Find Cheap Flights from Chicago Midway to Pittsburgh (MDW - PIT)

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Looking for a cheap flight? 25% of our users found flights on this route for $230 or less.

FAQs for Booking Chicago Midway to Pittsburgh Flights

How long does a flight from Chicago Midway to Pittsburgh take?
An average nonstop flight takes 3h 08m, covering a distance of 400 miles.
How many flights are there between Chicago Midway and Pittsburgh?
There are 117 (nonstop) flights between Chicago Midway and Pittsburgh per week, averaging 19 per day.
Which airlines provide the cheapest flights from Chicago Midway to Pittsburgh?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($182)
Do I need a passport to fly between Chicago Midway and Pittsburgh?
No.
Which airlines fly most frequently between Chicago Midway and Pittsburgh?
Southwest (16 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to Pittsburgh?
For Chicago Midway to Pittsburgh, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Pittsburgh back to Chicago Midway, the best deals are generally found on Wednesday, with Friday being the most expensive.

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

Airports
Origin
Chicago
$182
only
$182
Destination
Pittsburgh
$182
only
$182
Mon, Feb 5
MDW
PIT
3h 44m
Thu, Feb 8
PIT
MDW
3h 41m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
IND
ATL
Excellent 8.3

Ind-atl flight was absolutely amazing i couldn’t find really anything wrong with the flight besides spacing for seats

Spacing with seats

BUF
DTW
Okay 4.0

No help with baggage when boarding the plane, they hurry you up for nothing, because we had to wait 20 mi utes to take off.

SJC
SEA
Okay 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

MSN
LGA
Mediocre 3.3

3.5 hours late.

LAX
SYD
Excellent 10.0

adjustable head rest is great - being given a pillow is great - the plane was not too cold to sleep either (as they often are)

Wed, Apr 25
MDW
PIT
4h 45m
Sat, Apr 28
PIT
MDW
3h 12m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
BUF
DTW
Okay 4.0

No help with baggage when boarding the plane, they hurry you up for nothing, because we had to wait 20 mi utes to take off.

ATL
MGM
Okay 5.0

Very uncomfortable and cold. Wasn’t space didn’t serve anything no WiFi or tv like other flight

SEA
SFO
Excellent 10.0

Being on time.

ATL
BNA
Mediocre 2.0

They lost my bag.

SJC
SEA
Okay 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

Mon, May 14
MDW
PIT
5h 06m
Sat, May 19
PIT
MDW
3h 12m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
AUS
Excellent 10.0

i liked the aircraft and the fact that you could watch movies on your phone!

you couldn't hear the staff when they started boarding the plane

SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

SJC
SEA
Okay 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

DTW
MEX
Okay 4.0

Arriving to the destination

SJC
LAS
Good 7.3

Quick friendly service from crew and captain.

First class seat was broken was reclined and super uncomfortable the whole flight the plane was super outdated and old.

Fri, Jan 12
MDW
PIT
6h 11m
Mon, Jan 15
PIT
MDW
3h 43m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

BOS
AUS
Excellent 10.0

i liked the aircraft and the fact that you could watch movies on your phone!

you couldn't hear the staff when they started boarding the plane

SJC
SEA
Okay 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

ATL
MGM
Okay 5.0

Very uncomfortable and cold. Wasn’t space didn’t serve anything no WiFi or tv like other flight

BUF
DTW
Okay 4.0

No help with baggage when boarding the plane, they hurry you up for nothing, because we had to wait 20 mi utes to take off.

Fri, Jan 12
MDW
PIT
3h 44m
Sun, Jan 14
PIT
MDW
3h 43m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
BUF
DTW
Okay 4.0

No help with baggage when boarding the plane, they hurry you up for nothing, because we had to wait 20 mi utes to take off.

MSN
LGA
Mediocre 3.3

3.5 hours late.

LAX
SYD
Excellent 10.0

adjustable head rest is great - being given a pillow is great - the plane was not too cold to sleep either (as they often are)

ATL
MGM
Okay 5.0

Very uncomfortable and cold. Wasn’t space didn’t serve anything no WiFi or tv like other flight

SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

Mon, Dec 25
MDW
PIT
3h 08m
Mon, Jan 1
PIT
MDW
4h 04m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
SJC
LAS
Good 7.3

Quick friendly service from crew and captain.

First class seat was broken was reclined and super uncomfortable the whole flight the plane was super outdated and old.

SJC
SEA
Okay 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

IND
ATL
Excellent 8.3

Ind-atl flight was absolutely amazing i couldn’t find really anything wrong with the flight besides spacing for seats

Spacing with seats

MSN
LGA
Mediocre 3.3

3.5 hours late.

ATL
MGM
Okay 5.0

Very uncomfortable and cold. Wasn’t space didn’t serve anything no WiFi or tv like other flight

Thu, Mar 15
MDW
PIT
4h 25m
Sat, Mar 17
PIT
MDW
3h 27m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
MSN
LGA
Mediocre 3.3

3.5 hours late.

SJC
SEA
Okay 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

SEA
SFO
Excellent 10.0

Being on time.

SJC
LAS
Good 7.3

Quick friendly service from crew and captain.

First class seat was broken was reclined and super uncomfortable the whole flight the plane was super outdated and old.

IND
ATL
Excellent 8.3

Ind-atl flight was absolutely amazing i couldn’t find really anything wrong with the flight besides spacing for seats

Spacing with seats

Wed, Dec 20
MDW
PIT
4h 15m
Wed, Jan 3
PIT
MDW
3h 41m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
BNA
Mediocre 2.0

They lost my bag.

IND
ATL
Excellent 8.3

Ind-atl flight was absolutely amazing i couldn’t find really anything wrong with the flight besides spacing for seats

Spacing with seats

BUF
DTW
Okay 4.0

No help with baggage when boarding the plane, they hurry you up for nothing, because we had to wait 20 mi utes to take off.

BOS
AUS
Excellent 10.0

i liked the aircraft and the fact that you could watch movies on your phone!

you couldn't hear the staff when they started boarding the plane

MSN
LGA
Mediocre 3.3

3.5 hours late.

Fri, Jun 29
MDW
PIT
3h 39m
Sun, Jul 1
PIT
MDW
5h 52m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
IND
ATL
Excellent 8.3

Ind-atl flight was absolutely amazing i couldn’t find really anything wrong with the flight besides spacing for seats

Spacing with seats

SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

LAX
SYD
Excellent 10.0

adjustable head rest is great - being given a pillow is great - the plane was not too cold to sleep either (as they often are)

SEA
SFO
Excellent 10.0

Being on time.

ATL
BNA
Mediocre 2.0

They lost my bag.

Mon, Dec 11
MDW
PIT
4h 51m
Fri, Dec 15
PIT
MDW
5h 13m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

MSN
LGA
Mediocre 3.3

3.5 hours late.

SJC
SEA
Okay 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

BUF
DTW
Okay 4.0

No help with baggage when boarding the plane, they hurry you up for nothing, because we had to wait 20 mi utes to take off.

DTW
MEX
Okay 4.0

Arriving to the destination

*
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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.