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Flights Chicago – Miami, Southwest Airlines

1 passenger, economy

Flight schedule Chicago – Miami, Southwest Airlines

Compare prices, duration and stops

Southwest Airlines
WN 2412
14:25
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
3h
Direct
17:25
Miami (MIA)
Tue, 22 sep
S$368
Southwest Airlines
WN 2929
16:35
Chicago, Chicago Midway International Airport (MDW)
Tue, 20 oct
3h 10min
Direct
19:45
Miami (MIA)
Tue, 20 oct
S$110
Southwest Airlines
WN 2929 Best price
16:35
Chicago, Chicago Midway International Airport (MDW)
Wed, 28 oct
3h 10min
Direct
19:45
Miami (MIA)
Wed, 28 oct
S$103
Southwest Airlines
WN 1362 Best price
19:20
Chicago, Chicago Midway International Airport (MDW)
Wed, 11 nov
3h
Direct
22:20
Miami (MIA)
Wed, 11 nov
S$103
Southwest Airlines
WN 2939
18:25
Chicago, Chicago Midway International Airport (MDW)
Fri, 13 nov
10h 20min
1 stop
04:45
Miami (MIA)
Sat, 14 nov +1
S$191
Southwest Airlines
WN 1362
19:25
Chicago, Chicago Midway International Airport (MDW)
Tue, 17 nov
3h
Direct
22:25
Miami (MIA)
Tue, 17 nov
S$152
Southwest Airlines
WN 2972
13:35
Chicago, Chicago Midway International Airport (MDW)
Wed, 25 nov
3h
Direct
16:35
Miami (MIA)
Wed, 25 nov
S$155
Southwest Airlines
WN 1362
19:25
Chicago, Chicago Midway International Airport (MDW)
Tue, 1 dec
3h
Direct
22:25
Miami (MIA)
Tue, 1 dec
S$110
Southwest Airlines
WN 1940
12:50
Chicago, Chicago Midway International Airport (MDW)
Fri, 19 mar
10h 20min
1 stop
23:10
Miami (MIA)
Fri, 19 mar
S$362
Southwest Airlines
WN 400
12:45
Chicago, Chicago Midway International Airport (MDW)
Sat, 20 mar
11h 5min
1 stop
23:50
Miami (MIA)
Sat, 20 mar
S$343
Southwest Airlines
WN 225
15:10
Chicago, Chicago Midway International Airport (MDW)
Sat, 20 mar
12h 45min
1 stop
03:55
Miami (MIA)
Sun, 21 mar +1
S$341

Low price calendar

September 2026
Price chart (September 2026)
min: S$79 · max: S$197
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S$178
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S$79
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S$177
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S$105
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S$170

Popular Southwest Airlines flights Chicago – Miami

All →
Flight Departure days Price from
WN2929 TueWed S$103
WN1362 TueWed S$103
WN2972 Wed S$155
WN2939 Fri S$191
WN225 Sat S$341
WN400 Sat S$343
WN1940 Fri S$362
WN2412 Tue S$368

Popular destinations from Chicago

All →
CHI
Chicago — Orlando
United States → United States
ORL
from
S$27
CHI
Chicago — Orlando
United States → United States
MCO
from
S$27
CHI
Chicago — Atlanta
United States → United States
ATL
from
S$28
CHI
Chicago — Houston
United States → United States
IAH
from
S$28
CHI
Chicago — Houston
United States → United States
HOU
from
S$28
CHI
Chicago — New York
United States → United States
NYC
from
S$30
CHI
Chicago — Denver
United States → United States
DEN
from
S$31
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
S$31

Popular destinations to Miami

All →
ATL
Atlanta — Miami
United States → United States
MIA
from
S$26
BWI
Baltimore — Miami
United States → United States
MIA
from
S$27
HOU
Houston — Miami
United States → United States
MIA
from
S$29
DFW
Dallas — Miami
United States → United States
MIA
from
S$29
PHL
Philadelphia — Miami
United States → United States
MIA
from
S$29
WAS
Washington — Miami
United States → United States
MIA
from
S$30
RDU
Raleigh — Miami
United States → United States
MIA
from
S$30
CLT
Charlotte — Miami
United States → United States
MIA
from
S$34

Flight statistics Chicago – Miami, Southwest Airlines

We gathered interesting facts about the flight for you

Cheapest flight

WN 2929

S$103

Fastest flight

WN 1362

3h

Average time

5h 59min

Distance

12 127 km

Passenger reviews

No reviews for this route yet

Other airlines Chicago – Miami

Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$65
American Airlines
American Airlines
Tue, Wed, Thu, Fri, Sat
Price from
S$101
United Airlines
United Airlines
Mon, Tue, Wed, Thu, Sat, Sun
Price from
S$102
Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$122
Allegiant Air
Allegiant Air
Sun
Price from
S$204

Internet abroad

eSIM · United States

All plans

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3 GB

data

30

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S$11

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2 GB

data

15

days

S$16

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5 GB

data

30

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S$18

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3 GB

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30

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S$20

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data

30

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S$29

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Frequently Asked Questions

The cheapest Southwest Airlines ticket Chicago – Miami costs S$103, flight WN2929, departing at 16:35.
The fastest Southwest Airlines flight Chicago – Miami takes 3h, flight WN2412, departing at 14:25.
The earliest Southwest Airlines flight Chicago – Miami(WN2412)departs at 14:25.