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

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Sat 12/16
Sat 12/23
Any month
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Good to Know

Low Season:
January
Best time to beat the crowds
2%
expected price decrease
High Season:
August
Most popular time to fly
9%
expected price increase
Average Price:
$300
(avg. price over the last 2 weeks)
Good Deal:
$212
or less (round trip)

When to Book Flights from Chicago Midway to Orlando

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 $211 or less.
The cheapest flight from Chicago Midway to Orlando was found 17 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
High season is considered to be July, August and September. The cheapest month to fly is January.
Morning departure is around 15% 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

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

Airports
Origin
Chicago
$174
only
$174
Destination
Orlando
$174
only
$174
Wed, Jan 3
MDW
MCO
5h 52m
Tue, Jan 9
MCO
MDW
7h 09m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

Thu, Jan 4
MDW
MCO
5h 52m
Tue, Jan 9
MCO
MDW
5h 32m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

Sat, Jan 13
MDW
MCO
5h 38m
Wed, Jan 17
MCO
MDW
4h 39m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ZAG
CDG
Good 6.0

Old plane, bad food & old crew

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Sun, Jan 21
MDW
MCO
4h 27m
Fri, Jan 26
MCO
MDW
5h 09m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

Mon, Feb 5
MDW
MCO
6h 31m
Tue, Feb 6
MCO
MDW
7h 09m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

Wed, Feb 7
MDW
MCO
5h 25m
Tue, Feb 13
MCO
MDW
4h 32m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ZAG
CDG
Good 6.0

Old plane, bad food & old crew

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

Sun, Feb 11
MDW
MCO
5h 25m
Wed, Feb 14
MCO
MDW
5h 09m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

Tue, Mar 6
MDW
MCO
4h 47m
Tue, Mar 20
MCO
MDW
6h 28m
Trip: 14 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

Wed, Apr 11
MDW
MCO
5h 59m
Tue, Apr 17
MCO
MDW
4h 40m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

Sun, Feb 11
MDW
MCO
4h 27m
Wed, Feb 14
MCO
MDW
4h 09m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Thu, Mar 1
MDW
MCO
6h 23m
Tue, Mar 6
MCO
MDW
5h 09m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Wed, May 2
MDW
MCO
5h 49m
Wed, May 9
MCO
MDW
4h 15m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

Sun, May 20
MDW
MCO
5h 49m
Sat, May 26
MCO
MDW
5h 44m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

Sat, Jun 2
MDW
MCO
4h 31m
Sat, Jun 9
MCO
MDW
7h 10m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

Mon, Jun 4
MDW
MCO
4h 31m
Tue, Jun 12
MCO
MDW
4h 35m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Sat, Dec 16
MDW
MCO
5h 24m
Thu, Feb 1
MCO
MDW
4h 32m
Trip: 48 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
GSO
ATL
Excellent 10.0

Plane nice and comfortable

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

Sun, Apr 8
MDW
MCO
5h 49m
Fri, Apr 13
MCO
MDW
5h 39m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

Thu, May 31
MDW
MCO
4h 49m
Sun, Jun 3
MCO
MDW
5h 15m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

Thu, Mar 1
MDW
MCO
6h 23m
Sun, Mar 4
MCO
MDW
4h 49m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
Okay 5.3

Some of the flight attendants were rude and not very welcoming at all.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

Sat, Dec 16
MDW
MCO
6h 03m
Sun, Dec 17
MCO
MDW
4h 44m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ZAG
CDG
Good 6.0

Old plane, bad food & old crew

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.