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Cheap flights from Chicago Midway Airport to Sao Paulo from $280

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 12/24. 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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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
12:47 pm - 1:40 pm
MDW
-
GRU
22h 53m2 stops
LATAM Airlines Logo
10:40 am - 10:29 pm
GRU
-
MDW
13h 49m1 stop
$607LATAM Airlines
Wed, Mar 11 - Sun, Mar 15
LATAM Airlines Logo
10:49 am - 5:40 am
MDW
-
GRU
16h 51m1 stop
LATAM Airlines Logo
4:25 pm - 9:55 am
GRU
-
MDW
19h 30m2 stops
$640LATAM Airlines
Tue, Mar 10 - Tue, Mar 17
Delta Logo
9:32 am - 5:20 am
MDW
-
GRU
17h 48m2 stops
Delta Logo
4:30 pm - 9:55 am
GRU
-
MDW
19h 25m2 stops
$645Delta
Wed, Mar 18 - Wed, Mar 25
LATAM Airlines Logo
5:38 pm - 9:35 am
MDW
-
GRU
13h 57m1 stop
LATAM Airlines Logo
10:40 am - 10:29 pm
GRU
-
MDW
13h 49m1 stop
$662LATAM Airlines
Sun, Mar 8 - Sun, Mar 15
Multiple Airlines Logo
6:30 am - 5:20 am
MDW
-
GRU
19h 50m1 stop
Multiple Airlines Logo
10:55 pm - 2:05 pm
GRU
-
MDW
18h 10m1 stop
$671Multiple Airlines
Thu, Feb 12 - Wed, Feb 18
LATAM Airlines Logo
6:30 am - 5:40 am
MDW
-
GRU
21h 10m1 stop
LATAM Airlines Logo
11:55 pm - 9:55 am
GRU
-
MDW
36h 00m2 stops
$676LATAM Airlines
Fri, Mar 13 - Sun, Mar 22
Multiple Airlines Logo
1:00 pm - 3:25 am
MDW
-
GRU
35h 25m2 stops
Multiple Airlines Logo
10:20 am - 9:58 pm
GRU
-
MDW
13h 38m1 stop
$717Multiple Airlines
Mon, Feb 9 - Wed, Mar 11
Multiple Airlines Logo
6:30 am - 5:20 am
MDW
-
GRU
19h 50m1 stop
Multiple Airlines Logo
6:00 am - 7:50 pm
GRU
-
MDW
16h 50m2 stops
$725Multiple Airlines
Thu, Feb 12 - Fri, Feb 20
LATAM Airlines Logo
12:47 pm - 12:40 pm
MDW
-
GRU
21h 53m2 stops
LATAM Airlines Logo
11:45 pm - 12:02 pm
GRU
-
MDW
14h 17m1 stop
$736LATAM Airlines
Mon, Mar 9 - Wed, Mar 11
LATAM Airlines Logo
10:53 am - 5:40 am
MDW
-
GRU
15h 47m1 stop
LATAM Airlines Logo
11:45 pm - 11:02 am
GRU
-
MDW
14h 17m1 stop
$744LATAM Airlines
Fri, Feb 27 - Sat, Mar 7

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
Mar 11
MDW12:47 pmChicago Midway
22h 53m
2 stops
GRU1:40 pmSao Paulo Guarulhos Intl
Mar 15
GRU10:40 amSao Paulo Guarulhos Intl
13h 49m
1 stop
MDW10:29 pmChicago Midway
$607
Find similar
LATAM Airlines
Mar 10
MDW10:49 amChicago Midway
16h 51m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Mar 17
GRU4:25 pmSao Paulo Guarulhos Intl
19h 30m
2 stops
MDW9:55 amChicago Midway
$640
Find similar
LATAM Airlines
Mar 8
MDW5:38 pmChicago Midway
13h 57m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Mar 15
GRU10:40 amSao Paulo Guarulhos Intl
13h 49m
1 stop
MDW10:29 pmChicago Midway
$662
Find similar

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
Mar 18
MDW9:32 amChicago Midway
17h 48m
2 stops
GRU5:20 amSao Paulo Guarulhos Intl
Mar 25
GRU4:30 pmSao Paulo Guarulhos Intl
19h 25m
2 stops
MDW9:55 amChicago Midway
$645
Find similar
Delta
Feb 9
MDW10:46 amChicago Midway
15h 54m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Mar 10
GRU10:40 amSao Paulo Guarulhos Intl
13h 49m
1 stop
MDW10:29 pmChicago Midway
$812
Find similar
Delta
Feb 9
MDW1:26 pmChicago Midway
17h 09m
2 stops
GRU9:35 amSao Paulo Guarulhos Intl
Mar 10
GRU10:40 amSao Paulo Guarulhos Intl
13h 49m
1 stop
MDW10:29 pmChicago Midway
$817
Find similar

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 December 4, 2025.
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

Wed 3/11

12:47 pm-1:40 pm

2 stops22h 53m

Sao Paulo Guarulhos Intl

Sun 3/15

10:40 am-10:29 pm

1 stop13h 49m

$607

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 3/10

10:49 am-5:40 am

1 stop16h 51m

Sao Paulo Guarulhos Intl

Tue 3/17

4:25 pm-9:55 am

2 stops19h 30m

$640

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 3/18

9:32 am-5:20 am

2 stops17h 48m

Sao Paulo Guarulhos Intl

Wed 3/25

4:30 pm-9:55 am

2 stops19h 25m

$645

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 3/8

5:38 pm-9:35 am

1 stop13h 57m

Sao Paulo Guarulhos Intl

Sun 3/15

10:40 am-10:29 pm

1 stop13h 49m

$662

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/12

6:30 am-5:20 am

1 stop19h 50m

Sao Paulo Guarulhos Intl

Wed 2/18

10:55 pm-2:05 pm

1 stop18h 10m

$671

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 3/13

6:30 am-5:40 am

1 stop21h 10m

Sao Paulo Guarulhos Intl

Sun 3/22

11:55 pm-9:55 am

2 stops36h 00m

$676

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 2/9

1:00 pm-3:25 am

2 stops35h 25m

Sao Paulo Guarulhos Intl

Wed 3/11

10:20 am-9:58 pm

1 stop13h 38m

$717

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/12

6:30 am-5:20 am

1 stop19h 50m

Sao Paulo Guarulhos Intl

Fri 2/20

6:00 am-7:50 pm

2 stops16h 50m

$725

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/9

12:47 pm-12:40 pm

2 stops21h 53m

Sao Paulo Guarulhos Intl

Wed 3/11

11:45 pm-12:02 pm

1 stop14h 17m

$736

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 2/27

10:53 am-5:40 am

1 stop15h 47m

Sao Paulo Guarulhos Intl

Sat 3/7

11:45 pm-11:02 am

1 stop14h 17m

$744

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 $945. 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 $1,097.

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 at noon. Our users have found flights to Sao Paulo Guarulhos Intl Airport at noon for as low as $956. Flights in the afternoon are often more expensive with an average ticket price of $1,045.

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 22m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport takes 13h 22m
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 57m.

  • 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
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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