Find Cheap Flights from São Paulo Guarulhos Intl to Chicago Midway (GRU - MDW)

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Wed 1/17
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FAQs for Booking São Paulo Guarulhos Intl to Chicago Midway Flights

How long does a flight from São Paulo Guarulhos Intl to Chicago Midway take?
An average nonstop flight takes 16h 24m, covering a distance of 5222 miles.
Which airlines provide the cheapest flights from São Paulo Guarulhos Intl to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Aeromexico ($955) and Delta ($1345)
Do I need a passport to fly between São Paulo Guarulhos Intl and Chicago Midway?
Yes.
What’s the cheapest day of the week to fly São Paulo Guarulhos Intl to Chicago Midway?
For São Paulo Guarulhos Intl to Chicago Midway, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway back to São Paulo Guarulhos Intl, the best deals are generally found on Saturday, with Tuesday being the most expensive.

Book cheap flights from São Paulo Guarulhos Intl to Chicago Midway (round-trip)

Airports
Origin
São Paulo
$955
only
$955
Destination
Chicago
$955
only
$955
Tue, Apr 3
GRU
MDW
25h 18m
Mon, Apr 9
MDW
GRU
30h 50m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5152 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
IAH
Good 7.3

The plane was comfortable and the crew was great.

The boarding was ridiculous. They never posted what gate the flight went out of. If it wasn't for Kayak we would not have known when to go. The flight was delayed but they never did update that information. It did not leave on time like the board said. They just all of a sudden said they were boarding the flight.

GDL
SJC
Excellent 9.6

The service and food

Some crew had attitude

MEX
LAX
Okay 5.3

My flight was changed...

MEX
SEA
Good 7.3

They offer food and entertainment its good. Also is amazing to flight none stop to Mexico City

Getting to Mexico or leaving Mexico is a hassle if you are in a wheelchair. They have a really poor service, I really struggle since I was flying by myself.

CUN
MEX
Excellent 9.6

Thu, May 17
GRU
MDW
17h 04m
Tue, Jun 5
MDW
GRU
17h 50m
$1345
Trip: 20 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

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.

HOU
ATL
Excellent 10.0

Service

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.

Thu, May 31
GRU
MDW
17h 04m
Fri, Jun 29
MDW
GRU
17h 40m
$1345
Trip: 30 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. :))

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.

BOS
MKE
Excellent 10.0

Direct flight, on time, friendly crew, smooth flight

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.

Wed, Jun 6
GRU
MDW
17h 04m
Mon, Jun 18
MDW
GRU
18h 00m
$1345
Trip: 13 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

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

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.

BOS
MKE
Excellent 10.0

Direct flight, on time, friendly crew, smooth flight

Thu, Mar 8
GRU
MDW
17h 59m
Tue, Mar 20
MDW
GRU
17h 55m
$1356
Trip: 12 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
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.

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.

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.

JFK
CMH
Excellent 9.6

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

Sat, Apr 28
GRU
MDW
20h 17m
Sat, May 19
MDW
GRU
18h 00m
$1370
Trip: 22 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

SEA
ANC
Excellent 10.0

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

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.

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.

JFK
CMH
Excellent 9.6

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

Wed, Apr 18
GRU
MDW
17h 04m
Wed, Apr 25
MDW
GRU
17h 30m
$1381
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. :))

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.

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.

SAN
LAX
Excellent 10.0

on time

BOS
MKE
Excellent 10.0

Direct flight, on time, friendly crew, smooth flight

Tue, Jun 26
GRU
MDW
16h 54m
Sun, Jul 8
MDW
GRU
18h 00m
$1431
Trip: 13 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

SYR
JFK
Good 7.0

Nothing Special

HOU
ATL
Excellent 10.0

Service

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.

Tue, Feb 13
GRU
MDW
18h 09m
Sun, Mar 4
MDW
GRU
17h 15m
$1432
Trip: 20 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. :))

HOU
ATL
Excellent 10.0

Service

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.

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.

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.

Mon, Feb 19
GRU
MDW
16h 27m
Tue, Feb 27
MDW
GRU
16h 55m
$1432
Trip: 9 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.

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

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.

Wed, Feb 14
GRU
MDW
16h 34m
Sat, Mar 10
MDW
GRU
16h 55m
$1457
Trip: 25 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
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.

YUL
DTW
Mediocre 2.0

Not applied

Not applied

HOU
ATL
Excellent 10.0

Service

DEN
SLC
Excellent 10.0

Delta is great

Wed, Jul 25
GRU
MDW
16h 24m
Tue, Aug 7
MDW
GRU
18h 10m
$1478
Trip: 14 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.

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.

HOU
ATL
Excellent 10.0

Service

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

Mon, Jul 2
GRU
MDW
20h 23m
Sat, Jul 14
MDW
GRU
18h 10m
$1693
Trip: 13 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.

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.

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.

SAN
LAX
Excellent 10.0

on time

Mon, Jan 22
GRU
MDW
20h 39m
Thu, Jan 25
MDW
GRU
18h 58m
$2272
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
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.

SEA
ANC
Excellent 10.0

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

Nothing.

SYR
JFK
Good 7.0

Nothing Special

SAN
LAX
Excellent 10.0

on time

*
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São Paulo Guarulhos Intl to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from São Paulo Guarulhos Intl
Flight Price $955
Distance 5222 miles
Airlines Aeromexico, Delta