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Cheap flights Philadelphia (Philadelphia International) to Chicago Midway International Airport

1 passenger, economy

Cheap flights Philadelphia to Chicago Midway International Airport

Compare prices, duration and stops

Frontier Airlines
F9 1101
16:40
Philadelphia, Philadelphia International (PHL)
Tue, 15 sep
6h 6min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep
214 S$
Frontier Airlines
F9 1101
16:40
Philadelphia, Philadelphia International (PHL)
Wed, 16 sep
6h 11min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
190 S$
Frontier Airlines
F9 1101
16:40
Philadelphia, Philadelphia International (PHL)
Thu, 17 sep
6h 6min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
194 S$
Frontier Airlines
F9 1147
21:32
Philadelphia, Philadelphia International (PHL)
Fri, 18 sep
7h 12min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep +1
147 S$
Southwest Airlines
WN 4337
22:05
Philadelphia, Philadelphia International (PHL)
Fri, 18 sep
2h 5min
Direct
00:10
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep +1
305 S$
Frontier Airlines
F9 3985
10:00
Philadelphia, Philadelphia International (PHL)
Sat, 19 sep
6h 59min
1 stop
16:59
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
182 S$
Frontier Airlines
F9 3985
10:00
Philadelphia, Philadelphia International (PHL)
Sun, 20 sep
6h 59min
1 stop
16:59
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep
214 S$
Frontier Airlines
F9 1101
16:40
Philadelphia, Philadelphia International (PHL)
Mon, 21 sep
6h 11min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
125 S$
Frontier Airlines
F9 1147
21:40
Philadelphia, Philadelphia International (PHL)
Mon, 21 sep
7h 4min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep +1
208 S$
Frontier Airlines
F9 1101
16:40
Philadelphia, Philadelphia International (PHL)
Tue, 22 sep
6h 6min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
194 S$
Frontier Airlines
F9 1101 🔥 Hot deal
16:40
Philadelphia, Philadelphia International (PHL)
Wed, 23 sep
6h 11min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 23 sep
189 S$
Frontier Airlines
F9 3985
10:00
Philadelphia, Philadelphia International (PHL)
Thu, 24 sep
6h 59min
1 stop
16:59
Chicago, Chicago Midway International Airport (MDW)
Thu, 24 sep
163 S$
Frontier Airlines
F9 1101
16:40
Philadelphia, Philadelphia International (PHL)
Thu, 24 sep
6h 6min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 24 sep
216 S$
Frontier Airlines
F9 1101
16:40
Philadelphia, Philadelphia International (PHL)
Sat, 26 sep
6h 11min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep
163 S$
Frontier Airlines
F9 1147
21:32
Philadelphia, Philadelphia International (PHL)
Mon, 28 sep
7h 12min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep +1
199 S$
Frontier Airlines
F9 1101
16:40
Philadelphia, Philadelphia International (PHL)
Tue, 29 sep
6h 6min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
149 S$
Frontier Airlines
F9 1101
16:40
Philadelphia, Philadelphia International (PHL)
Wed, 30 sep
6h 11min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 sep
133 S$
Frontier Airlines
F9 3985
10:00
Philadelphia, Philadelphia International (PHL)
Thu, 1 oct
6h 59min
1 stop
16:59
Chicago, Chicago Midway International Airport (MDW)
Thu, 1 oct
153 S$
Frontier Airlines
F9 1147
21:32
Philadelphia, Philadelphia International (PHL)
Thu, 1 oct
7h 12min
1 stop
04:44
Chicago, Chicago Midway International Airport (MDW)
Fri, 2 oct +1
165 S$
Frontier Airlines
F9 1101 Best price
16:40
Philadelphia, Philadelphia International (PHL)
Sat, 3 oct
6h 11min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
125 S$
Frontier Airlines
F9 2297
12:30
Philadelphia, Philadelphia International (PHL)
Thu, 8 oct
10h 15min
1 stop
22:45
Chicago, Chicago Midway International Airport (MDW)
Thu, 8 oct
164 S$
Frontier Airlines
F9 3985
10:00
Philadelphia, Philadelphia International (PHL)
Tue, 13 oct
9h 35min
1 stop
19:35
Chicago, Chicago Midway International Airport (MDW)
Tue, 13 oct
151 S$
Southwest Airlines
WN 3372
12:25
Philadelphia, Philadelphia International (PHL)
Tue, 1 dec
2h 25min
Direct
14:50
Chicago, Chicago Midway International Airport (MDW)
Tue, 1 dec
158 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 133 S$ · max: 305 S$
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Sun
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214 S$
16
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190 S$
17
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194 S$
18
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305 S$
19
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182 S$
20
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214 S$
21
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208 S$
22
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194 S$
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189 S$
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163 S$
25
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Good deal
163 S$
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199 S$
29
Good deal
149 S$
30
Good deal
133 S$

Cheap flights Philadelphia to Chicago Midway International Airport

Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
S$125
Southwest Airlines
Southwest Airlines
Tue, Fri
Price from
S$158

Popular destinations from Philadelphia

All →
PHL
Philadelphia — Atlanta
United States → United States
ATL
from
S$24
PHL
Philadelphia — Miami
United States → United States
MIA
from
S$29
PHL
Philadelphia — Fort Lauderdale
United States → United States
FLL
from
S$29
PHL
Philadelphia — Tampa
United States → United States
TPA
from
S$33
PHL
Philadelphia — Myrtle Beach
United States → United States
MYR
from
S$37
PHL
Philadelphia — Orlando
United States → United States
ORL
from
S$38
PHL
Philadelphia — Tampa
United States → United States
PIE
from
S$41
PHL
Philadelphia — Orlando
United States → United States
MCO
from
S$56
PHL
Philadelphia — Denver
United States → United States
DEN
from
S$58

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
TPA
Tampa — Chicago
United States → United States
MDW
from
S$94
MIA
Miami — Chicago
United States → United States
MDW
from
S$96
DEN
Denver — Chicago
United States → United States
MDW
from
S$97

Cheap flights Philadelphia to Chicago Midway International Airport

Interesting facts about the route

Flight time

6h 11min

Distance

1 071 km

Average price

S$182

Most frequent flight

F9 1101

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 Philadelphia Chicago Midway International Airport is S$182. The cheapest ticket costs S$190, operated by Frontier Airlines, flight 1101, departing Philadelphia on 16 September at 16:40, arriving Chicago Midway International Airport on 16 September at 22:51.
The average flight time is 6 hours 6 minutes. The fastest flight takes 6 hours 6 minutes, flight 1101 operated by Frontier Airlines, departing Philadelphia on 15 September at 16:40, arriving Chicago Midway International Airport on 15 September at 22:46.
Flights on the Philadelphia - Chicago Midway International Airport route are operated by the following airlines: Frontier Airlines, Southwest Airlines.
The distance from Philadelphia to Chicago Midway International Airport is 1071 km.