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Cheap flights from Chicago Midway Airport to Sao Paulo from $309

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 3/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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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
10:45 am - 5:30 am
MDW
-
GRU
16h 45m
2 stops
LATAM Airlines Logo
2:20 pm - 9:56 am
GRU
-
MDW
21h 36m
2 stops
$737LATAM Airlines
Fri, Apr 3 - Thu, Apr 9
Multiple Airlines Logo
3:20 pm - 9:37 pm
MDW
-
GRU
28h 17m
3 stops
Multiple Airlines Logo
11:10 am - 9:40 am
GRU
-
MDW
24h 30m
3 stops
$827Multiple Airlines
Thu, May 7 - Tue, May 19
LATAM Airlines Logo
6:07 pm - 9:35 am
MDW
-
GRU
13h 28m
1 stop
LATAM Airlines Logo
3:20 pm - 9:56 am
GRU
-
MDW
20h 36m
2 stops
$866LATAM Airlines
Wed, Mar 18 - Tue, Mar 24
LATAM Airlines Logo
6:07 pm - 9:35 am
MDW
-
GRU
13h 28m
1 stop
LATAM Airlines Logo
3:20 pm - 9:56 am
GRU
-
MDW
20h 36m
2 stops
$873LATAM Airlines
Thu, Mar 19 - Wed, Mar 25
LATAM Airlines Logo
10:45 am - 5:40 am
MDW
-
GRU
16h 55m
1 stop
LATAM Airlines Logo
3:25 pm - 9:56 am
GRU
-
MDW
20h 31m
2 stops
$874LATAM Airlines
Fri, Mar 20 - Thu, Mar 26
LATAM Airlines Logo
6:07 pm - 5:30 am
MDW
-
GRU
33h 23m
2 stops
LATAM Airlines Logo
2:20 pm - 9:56 am
GRU
-
MDW
21h 36m
2 stops
$929LATAM Airlines
Thu, Apr 2 - Thu, Apr 9
LATAM Airlines Logo
10:41 am - 5:40 am
MDW
-
GRU
16h 59m
1 stop
LATAM Airlines Logo
10:50 pm - 12:07 pm
GRU
-
MDW
15h 17m
1 stop
$951LATAM Airlines
Tue, Apr 14 - Tue, Apr 21
LATAM Airlines Logo
12:52 pm - 5:20 am
MDW
-
GRU
14h 28m
2 stops
LATAM Airlines Logo
8:30 am - 10:28 pm
GRU
-
MDW
15h 58m
2 stops
$953LATAM Airlines
Tue, Apr 14 - Tue, Apr 28
Multiple Airlines Logo
3:20 pm - 9:05 am
MDW
-
GRU
15h 45m
1 stop
Multiple Airlines Logo
5:15 pm - 2:35 pm
GRU
-
MDW
23h 20m
2 stops
$957Multiple Airlines
Thu, May 14 - Wed, May 27
LATAM Airlines Logo
1:05 pm - 5:40 am
MDW
-
GRU
14h 35m
1 stop
LATAM Airlines Logo
10:50 pm - 9:46 pm
GRU
-
MDW
24h 56m
1 stop
$960LATAM Airlines
Tue, Aug 18 - Fri, Aug 28

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
Apr 3
MDW10:45 amChicago Midway
16h 45m
2 stops
GRU5:30 amSao Paulo Guarulhos Intl
Apr 9
GRU2:20 pmSao Paulo Guarulhos Intl
21h 36m
2 stops
MDW9:56 amChicago Midway
$737
LATAM Airlines
Apr 2
MDW6:07 pmChicago Midway
33h 23m
2 stops
GRU5:30 amSao Paulo Guarulhos Intl
Apr 9
GRU2:20 pmSao Paulo Guarulhos Intl
21h 36m
2 stops
MDW9:56 amChicago Midway
$800
LATAM Airlines
Mar 18
MDW6:07 pmChicago Midway
13h 28m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Mar 24
GRU3:20 pmSao Paulo Guarulhos Intl
20h 36m
2 stops
MDW9:56 amChicago Midway
$866

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
Apr 16
MDW12:52 pmChicago Midway
14h 48m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Apr 23
GRU10:50 pmSao Paulo Guarulhos Intl
15h 17m
1 stop
MDW12:07 pmChicago Midway
$963
Delta
Apr 16
MDW9:27 amChicago Midway
18h 13m
2 stops
GRU5:40 amSao Paulo Guarulhos Intl
Apr 23
GRU8:35 pmSao Paulo Guarulhos Intl
18h 08m
2 stops
MDW12:43 pmChicago Midway
$967
Delta
Mar 16
MDW6:07 pmChicago Midway
13h 28m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Mar 30
GRU10:50 pmSao Paulo Guarulhos Intl
15h 12m
1 stop
MDW12:02 pmChicago Midway
$1,483

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 March 3, 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

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 4/3

10:45 am-5:30 am

2 stops16h 45m

Sao Paulo Guarulhos Intl

Thu 4/9

2:20 pm-9:56 am

2 stops21h 36m

$737

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 5/7

3:20 pm-9:37 pm

3 stops28h 17m

Sao Paulo Guarulhos Intl

Tue 5/19

11:10 am-9:40 am

3 stops24h 30m

$827

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 3/18

6:07 pm-9:35 am

1 stop13h 28m

Sao Paulo Guarulhos Intl

Tue 3/24

3:20 pm-9:56 am

2 stops20h 36m

$866

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 3/19

6:07 pm-9:35 am

1 stop13h 28m

Sao Paulo Guarulhos Intl

Wed 3/25

3:20 pm-9:56 am

2 stops20h 36m

$873

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 3/20

10:45 am-5:40 am

1 stop16h 55m

Sao Paulo Guarulhos Intl

Thu 3/26

3:25 pm-9:56 am

2 stops20h 31m

$874

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 4/2

6:07 pm-5:30 am

2 stops33h 23m

Sao Paulo Guarulhos Intl

Thu 4/9

2:20 pm-9:56 am

2 stops21h 36m

$929

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 4/14

10:41 am-5:40 am

1 stop16h 59m

Sao Paulo Guarulhos Intl

Tue 4/21

10:50 pm-12:07 pm

1 stop15h 17m

$951

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 4/14

12:52 pm-5:20 am

2 stops14h 28m

Sao Paulo Guarulhos Intl

Tue 4/28

8:30 am-10:28 pm

2 stops15h 58m

$953

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 5/14

3:20 pm-9:05 am

1 stop15h 45m

Sao Paulo Guarulhos Intl

Wed 5/27

5:15 pm-2:35 pm

2 stops23h 20m

$957

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 8/18

1:05 pm-5:40 am

1 stop14h 35m

Sao Paulo Guarulhos Intl

Fri 8/28

10:50 pm-9:46 pm

1 stop24h 56m

$960

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Sao Paulo from

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 $947. 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 Friday, with ticket prices averaging around $1,079.

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 $982. Flights in the evening are often more expensive with an average ticket price of $1,051.

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

13h 55m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport takes 13h 55m
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

  • 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 13h 55m.

  • 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
Santos
Guarulhos
Guarujá
Campinas
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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