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Cheap flights from Chicago Midway Airport to Sao Paulo from $285

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Sao Paulo departing on 6/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Find the cheapest flights from Chicago Midway Airport to Sao Paulo

Cheap round-trip flights

Enter your travel dates to find the best prices.
LATAM Airlines Logo
5:10 pm - 5:40 am
MDW
-
GRU
34h 30m
1 stop
LATAM Airlines Logo
3:20 pm - 10:00 am
GRU
-
MDW
20h 40m
2 stops
$660LATAM Airlines
Tue, May 12 - Tue, May 19
Delta Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
Delta Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
$823Delta
Mon, May 4 - Sun, May 17
LATAM Airlines Logo
5:10 pm - 5:20 am
MDW
-
GRU
34h 10m
2 stops
LATAM Airlines Logo
3:20 pm - 10:00 am
GRU
-
MDW
20h 40m
2 stops
$842LATAM Airlines
Tue, May 12 - Tue, May 19
Multiple Airlines Logo
8:23 pm - 1:10 am
MDW
-
GRU
26h 47m
3 stops
Multiple Airlines Logo
7:35 am - 9:40 am
GRU
-
MDW
28h 05m
3 stops
$851Multiple Airlines
Mon, Jun 1 - Mon, Jun 15
Multiple Airlines Logo
3:20 pm - 10:30 pm
MDW
-
GRU
29h 10m
3 stops
Multiple Airlines Logo
7:35 am - 9:40 am
GRU
-
MDW
28h 05m
3 stops
$857Multiple Airlines
Thu, May 28 - Tue, Jun 2
LATAM Airlines Logo
11:18 am - 6:05 am
MDW
-
GRU
16h 47m
2 stops
LATAM Airlines Logo
3:20 pm - 10:00 am
GRU
-
MDW
20h 40m
2 stops
$867LATAM Airlines
Sat, May 2 - Thu, May 7
LATAM Airlines Logo
5:12 pm - 1:25 pm
MDW
-
GRU
18h 13m
2 stops
LATAM Airlines Logo
7:15 pm - 11:56 am
GRU
-
MDW
18h 41m
2 stops
$868LATAM Airlines
Wed, May 27 - Mon, Jun 1
LATAM Airlines Logo
5:11 pm - 5:40 am
MDW
-
GRU
34h 29m
1 stop
LATAM Airlines Logo
11:05 pm - 10:07 am
GRU
-
MDW
37h 02m
2 stops
$925LATAM Airlines
Tue, Jun 23 - Sun, Jun 28
LATAM Airlines Logo
5:29 pm - 5:40 am
MDW
-
GRU
34h 11m
1 stop
LATAM Airlines Logo
3:20 pm - 9:59 am
GRU
-
MDW
20h 39m
2 stops
$938LATAM Airlines
Sat, May 16 - Sat, May 23
LATAM Airlines Logo
5:25 pm - 5:40 am
MDW
-
GRU
34h 15m
1 stop
LATAM Airlines Logo
5:45 pm - 9:50 am
GRU
-
MDW
18h 05m
2 stops
$951LATAM Airlines
Thu, Sep 17 - Thu, Sep 24

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LATAM Airlines flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Our best LATAM Airlines deals on Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport flight tickets
LATAM Airlines
May 12
MDW5:10 pmChicago Midway
34h 30m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
May 19
GRU3:20 pmSao Paulo Guarulhos Intl
20h 40m
2 stops
MDW10:00 amChicago Midway
$660
LATAM Airlines
May 12
MDW5:10 pmChicago Midway
34h 10m
2 stops
GRU5:20 amSao Paulo Guarulhos Intl
May 19
GRU3:20 pmSao Paulo Guarulhos Intl
20h 40m
2 stops
MDW10:00 amChicago Midway
$842
LATAM Airlines
May 27
MDW5:12 pmChicago Midway
18h 13m
2 stops
GRU1:25 pmSao Paulo Guarulhos Intl
Jun 1
GRU7:15 pmSao Paulo Guarulhos Intl
18h 41m
2 stops
MDW11:56 amChicago Midway
$868

Delta flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Our best Delta deals on Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport flight tickets
Delta
May 4
MDW6:00 amChicago Midway
21h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
May 17
GRU10:50 pmSao Paulo Guarulhos Intl
15h 06m
1 stop
MDW11:56 amChicago Midway
$823
Delta
May 30
MDW6:23 amChicago Midway
21h 17m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Jun 23
GRU10:50 pmSao Paulo Guarulhos Intl
13h 17m
1 stop
MDW10:07 amChicago Midway
$961
Delta
Jul 3
MDW1:16 pmChicago Midway
17h 34m
2 stops
GRU8:50 amSao Paulo Guarulhos Intl
Jul 14
GRU10:45 pmSao Paulo Guarulhos Intl
15h 48m
2 stops
MDW12:33 pmChicago Midway
$966

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 16, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 5/12

5:10 pm-5:40 am

1 stop34h 30m

Sao Paulo Guarulhos Intl

Tue 5/19

3:20 pm-10:00 am

2 stops20h 40m

$660
Quickest round-trip

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 5/4

6:00 am-5:40 am

1 stop21h 40m

Sao Paulo Guarulhos Intl

Sun 5/17

10:50 pm-11:56 am

1 stop15h 06m

$823

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 5/12

5:10 pm-5:20 am

2 stops34h 10m

Sao Paulo Guarulhos Intl

Tue 5/19

3:20 pm-10:00 am

2 stops20h 40m

$842

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 6/1

8:23 pm-1:10 am

3 stops26h 47m

Sao Paulo Guarulhos Intl

Mon 6/15

7:35 am-9:40 am

3 stops28h 05m

$851

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 5/28

3:20 pm-10:30 pm

3 stops29h 10m

Sao Paulo Guarulhos Intl

Tue 6/2

7:35 am-9:40 am

3 stops28h 05m

$857

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 5/2

11:18 am-6:05 am

2 stops16h 47m

Sao Paulo Guarulhos Intl

Thu 5/7

3:20 pm-10:00 am

2 stops20h 40m

$867

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 5/27

5:12 pm-1:25 pm

2 stops18h 13m

Sao Paulo Guarulhos Intl

Mon 6/1

7:15 pm-11:56 am

2 stops18h 41m

$868

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 6/23

5:11 pm-5:40 am

1 stop34h 29m

Sao Paulo Guarulhos Intl

Sun 6/28

11:05 pm-10:07 am

2 stops37h 02m

$925

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 5/16

5:29 pm-5:40 am

1 stop34h 11m

Sao Paulo Guarulhos Intl

Sat 5/23

3:20 pm-9:59 am

2 stops20h 39m

$938

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 9/17

5:25 pm-5:40 am

1 stop34h 15m

Sao Paulo Guarulhos Intl

Thu 9/24

5:45 pm-9:50 am

2 stops18h 05m

$951

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Sao Paulo Guarulhos Intl Airport?

On average, the least expensive day to fly to Sao Paulo Guarulhos Intl Airport from Chicago Midway Airport is on a Thursday. momondo users have found tickets for Thursday departures for as low as $946. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Sao Paulo Guarulhos Intl Airport is Tuesday, with ticket prices averaging around $1,098.

What is the cheapest time of day to depart on your flight to Sao Paulo Guarulhos Intl Airport?

Our data shows that the cheapest Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport flights are usually those with departure times in the afternoon. Our users have found flights to Sao Paulo Guarulhos Intl Airport in the afternoon for as low as $986. Flights in the evening are often more expensive with an average ticket price of $1,058.

Can stopping save me money on Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport flights?

You could potentially save up to 59% on your flight if you consider stops on a Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport flight.

When to book flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport (MDW to GRU) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Fastest flight time

14h 35m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport takes 14h 35m
There are no direct flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport. There are no popular flight routes from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

  • How far is Chicago Midway to Sao Paulo Guarulhos Intl by plane?

    A flight from Chicago Midway to Sao Paulo Guarulhos Intl will travel around 5217.7 mi. In terms of flight time, this usually takes a little over 14h 35m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport?

    Prices for flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport.

  • What documentation or ID do you need to fly to Sao Paulo Guarulhos Intl Airport?

    The travel and health documents required for your trip to Sao Paulo Guarulhos Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Sao Paulo Guarulhos Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Sao Paulo?

Book flights to Sao Paulo if you plan to visit one of these locations
Guarulhos
Santos
Campinas
Guarujá
Aparecida

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Sao Paulo?

Finding the right flight to Sao Paulo from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Sao Paulo quick and easy, saving you time and money.

Can I find flights from Chicago to Sao Paulo with flexible booking policies on momondo?

All flight searches from Chicago to Sao Paulo on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Sao Paulo?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Sao Paulo from Chicago.

I’m not ready to book a flight from Chicago to Sao Paulo right now. Can momondo alert me if prices change?

Price alerts on flights to Sao Paulo from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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