓ Refundable8 fare options
United Airlines
UA-1498
17:08
05/11/2026
CHS
Charleston Air Force Base-International Airport
1h 37m
Non-stop
18:45
05/11/2026
ORD
Chicago Midway International Airport
₹20,235
per person
✕ Non-refundable5 fare options
United Airlines
UA-5525
18:53
05/11/2026
CHS
Charleston Air Force Base-International Airport
1h 47m
Non-stop
20:40
05/11/2026
ORD
Chicago Midway International Airport
₹20,235
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-1524
17:45
05/11/2026
CHS
Charleston Air Force Base-International Airport
6h 10m
1 Stop
⏱ DAL · 2h 10mDAL Airport
23:55
05/11/2026
MDW
Chicago Midway International Airport
₹20,630
per person
✕ Non-refundable🔥 Last 5 seats9 fare options
American Airlines
AA-2991
12:29
05/11/2026
CHS
Charleston Air Force Base-International Airport
1h 36m
Non-stop
14:05
05/11/2026
ORD
Chicago Midway International Airport
₹20,697
per person
✕ Non-refundable9 fare options
American Airlines
AA-2014
07:07
05/11/2026
CHS
Charleston Air Force Base-International Airport
1h 40m
Non-stop
08:47
05/11/2026
ORD
Chicago Midway International Airport
₹20,697
per person
✕ Non-refundable9 fare options
American Airlines
AA-4711
18:32
05/11/2026
CHS
Charleston Air Force Base-International Airport
1h 53m
Non-stop
20:25
05/11/2026
ORD
Chicago Midway International Airport
₹20,697
per person
✕ Non-refundable🔥 Last 5 seats9 fare options
United Airlines
UA-6161
19:44
05/11/2026
CHS
Charleston Air Force Base-International Airport
4h 0m
1 Stop
⏱ IAD · 1h 5mIAD Airport
23:44
05/11/2026
ORD
Chicago Midway International Airport
₹21,143
per person
✕ Non-refundable5 fare options
United Airlines
UA-1858
10:15
05/11/2026
CHS
Charleston Air Force Base-International Airport
6h 15m
1 Stop
⏱ IAD · 3h 23mIAD Airport
16:30
05/11/2026
ORD
Chicago Midway International Airport
₹21,143
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-1086
14:15
05/11/2026
CHS
Charleston Air Force Base-International Airport
9h 25m
2 Stops
⏱ STL · 1h 45mSTL Airport⏱ DEN · 1h 45mDEN Airport
23:40
05/11/2026
MDW
Chicago Midway International Airport
₹21,307
per person
✕ Non-refundable🔥 Last 2 seats4 fare options
Southwest Airlines
WN-1441
06:00
05/11/2026
CHS
Charleston Air Force Base-International Airport
8h 30m
2 Stops
⏱ BNA · 1h 5mBNA Airport⏱ AUS · 1h 55mAUS Airport
14:30
05/11/2026
MDW
Chicago Midway International Airport
₹21,307
per person
✕ Non-refundable🔥 Last 1 seats4 fare options
Southwest Airlines
WN-1503
13:15
05/11/2026
CHS
Charleston Air Force Base-International Airport
7h 25m
2 Stops
⏱ BNA · 1h 35mBNA Airport⏱ BUF · 1h 45mBUF Airport
20:40
05/11/2026
MDW
Chicago Midway International Airport
₹21,307
per person
✕ Non-refundable🔥 Last 1 seats4 fare options
Southwest Airlines
WN-1503
13:15
05/11/2026
CHS
Charleston Air Force Base-International Airport
7h 0m
2 Stops
⏱ BNA · 2h 0mBNA Airport⏱ CMH · 1h 50mCMH Airport
20:15
05/11/2026
MDW
Chicago Midway International Airport
₹21,307
per person
✕ Non-refundable🔥 Last 1 seats4 fare options
😕 No flights match your filters.
Charleston (CHS)
📍 Charleston Air Force Base-International Airport
🌍 United States
🕐 GMT -5
📐 Latitude: 32.89860153
📐 Longitude: -80.04049683
Chicago (MDW)
📍 Chicago Midway International Airport
🌍 United States
🕐 GMT -6
📐 Latitude: 41.785999
📐 Longitude: -87.752403

✈ Distance: Charleston,USA to Chicago,USA1199.41 km

📅 Results on this page are loaded for 11 May 2026. Click View all flights for the complete live search.

Charleston to Chicago — what to expect when booking

The CHS–MDW route is served by multiple carriers throughout the year. Fares on this route can move quickly — a price available now may not be there 30 minutes later.

If your dates are flexible, try shifting your departure by a day or two using the date strip above. Mid-week departures often show lower base fares compared to weekend starts on many routes.

The distance between Charleston,USA and Chicago,USA is approximately 1199.41 km.

Before you book

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More flights from Charleston (CHS)
14 routes
More flights from Chicago (MDW)
69 routes
Chicago Albany
MDW → ALB
Chicago Albuquerque
MDW → ABQ
Chicago Amarillo
MDW → AMA
Chicago Atlanta
MDW → ATL
Chicago Austin
MDW → AUS
Chicago Birmingham
MDW → BHM
Chicago Boston
MDW → BOS
Chicago Buffalo
MDW → BUF
Chicago Cancun
MDW → CUN
Chicago Charleston
MDW → CHS
Chicago Charlotte
MDW → CLT
Chicago Cleveland
MDW → CLE
Chicago Columbus
MDW → CMH
Chicago Denver
MDW → DEN
Chicago Des Moines
MDW → DSM
Chicago Detroit
MDW → DTW
Chicago Fort Lauderdale
MDW → FLL
Chicago Fort Myers
MDW → RSW
Chicago Greenville
MDW → GSP
Chicago Guadalajara
MDW → GDL
Chicago Hartford
MDW → BDL
Chicago Houston
MDW → HOU
Chicago Jackson
MDW → JAN
Chicago Jacksonville
MDW → JAX
Chicago Kansas City
MDW → MCI
Chicago Las Vegas
MDW → LAS
Chicago Leon
MDW → BJX
Chicago Little Rock
MDW → LIT
Chicago Los Angeles
MDW → LAX
Chicago Louisville
MDW → SDF
Chicago Manchester
MDW → MHT
Chicago Memphis
MDW → MEM
Chicago Minneapolis
MDW → MSP
Chicago Montego Bay
MDW → MBJ
Chicago Morelia
MDW → MLM
Chicago Nashville
MDW → BNA
Chicago New Orleans
MDW → MSY
Chicago New York
MDW → LGA
Chicago Norfolk
MDW → ORF
Chicago Oakland
MDW → OAK
Chicago Oklahoma City
MDW → OKC
Chicago Omaha
MDW → OMA
Chicago Ontario
MDW → ONT
Chicago Orlando
MDW → MCO
Chicago Philadelphia
MDW → PHL
Chicago Phoenix
MDW → PHX
Chicago Pittsburgh International Airport
MDW → PIT
Chicago Portland International
MDW → PDX
Chicago Providence
MDW → PVD
Chicago Punta Cana
MDW → PUJ
Chicago Raleigh
MDW → RDU
Chicago Reno
MDW → RNO
Chicago Rochester
MDW → ROC
Chicago Sacramento
MDW → SMF
Chicago Salt Lake City
MDW → SLC
Chicago San Antonio
MDW → SAT
Chicago San Diego
MDW → SAN
Chicago San Francisco
MDW → SFO
Chicago San Jose
MDW → SJC
Chicago Seattle
MDW → SEA
Chicago St. Louis
MDW → STL
Chicago Tampa
MDW → TPA
Chicago Toronto
MDW → YTZ
Chicago Trenton
MDW → TTN
Chicago Tucson
MDW → TUS
Chicago Tulsa
MDW → TUL
Chicago Washington DC
MDW → IAD
Chicago Wichita
MDW → ICT
Chicago Zacatecas
MDW → ZCL
❓ Frequently asked questions — Charleston to Chicago flights

Generally yes — fares on most routes are most competitive around 4–6 weeks before departure. Booking earlier usually means better availability and a lower base fare when your dates are fixed.

The straight-line distance between Charleston,USA (CHS) and Chicago,USA (MDW) is approximately 1199.41 km. Actual flying distance may vary slightly depending on routing.

Non-stop availability on this route varies by airline schedule and season. Use the filters below to quickly check whether direct options are available on your selected date.

Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.