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Cheap flights from Chicago Midway Airport to Sao Paulo from $298

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 3/16. 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.
Delta Logo
12:47 pm - 9:35 am
MDW
-
GRU
18h 48m
1 stop
Delta Logo
11:45 pm - 12:02 pm
GRU
-
MDW
14h 17m
1 stop
$692Delta
Sun, Mar 8 - Tue, Mar 24
Delta Logo
6:07 pm - 9:35 am
MDW
-
GRU
13h 28m
1 stop
Delta Logo
11:45 pm - 5:22 pm
GRU
-
MDW
19h 37m
1 stop
$701Delta
Sun, Mar 8 - Tue, Mar 24
LATAM Airlines Logo
10:41 am - 5:40 am
MDW
-
GRU
16h 59m
1 stop
LATAM Airlines Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
$702LATAM Airlines
Mon, May 4 - Tue, May 12
Delta Logo
12:47 pm - 7:50 am
MDW
-
GRU
17h 03m
2 stops
Delta Logo
11:45 pm - 12:02 pm
GRU
-
MDW
14h 17m
1 stop
$705Delta
Sun, Mar 8 - Sun, Mar 15
LATAM Airlines Logo
10:45 am - 5:40 am
MDW
-
GRU
16h 55m
1 stop
LATAM Airlines Logo
10:50 pm - 12:07 pm
GRU
-
MDW
15h 17m
1 stop
$732LATAM Airlines
Fri, Apr 10 - Sun, Apr 26
LATAM Airlines Logo
10:45 am - 8:20 pm
MDW
-
GRU
31h 35m
2 stops
LATAM Airlines Logo
7:30 am - 9:56 am
GRU
-
MDW
28h 26m
2 stops
$738LATAM Airlines
Thu, Apr 2 - Thu, Apr 9
LATAM Airlines Logo
4:30 pm - 5:40 am
MDW
-
GRU
35h 10m
1 stop
LATAM Airlines Logo
10:40 am - 10:31 pm
GRU
-
MDW
13h 51m
1 stop
$740LATAM Airlines
Sat, Mar 14 - Sat, Mar 21
LATAM Airlines Logo
4:30 pm - 11:55 pm
MDW
-
GRU
29h 25m
2 stops
LATAM Airlines Logo
10:50 pm - 9:09 pm
GRU
-
MDW
24h 19m
1 stop
$741LATAM Airlines
Sat, May 16 - Sat, May 30
LATAM Airlines Logo
6:00 am - 8:20 pm
MDW
-
GRU
36h 20m
2 stops
LATAM Airlines Logo
10:50 pm - 5:22 pm
GRU
-
MDW
20h 32m
1 stop
$743LATAM Airlines
Thu, Apr 2 - Thu, Apr 9
LATAM Airlines Logo
4:30 pm - 11:55 pm
MDW
-
GRU
29h 25m
2 stops
LATAM Airlines Logo
8:15 am - 9:51 am
GRU
-
MDW
27h 36m
2 stops
$747LATAM Airlines
Sat, May 16 - Sat, May 30

LATAM Airlines flights from Chicago Midway Airport to Sao Paulo

Our best LATAM Airlines deals on Chicago Midway Airport to Sao Paulo flight tickets
LATAM Airlines
May 4
MDW10:41 amChicago Midway
16h 59m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
May 12
GRU10:50 pmSao Paulo Guarulhos Intl
15h 06m
1 stop
MDW11:56 amChicago Midway
$702
LATAM Airlines
Apr 10
MDW10:45 amChicago Midway
16h 55m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Apr 26
GRU10:50 pmSao Paulo Guarulhos Intl
15h 17m
1 stop
MDW12:07 pmChicago Midway
$732
LATAM Airlines
Apr 2
MDW10:45 amChicago Midway
31h 35m
2 stops
GRU8:20 pmSao Paulo Guarulhos Intl
Apr 9
GRU7:30 amSao Paulo Guarulhos Intl
28h 26m
2 stops
MDW9:56 amChicago Midway
$738

Delta flights from Chicago Midway Airport to Sao Paulo

Our best Delta deals on Chicago Midway Airport to Sao Paulo flight tickets
Delta
Mar 8
MDW12:47 pmChicago Midway
18h 48m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Mar 24
GRU11:45 pmSao Paulo Guarulhos Intl
14h 17m
1 stop
MDW12:02 pmChicago Midway
$692
Delta
Mar 8
MDW6:07 pmChicago Midway
13h 28m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Mar 24
GRU11:45 pmSao Paulo Guarulhos Intl
19h 37m
1 stop
MDW5:22 pmChicago Midway
$701
Delta
Mar 8
MDW12:47 pmChicago Midway
17h 03m
2 stops
GRU7:50 amSao Paulo Guarulhos Intl
Mar 15
GRU11:45 pmSao Paulo Guarulhos Intl
14h 17m
1 stop
MDW12:02 pmChicago Midway
$705

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Sao Paulo 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 February 18, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Sao Paulo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 3/8

12:47 pm-9:35 am

1 stop18h 48m

Sao Paulo Guarulhos Intl

Tue 3/24

11:45 pm-12:02 pm

1 stop14h 17m

$692

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 3/8

6:07 pm-9:35 am

1 stop13h 28m

Sao Paulo Guarulhos Intl

Tue 3/24

11:45 pm-5:22 pm

1 stop19h 37m

$701

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 5/4

10:41 am-5:40 am

1 stop16h 59m

Sao Paulo Guarulhos Intl

Tue 5/12

10:50 pm-11:56 am

1 stop15h 06m

$702

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 3/8

12:47 pm-7:50 am

2 stops17h 03m

Sao Paulo Guarulhos Intl

Sun 3/15

11:45 pm-12:02 pm

1 stop14h 17m

$705

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 4/10

10:45 am-5:40 am

1 stop16h 55m

Sao Paulo Guarulhos Intl

Sun 4/26

10:50 pm-12:07 pm

1 stop15h 17m

$732

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 4/2

10:45 am-8:20 pm

2 stops31h 35m

Sao Paulo Guarulhos Intl

Thu 4/9

7:30 am-9:56 am

2 stops28h 26m

$738

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 3/14

4:30 pm-5:40 am

1 stop35h 10m

Sao Paulo Guarulhos Intl

Sat 3/21

10:40 am-10:31 pm

1 stop13h 51m

$740

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 5/16

4:30 pm-11:55 pm

2 stops29h 25m

Sao Paulo Guarulhos Intl

Sat 5/30

10:50 pm-9:09 pm

1 stop24h 19m

$741

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 4/2

6:00 am-8:20 pm

2 stops36h 20m

Sao Paulo Guarulhos Intl

Thu 4/9

10:50 pm-5:22 pm

1 stop20h 32m

$743

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 5/16

4:30 pm-11:55 pm

2 stops29h 25m

Sao Paulo Guarulhos Intl

Sat 5/30

8:15 am-9:51 am

2 stops27h 36m

$747

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

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?

The cheapest day to depart on your flight to Sao Paulo is on a Thursday when prices can be found for as low as $937. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,079.

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

In the afternoon is the cheapest time of day to fly from Chicago Midway Airport to Sao Paulo when you can find flight prices for as low as $993. Flying to Sao Paulo in the afternoon is an ideal time because this is during off-peak travel hours. Flights to Sao Paulo are more costly in the evening, with an average ticket price of $1,035. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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

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

When to book flights from Chicago Midway Airport to Sao Paulo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Sao Paulo 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 (MDW to SAO) flight deals and tips

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

Fastest flight time

14h 35m

Direct flights

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

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

    The distance between Chicago Midway and Sao Paulo is about 5219.4 mi. A reasonable flight in good conditions will take 14h 35m.

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

    Prices for flights from Chicago Midway Airport to Sao Paulo are updated daily.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Sao Paulo.

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

    The necessary travel and health documents for your Sao Paulo trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Sao Paulo?

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

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Sao Paulo from Chicago.

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

Flights from Chicago to Sao Paulo with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Chicago to Sao Paulo flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Chicago to Sao Paulo flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to Brazil

Fly into one of these airports located in Sao Paulo

Airports listed have a maximum distance of 48.9 mi from Sao Paulo
Sao Paulo Congonhas Airport
Sao Paulo Guarulhos Intl Airport
Sao Paulo Viracopos Airport