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Cheap flights from Chicago Midway Airport to Sao Paulo from $277

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 2/23. 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
12:46 pm - 1:40 pm
MDW
-
GRU
21h 54m
2 stops
LATAM Airlines Logo
9:15 pm - 11:59 am
GRU
-
MDW
17h 44m
1 stop
$629LATAM Airlines
Mon, Feb 9 - Sun, Feb 15
Delta Logo
10:49 am - 9:35 am
MDW
-
GRU
19h 46m
1 stop
Delta Logo
10:40 am - 10:31 pm
GRU
-
MDW
13h 51m
1 stop
$700Delta
Sun, Mar 1 - Sun, Mar 8
Delta Logo
10:49 am - 5:40 am
MDW
-
GRU
15h 51m
1 stop
Delta Logo
10:55 pm - 11:59 am
GRU
-
MDW
16h 04m
2 stops
$705Delta
Thu, Feb 19 - Thu, Feb 26
LATAM Airlines Logo
4:13 pm - 9:35 am
MDW
-
GRU
14h 22m
1 stop
LATAM Airlines Logo
10:40 am - 10:31 pm
GRU
-
MDW
13h 51m
1 stop
$729LATAM Airlines
Sat, Mar 7 - Sat, Mar 14
LATAM Airlines Logo
5:40 pm - 9:35 am
MDW
-
GRU
13h 55m
1 stop
LATAM Airlines Logo
3:20 pm - 3:25 pm
GRU
-
MDW
26h 05m
2 stops
$747LATAM Airlines
Tue, Mar 10 - Fri, Mar 13
Multiple Airlines Logo
11:00 am - 7:50 am
MDW
-
GRU
18h 50m
1 stop
Multiple Airlines Logo
5:50 am - 8:53 pm
GRU
-
MDW
17h 03m
2 stops
$749Multiple Airlines
Sun, Mar 15 - Mon, Mar 30
Multiple Airlines Logo
12:25 pm - 7:10 am
MDW
-
GRU
39h 45m
2 stops
Multiple Airlines Logo
12:50 pm - 2:26 pm
GRU
-
MDW
28h 36m
1 stop
$795Multiple Airlines
Thu, Feb 12 - Sat, Feb 21
Multiple Airlines Logo
6:15 am - 8:10 pm
MDW
-
GRU
34h 55m
1 stop
Multiple Airlines Logo
12:50 pm - 2:26 pm
GRU
-
MDW
28h 36m
1 stop
$845Multiple Airlines
Thu, Feb 12 - Sat, Feb 21
LATAM Airlines Logo
10:35 am - 6:45 am
MDW
-
GRU
18h 10m
2 stops
LATAM Airlines Logo
3:20 pm - 9:51 am
GRU
-
MDW
20h 31m
2 stops
$870LATAM Airlines
Thu, May 14 - Tue, May 19
LATAM Airlines Logo
12:45 pm - 5:40 am
MDW
-
GRU
13h 55m
1 stop
LATAM Airlines Logo
3:10 pm - 8:56 am
GRU
-
MDW
20h 46m
2 stops
$876LATAM Airlines
Fri, Feb 27 - Sat, Mar 7

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
Feb 19
MDW10:49 amChicago Midway
15h 51m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Feb 26
GRU11:45 pmSao Paulo Guarulhos Intl
21h 00m
1 stop
MDW5:45 pmChicago Midway
$700
Delta
Feb 19
MDW9:34 amChicago Midway
16h 46m
2 stops
GRU5:20 amSao Paulo Guarulhos Intl
Feb 26
GRU10:55 pmSao Paulo Guarulhos Intl
16h 51m
2 stops
MDW12:46 pmChicago Midway
$705
Delta
Feb 15
MDW1:29 pmChicago Midway
17h 06m
2 stops
GRU9:35 amSao Paulo Guarulhos Intl
Feb 28
GRU9:15 pmSao Paulo Guarulhos Intl
15h 39m
1 stop
MDW9:54 amChicago Midway
$919

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
Feb 9
MDW12:46 pmChicago Midway
21h 54m
2 stops
GRU1:40 pmSao Paulo Guarulhos Intl
Feb 15
GRU9:15 pmSao Paulo Guarulhos Intl
17h 44m
1 stop
MDW11:59 amChicago Midway
$629
LATAM Airlines
Mar 7
MDW4:13 pmChicago Midway
14h 22m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Mar 14
GRU10:40 amSao Paulo Guarulhos Intl
13h 51m
1 stop
MDW10:31 pmChicago Midway
$729
LATAM Airlines
Mar 10
MDW5:40 pmChicago Midway
13h 55m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Mar 13
GRU3:20 pmSao Paulo Guarulhos Intl
26h 05m
2 stops
MDW3:25 pmChicago Midway
$747

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 January 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

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 2/9

12:46 pm-1:40 pm

2 stops21h 54m

Sao Paulo Guarulhos Intl

Sun 2/15

9:15 pm-11:59 am

1 stop17h 44m

$629

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 3/1

10:49 am-9:35 am

1 stop19h 46m

Sao Paulo Guarulhos Intl

Sun 3/8

10:40 am-10:31 pm

1 stop13h 51m

$700

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/19

10:49 am-5:40 am

1 stop15h 51m

Sao Paulo Guarulhos Intl

Thu 2/26

10:55 pm-11:59 am

2 stops16h 04m

$705

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 3/7

4:13 pm-9:35 am

1 stop14h 22m

Sao Paulo Guarulhos Intl

Sat 3/14

10:40 am-10:31 pm

1 stop13h 51m

$729

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 3/10

5:40 pm-9:35 am

1 stop13h 55m

Sao Paulo Guarulhos Intl

Fri 3/13

3:20 pm-3:25 pm

2 stops26h 05m

$747

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 3/15

11:00 am-7:50 am

1 stop18h 50m

Sao Paulo Guarulhos Intl

Mon 3/30

5:50 am-8:53 pm

2 stops17h 03m

$749

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/12

12:25 pm-7:10 am

2 stops39h 45m

Sao Paulo Guarulhos Intl

Sat 2/21

12:50 pm-2:26 pm

1 stop28h 36m

$795

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/12

6:15 am-8:10 pm

1 stop34h 55m

Sao Paulo Guarulhos Intl

Sat 2/21

12:50 pm-2:26 pm

1 stop28h 36m

$845

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 5/14

10:35 am-6:45 am

2 stops18h 10m

Sao Paulo Guarulhos Intl

Tue 5/19

3:20 pm-9:51 am

2 stops20h 31m

$870

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 2/27

12:45 pm-5:40 am

1 stop13h 55m

Sao Paulo Guarulhos Intl

Sat 3/7

3:10 pm-8:56 am

2 stops20h 46m

$876

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 $939. 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 $1,093.

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 evening. Our users have found flights to Sao Paulo Guarulhos Intl Airport in the evening for as low as $1,008. Flights in the afternoon are often more expensive with an average ticket price of $1,023.

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 53m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport takes 14h 53m
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 14h 53m.

  • 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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