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Find Cheap Flights from Chicago Midway to Orlando (MDW - MCO)

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Chicago Midway to Orlando Flight Information

Avg. Flight Duration 2h 40m
Flights Arrive in Orlando
Flights Depart from Chicago Midway
Flight Price $228
Distance 989 miles
Airlines Delta, Major Airline

Good to Know

Average Price:
$324
(avg. price over the last 2 weeks)
Good Deal:
$256
or less (round trip)

When to Book Flights from Chicago Midway to Orlando

Top Tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $256 or less.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 29% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago Midway to Orlando Flights

How long does a flight from Chicago Midway to Orlando take?
An average nonstop flight takes 2h 35m, covering a distance of 989 miles.
How many flights are there between Chicago Midway and Orlando?
There are 97 (nonstop) flights between Chicago Midway and Orlando per week, averaging 13 per day.
Which airlines provide the cheapest flights from Chicago Midway to Orlando?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($228)
Do I need a passport to fly between Chicago Midway and Orlando?
No.
Which airlines fly most frequently between Chicago Midway and Orlando?
Southwest (13 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to Orlando?
For Chicago Midway to Orlando, Tuesday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Orlando back to Chicago Midway, the best deals are generally found on Wednesday, with Monday being the most expensive.

Book cheap flights from Chicago Midway to Orlando (round-trip)

Airports
Origin
Chicago
$228
only
$228
Destination
Orlando
$228
only
$228
Tue, Oct 2
MDW
Chicago Midway
MCO
Orlando
4h 36m
Wed, Oct 10
MCO
Orlando
MDW
Chicago Midway
5h 08m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SJD
LAX
Excellent 8.3

Crews were nice

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

Tue, Oct 9
MDW
Chicago Midway
MCO
Orlando
4h 36m
Tue, Oct 16
MCO
Orlando
MDW
Chicago Midway
4h 16m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

Wed, Sep 26
MDW
Chicago Midway
MCO
Orlando
2h 35m
Sun, Oct 14
MCO
Orlando
MDW
Chicago Midway
2h 45m
Trip: 19 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Oct 15
MDW
Chicago Midway
MCO
Orlando
4h 36m
Tue, Oct 16
MCO
Orlando
MDW
Chicago Midway
4h 16m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SJD
LAX
Excellent 8.3

Crews were nice

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

Tue, Oct 16
MDW
Chicago Midway
MCO
Orlando
4h 36m
Tue, Oct 23
MCO
Orlando
MDW
Chicago Midway
5h 08m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

Mon, Oct 22
MDW
Chicago Midway
MCO
Orlando
5h 15m
Tue, Oct 30
MCO
Orlando
MDW
Chicago Midway
4h 53m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

Tue, Oct 23
MDW
Chicago Midway
MCO
Orlando
6h 05m
Wed, Oct 24
MCO
Orlando
MDW
Chicago Midway
6h 24m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

Mon, Oct 29
MDW
Chicago Midway
MCO
Orlando
4h 44m
Thu, Nov 1
MCO
Orlando
MDW
Chicago Midway
5h 25m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

Tue, Oct 30
MDW
Chicago Midway
MCO
Orlando
6h 09m
Wed, Oct 31
MCO
Orlando
MDW
Chicago Midway
4h 53m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

SJD
LAX
Excellent 8.3

Crews were nice

Tue, Nov 6
MDW
Chicago Midway
MCO
Orlando
4h 40m
Tue, Nov 27
MCO
Orlando
MDW
Chicago Midway
5h 50m
Trip: 22 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

Tue, Nov 13
MDW
Chicago Midway
MCO
Orlando
5h 01m
Tue, Nov 27
MCO
Orlando
MDW
Chicago Midway
5h 07m
Trip: 15 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

Mon, Nov 26
MDW
Chicago Midway
MCO
Orlando
4h 38m
Thu, Dec 6
MCO
Orlando
MDW
Chicago Midway
5h 57m
Trip: 11 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

SJD
LAX
Excellent 8.3

Crews were nice

Tue, Nov 27
MDW
Chicago Midway
MCO
Orlando
4h 40m
Wed, Dec 5
MCO
Orlando
MDW
Chicago Midway
5h 06m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

Mon, Dec 3
MDW
Chicago Midway
MCO
Orlando
4h 48m
Fri, Dec 7
MCO
Orlando
MDW
Chicago Midway
5h 06m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

Tue, Dec 4
MDW
Chicago Midway
MCO
Orlando
4h 15m
Thu, Dec 6
MCO
Orlando
MDW
Chicago Midway
5h 27m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

Mon, Dec 10
MDW
Chicago Midway
MCO
Orlando
5h 41m
Fri, Dec 14
MCO
Orlando
MDW
Chicago Midway
5h 06m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

Wed, Dec 12
MDW
Chicago Midway
MCO
Orlando
4h 15m
Thu, Dec 13
MCO
Orlando
MDW
Chicago Midway
5h 06m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

SJD
LAX
Excellent 8.3

Crews were nice

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

Sun, Jan 6
MDW
Chicago Midway
MCO
Orlando
5h 46m
Thu, Jan 10
MCO
Orlando
MDW
Chicago Midway
4h 53m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SJD
LAX
Excellent 8.3

Crews were nice

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

Mon, Jan 7
MDW
Chicago Midway
MCO
Orlando
5h 20m
Fri, Jan 11
MCO
Orlando
MDW
Chicago Midway
6h 03m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

Tue, Jan 8
MDW
Chicago Midway
MCO
Orlando
4h 18m
Tue, Jan 15
MCO
Orlando
MDW
Chicago Midway
4h 34m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

SJD
LAX
Excellent 8.3

Crews were nice

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

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