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

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Wed 1/17
Wed 1/24
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Good to Know

Low Season:
January
Best time to beat the crowds
4%
expected price decrease
High Season:
October
Most popular time to fly
11%
expected price increase
Average Price:
$304
(avg. price over the last 2 weeks)
Good Deal:
$213
or less (round trip)

When to Book Flights from Orlando to Chicago Midway

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $213 or less.
The cheapest flight from Orlando to Chicago Midway was found 65 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be September, October and November. The cheapest month to fly is January.
Morning departure is around 21% 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 Orlando to Chicago Midway Flights

How long does a flight from Orlando to Chicago Midway take?
An average nonstop flight takes 4h 32m, covering a distance of 989 miles.
How many flights are there between Orlando and Chicago Midway?
There are 66 (nonstop) flights between Orlando and Chicago Midway per week, averaging 9 per day.
Which airlines provide the cheapest flights from Orlando to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($174)
Do I need a passport to fly between Orlando and Chicago Midway?
No.
Which airlines fly most frequently between Orlando and Chicago Midway?
Southwest (9 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Orlando to Chicago Midway?
For Orlando to Chicago Midway, Thursday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago Midway back to Orlando, the best deals are generally found on Monday, with Friday being the most expensive.

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

Airports
Origin
Orlando
$174
only
$174
Destination
Chicago
$174
only
$174
Thu, Feb 8
MCO
MDW
7h 24m
Sun, Feb 11
MDW
MCO
5h 44m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

DEN
SLC
Excellent 10.0

Delta is great

BOS
MKE
Excellent 10.0

Direct flight, on time, friendly crew, smooth flight

Fri, Feb 23
MCO
MDW
7h 19m
Sun, Feb 25
MDW
MCO
5h 14m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

TUS
SEA
Excellent 10.0

Delta did a really good job as always. Cheaper, more comfortable, and a WAY better experience than Alaska Airlines.

Nothing.

SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

SAN
LAX
Excellent 10.0

on time

Thu, Mar 1
MCO
MDW
4h 49m
Tue, Mar 6
MDW
MCO
5h 03m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

SAN
LAX
Excellent 10.0

on time

YUL
DTW
Mediocre 2.0

Not applied

Not applied

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

Wed, Apr 25
MCO
MDW
5h 39m
Sat, Apr 28
MDW
MCO
4h 57m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Excellent 10.0

Delta is great

YUL
DTW
Mediocre 2.0

Not applied

Not applied

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

SYR
JFK
Good 7.0

Nothing Special

TUS
SEA
Excellent 10.0

Delta did a really good job as always. Cheaper, more comfortable, and a WAY better experience than Alaska Airlines.

Nothing.

Tue, Jan 23
MCO
MDW
4h 55m
Tue, Jan 30
MDW
MCO
4h 20m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAN
LAX
Excellent 10.0

on time

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

SYR
JFK
Good 7.0

Nothing Special

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

Thu, Apr 26
MCO
MDW
5h 40m
Tue, May 1
MDW
MCO
4h 57m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

DEN
SLC
Excellent 10.0

Delta is great

HOU
ATL
Excellent 10.0

Service

SAN
LAX
Excellent 10.0

on time

SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

Tue, May 1
MCO
MDW
5h 15m
Tue, May 8
MDW
MCO
4h 48m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

DEN
SLC
Excellent 10.0

Delta is great

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

Thu, May 10
MCO
MDW
5h 15m
Tue, May 15
MDW
MCO
5h 53m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAN
LAX
Excellent 10.0

on time

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

DEN
SLC
Excellent 10.0

Delta is great

SYR
JFK
Good 7.0

Nothing Special

Thu, Jul 26
MCO
MDW
6h 39m
Mon, Jul 30
MDW
MCO
5h 56m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YUL
DTW
Mediocre 2.0

Not applied

Not applied

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

TUS
SEA
Excellent 10.0

Delta did a really good job as always. Cheaper, more comfortable, and a WAY better experience than Alaska Airlines.

Nothing.

SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

DEN
SLC
Excellent 10.0

Delta is great

Fri, Jan 26
MCO
MDW
4h 32m
Mon, Jan 29
MDW
MCO
4h 37m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

YUL
DTW
Mediocre 2.0

Not applied

Not applied

HOU
ATL
Excellent 10.0

Service

DEN
SLC
Excellent 10.0

Delta is great

SYR
JFK
Good 7.0

Nothing Special

Fri, Feb 16
MCO
MDW
5h 45m
Mon, Feb 19
MDW
MCO
5h 14m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SYR
JFK
Good 7.0

Nothing Special

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

HOU
ATL
Excellent 10.0

Service

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

Thu, Jun 21
MCO
MDW
5h 20m
Mon, Jun 25
MDW
MCO
6h 00m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BOS
MKE
Excellent 10.0

Direct flight, on time, friendly crew, smooth flight

TUS
SEA
Excellent 10.0

Delta did a really good job as always. Cheaper, more comfortable, and a WAY better experience than Alaska Airlines.

Nothing.

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

HOU
ATL
Excellent 10.0

Service

SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

Thu, Jul 5
MCO
MDW
5h 05m
Mon, Jul 9
MDW
MCO
4h 57m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

SAN
LAX
Excellent 10.0

on time

HOU
ATL
Excellent 10.0

Service

Fri, Jun 8
MCO
MDW
4h 49m
Mon, Jun 11
MDW
MCO
6h 07m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SYR
JFK
Good 7.0

Nothing Special

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

Wed, Mar 21
MCO
MDW
5h 02m
Tue, Mar 27
MDW
MCO
4h 44m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
HOU
ATL
Excellent 10.0

Service

BOS
MKE
Excellent 10.0

Direct flight, on time, friendly crew, smooth flight

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

JFK
CMH
Excellent 9.6

Always nice to be on an American plane out of an American airport.....SO much more professional. :))

Fri, Jan 19
MCO
MDW
4h 32m
Sun, Jan 21
MDW
MCO
5h 44m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

CUN
MSY
Good 7.0

The outbound crew was terrific. The flight itself was fine. We even arrived early.

Upon deplaning in Cancun, ALL passengers are put on a bus and driven far away from the terminals to an arrivals area. Those of us with connecting flights are royally f*cked at that point, especially if your connection is short, as mine was. The so-called shuttle to the departure terminals, which are entire kilometers away, was to arrive in like half an hour. HALF AN HOUR. Who has this time to spare?? The alternative to the shuttle is paying a taxi that charges a hefty fare--and God help you if you don't have cash. The departures terminal was swamped and only thru begging assistance and line cuts did I make my connection...and then only by the skin of my teeth. It was a complete nightmare.

SYR
JFK
Good 7.0

Nothing Special

HOU
ATL
Excellent 10.0

Service

YUL
DTW
Mediocre 2.0

Not applied

Not applied

Show more results
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Orlando to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Orlando
Flight Price $174
Distance 989 miles
Airlines Delta