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Cheap flights Denver to Chicago Midway International Airport

1 passenger, economy

Cheap flights Denver to Chicago Midway International Airport

Compare prices, duration and stops

Frontier Airlines
F9 3600
16:44
Denver (DEN)
Tue, 15 sep
6h 2min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 15 sep
139 £
Southwest Airlines
WN 1564
12:30
Denver (DEN)
Wed, 16 sep
2h 20min
Direct
14:50
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
210 £
Southwest Airlines
WN 1547
17:00
Denver (DEN)
Wed, 16 sep
5h
1 stop
22:00
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
119 £
Southwest Airlines
WN 379
17:15
Denver (DEN)
Wed, 16 sep
3h 50min
Direct
21:05
Chicago, Chicago Midway International Airport (MDW)
Wed, 16 sep
188 £
Southwest Airlines
WN 1806
02:25
Denver (DEN)
Fri, 18 sep
2h 25min
Direct
04:50
Chicago, Chicago Midway International Airport (MDW)
Fri, 18 sep
195 £
Frontier Airlines
F9 3600
16:44
Denver (DEN)
Fri, 18 sep
6h 7min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Fri, 18 sep
138 £
Southwest Airlines
WN 1806
02:25
Denver (DEN)
Sat, 19 sep
2h 25min
Direct
04:50
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
78 £
Frontier Airlines
F9 3600
16:44
Denver (DEN)
Sat, 19 sep
6h 7min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
125 £
Southwest Airlines
WN 1561
21:05
Denver (DEN)
Sat, 19 sep
2h 25min
Direct
23:30
Chicago, Chicago Midway International Airport (MDW)
Sat, 19 sep
192 £
Southwest Airlines
WN 3439
23:20
Denver (DEN)
Sat, 19 sep
2h 30min
Direct
01:50
Chicago, Chicago Midway International Airport (MDW)
Sun, 20 sep +1
200 £
Southwest Airlines
WN 290
22:55
Denver (DEN)
Mon, 21 sep
2h 20min
Direct
01:15
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep +1
226 £
Southwest Airlines
WN 1564
12:30
Denver (DEN)
Tue, 22 sep
2h 20min
Direct
14:50
Chicago, Chicago Midway International Airport (MDW)
Tue, 22 sep
187 £
Southwest Airlines
WN 4022
02:40
Denver (DEN)
Fri, 25 sep
6h 50min
1 stop
09:30
Chicago, Chicago Midway International Airport (MDW)
Fri, 25 sep
125 £
Southwest Airlines
WN 4717
21:15
Denver (DEN)
Fri, 25 sep
3h 30min
1 stop
00:45
Chicago, Chicago Midway International Airport (MDW)
Sat, 26 sep +1
107 £
Southwest Airlines
WN 1563 Best price
00:30
Denver (DEN)
Tue, 29 sep
2h 35min
Direct
03:05
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
69 £
Southwest Airlines
WN 1806
02:25
Denver (DEN)
Tue, 29 sep
2h 25min
Direct
04:50
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
152 £
Frontier Airlines
F9 3600
16:44
Denver (DEN)
Tue, 29 sep
6h 2min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 29 sep
88 £
Southwest Airlines
WN 1563
01:25
Denver (DEN)
Wed, 30 sep
2h 30min
Direct
03:55
Chicago, Chicago Midway International Airport (MDW)
Wed, 30 sep
72 £
Southwest Airlines
WN 1563
01:25
Denver (DEN)
Thu, 1 oct
2h 30min
Direct
03:55
Chicago, Chicago Midway International Airport (MDW)
Thu, 1 oct
72 £
Southwest Airlines
WN 1673
11:50
Denver (DEN)
Thu, 1 oct
2h 20min
Direct
14:10
Chicago, Chicago Midway International Airport (MDW)
Thu, 1 oct
89 £
Southwest Airlines
WN 2927
12:55
Denver (DEN)
Sat, 3 oct
4h 10min
1 stop
17:05
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
89 £
Frontier Airlines
F9 3600
16:44
Denver (DEN)
Sat, 3 oct
6h 7min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Sat, 3 oct
92 £
Frontier Airlines
F9 3600
16:44
Denver (DEN)
Sun, 4 oct
6h 2min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Sun, 4 oct
100 £
Southwest Airlines
WN 1673
11:50
Denver (DEN)
Mon, 5 oct
2h 20min
Direct
14:10
Chicago, Chicago Midway International Airport (MDW)
Mon, 5 oct
91 £
Frontier Airlines
F9 3600
16:44
Denver (DEN)
Mon, 5 oct
6h 7min
1 stop
22:51
Chicago, Chicago Midway International Airport (MDW)
Mon, 5 oct
96 £
Southwest Airlines
WN 1683
02:55
Denver (DEN)
Tue, 6 oct
2h 25min
Direct
05:20
Chicago, Chicago Midway International Airport (MDW)
Tue, 6 oct
84 £
Frontier Airlines
F9 3600
16:44
Denver (DEN)
Tue, 6 oct
6h 2min
1 stop
22:46
Chicago, Chicago Midway International Airport (MDW)
Tue, 6 oct
89 £
Southwest Airlines
WN 455
13:00
Denver (DEN)
Wed, 7 oct
2h 20min
Direct
15:20
Chicago, Chicago Midway International Airport (MDW)
Wed, 7 oct
106 £
Southwest Airlines
WN 1676
20:35
Denver (DEN)
Thu, 8 oct
2h 20min
Direct
22:55
Chicago, Chicago Midway International Airport (MDW)
Thu, 8 oct
109 £
Southwest Airlines
WN 290
18:30
Denver (DEN)
Sat, 10 oct
4h 30min
Direct
23:00
Chicago, Chicago Midway International Airport (MDW)
Sat, 10 oct
95 £
Southwest Airlines
WN 455
13:00
Denver (DEN)
Tue, 13 oct
2h 20min
Direct
15:20
Chicago, Chicago Midway International Airport (MDW)
Tue, 13 oct
76 £
Southwest Airlines
WN 2565
23:40
Denver (DEN)
Tue, 13 oct
2h 20min
Direct
02:00
Chicago, Chicago Midway International Airport (MDW)
Wed, 14 oct +1
106 £
Southwest Airlines
WN 1338
01:50
Denver (DEN)
Wed, 14 oct
2h 25min
Direct
04:15
Chicago, Chicago Midway International Airport (MDW)
Wed, 14 oct
89 £
Southwest Airlines
WN 455
13:00
Denver (DEN)
Wed, 14 oct
2h 20min
Direct
15:20
Chicago, Chicago Midway International Airport (MDW)
Wed, 14 oct
107 £
Southwest Airlines
WN 2565
23:40
Denver (DEN)
Wed, 14 oct
2h 20min
Direct
02:00
Chicago, Chicago Midway International Airport (MDW)
Thu, 15 oct +1
89 £
Southwest Airlines
WN 1338
01:50
Denver (DEN)
Thu, 15 oct
2h 25min
Direct
04:15
Chicago, Chicago Midway International Airport (MDW)
Thu, 15 oct
76 £
Southwest Airlines
WN 1683
02:55
Denver (DEN)
Fri, 16 oct
2h 20min
Direct
05:15
Chicago, Chicago Midway International Airport (MDW)
Fri, 16 oct
76 £
Southwest Airlines
WN 1092
13:35
Denver (DEN)
Sat, 14 nov
2h 20min
Direct
15:55
Chicago, Chicago Midway International Airport (MDW)
Sat, 14 nov
81 £
Southwest Airlines
WN 1697
15:55
Denver (DEN)
Wed, 2 dec
2h 20min
Direct
18:15
Chicago, Chicago Midway International Airport (MDW)
Wed, 2 dec
85 £
Southwest Airlines
WN 1092
13:35
Denver (DEN)
Sat, 5 dec
2h 20min
Direct
15:55
Chicago, Chicago Midway International Airport (MDW)
Sat, 5 dec
85 £
Eagle Aviation
Y4 761
19:53
Denver (DEN)
Thu, 6 May
26h 54min
2 stops
22:47
Chicago, Chicago Midway International Airport (MDW)
Fri, 7 May +1
354 £

Low price calendar

September 2026
Price chart (September 2026)
min: 69 £ · max: 226 £
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139 £
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188 £
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138 £
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125 £
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226 £
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187 £
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107 £
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Good deal
69 £
30
Good deal
72 £

Cheap flights Denver to Chicago Midway International Airport

Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat
Price from
£69
Frontier Airlines
Frontier Airlines
Mon, Tue, Fri, Sat, Sun
Price from
£88

Popular destinations from Denver

All →
DEN
Denver — Las Vegas
United States → United States
LAS
from
£16
DEN
Denver — Dallas
United States → United States
DFW
from
£17
DEN
Denver — Los Angeles
United States → United States
LAX
from
£18
DEN
Denver — Salt Lake City
United States → United States
SLC
from
£18
DEN
Denver — Minneapolis
United States → United States
MSP
from
£19
DEN
Denver — Houston
United States → United States
HOU
from
£21
DEN
Denver — Chicago
United States → United States
CHI
from
£25
DEN
Denver — Chicago
United States → United States
ORD
from
£25
DEN
Denver — Phoenix
United States → United States
PHX
from
£25

Popular destinations to Chicago Midway International Airport

All →
NYC
New York — Chicago
United States → United States
MDW
from
£17
ATL
Atlanta — Chicago
United States → United States
MDW
from
£27
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
£40
HOU
Houston — Chicago
United States → United States
MDW
from
£44
DFW
Dallas — Chicago
United States → United States
MDW
from
£52
PHL
Philadelphia — Chicago
United States → United States
MDW
from
£52
TPA
Tampa — Chicago
United States → United States
MDW
from
£54
MIA
Miami — Chicago
United States → United States
MDW
from
£56

Cheap flights Denver to Chicago Midway International Airport

Interesting facts about the route

Flight time

2h 25min

Distance

1 438 km

Average price

£96

Most frequent flight

WN 1563

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

£7

Buy

change

2 GB

data

15

days

£9

Buy

change

5 GB

data

30

days

£10

Buy

change

3 GB

data

30

days

£12

Buy

change

5 GB

data

30

days

£17

Buy

Frequently Asked Questions

The average ticket price Denver Chicago Midway International Airport is £96. The cheapest ticket costs £119, operated by Southwest Airlines, flight 1547, departing Denver on 16 September at 17:00, arriving Chicago Midway International Airport on 16 September at 22:00.
The average flight time is 5 hours. The fastest flight takes 2 hours 20 minutes, flight 1564 operated by Southwest Airlines, departing Denver on 16 September at 12:30, arriving Chicago Midway International Airport on 16 September at 14:50.
Flights on the Denver - Chicago Midway International Airport route are operated by the following airlines: Frontier Airlines, Southwest Airlines.
The distance from Denver to Chicago Midway International Airport is 1438 km.