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Cheap flights from Chicago Midway Airport to Sao Paulo from $307

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
10:54 am - 5:25 am
MDW
-
GRU
16h 31m
2 stops
LATAM Airlines Logo
9:45 am - 9:59 am
GRU
-
MDW
26h 14m
2 stops
$689LATAM Airlines
Sun, Aug 23 - Mon, Aug 24
LATAM Airlines Logo
10:54 am - 8:40 am
MDW
-
GRU
19h 46m
2 stops
LATAM Airlines Logo
5:45 pm - 11:51 am
GRU
-
MDW
20h 06m
2 stops
$780LATAM Airlines
Wed, Aug 19 - Mon, Aug 24
LATAM Airlines Logo
12:46 pm - 5:40 am
MDW
-
GRU
14h 54m
1 stop
LATAM Airlines Logo
5:45 pm - 9:59 am
GRU
-
MDW
18h 14m
2 stops
$785LATAM Airlines
Wed, Aug 19 - Mon, Aug 24
Multiple Airlines Logo
7:30 pm - 5:35 am
MDW
-
GRU
32h 05m
3 stops
Multiple Airlines Logo
10:45 pm - 2:35 pm
GRU
-
MDW
17h 50m
2 stops
$915Multiple Airlines
Sat, Sep 12 - Sat, Sep 19
LATAM Airlines Logo
5:15 pm - 4:15 pm
MDW
-
GRU
21h 00m
2 stops
LATAM Airlines Logo
3:50 pm - 10:03 am
GRU
-
MDW
20h 13m
2 stops
$916LATAM Airlines
Wed, Oct 21 - Sun, Oct 25
LATAM Airlines Logo
5:15 pm - 1:15 pm
MDW
-
GRU
18h 00m
2 stops
LATAM Airlines Logo
9:30 pm - 9:52 am
GRU
-
MDW
14h 22m
1 stop
$917LATAM Airlines
Fri, Oct 23 - Wed, Oct 28
LATAM Airlines Logo
12:46 pm - 5:40 am
MDW
-
GRU
14h 54m
1 stop
LATAM Airlines Logo
5:45 pm - 9:59 am
GRU
-
MDW
18h 14m
2 stops
$944LATAM Airlines
Sun, Aug 16 - Mon, Aug 24
Multiple Airlines Logo
7:30 pm - 5:35 am
MDW
-
GRU
32h 05m
3 stops
Multiple Airlines Logo
10:45 pm - 2:35 pm
GRU
-
MDW
17h 50m
2 stops
$985Multiple Airlines
Sat, Sep 12 - Sat, Sep 19
Multiple Airlines Logo
7:30 pm - 5:35 am
MDW
-
GRU
32h 05m
3 stops
Multiple Airlines Logo
10:45 pm - 2:35 pm
GRU
-
MDW
17h 50m
2 stops
$990Multiple Airlines
Sat, Sep 12 - Sat, Sep 19
Multiple Airlines Logo
8:23 pm - 3:08 am
MDW
-
GRU
28h 45m
3 stops
Multiple Airlines Logo
4:08 am - 11:00 am
GRU
-
MDW
32h 52m
3 stops
$992Multiple Airlines
Fri, Aug 28 - Sun, Sep 6

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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
Aug 23
MDW10:54 amChicago Midway
16h 31m
2 stops
GRU5:25 amSao Paulo Guarulhos Intl
Aug 24
GRU9:45 amSao Paulo Guarulhos Intl
26h 14m
2 stops
MDW9:59 amChicago Midway
$689
LATAM Airlines
Aug 19
MDW10:54 amChicago Midway
19h 46m
2 stops
GRU8:40 amSao Paulo Guarulhos Intl
Aug 24
GRU5:45 pmSao Paulo Guarulhos Intl
20h 06m
2 stops
MDW11:51 amChicago Midway
$780
LATAM Airlines
Aug 19
MDW12:46 pmChicago Midway
14h 54m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Aug 24
GRU5:45 pmSao Paulo Guarulhos Intl
18h 14m
2 stops
MDW9:59 amChicago Midway
$785

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 July 29, 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

Cheapest round-trip

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 8/23

10:54 am-5:25 am

2 stops16h 31m

Sao Paulo Guarulhos Intl

Mon 8/24

9:45 am-9:59 am

2 stops26h 14m

$689

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 8/19

10:54 am-8:40 am

2 stops19h 46m

Sao Paulo Guarulhos Intl

Mon 8/24

5:45 pm-11:51 am

2 stops20h 06m

$780

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 8/19

12:46 pm-5:40 am

1 stop14h 54m

Sao Paulo Guarulhos Intl

Mon 8/24

5:45 pm-9:59 am

2 stops18h 14m

$785

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 9/12

7:30 pm-5:35 am

3 stops32h 05m

Sao Paulo Guarulhos Intl

Sat 9/19

10:45 pm-2:35 pm

2 stops17h 50m

$915

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 10/21

5:15 pm-4:15 pm

2 stops21h 00m

Sao Paulo Guarulhos Intl

Sun 10/25

3:50 pm-10:03 am

2 stops20h 13m

$916
Quickest round-trip

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 10/23

5:15 pm-1:15 pm

2 stops18h 00m

Sao Paulo Guarulhos Intl

Wed 10/28

9:30 pm-9:52 am

1 stop14h 22m

$917

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 8/16

12:46 pm-5:40 am

1 stop14h 54m

Sao Paulo Guarulhos Intl

Mon 8/24

5:45 pm-9:59 am

2 stops18h 14m

$944

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 9/12

7:30 pm-5:35 am

3 stops32h 05m

Sao Paulo Guarulhos Intl

Sat 9/19

10:45 pm-2:35 pm

2 stops17h 50m

$985

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 9/12

7:30 pm-5:35 am

3 stops32h 05m

Sao Paulo Guarulhos Intl

Sat 9/19

10:45 pm-2:35 pm

2 stops17h 50m

$990

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 8/28

8:23 pm-3:08 am

3 stops28h 45m

Sao Paulo Guarulhos Intl

Sun 9/6

4:08 am-11:00 am

3 stops32h 52m

$992

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 Monday when prices can be found for as low as $992. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday 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 $1,196.

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 $996. 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 $1,103. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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

13h 10m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sao Paulo takes 13h 10m
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

Frequently asked questions about flying from Chicago Midway Airport to Sao Paulo

  • 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 13h 10m.

  • 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