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Cheap flights Dallas (Fort Worth) to Chicago Midway International Airport

1 passenger, economy

Cheap flights Dallas to Chicago Midway International Airport

Compare prices, duration and stops

Southwest Airlines
WN 130
11:00
Dallas, Dallas Love Field (DAL)
Tue, 15 sep
2h 10min
Direct
13:10
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep
292 S$
Southwest Airlines
WN 130
11:00
Dallas, Dallas Love Field (DAL)
Wed, 16 sep
2h 10min
Direct
13:10
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
294 S$
Frontier Airlines
F9 2882
14:36
Dallas, Fort Worth (DFW)
Thu, 17 sep
2h 23min
Direct
16:59
Chicago, Chicago Midway International Airport (MDW)
Thu, 17 sep
207 S$
Frontier Airlines
F9 2882
14:36
Dallas, Fort Worth (DFW)
Sat, 19 sep
2h 23min
Direct
16:59
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
200 S$
Frontier Airlines
F9 2882
14:36
Dallas, Fort Worth (DFW)
Sun, 20 sep
2h 23min
Direct
16:59
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep
198 S$
Frontier Airlines
F9 2882
14:36
Dallas, Fort Worth (DFW)
Mon, 21 sep
2h 23min
Direct
16:59
Chicago, Chicago Midway International Airport (MDW)
Mon, 21 sep
223 S$
Southwest Airlines
WN 3613
18:10
Dallas, Dallas Love Field (DAL)
Tue, 22 sep
2h 10min
Direct
20:20
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
180 S$
Frontier Airlines
F9 3022
00:48
Dallas, Fort Worth (DFW)
Thu, 24 sep
21h 58min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Thu, 24 sep
229 S$
Frontier Airlines
F9 2882
14:36
Dallas, Fort Worth (DFW)
Fri, 25 sep
2h 23min
Direct
16:59
Chicago, Chicago Midway International Airport (MDW)
Fri, 25 sep
142 S$
Frontier Airlines
F9 2882
14:54
Dallas, Fort Worth (DFW)
Sun, 11 oct
2h 23min
Direct
17:17
Chicago, Chicago Midway International Airport (MDW)
Sun, 11 oct
173 S$
Frontier Airlines
F9 2882
14:44
Dallas, Fort Worth (DFW)
Mon, 12 oct
2h 23min
Direct
17:07
Chicago, Chicago Midway International Airport (MDW)
Mon, 12 oct
126 S$
Frontier Airlines
F9 2882
14:54
Dallas, Fort Worth (DFW)
Mon, 12 oct
2h 23min
Direct
17:17
Chicago, Chicago Midway International Airport (MDW)
Mon, 12 oct
182 S$
Frontier Airlines
F9 2882
14:54
Dallas, Fort Worth (DFW)
Sat, 17 oct
2h 23min
Direct
17:17
Chicago, Chicago Midway International Airport (MDW)
Sat, 17 oct
137 S$
Frontier Airlines
F9 2882 Best price
17:12
Dallas, Fort Worth (DFW)
Wed, 21 oct
2h 23min
Direct
19:35
Chicago, Chicago Midway International Airport (MDW)
Wed, 21 oct
113 S$
Frontier Airlines
F9 2882
13:54
Dallas, Fort Worth (DFW)
Thu, 29 oct
2h 31min
Direct
16:25
Chicago, Chicago Midway International Airport (MDW)
Thu, 29 oct
159 S$
Frontier Airlines
F9 2882
11:40
Dallas, Fort Worth (DFW)
Mon, 23 nov
2h 22min
Direct
14:02
Chicago, Chicago Midway International Airport (MDW)
Mon, 23 nov
175 S$
Frontier Airlines
F9 2882
23:56
Dallas, Fort Worth (DFW)
Wed, 2 dec
2h 22min
Direct
02:18
Chicago, Chicago Midway International Airport (MDW)
Thu, 3 dec +1
133 S$
Frontier Airlines
F9 4018
16:00
Dallas, Fort Worth (DFW)
Thu, 3 dec
9h 2min
1 stop
01:02
Chicago, Chicago Midway International Airport (MDW)
Fri, 4 dec +1
169 S$
Frontier Airlines
F9 2882
23:56
Dallas, Fort Worth (DFW)
Fri, 4 dec
2h 22min
Direct
02:18
Chicago, Chicago Midway International Airport (MDW)
Sat, 5 dec +1
165 S$
Southwest Airlines
WN 1432
12:00
Dallas, Dallas Love Field (DAL)
Sun, 27 dec
2h 15min
Direct
14:15
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 dec
279 S$
Southwest Airlines
WN 1432
12:05
Dallas, Dallas Love Field (DAL)
Sun, 27 dec
2h 10min
Direct
14:15
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 dec
326 S$
Southwest Airlines
WN 1430
14:10
Dallas, Dallas Love Field (DAL)
Sun, 27 dec
2h 20min
Direct
16:30
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 dec
327 S$
Southwest Airlines
WN 1430
14:15
Dallas, Dallas Love Field (DAL)
Sun, 27 dec
2h 15min
Direct
16:30
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 dec
276 S$
Southwest Airlines
WN 1441
18:40
Dallas, Dallas Love Field (DAL)
Sun, 27 dec
2h 15min
Direct
20:55
Chicago, Chicago Midway International Airport (MDW)
Sun, 27 dec
358 S$
Southwest Airlines
WN 1724
02:10
Dallas, Dallas Love Field (DAL)
Mon, 28 dec
2h 10min
Direct
04:20
Chicago, Chicago Midway International Airport (MDW)
Mon, 28 dec
314 S$
Southwest Airlines
WN 805
03:35
Dallas, Dallas Love Field (DAL)
Mon, 28 dec
2h 10min
Direct
05:45
Chicago, Chicago Midway International Airport (MDW)
Mon, 28 dec
278 S$
Southwest Airlines
WN 805
03:35
Dallas, Dallas Love Field (DAL)
Wed, 30 dec
2h 10min
Direct
05:45
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 dec
214 S$

Low price calendar

September 2026
Price chart (September 2026)
min: 142 S$ · max: 294 S$
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186 S$
15
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292 S$
16
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294 S$
17
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207 S$
18
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19
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200 S$
20
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198 S$
21
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223 S$
22
Good deal
180 S$
23
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229 S$
25
Good deal
142 S$
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Cheap flights Dallas to Chicago Midway International Airport

Frontier Airlines
Frontier Airlines
Mon, Wed, Thu, Fri, Sat, Sun
Price from
S$113
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Sun
Price from
S$214

Popular destinations from Dallas

All →
DFW
Dallas — Atlanta
United States → United States
ATL
from
S$25
DFW
Dallas — New Orleans
United States → United States
MSY
from
S$28
DFW
Dallas — Miami
United States → United States
MIA
from
S$29
DFW
Dallas — Fort Lauderdale
United States → United States
FLL
from
S$31
DFW
Dallas — Orlando
United States → United States
ORL
from
S$32
DFW
Dallas — Denver
United States → United States
DEN
from
S$33
DFW
Dallas — Phoenix
United States → United States
PHX
from
S$38
DFW
Dallas — Las Vegas
United States → United States
LAS
from
S$46
DFW
Dallas — Detroit
United States → United States
DTT
from
S$47

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
PHL
Philadelphia — Chicago
United States → United States
MDW
from
S$90
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 Dallas to Chicago Midway International Airport

Interesting facts about the route

Flight time

2h 23min

Distance

1 283 km

Average price

S$198

Most frequent flight

F9 2882

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 Dallas Chicago Midway International Airport is S$198. The cheapest ticket costs S$207, operated by Frontier Airlines, flight 2882, departing Dallas on 17 September at 14:36, arriving Chicago Midway International Airport on 17 September at 16:59.
The average flight time is 2 hours 10 minutes. The fastest flight takes 2 hours 10 minutes, flight 130 operated by Southwest Airlines, departing Dallas on 15 September at 11:00, arriving Chicago Midway International Airport on 15 September at 13:10.
Flights on the Dallas - Chicago Midway International Airport route are operated by the following airlines: Frontier Airlines, Southwest Airlines.
The distance from Dallas to Chicago Midway International Airport is 1283 km.