Find Cheap Flights from São Paulo to Chicago Midway (SAO - MDW)

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FAQs for Booking São Paulo to Chicago Midway Flights

How long does a flight from São Paulo to Chicago Midway take?
An average nonstop flight takes 16h 24m, covering a distance of 5223 miles.
Which airlines provide the cheapest flights from São Paulo to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Aeromexico ($1323) and Delta ($1478)
Do I need a passport to fly between São Paulo and Chicago Midway?
Yes.
What’s the cheapest day of the week to fly São Paulo to Chicago Midway?
For São Paulo to Chicago Midway, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago Midway back to São Paulo, the best deals are generally found on Wednesday, with Tuesday being the most expensive.

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

Airports
Origin
São Paulo
$1323
only
$1323
Destination
Chicago
$1323
only
$1323
Tue, Apr 10
GRU
MDW
20h 33m
Tue, Apr 17
MDW
GRU
22h 25m
$1323
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5229 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
PDX
Excellent 10.0

Best entertainment

PDX
MEX
Excellent 8.0

Seemed fine!

GDL
SFO
Okay 4.3

swift flight so that we could get off of the plane quicker.

getting in and out of the seat was awful. especially when the seat in front is reclined. the armrest on the aisle seat should be able to move up as the others in the row did. the metal underneath the armrest is pretty sharp and jagged, scraped my palm as i was trying to get the seatbelt to buckle.

ORD
GDL
Excellent 10.0

free meal and free alcoholic beverage!

GDL
MEX
Excellent 10.0

Aeromexico treats everyone like there in first class

Tue, Jul 31
GRU
MDW
17h 04m
Tue, Aug 7
MDW
GRU
18h 00m
$1478
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
TYS
ATL
Excellent 8.4

Everything went well...on time, quick boarding and free gate check of bag.

DEN
SLC
Mediocre 2.0

Nothing!

Everything

SJD
ATL
Good 7.6

Our Delta plane was brand spanking new. Everything worked and the inflight entertainment system was fantastic with many movies to choose from, free headphones, games, tv shows, etc. The crew was polite and the seating at least as comfortable as expected for a 4 hour flight.

The restrooms in the rear of the plane were remarkably small, even by airline standards. I'm a somewhat larger person and I fit, but I know a lot of people who would literally not be able to fit on the toilet without touching both of the sidewalls or risk getting stuck in there. The boarding process at San Jose Del Cabo was the most ridiculous setup I've ever experienced. There were numerous flights boarding out of the same gates and at least 3 or 4 lines for different destinations forming on a ramp just outside the gates. There were guys with signs trying to herd people into the correct lines and then loading the people onto buses which took you out to the planes. The planes were loading from both the front and rear doors and people were getting tangled up inside because of the haphazard loading process. Very easy for a person to end up on an incorrect plane!!

ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

Fri, Jun 8
GRU
MDW
62h 12m
Sat, Jun 16
MDW
GRU
60h 25m
$1405
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5229 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
GDL
SFO
Okay 4.3

swift flight so that we could get off of the plane quicker.

getting in and out of the seat was awful. especially when the seat in front is reclined. the armrest on the aisle seat should be able to move up as the others in the row did. the metal underneath the armrest is pretty sharp and jagged, scraped my palm as i was trying to get the seatbelt to buckle.

PDX
MEX
Excellent 8.0

Seemed fine!

ORD
GDL
Excellent 10.0

free meal and free alcoholic beverage!

MEX
YVR
Good 6.3

Overall planes were ontime Staff pleasant. Tv entertainment was certainly adequate

Food was terrible Both trips a bun with mystery meat and cheese And a pudding on the side My last overnight trip my seat didn’t recline making sleeping almost impossible

MEX
GDL
Good 6.0

Fight crew were professional and courteous.

Delayed flight and no tv

Sat, May 5
GRU
MDW
16h 24m
Mon, Jun 11
MDW
GRU
18h 10m
$1483
Trip: 38 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SJD
ATL
Good 7.6

Our Delta plane was brand spanking new. Everything worked and the inflight entertainment system was fantastic with many movies to choose from, free headphones, games, tv shows, etc. The crew was polite and the seating at least as comfortable as expected for a 4 hour flight.

The restrooms in the rear of the plane were remarkably small, even by airline standards. I'm a somewhat larger person and I fit, but I know a lot of people who would literally not be able to fit on the toilet without touching both of the sidewalls or risk getting stuck in there. The boarding process at San Jose Del Cabo was the most ridiculous setup I've ever experienced. There were numerous flights boarding out of the same gates and at least 3 or 4 lines for different destinations forming on a ramp just outside the gates. There were guys with signs trying to herd people into the correct lines and then loading the people onto buses which took you out to the planes. The planes were loading from both the front and rear doors and people were getting tangled up inside because of the haphazard loading process. Very easy for a person to end up on an incorrect plane!!

ATL
MEX
Excellent 10.0

In some Delta flights that I had in the past the plane was just ok, not bad, not good. But this plane ATL-MEX was great, very nice and conformable plane, it looks and feels excellent!

TYS
ATL
Excellent 8.4

Everything went well...on time, quick boarding and free gate check of bag.

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

Tue, Mar 13
GRU
MDW
24h 05m
Tue, Mar 20
MDW
GRU
23h 45m
$1406
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5229 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
YVR
Good 6.3

Overall planes were ontime Staff pleasant. Tv entertainment was certainly adequate

Food was terrible Both trips a bun with mystery meat and cheese And a pudding on the side My last overnight trip my seat didn’t recline making sleeping almost impossible

MEX
CUN
Excellent 8.0

Surprise first class!

DTW
MEX
Okay 5.3

Plane waited on another family to connect to this flight, in turn causing our flight to arrivw in Mexico City an hour later. Baggage was slow staff in airport were aware of us trying to connect. They radiod that we were on our way to gate yet still closed gate doors before we arrived at the gate

GDL
SFO
Okay 4.3

swift flight so that we could get off of the plane quicker.

getting in and out of the seat was awful. especially when the seat in front is reclined. the armrest on the aisle seat should be able to move up as the others in the row did. the metal underneath the armrest is pretty sharp and jagged, scraped my palm as i was trying to get the seatbelt to buckle.

MEX
GDL
Good 6.0

Fight crew were professional and courteous.

Delayed flight and no tv

Sat, Apr 28
GRU
MDW
17h 04m
Mon, May 21
MDW
GRU
17h 50m
$1493
Trip: 24 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Mediocre 2.0

Nothing!

Everything

ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

SJD
ATL
Good 7.6

Our Delta plane was brand spanking new. Everything worked and the inflight entertainment system was fantastic with many movies to choose from, free headphones, games, tv shows, etc. The crew was polite and the seating at least as comfortable as expected for a 4 hour flight.

The restrooms in the rear of the plane were remarkably small, even by airline standards. I'm a somewhat larger person and I fit, but I know a lot of people who would literally not be able to fit on the toilet without touching both of the sidewalls or risk getting stuck in there. The boarding process at San Jose Del Cabo was the most ridiculous setup I've ever experienced. There were numerous flights boarding out of the same gates and at least 3 or 4 lines for different destinations forming on a ramp just outside the gates. There were guys with signs trying to herd people into the correct lines and then loading the people onto buses which took you out to the planes. The planes were loading from both the front and rear doors and people were getting tangled up inside because of the haphazard loading process. Very easy for a person to end up on an incorrect plane!!

DTW
PVR
Excellent 8.6

Easy flight from check-in to boarding to deplaning.

Nothing really! No entertainment and nothing but almonds eaten.

Mon, Feb 19
GRU
MDW
18h 02m
Mon, Mar 5
MDW
GRU
19h 00m
$1545
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

ATL
TYS
Excellent 9.5

Flight less than 2/3 full, lots of room for comfort. On time, no need to gate check carry on.

nothing, it was great.

DEN
SLC
Mediocre 2.0

Nothing!

Everything

MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

Tue, Feb 20
GRU
MDW
18h 02m
Tue, Mar 20
MDW
GRU
17h 55m
$1545
Trip: 28 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
SJD
Excellent 8.0

On time departure, actually got to Cabo early.

The seat in front of mine had a broken reclining lock mechanism and the passenger kept trying to switch from recline to sitting up and it wouldn't latch in the upright position, so he kept jerking the seatback up and down for the entire 4 hour flight. Also the rows were so tight, and seatbacks were so close together, that the reclining seat in front of me was 6 inches from my face.

DTW
PVR
Excellent 8.6

Easy flight from check-in to boarding to deplaning.

Nothing really! No entertainment and nothing but almonds eaten.

DEN
SLC
Mediocre 2.0

Nothing!

Everything

ORD
ATL
Excellent 10.0

My flight was great. Boarding was easy and the seats were comfortable.

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

Mon, Mar 5
GRU
MDW
20h 03m
Mon, Mar 26
MDW
GRU
17h 55m
$1545
Trip: 21 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

ORD
ATL
Excellent 10.0

My flight was great. Boarding was easy and the seats were comfortable.

ATL
MEX
Excellent 10.0

In some Delta flights that I had in the past the plane was just ok, not bad, not good. But this plane ATL-MEX was great, very nice and conformable plane, it looks and feels excellent!

SJD
ATL
Good 7.6

Our Delta plane was brand spanking new. Everything worked and the inflight entertainment system was fantastic with many movies to choose from, free headphones, games, tv shows, etc. The crew was polite and the seating at least as comfortable as expected for a 4 hour flight.

The restrooms in the rear of the plane were remarkably small, even by airline standards. I'm a somewhat larger person and I fit, but I know a lot of people who would literally not be able to fit on the toilet without touching both of the sidewalls or risk getting stuck in there. The boarding process at San Jose Del Cabo was the most ridiculous setup I've ever experienced. There were numerous flights boarding out of the same gates and at least 3 or 4 lines for different destinations forming on a ramp just outside the gates. There were guys with signs trying to herd people into the correct lines and then loading the people onto buses which took you out to the planes. The planes were loading from both the front and rear doors and people were getting tangled up inside because of the haphazard loading process. Very easy for a person to end up on an incorrect plane!!

JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

Sat, Jan 27
GRU
MDW
16h 39m
Sat, Feb 17
MDW
GRU
20h 45m
$2479
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DTW
PVR
Excellent 8.6

Easy flight from check-in to boarding to deplaning.

Nothing really! No entertainment and nothing but almonds eaten.

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

TYS
ATL
Excellent 8.4

Everything went well...on time, quick boarding and free gate check of bag.

ORD
ATL
Excellent 10.0

My flight was great. Boarding was easy and the seats were comfortable.

DEN
SLC
Mediocre 2.0

Nothing!

Everything

São Paulo to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from São Paulo
Flight Price $1323
Distance 5223 miles
Airlines Aeromexico, Delta
*
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