Cheap flights Orlando (Executive) to Chicago Midway International Airport

From

To

Depart

Return

Passengers

1 passenger, economy

Cheap flights Orlando to Chicago Midway International Airport

Compare prices, duration and stops

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Stops

Direct only 1 stop

Price

79 € 272 € 272 €

Airlines

Frontier Airlines Southwest Airlines

F9 3507

16:50

Orlando, Orlando International Airport (MCO)

Sat, 19 sep

6h 1min

1 stop

22:51

Chicago, Chicago Midway International Airport (MDW)

Sat, 19 sep

179 €

F9 4017

10:00

Orlando, Orlando International Airport (MCO)

Sun, 20 sep

6h 59min

1 stop

16:59

Chicago, Chicago Midway International Airport (MDW)

Sun, 20 sep

176 €

WN 693

00:55

Orlando, Orlando International Airport (MCO)

Tue, 22 sep

2h 50min

Direct

03:45

Chicago, Chicago Midway International Airport (MDW)

Tue, 22 sep

161 €

WN 2110

15:10

Orlando, Orlando International Airport (MCO)

Tue, 22 sep

5h 10min

1 stop

20:20

Chicago, Chicago Midway International Airport (MDW)

Tue, 22 sep

151 €

F9 3507

16:50

Orlando, Orlando International Airport (MCO)

Tue, 22 sep

5h 56min

1 stop

22:46

Chicago, Chicago Midway International Airport (MDW)

Tue, 22 sep

146 €

F9 4025

21:19

Orlando, Orlando International Airport (MCO)

Tue, 22 sep

25h 32min

1 stop

22:51

Chicago, Chicago Midway International Airport (MDW)

Wed, 23 sep +1

101 €

WN 359

11:40

Orlando, Orlando International Airport (MCO)

Wed, 23 sep

2h 45min

Direct

14:25

Chicago, Chicago Midway International Airport (MDW)

Wed, 23 sep

95 €

F9 3507

16:50

Orlando, Orlando International Airport (MCO)

Thu, 24 sep

5h 56min

1 stop

22:46

Chicago, Chicago Midway International Airport (MDW)

Thu, 24 sep

149 €

F9 4025

21:19

Orlando, Orlando International Airport (MCO)

Fri, 25 sep

7h 25min

1 stop

04:44

Chicago, Chicago Midway International Airport (MDW)

Sat, 26 sep +1

112 €

F9 4017

10:00

Orlando, Orlando International Airport (MCO)

Sat, 26 sep

6h 59min

1 stop

16:59

Chicago, Chicago Midway International Airport (MDW)

Sat, 26 sep

139 €

F9 1241

13:30

Orlando, Orlando International Airport (MCO)

Tue, 29 sep

9h 16min

1 stop

22:46

Chicago, Chicago Midway International Airport (MDW)

Tue, 29 sep

107 €

F9 3507

16:50

Orlando, Orlando International Airport (MCO)

Tue, 29 sep

5h 56min

1 stop

22:46

Chicago, Chicago Midway International Airport (MDW)

Tue, 29 sep

147 €

F9 3507

16:50

Orlando, Orlando International Airport (MCO)

Wed, 30 sep

6h 1min

1 stop

22:51

Chicago, Chicago Midway International Airport (MDW)

Wed, 30 sep

104 €

F9 4025

21:19

Orlando, Orlando International Airport (MCO)

Fri, 2 oct

7h 25min

1 stop

04:44

Chicago, Chicago Midway International Airport (MDW)

Sat, 3 oct +1

110 €

F9 3507

16:50

Orlando, Orlando International Airport (MCO)

Sat, 3 oct

6h 1min

1 stop

22:51

Chicago, Chicago Midway International Airport (MDW)

Sat, 3 oct

89 €

F9 1241

13:30

Orlando, Orlando International Airport (MCO)

Wed, 7 oct

9h 21min

1 stop

22:51

Chicago, Chicago Midway International Airport (MDW)

Wed, 7 oct

92 €

F9 3507

16:50

Orlando, Orlando International Airport (MCO)

Wed, 7 oct

6h 1min

1 stop

22:51

Chicago, Chicago Midway International Airport (MDW)

Wed, 7 oct

82 €

F9 1563

09:25

Orlando, Orlando International Airport (MCO)

Fri, 9 oct

17h 57min

1 stop

03:22

Chicago, Chicago Midway International Airport (MDW)

Sat, 10 oct +1

127 €

F9 3975

18:52

Orlando, Orlando International Airport (MCO)

Fri, 9 oct

8h 30min

1 stop

03:22

Chicago, Chicago Midway International Airport (MDW)

Sat, 10 oct +1

133 €

F9 1241 Best price

11:10

Orlando, Orlando International Airport (MCO)

Sat, 10 oct

17h 33min

1 stop

04:43

Chicago, Chicago Midway International Airport (MDW)

Sun, 11 oct +1

79 €

F9 1563

10:07

Orlando, Orlando International Airport (MCO)

Sun, 11 oct

18h 36min

1 stop

04:43

Chicago, Chicago Midway International Airport (MDW)

Mon, 12 oct +1

138 €

WN 2825

11:30

Orlando, Orlando International Airport (MCO)

Sat, 31 oct

2h 50min

Direct

14:20

Chicago, Chicago Midway International Airport (MDW)

Sat, 31 oct

104 €

F9 1563

13:07

Orlando, Orlando International Airport (MCO)

Sun, 1 nov

10h 40min

1 stop

23:47

Chicago, Chicago Midway International Airport (MDW)

Sun, 1 nov

140 €

WN 2595

00:20

Orlando, Orlando International Airport (MCO)

Thu, 5 nov

2h 55min

Direct

03:15

Chicago, Chicago Midway International Airport (MDW)

Thu, 5 nov

107 €

F9 1915

11:25

Orlando, Orlando International Airport (MCO)

Thu, 5 nov

15h 5min

1 stop

02:30

Chicago, Chicago Midway International Airport (MDW)

Fri, 6 nov +1

93 €

WN 246

14:05

Orlando, Orlando International Airport (MCO)

Thu, 5 nov

4h 15min

Direct

18:20

Chicago, Chicago Midway International Airport (MDW)

Thu, 5 nov

108 €

WN 2806

23:40

Orlando, Orlando International Airport (MCO)

Thu, 5 nov

2h 55min

Direct

02:35

Chicago, Chicago Midway International Airport (MDW)

Fri, 6 nov +1

107 €

F9 1915

11:25

Orlando, Orlando International Airport (MCO)

Fri, 6 nov

27h 35min

1 stop

15:00

Chicago, Chicago Midway International Airport (MDW)

Sat, 7 nov +1

96 €

WN 1376

18:00

Orlando, Orlando International Airport (MCO)

Sat, 14 nov

8h

1 stop

02:00

Chicago, Chicago Midway International Airport (MDW)

Sun, 15 nov +1

107 €

F9 4025

22:03

Orlando, Orlando International Airport (MCO)

Sat, 14 nov

7h 44min

1 stop

05:47

Chicago, Chicago Midway International Airport (MDW)

Sun, 15 nov +1

114 €

F9 3507

17:54

Orlando, Orlando International Airport (MCO)

Thu, 19 nov

5h 53min

1 stop

23:47

Chicago, Chicago Midway International Airport (MDW)

Thu, 19 nov

97 €

F9 1457

15:23

Orlando, Orlando International Airport (MCO)

Tue, 24 nov

3h 1min

Direct

18:24

Chicago, Chicago Midway International Airport (MDW)

Tue, 24 nov

117 €

F9 1457

22:46

Orlando, Orlando International Airport (MCO)

Tue, 24 nov

3h 1min

Direct

01:47

Chicago, Chicago Midway International Airport (MDW)

Wed, 25 nov +1

115 €

F9 1457

15:23

Orlando, Orlando International Airport (MCO)

Fri, 27 nov

3h 1min

Direct

18:24

Chicago, Chicago Midway International Airport (MDW)

Fri, 27 nov

164 €

WN 2814

03:15

Orlando, Orlando International Airport (MCO)

Sun, 29 nov

9h 30min

1 stop

12:45

Chicago, Chicago Midway International Airport (MDW)

Sun, 29 nov

272 €

F9 1457

22:01

Orlando, Orlando International Airport (MCO)

Thu, 3 dec

3h 1min

Direct

01:02

Chicago, Chicago Midway International Airport (MDW)

Fri, 4 dec +1

84 €

F9 1457

22:01

Orlando, Orlando International Airport (MCO)

Wed, 23 dec

3h 1min

Direct

01:02

Chicago, Chicago Midway International Airport (MDW)

Thu, 24 dec +1

138 €

WN 1731

21:10

Orlando, Orlando International Airport (MCO)

Thu, 24 dec

2h 55min

Direct

00:05

Chicago, Chicago Midway International Airport (MDW)

Fri, 25 dec +1

92 €

WN 2595

00:20

Orlando, Orlando International Airport (MCO)

Fri, 25 dec

2h 55min

Direct

03:15

Chicago, Chicago Midway International Airport (MDW)

Fri, 25 dec

105 €

WN 1211

13:10

Orlando, Orlando International Airport (MCO)

Wed, 30 dec

4h 50min

Direct

18:00

Chicago, Chicago Midway International Airport (MDW)

Wed, 30 dec

132 €

F9 1457

22:01

Orlando, Orlando International Airport (MCO)

Wed, 30 dec

3h 1min

Direct

01:02

Chicago, Chicago Midway International Airport (MDW)

Thu, 31 dec +1

109 €

WN 2310

12:40

Orlando, Orlando International Airport (MCO)

Thu, 31 dec

9h 25min

1 stop

22:05

Chicago, Chicago Midway International Airport (MDW)

Thu, 31 dec

121 €

F9 1241

14:27

Orlando, Orlando International Airport (MCO)

Thu, 31 dec

7h 48min

1 stop

22:15

Chicago, Chicago Midway International Airport (MDW)

Thu, 31 dec

120 €

F9 1457

22:01

Orlando, Orlando International Airport (MCO)

Thu, 31 dec

3h 1min

Direct

01:02

Chicago, Chicago Midway International Airport (MDW)

Fri, 1 jan +1

151 €

WN 1346

22:15

Orlando, Orlando International Airport (MCO)

Thu, 31 dec

6h 25min

1 stop

04:40

Chicago, Chicago Midway International Airport (MDW)

Fri, 1 jan +1

137 €

F9 1241

14:27

Orlando, Orlando International Airport (MCO)

Sun, 3 jan

7h 48min

1 stop

22:15

Chicago, Chicago Midway International Airport (MDW)

Sun, 3 jan

173 €

F9 1241

15:01

Orlando, Orlando International Airport (MCO)

Wed, 3 mar

14h 45min

1 stop

05:46

Chicago, Chicago Midway International Airport (MDW)

Thu, 4 mar +1

93 €

Low price calendar

September 2026

Price chart (September 2026)

min: 95 € · max: 179 €

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179 €

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146 €

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95 €

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112 €

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139 €

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147 €

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Good deal

104 €

Cheap flights Orlando to Chicago Midway International Airport

Frontier Airlines

Tue, Wed, Thu, Fri, Sat, Sun

Price from

79 €

Southwest Airlines

Tue, Wed, Thu, Fri, Sat, Sun

Price from

95 €

Popular destinations from Orlando

All →

ORL

Orlando — New York

United States → United States

NYC

from

16 €

ORL

Orlando — New York

United States → United States

LGA

from

16 €

ORL

Orlando — Atlanta

United States → United States

ATL

from

17 €

ORL

Orlando — Houston

United States → United States

HOU

from

19 €

ORL

Orlando — Nashville

United States → United States

BNA

from

20 €

ORL

Orlando — Austin

United States → United States

AUS

from

22 €

ORL

Orlando — Las Vegas

United States → United States

LAS

from

23 €

ORL

Orlando — Houston

United States → United States

IAH

from

23 €

ORL

Orlando — Boston

United States → United States

BOS

from

24 €

Popular destinations to Chicago Midway International Airport

All →

NYC

New York — Chicago

United States → United States

MDW

from

20 €

ATL

Atlanta — Chicago

United States → United States

MDW

from

32 €

FLL

Fort Lauderdale — Chicago

United States → United States

MDW

from

48 €

HOU

Houston — Chicago

United States → United States

MDW

from

52 €

DFW

Dallas — Chicago

United States → United States

MDW

from

61 €

PHL

Philadelphia — Chicago

United States → United States

MDW

from

62 €

TPA

Tampa — Chicago

United States → United States

MDW

from

64 €

MIA

Miami — Chicago

United States → United States

MDW

from

66 €

Cheap flights Orlando to Chicago Midway International Airport

Interesting facts about the route

Flight time

6h 1min

Distance

1 594 km

Average price

114 €

Most frequent flight

F9 3507

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

change

3 GB

data

30

days

€8

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2 GB

data

15

days

€11

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5 GB

data

30

days

€12

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3 GB

data

30

days

€14

change

5 GB

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30

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€20

Frequently Asked Questions

The average ticket price Orlando Chicago Midway International Airport is €114. The cheapest ticket costs €146, operated by Frontier Airlines, flight 3507, departing Orlando on 22 September at 16:50, arriving Chicago Midway International Airport on 22 September at 22:46.

The average flight time is 5 hours 56 minutes.The fastest flight takes 2 hours 50 minutes, flight 693operated by Southwest Airlines, departing Orlando on 22 September at 00:55, arriving Chicago Midway International Airport on 22 September at 03:45.

Flights on the Orlando - Chicago Midway International Airport route are operated by the following airlines: Frontier Airlines, Southwest Airlines.

The distance from Orlando to Chicago Midway International Airport is 1594 km.