Cheap Flights from Charleston to Chicago
Browse current best options from Charleston. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Charleston
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Prices updated 24 days ago
486,190 searches this week
171 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Charleston to Chicago
Explore current cheapest deals departing from Charleston to Chicago
Round trip
Sort by: Cheapest
September 1 - September 21
CHS - Chicago
$220
$219
Round trip
August 25 - September 21
CHS - Chicago
$238
$219
Round trip
September 23 - September 29
CHS - Chicago
$276
$226
Round trip
September 23 - September 28
CHS - Chicago
$172
$228
Round trip
October 10 - October 14
CHS - Chicago
$190
$229
Round trip
August 26 - August 31
CHS - Chicago
$289
$232
Round trip
July 15 - July 22
CHS - Chicago
$159
$237
Round trip
July 7 - July 14
CHS - Chicago
$253
$237
Round trip
July 8 - July 14
CHS - Chicago
$254
$237
Round trip
July 14 - July 15
CHS - Chicago
$282
$237
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Charleston to Chicago
How much is a round trip from Charleston to Chicago
Regular price: $186 - $324
Prices for flights from Charleston to Chicago are currently within the regular range.
The regular price range for flights from Charleston to Chicago is between $186 and $324. The current lowest deal is $219 with Breeze Airways for travel from Sep 1-Sep 21.
now $219
Low $186
High $324
The cheapest time to fly from Charleston to Chicago
The cheapest month to fly from Charleston to Chicago is April, with a median price of $245. The most expensive month is June, with a median price of $631. Prices are generally lower from January to November.
April
Flights from $245
June
Flights from $631
Direct flights from Charleston to Chicago
American Airlines
Last-minute flights going from Charleston to Chicago
Sat, Jun 27
CHS - Chicago
Charleston (CHS) - Chicago (RFD)
JetBlue Airways
$369
$337
One-way
Wed, Jul 1
CHS - Chicago
Charleston (CHS) - Chicago (ORD)
American Airlines
$164
$279
One-way
Wed, Jul 1
CHS - Chicago
Charleston (CHS) - Chicago (ORD)
United Airlines
$164
$280
One-way
Sat, Jul 4
CHS - Chicago
Charleston (CHS) - Chicago (ORD)
United Airlines
$173
$280
One-way
Mon, Jul 6
CHS - Chicago
Charleston (CHS) - Chicago (MDW)
Breeze Airways
$293
$346
One-way
Tue, Jul 7
CHS - Chicago
Charleston (CHS) - Chicago (ORD)
$253
$237
One-way
Biggest price drops on these dates for flights from Charleston to Chicago
Aug 26 - Aug 31
$289 → $232
20%
Dec 1 - Dec 15
$301 → $247
18%
Sep 23 - Sep 29
$276 → $226
18%
Jul 14 - Jul 15
$282 → $237
16%
Popular Airports to fly from Charleston to Chicago
Charleston - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares for Charleston to Chicago are above the typical level, with a median price of $325.
📅 Best time to fly
April is historically cheapest at $245
Historically, April is the cheapest month to fly from Charleston to Chicago, with a median price of $245.
⏱️ Flight duration
Typically 5h 4m to Chicago
Flights from Charleston to Chicago typically take 5 hours and 4 minutes, covering 1199 km.
✈️ Airlines & availability
Mixed availability of direct flights
Approximately 49.6% of recent deals are for direct flights, indicating mixed availability.
🏆 Airline highlight
American Airlines offers direct flights
American Airlines has offered direct flights from Charleston to Chicago in recent deals.
🎯 Booking tip
Deals appear frequently
Deals for flights from Charleston to Chicago appear frequently, averaging 1.03 deals per day.
Charleston main airports to depart from
Charleston International (CHS)
Charleston International Airport (CHS) is a good option for flights from Charleston to Chicago.
📍 ~20 km from city center
💸 Flights from ~$219
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub, offering extensive connections for your arrival in Chicago.
📍 ~27 km from Chicago (reachable by car)
💸 Flights from ~$219
Chicago Midway International (MDW)
Chicago Midway International Airport provides a convenient arrival option for your trip to Chicago.
📍 ~14 km from Chicago (reachable by car)
💸 Flights from ~$237
Chicago Rockford International (RFD)
Chicago Rockford International Airport is an alternative arrival point for flights to the Chicago area.
📍 ~100 km from Chicago (reachable by car)
💸 Flights from ~$261
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from destination city (reachable by rail)
💸 Flights from ~$300
South Bend International (SBN)
South Bend International is geographically the closest alternative to Chicago, with direct commuter rail connections.
📍 ~120 km from destination city (reachable by rail)
💸 Flights from ~$227
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub offering a wide range of cabin classes.
📍 ~200 km from destination city (reachable by car)
💸 Flights from ~$274
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service and less congestion.
📍 ~200 km from destination city (reachable by car)
💸 Flights from ~$257
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service and is an alternative for southeastern Chicago suburbs.
📍 ~230 km from destination city (reachable by car)
💸 Flights from ~$288
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Charleston to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From CHS
Elite
Jul 28
Chicago, United States
81% AI deal score
$916
$547
Save $369
From CHS
Elite
Sep 29
Chicago, United States
81% AI deal score
$951
$547
Save $404
From CHS
Elite
Sep 09
Chicago, United States
81% AI deal score
$941
$547
Save $394
From CHS
Elite
Sep 08
Chicago, United States
81% AI deal score
$941
$548
Save $393
From CHS
Elite
Sep 28
Chicago, United States
80% AI deal score
$949
$579
Save $370
From CHS
Elite
Aug 27
Chicago, United States
78% AI deal score
$1,772
$669
Save $1,103
From CHS
Elite
Aug 11
Chicago, United States
76% AI deal score
$712
$537
Save $175
From CHS
Elite
Jul 14
Chicago, United States
76% AI deal score
$704
$537
Save $167
From CHS
Elite
Aug 06
Chicago, United States
76% AI deal score
$784
$569
Save $215
From CHS
Elite
Aug 06
Chicago, United States
75% AI deal score
$721
$569
Save $152
From CHS
Elite
Oct 28
Chicago, United States
74% AI deal score
$671
$537
Save $134
From CHS
Elite
Jul 10
Chicago, United States
74% AI deal score
$1,450
$914
Save $536
From CHS
Elite
Jul 07
Chicago, United States
74% AI deal score
$624
$519
Save $105
From CHS
Elite
Aug 06
Chicago, United States
74% AI deal score
$769
$551
Save $218
From CHS
Elite
Aug 27
Chicago, United States
71% AI deal score
$787
$551
Save $236
From CHS
Elite
Jul 14
Chicago, United States
70% AI deal score
$634
$537
Save $97
From CHS
Elite
Aug 24
Chicago, United States
70% AI deal score
$710
$569
Save $141
From CHS
Elite
Aug 20
Chicago, United States
70% AI deal score
$711
$569
Save $142
From CHS
Elite
Jul 01
Chicago, United States
70% AI deal score
$702
$579
Save $123
From CHS
Elite
Jul 01
Chicago, United States
70% AI deal score
$703
$579
Save $124
From CHS
Elite
Jul 14
Chicago, United States
70% AI deal score
$626
$519
Save $107
From CHS
Elite
Aug 29
Chicago, United States
69% AI deal score
$692
$569
Save $123
From CHS
Elite
Sep 24
Chicago, United States
69% AI deal score
$684
$570
Save $114
From CHS
Elite
Aug 21
Chicago, United States
69% AI deal score
$747
$613
Save $134
From CHS
Elite
Aug 27
Chicago, United States
69% AI deal score
$777
$629
Save $148
From CHS
Elite
Sep 09
Chicago, United States
69% AI deal score
$715
$519
Save $196
From CHS
Elite
Jul 14
Chicago, United States
69% AI deal score
$616
$519
Save $97
From CHS
Elite
Sep 05
Chicago, United States
69% AI deal score
$735
$535
Save $200
From CHS
Elite
Sep 17
Chicago, United States
69% AI deal score
$742
$551
Save $191
From CHS
Elite
Jul 01
Chicago, United States
69% AI deal score
$640
$561
Save $79
From CHS
Elite
Aug 26
Chicago, United States
69% AI deal score
$773
$595
Save $178
From CHS
Elite
Aug 05
Chicago, United States
69% AI deal score
$782
$595
Save $187
From CHS
Elite
Oct 31
Chicago, United States
68% AI deal score
$672
$569
Save $103
From CHS
Elite
Nov 25
Chicago, United States
68% AI deal score
$685
$579
Save $106
From CHS
Elite
Jul 15
Chicago, United States
68% AI deal score
$702
$613
Save $89
From CHS
Elite
Jun 27
Chicago, United States
68% AI deal score
$730
$639
Save $91
From CHS
Elite
Sep 16
Chicago, United States
68% AI deal score
$747
$595
Save $152
From CHS
Elite
Jul 13
Chicago, United States
67% AI deal score
$704
$623
Save $81
From CHS
Elite
Jul 08
Chicago, United States
67% AI deal score
$704
$623
Save $81
From CHS
Elite
Aug 30
Chicago, United States
67% AI deal score
$703
$629
Save $74
From CHS
Elite
Oct 09
Chicago, United States
67% AI deal score
$715
$629
Save $86
From CHS
Elite
Oct 07
Chicago, United States
67% AI deal score
$724
$595
Save $129
From CHS
Elite
Jul 29
Chicago, United States
66% AI deal score
$670
$613
Save $57
From CHS
Elite
Jul 16
Chicago, United States
66% AI deal score
$660
$613
Save $47
From CHS
Elite
Jul 08
Chicago, United States
66% AI deal score
$622
$579
Save $43
From CHS
Elite
Nov 26
Chicago, United States
65% AI deal score
$653
$611
Save $42
From CHS
Elite
Jul 29
Chicago, United States
50% AI deal score
$619
$595
Save $24
From CHS
Elite
Jul 16
Chicago, United States
50% AI deal score
$620
$595
Save $25
From CHS
Elite
Nov 08
Chicago, United States
50% AI deal score
$667
$628
Save $39
From CHS
Elite
Jul 18
Chicago, United States
49% AI deal score
$634
$621
Save $13
From CHS
Elite
Nov 23
Chicago, United States
49% AI deal score
$685
$664
Save $21
From CHS
Elite
Jul 24
Chicago, United States
48% AI deal score
$671
$613
Save $58
From CHS
Elite
Jul 30
Chicago, United States
48% AI deal score
$629
From CHS
Elite
Nov 06
Chicago, United States
48% AI deal score
$678
$671
Save $7
From CHS
Elite
Nov 20
Chicago, United States
46% AI deal score
$724
From CHS
Elite
Nov 01
Chicago, United States
46% AI deal score
$757
From CHS
Elite
Jun 20
Chicago, United States
44% AI deal score
$1,778
$1,755
Save $23
From CHS
Elite
Jul 01
Chicago, United States
42% AI deal score
$3,028
From CHS
Elite
Jul 01
Chicago, United States
42% AI deal score
$3,380
From CHS
Elite
Jun 19
Chicago, United States
42% AI deal score
$1,346
From CHS
Elite
Jul 01
Chicago, United States
41% AI deal score
$3,139
From CHS
Elite
Aug 28
Chicago, United States
41% AI deal score
$3,663
From CHS
Elite
Aug 01
Chicago, United States
41% AI deal score
$3,971
From CHS
Elite
Jun 22
Chicago, United States
40% AI deal score
$3,477
From CHS
Elite
Jul 01
Chicago, United States
40% AI deal score
$3,502
From CHS
Elite
Jun 22
Chicago, United States
40% AI deal score
$3,610
From CHS
Elite
Aug 28
Chicago, United States
40% AI deal score
$3,615
From CHS
Elite
Nov 19
Chicago, United States
40% AI deal score
$959
From CHS
Elite
Oct 26
Chicago, United States
40% AI deal score
$959
From CHS
Elite
Jun 22
Chicago, United States
39% AI deal score
$3,569
From CHS
Elite
Sep 04
Chicago, United States
39% AI deal score
$3,614
From CHS
Elite
Jul 14
Chicago, United States
39% AI deal score
$3,649
From CHS
Elite
Jul 01
Chicago, United States
39% AI deal score
$3,684
From CHS
Elite
Jul 24
Chicago, United States
39% AI deal score
$3,690
From CHS
Elite
Jul 25
Chicago, United States
39% AI deal score
$3,728
From CHS
Elite
Jul 17
Chicago, United States
39% AI deal score
$3,733
From CHS
Elite
Jul 24
Chicago, United States
39% AI deal score
$3,736
From CHS
Elite
Jul 28
Chicago, United States
39% AI deal score
$3,765
From CHS
Elite
Jul 25
Chicago, United States
39% AI deal score
$3,774
From CHS
Elite
Jul 28
Chicago, United States
39% AI deal score
$3,812
From CHS
Elite
Jul 31
Chicago, United States
39% AI deal score
$3,835
From CHS
Elite
Jul 24
Chicago, United States
39% AI deal score
$3,960
From CHS
Elite
Jun 18
Chicago, United States
39% AI deal score
$3,984
From CHS
Elite
Jul 27
Chicago, United States
39% AI deal score
$3,998
From CHS
Elite
Aug 11
Chicago, United States
39% AI deal score
$4,041
From CHS
Elite
Jul 17
Chicago, United States
38% AI deal score
$3,687
From CHS
Elite
Jun 22
Chicago, United States
38% AI deal score
$3,691
From CHS
Elite
Jul 14
Chicago, United States
38% AI deal score
$3,695
From CHS
Elite
Jul 10
Chicago, United States
38% AI deal score
$3,748
From CHS
Elite
Jun 18
Chicago, United States
38% AI deal score
$3,776
From CHS
Elite
Jul 10
Chicago, United States
38% AI deal score
$3,794
From CHS
Elite
Jul 23
Chicago, United States
38% AI deal score
$3,819
From CHS
Elite
Jul 23
Chicago, United States
38% AI deal score
$3,865
From CHS
Elite
Jun 18
Chicago, United States
38% AI deal score
$3,868
From CHS
Elite
Jul 11
Chicago, United States
38% AI deal score
$3,871
From CHS
Elite
Jun 18
Chicago, United States
38% AI deal score
$3,910
From CHS
Elite
Jul 11
Chicago, United States
38% AI deal score
$3,917
From CHS
Elite
Jul 14
Chicago, United States
38% AI deal score
$3,919
From CHS
Elite
Jul 03
Chicago, United States
38% AI deal score
$3,948
From CHS
Elite
Jul 27
Chicago, United States
38% AI deal score
$3,951