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Cheap flights from Chicago Midway Airport to Sao Paulo from $360

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 8/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 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
5:11 pm - 5:40 am
MDW
-
GRU
34h 29m
1 stop
LATAM Airlines Logo
3:20 pm - 10:09 am
GRU
-
MDW
20h 49m
2 stops
$732LATAM Airlines
Tue, Jun 23 - Tue, Jun 30
LATAM Airlines Logo
5:25 pm - 5:40 am
MDW
-
GRU
34h 15m
1 stop
LATAM Airlines Logo
8:45 pm - 11:55 am
GRU
-
MDW
41h 10m
2 stops
$983LATAM Airlines
Sun, Sep 13 - Sun, Sep 20
LATAM Airlines Logo
10:54 am - 5:40 am
MDW
-
GRU
16h 46m
1 stop
LATAM Airlines Logo
1:10 pm - 9:53 am
GRU
-
MDW
22h 43m
2 stops
$1,002LATAM Airlines
Tue, Sep 1 - Mon, Sep 14
LATAM Airlines Logo
11:05 am - 5:30 am
MDW
-
GRU
16h 25m
2 stops
LATAM Airlines Logo
3:20 pm - 10:09 am
GRU
-
MDW
20h 49m
2 stops
$1,003LATAM Airlines
Fri, Jun 19 - Sat, Jun 27
LATAM Airlines Logo
5:11 pm - 1:15 pm
MDW
-
GRU
18h 04m
2 stops
LATAM Airlines Logo
10:50 pm - 10:09 am
GRU
-
MDW
13h 19m
1 stop
$1,004LATAM Airlines
Fri, Jun 19 - Sat, Jun 27
LATAM Airlines Logo
12:46 pm - 5:40 am
MDW
-
GRU
14h 54m
1 stop
LATAM Airlines Logo
8:45 pm - 10:37 am
GRU
-
MDW
39h 52m
2 stops
$1,058LATAM Airlines
Thu, Sep 3 - Mon, Sep 7
LATAM Airlines Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
LATAM Airlines Logo
7:55 am - 9:53 am
GRU
-
MDW
27h 58m
2 stops
$1,063LATAM Airlines
Thu, Sep 10 - Mon, Sep 14
LATAM Airlines Logo
5:25 pm - 5:30 am
MDW
-
GRU
34h 05m
2 stops
LATAM Airlines Logo
8:45 pm - 11:55 am
GRU
-
MDW
41h 10m
2 stops
$1,090LATAM Airlines
Sun, Sep 13 - Sun, Sep 20
Multiple Airlines Logo
10:25 am - 9:50 am
MDW
-
GRU
21h 25m
2 stops
Multiple Airlines Logo
4:08 am - 9:40 am
GRU
-
MDW
31h 32m
2 stops
$1,115Multiple Airlines
Sun, Jul 12 - Sun, Aug 23
Multiple Airlines Logo
10:25 am - 9:00 am
MDW
-
GRU
20h 35m
1 stop
Multiple Airlines Logo
4:08 am - 9:40 am
GRU
-
MDW
31h 32m
2 stops
$1,117Multiple Airlines
Sun, Jul 12 - Sun, Aug 23

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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
Jun 23
MDW5:11 pmChicago Midway
34h 29m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Jun 30
GRU3:20 pmSao Paulo Guarulhos Intl
20h 49m
2 stops
MDW10:09 amChicago Midway
$732
LATAM Airlines
Sep 13
MDW5:25 pmChicago Midway
34h 15m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Sep 20
GRU8:45 pmSao Paulo Guarulhos Intl
41h 10m
2 stops
MDW11:55 amChicago Midway
$983
LATAM Airlines
Jun 16
MDW11:05 amChicago Midway
16h 35m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Jun 30
GRU3:20 pmSao Paulo Guarulhos Intl
20h 49m
2 stops
MDW10:09 amChicago Midway
$1,001

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
Jul 8
MDW12:41 pmChicago Midway
14h 59m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Aug 9
GRU10:50 pmSao Paulo Guarulhos Intl
13h 09m
1 stop
MDW9:59 amChicago Midway
$1,181
Delta
Jul 2
MDW1:26 pmChicago Midway
15h 49m
2 stops
GRU7:15 amSao Paulo Guarulhos Intl
Jul 20
GRU10:50 pmSao Paulo Guarulhos Intl
19h 25m
1 stop
MDW4:15 pmChicago Midway
$1,185
Delta
Jul 6
MDW5:11 pmChicago Midway
34h 29m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Aug 12
GRU10:50 pmSao Paulo Guarulhos Intl
19h 25m
1 stop
MDW4:15 pmChicago Midway
$1,191

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 June 15, 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 6/23

5:11 pm-5:40 am

1 stop34h 29m

Sao Paulo Guarulhos Intl

Tue 6/30

3:20 pm-10:09 am

2 stops20h 49m

$732

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 9/13

5:25 pm-5:40 am

1 stop34h 15m

Sao Paulo Guarulhos Intl

Sun 9/20

8:45 pm-11:55 am

2 stops41h 10m

$983

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 9/1

10:54 am-5:40 am

1 stop16h 46m

Sao Paulo Guarulhos Intl

Mon 9/14

1:10 pm-9:53 am

2 stops22h 43m

$1,002

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 6/19

11:05 am-5:30 am

2 stops16h 25m

Sao Paulo Guarulhos Intl

Sat 6/27

3:20 pm-10:09 am

2 stops20h 49m

$1,003
Quickest round-trip

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 6/19

5:11 pm-1:15 pm

2 stops18h 04m

Sao Paulo Guarulhos Intl

Sat 6/27

10:50 pm-10:09 am

1 stop13h 19m

$1,004

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 9/3

12:46 pm-5:40 am

1 stop14h 54m

Sao Paulo Guarulhos Intl

Mon 9/7

8:45 pm-10:37 am

2 stops39h 52m

$1,058

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 9/10

6:00 am-5:40 am

1 stop21h 40m

Sao Paulo Guarulhos Intl

Mon 9/14

7:55 am-9:53 am

2 stops27h 58m

$1,063

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 9/13

5:25 pm-5:30 am

2 stops34h 05m

Sao Paulo Guarulhos Intl

Sun 9/20

8:45 pm-11:55 am

2 stops41h 10m

$1,090

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 7/12

10:25 am-9:50 am

2 stops21h 25m

Sao Paulo Guarulhos Intl

Sun 8/23

4:08 am-9:40 am

2 stops31h 32m

$1,115

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 7/12

10:25 am-9:00 am

1 stop20h 35m

Sao Paulo Guarulhos Intl

Sun 8/23

4:08 am-9:40 am

2 stops31h 32m

$1,117

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 $957. 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 $1,192.

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 $996. Flights in the evening are often more expensive with an average ticket price of $1,091.

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

15h 45m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport takes 15h 45m
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 15h 45m.

  • 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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