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Cheap flights Miami to Chicago Midway International Airport

1 passenger, economy

Cheap flights Miami to Chicago Midway International Airport

Compare prices, duration and stops

Frontier Airlines
F9 4954
00:50
Miami (MIA)
Mon, 14 sep
16h 9min
2 stops
16:59
Chicago, Chicago Midway International Airport (MDW)
Mon, 14 sep
357 S$
Frontier Airlines
F9 2271
01:30
Miami (MIA)
Mon, 14 sep
15h 29min
2 stops
16:59
Chicago, Chicago Midway International Airport (MDW)
Mon, 14 sep
173 S$
Southwest Airlines
WN 2368
11:15
Miami (MIA)
Mon, 14 sep
3h 5min
Direct
14:20
Chicago, Chicago Midway International Airport (MDW)
Mon, 14 sep
441 S$
Frontier Airlines
F9 4405
21:34
Miami (MIA)
Mon, 14 sep
7h 10min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep +1
448 S$
Frontier Airlines
F9 2483
09:32
Miami (MIA)
Tue, 15 sep
13h 14min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep
271 S$
Southwest Airlines
WN 2866
20:00
Miami (MIA)
Tue, 15 sep
3h 5min
Direct
23:05
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep
361 S$
Southwest Airlines
WN 2866
20:00
Miami (MIA)
Wed, 16 sep
3h 5min
Direct
23:05
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
361 S$
Southwest Airlines
WN 2368
11:15
Miami (MIA)
Thu, 17 sep
3h 5min
Direct
14:20
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
115 S$
Frontier Airlines
F9 4405
20:30
Miami (MIA)
Thu, 17 sep
8h 14min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Fri, 18 sep +1
195 S$
Southwest Airlines
WN 2368
11:15
Miami (MIA)
Fri, 18 sep
3h 5min
Direct
14:20
Chicago, Chicago Midway International Airport (MDW)
Fri, 18 sep
125 S$
Frontier Airlines
F9 4405
21:34
Miami (MIA)
Fri, 18 sep
7h 10min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep +1
164 S$
Frontier Airlines
F9 2483
09:22
Miami (MIA)
Sat, 19 sep
13h 29min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
254 S$
Frontier Airlines
F9 2173
10:45
Fort Lauderdale (FLL)
Sun, 20 sep
12h 1min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep
208 S$
Frontier Airlines
F9 4405
20:30
Miami (MIA)
Sun, 20 sep
8h 14min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep +1
251 S$
Frontier Airlines
F9 3013
01:54
Fort Lauderdale (FLL)
Mon, 21 sep
20h 57min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
165 S$
Frontier Airlines
F9 4405
21:34
Miami (MIA)
Mon, 21 sep
7h 10min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep +1
250 S$
Southwest Airlines
WN 2866
20:00
Miami (MIA)
Tue, 22 sep
3h 5min
Direct
23:05
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
106 S$
Frontier Airlines
F9 2271
01:43
Miami (MIA)
Wed, 23 sep
21h 8min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
190 S$
Frontier Airlines
F9 3013
01:54
Fort Lauderdale (FLL)
Wed, 23 sep
20h 57min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
190 S$
Frontier Airlines
F9 2483
09:32
Miami (MIA)
Wed, 23 sep
13h 19min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
261 S$
Southwest Airlines
WN 2866
20:00
Miami (MIA)
Wed, 23 sep
3h 5min
Direct
23:05
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
110 S$
Frontier Airlines
F9 4405
20:30
Miami (MIA)
Thu, 24 sep
8h 14min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Fri, 25 sep +1
215 S$
Frontier Airlines
F9 4405
21:34
Miami (MIA)
Fri, 25 sep
7h 10min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep +1
188 S$
Frontier Airlines
F9 2483
09:22
Miami (MIA)
Sat, 26 sep
13h 29min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
182 S$
Frontier Airlines
F9 2271
01:43
Miami (MIA)
Sun, 27 sep
15h 16min
2 stops
16:59
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 sep
287 S$
Frontier Airlines
F9 4135
20:05
Miami (MIA)
Sun, 27 sep
50h 41min
2 stops
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep +1
311 S$
Frontier Airlines
F9 2271
01:43
Miami (MIA)
Wed, 30 sep
21h 8min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 sep
200 S$
Frontier Airlines
F9 4405
20:30
Miami (MIA)
Thu, 1 oct
8h 14min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Fri, 2 oct +1
183 S$
Frontier Airlines
F9 4405
21:34
Miami (MIA)
Mon, 5 oct
7h 9min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Tue, 6 oct +1
180 S$
Southwest Airlines
WN 2547
16:35
Miami (MIA)
Tue, 6 oct
3h 5min
Direct
19:40
Chicago, Chicago Midway International Airport (MDW)
Tue, 6 oct
113 S$
Frontier Airlines
F9 2271
01:43
Miami (MIA)
Wed, 7 oct
21h 8min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 7 oct
205 S$
Frontier Airlines
F9 2483
09:32
Miami (MIA)
Wed, 7 oct
13h 19min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 7 oct
194 S$
Southwest Airlines
WN 3039
10:40
Miami (MIA)
Thu, 8 oct
3h 5min
Direct
13:45
Chicago, Chicago Midway International Airport (MDW)
Thu, 8 oct
109 S$
Southwest Airlines
WN 3039
10:40
Miami (MIA)
Fri, 9 oct
3h 5min
Direct
13:45
Chicago, Chicago Midway International Airport (MDW)
Fri, 9 oct
126 S$
Frontier Airlines
F9 2271
02:55
Miami (MIA)
Sat, 10 oct
25h 48min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Sun, 11 oct +1
208 S$
Frontier Airlines
F9 2173
10:39
Fort Lauderdale (FLL)
Sat, 10 oct
18h 4min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Sun, 11 oct +1
208 S$
Frontier Airlines
F9 2173
10:39
Fort Lauderdale (FLL)
Sat, 17 oct
18h 4min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Sun, 18 oct +1
186 S$
Frontier Airlines
F9 2483
11:00
Miami (MIA)
Mon, 19 oct
28h 58min
1 stop
15:58
Chicago, Chicago Midway International Airport (MDW)
Tue, 20 oct +1
209 S$
Southwest Airlines
WN 2929
22:10
Miami (MIA)
Mon, 19 oct
7h 10min
1 stop
05:20
Chicago, Chicago Midway International Airport (MDW)
Tue, 20 oct +1
238 S$
Frontier Airlines
F9 2271
02:55
Miami (MIA)
Tue, 20 oct
25h 48min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Wed, 21 oct +1
196 S$
Southwest Airlines
WN 3039
10:40
Miami (MIA)
Thu, 22 oct
3h 5min
Direct
13:45
Chicago, Chicago Midway International Airport (MDW)
Thu, 22 oct
105 S$
Southwest Airlines
WN 3039
10:40
Miami (MIA)
Fri, 23 oct
3h 5min
Direct
13:45
Chicago, Chicago Midway International Airport (MDW)
Fri, 23 oct
125 S$
Frontier Airlines
F9 4405
20:30
Miami (MIA)
Sun, 25 oct
8h 13min
1 stop
04:43
Chicago, Chicago Midway International Airport (MDW)
Mon, 26 oct +1
193 S$
Frontier Airlines
F9 2135
10:00
Miami (MIA)
Mon, 26 oct
7h 7min
1 stop
17:07
Chicago, Chicago Midway International Airport (MDW)
Mon, 26 oct
118 S$
Southwest Airlines
WN 2547 Best price
16:35
Miami (MIA)
Wed, 28 oct
3h 5min
Direct
19:40
Chicago, Chicago Midway International Airport (MDW)
Wed, 28 oct
104 S$
Frontier Airlines
F9 2271
03:55
Miami (MIA)
Tue, 10 nov
19h 52min
1 stop
23:47
Chicago, Chicago Midway International Airport (MDW)
Tue, 10 nov
183 S$
Southwest Airlines
WN 942
17:40
Miami (MIA)
Tue, 17 nov
3h 15min
Direct
20:55
Chicago, Chicago Midway International Airport (MDW)
Tue, 17 nov
156 S$
Frontier Airlines
F9 4405
02:35
Miami (MIA)
Thu, 26 nov
11h 31min
1 stop
14:06
Chicago, Chicago Midway International Airport (MDW)
Thu, 26 nov
234 S$
Frontier Airlines
F9 4405
03:59
Miami (MIA)
Thu, 26 nov
9h 3min
1 stop
13:02
Chicago, Chicago Midway International Airport (MDW)
Thu, 26 nov
182 S$
Frontier Airlines
F9 2483
13:00
Miami (MIA)
Thu, 26 nov
6h 33min
1 stop
19:33
Chicago, Chicago Midway International Airport (MDW)
Thu, 26 nov
195 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 106 S$ · max: 458 S$
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Sun
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458 S$
14
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441 S$
15
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361 S$
16
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361 S$
17
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195 S$
18
Good deal
125 S$
19
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208 S$
20
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208 S$
21
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250 S$
22
Good deal
106 S$
23
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190 S$
24
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215 S$
25
Good deal
188 S$
26
Good deal
182 S$
27
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287 S$
28
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29
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30
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200 S$

Cheap flights Miami to Chicago Midway International Airport

Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$105
Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$118

Popular destinations from Miami

All →
MIA
Miami — Baltimore
United States → United States
BWI
from
S$36
MIA
Miami — Raleigh
United States → United States
RDU
from
S$37
MIA
Miami — Atlanta
United States → United States
ATL
from
S$37
MIA
Miami — Chicago
United States → United States
CHI
from
S$41
MIA
Miami — Philadelphia
United States → United States
PHL
from
S$44
MIA
Miami — New York
United States → United States
NYC
from
S$44
MIA
Miami — San Juan
United States → Puerto Rico
SJU
from
S$45
MIA
Miami — Cleveland
United States → United States
CLE
from
S$50
MIA
Miami — Houston
United States → United States
IAH
from
S$51

Popular destinations to Chicago Midway International Airport

All →
NYC
New York — Chicago
United States → United States
MDW
from
S$28
ATL
Atlanta — Chicago
United States → United States
MDW
from
S$47
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
S$69
HOU
Houston — Chicago
United States → United States
MDW
from
S$76
DFW
Dallas — Chicago
United States → United States
MDW
from
S$89
PHL
Philadelphia — Chicago
United States → United States
MDW
from
S$90
TPA
Tampa — Chicago
United States → United States
MDW
from
S$94
DEN
Denver — Chicago
United States → United States
MDW
from
S$97

Cheap flights Miami to Chicago Midway International Airport

Interesting facts about the route

Flight time

8h 5min

Distance

1 905 km

Average price

S$208

Most frequent flight

F9 2483

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

S$11

Buy

change

2 GB

data

15

days

S$16

Buy

change

5 GB

data

30

days

S$18

Buy

change

3 GB

data

30

days

S$20

Buy

change

5 GB

data

30

days

S$29

Buy

Frequently Asked Questions

The average ticket price Miami Chicago Midway International Airport is S$208. The cheapest ticket costs S$115, operated by Southwest Airlines, flight 2368, departing Miami on 17 September at 11:15, arriving Chicago Midway International Airport on 17 September at 14:20.
The average flight time is 7 hours 10 minutes. The fastest flight takes 3 hours 5 minutes, flight 2368 operated by Southwest Airlines, departing Miami on 14 September at 11:15, arriving Chicago Midway International Airport on 14 September at 14:20.
Flights on the Miami - Chicago Midway International Airport route are operated by the following airlines: Frontier Airlines, Southwest Airlines.
The distance from Miami to Chicago Midway International Airport is 1905 km.