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

Filters

Stops

Direct only 1 stop

Price

72 $ 312 $ 312 $

Airlines

Frontier Airlines Southwest Airlines

F9 4017

10:00

Orlando, Орландо (MCO)

Thu, 17 sep

6h 59min

1 stop

16:59

Chicago, Чикаго-Мидвей (MDW)

Thu, 17 sep

202 $

F9 3507

16:50

Orlando, Орландо (MCO)

Thu, 17 sep

5h 56min

1 stop

22:46

Chicago, Чикаго-Мидвей (MDW)

Thu, 17 sep

177 $

F9 3507

16:50

Orlando, Орландо (MCO)

Fri, 18 sep

6h 1min

1 stop

22:51

Chicago, Чикаго-Мидвей (MDW)

Fri, 18 sep

211 $

F9 3507

16:50

Orlando, Орландо (MCO)

Sat, 19 sep

6h 1min

1 stop

22:51

Chicago, Чикаго-Мидвей (MDW)

Sat, 19 sep

206 $

F9 4017

10:00

Orlando, Орландо (MCO)

Sun, 20 sep

6h 59min

1 stop

16:59

Chicago, Чикаго-Мидвей (MDW)

Sun, 20 sep

202 $

F9 3507

16:50

Orlando, Орландо (MCO)

Tue, 22 sep

5h 56min

1 stop

22:46

Chicago, Чикаго-Мидвей (MDW)

Tue, 22 sep

168 $

F9 4025

21:19

Orlando, Орландо (MCO)

Tue, 22 sep

25h 32min

1 stop

22:51

Chicago, Чикаго-Мидвей (MDW)

Wed, 23 sep +1

116 $

WN 359

11:40

Orlando, Орландо (MCO)

Wed, 23 sep

2h 45min

Direct

14:25

Chicago, Чикаго-Мидвей (MDW)

Wed, 23 sep

109 $

F9 3507

16:50

Orlando, Орландо (MCO)

Thu, 24 sep

5h 56min

1 stop

22:46

Chicago, Чикаго-Мидвей (MDW)

Thu, 24 sep

171 $

F9 4025

21:19

Orlando, Орландо (MCO)

Fri, 25 sep

7h 25min

1 stop

04:44

Chicago, Чикаго-Мидвей (MDW)

Sat, 26 sep +1

128 $

F9 4017

10:00

Orlando, Орландо (MCO)

Sat, 26 sep

6h 59min

1 stop

16:59

Chicago, Чикаго-Мидвей (MDW)

Sat, 26 sep

160 $

F9 1241

13:30

Orlando, Орландо (MCO)

Tue, 29 sep

9h 16min

1 stop

22:46

Chicago, Чикаго-Мидвей (MDW)

Tue, 29 sep

122 $

F9 3507

16:50

Orlando, Орландо (MCO)

Tue, 29 sep

5h 56min

1 stop

22:46

Chicago, Чикаго-Мидвей (MDW)

Tue, 29 sep

169 $

F9 3507

16:50

Orlando, Орландо (MCO)

Wed, 30 sep

6h 1min

1 stop

22:51

Chicago, Чикаго-Мидвей (MDW)

Wed, 30 sep

119 $

F9 4025

21:19

Orlando, Орландо (MCO)

Fri, 2 oct

7h 25min

1 stop

04:44

Chicago, Чикаго-Мидвей (MDW)

Sat, 3 oct +1

127 $

F9 3507

16:50

Orlando, Орландо (MCO)

Sat, 3 oct

6h 1min

1 stop

22:51

Chicago, Чикаго-Мидвей (MDW)

Sat, 3 oct

102 $

F9 1241

13:30

Orlando, Орландо (MCO)

Wed, 7 oct

9h 21min

1 stop

22:51

Chicago, Чикаго-Мидвей (MDW)

Wed, 7 oct

106 $

F9 3507 Best price

16:50

Orlando, Орландо (MCO)

Wed, 7 oct

6h 1min

1 stop

22:51

Chicago, Чикаго-Мидвей (MDW)

Wed, 7 oct

72 $

F9 1563

09:25

Orlando, Орландо (MCO)

Fri, 9 oct

17h 57min

1 stop

03:22

Chicago, Чикаго-Мидвей (MDW)

Sat, 10 oct +1

146 $

F9 3975

18:52

Orlando, Орландо (MCO)

Fri, 9 oct

8h 30min

1 stop

03:22

Chicago, Чикаго-Мидвей (MDW)

Sat, 10 oct +1

153 $

F9 1241

11:10

Orlando, Орландо (MCO)

Sat, 10 oct

17h 33min

1 stop

04:43

Chicago, Чикаго-Мидвей (MDW)

Sun, 11 oct +1

91 $

F9 1563

10:07

Orlando, Орландо (MCO)

Sun, 11 oct

18h 36min

1 stop

04:43

Chicago, Чикаго-Мидвей (MDW)

Mon, 12 oct +1

159 $

WN 2825

11:30

Orlando, Орландо (MCO)

Sat, 31 oct

2h 50min

Direct

14:20

Chicago, Чикаго-Мидвей (MDW)

Sat, 31 oct

119 $

F9 1563

13:07

Orlando, Орландо (MCO)

Sun, 1 nov

10h 40min

1 stop

23:47

Chicago, Чикаго-Мидвей (MDW)

Sun, 1 nov

161 $

WN 2595

00:20

Orlando, Орландо (MCO)

Thu, 5 nov

2h 55min

Direct

03:15

Chicago, Чикаго-Мидвей (MDW)

Thu, 5 nov

123 $

F9 1915

11:25

Orlando, Орландо (MCO)

Thu, 5 nov

15h 5min

1 stop

02:30

Chicago, Чикаго-Мидвей (MDW)

Fri, 6 nov +1

107 $

WN 246

14:05

Orlando, Орландо (MCO)

Thu, 5 nov

4h 15min

Direct

18:20

Chicago, Чикаго-Мидвей (MDW)

Thu, 5 nov

124 $

WN 2806

23:40

Orlando, Орландо (MCO)

Thu, 5 nov

2h 55min

Direct

02:35

Chicago, Чикаго-Мидвей (MDW)

Fri, 6 nov +1

123 $

F9 1915

11:25

Orlando, Орландо (MCO)

Fri, 6 nov

27h 35min

1 stop

15:00

Chicago, Чикаго-Мидвей (MDW)

Sat, 7 nov +1

110 $

WN 1376

18:00

Orlando, Орландо (MCO)

Sat, 14 nov

8h

1 stop

02:00

Chicago, Чикаго-Мидвей (MDW)

Sun, 15 nov +1

123 $

F9 4025

22:03

Orlando, Орландо (MCO)

Sat, 14 nov

7h 44min

1 stop

05:47

Chicago, Чикаго-Мидвей (MDW)

Sun, 15 nov +1

131 $

F9 3507

17:54

Orlando, Орландо (MCO)

Thu, 19 nov

5h 53min

1 stop

23:47

Chicago, Чикаго-Мидвей (MDW)

Thu, 19 nov

111 $

F9 1457

15:23

Orlando, Орландо (MCO)

Tue, 24 nov

3h 1min

Direct

18:24

Chicago, Чикаго-Мидвей (MDW)

Tue, 24 nov

134 $

F9 1457

22:46

Orlando, Орландо (MCO)

Tue, 24 nov

3h 1min

Direct

01:47

Chicago, Чикаго-Мидвей (MDW)

Wed, 25 nov +1

132 $

F9 1457

15:23

Orlando, Орландо (MCO)

Fri, 27 nov

3h 1min

Direct

18:24

Chicago, Чикаго-Мидвей (MDW)

Fri, 27 nov

188 $

WN 2814

03:15

Orlando, Орландо (MCO)

Sun, 29 nov

9h 30min

1 stop

12:45

Chicago, Чикаго-Мидвей (MDW)

Sun, 29 nov

312 $

F9 1457

22:01

Orlando, Орландо (MCO)

Thu, 3 dec

3h 1min

Direct

01:02

Chicago, Чикаго-Мидвей (MDW)

Fri, 4 dec +1

97 $

F9 1457

22:01

Orlando, Орландо (MCO)

Wed, 23 dec

3h 1min

Direct

01:02

Chicago, Чикаго-Мидвей (MDW)

Thu, 24 dec +1

159 $

WN 1731

21:10

Orlando, Орландо (MCO)

Thu, 24 dec

2h 55min

Direct

00:05

Chicago, Чикаго-Мидвей (MDW)

Fri, 25 dec +1

106 $

WN 2595

00:20

Orlando, Орландо (MCO)

Fri, 25 dec

2h 55min

Direct

03:15

Chicago, Чикаго-Мидвей (MDW)

Fri, 25 dec

121 $

WN 1211

13:10

Orlando, Орландо (MCO)

Wed, 30 dec

4h 50min

Direct

18:00

Chicago, Чикаго-Мидвей (MDW)

Wed, 30 dec

151 $

F9 1457

22:01

Orlando, Орландо (MCO)

Wed, 30 dec

3h 1min

Direct

01:02

Chicago, Чикаго-Мидвей (MDW)

Thu, 31 dec +1

78 $

WN 2310

12:40

Orlando, Орландо (MCO)

Thu, 31 dec

9h 25min

1 stop

22:05

Chicago, Чикаго-Мидвей (MDW)

Thu, 31 dec

139 $

F9 1241

14:27

Orlando, Орландо (MCO)

Thu, 31 dec

7h 48min

1 stop

22:15

Chicago, Чикаго-Мидвей (MDW)

Thu, 31 dec

146 $

F9 1457

22:01

Orlando, Орландо (MCO)

Thu, 31 dec

3h 1min

Direct

01:02

Chicago, Чикаго-Мидвей (MDW)

Fri, 1 jan +1

174 $

WN 1346

22:15

Orlando, Орландо (MCO)

Thu, 31 dec

6h 25min

1 stop

04:40

Chicago, Чикаго-Мидвей (MDW)

Fri, 1 jan +1

157 $

F9 1241

14:27

Orlando, Орландо (MCO)

Sun, 3 jan

7h 48min

1 stop

22:15

Chicago, Чикаго-Мидвей (MDW)

Sun, 3 jan

199 $

Low price calendar

September 2026

Price chart (September 2026)

min: 109 $ · max: 211 $

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177 $

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116 $

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109 $

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119 $

Cheap flights Orlando to Chicago Midway International Airport

Frontier Airlines

Tue, Wed, Thu, Fri, Sat, Sun

Price from

$72

Southwest Airlines

Wed, Thu, Fri, Sat, Sun

Price from

$109

Popular destinations from Orlando

All →

ORL

Orlando — New York

United States → United States

NYC

from

$18

ORL

Orlando — New York

United States → United States

LGA

from

$18

ORL

Orlando — Atlanta

United States → United States

ATL

from

$20

ORL

Orlando — Houston

United States → United States

HOU

from

$21

ORL

Orlando — Nashville

United States → United States

BNA

from

$23

ORL

Orlando — Austin

United States → United States

AUS

from

$26

ORL

Orlando — Las Vegas

United States → United States

LAS

from

$26

ORL

Orlando — Houston

United States → United States

IAH

from

$27

ORL

Orlando — Boston

United States → United States

BOS

from

$27

Popular destinations to Chicago Midway International Airport

All →

NYC

New York — Chicago

United States → United States

MDW

from

$22

ATL

Atlanta — Chicago

United States → United States

MDW

from

$37

FLL

Fort Lauderdale — Chicago

United States → United States

MDW

from

$55

HOU

Houston — Chicago

United States → United States

MDW

from

$60

DFW

Dallas — Chicago

United States → United States

MDW

from

$70

PHL

Philadelphia — Chicago

United States → United States

MDW

from

$71

TPA

Tampa — Chicago

United States → United States

MDW

from

$74

MIA

Miami — Chicago

United States → United States

MDW

from

$75

Cheap flights Orlando to Chicago Midway International Airport

Interesting facts about the route

Flight time

6h 1min

Distance

1 594 km

Average price

$132

Most frequent flight

F9 3507

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

change

3 GB

data

30

days

$9

change

2 GB

data

15

days

$13

change

5 GB

data

30

days

$14

change

3 GB

data

30

days

$16

change

5 GB

data

30

days

$23

Frequently Asked Questions

The average ticket price Orlando Chicago Midway International Airport is $132. The cheapest ticket costs $177, operated by Frontier Airlines, flight 3507, departing Orlando on 17 September at 16:50, arriving Chicago Midway International Airport on 17 September at 22:46.

The average flight time is 6 hours 1 minute. The fastest flight takes 5 hours 56 minutes, flight 3507 operated by Frontier Airlines, departing Orlando on 17 September at 16:50, arriving Chicago Midway International Airport on 17 September at 22:46.

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.