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Cheap flights from Chicago Midway Airport to Sao Paulo from $345

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 - 6:10 am
MDW
-
GRU
17h 16m
2 stops
LATAM Airlines Logo
5:45 pm - 9:59 am
GRU
-
MDW
18h 14m
2 stops
$643LATAM Airlines
Mon, Aug 24 - Sat, Aug 29
LATAM Airlines Logo
5:15 pm - 8:45 pm
MDW
-
GRU
25h 30m
2 stops
LATAM Airlines Logo
7:15 pm - 12:05 pm
GRU
-
MDW
18h 50m
2 stops
$754LATAM Airlines
Fri, Oct 23 - Thu, Oct 29
Multiple Airlines Logo
8:49 pm - 9:20 am
MDW
-
GRU
34h 31m
3 stops
Multiple Airlines Logo
11:10 am - 9:45 am
GRU
-
MDW
24h 35m
3 stops
$807Multiple Airlines
Tue, Aug 11 - Tue, Aug 25
LATAM Airlines Logo
6:00 am - 5:30 am
MDW
-
GRU
21h 30m
2 stops
LATAM Airlines Logo
8:10 am - 9:59 am
GRU
-
MDW
27h 49m
2 stops
$820LATAM Airlines
Fri, Jul 31 - Thu, Aug 6
LATAM Airlines Logo
5:11 pm - 4:10 pm
MDW
-
GRU
20h 59m
2 stops
LATAM Airlines Logo
10:50 pm - 11:55 am
GRU
-
MDW
15h 05m
1 stop
$1,019LATAM Airlines
Mon, Sep 21 - Tue, Sep 22
Multiple Airlines Logo
10:25 am - 9:50 am
MDW
-
GRU
21h 25m
2 stops
Multiple Airlines Logo
11:10 am - 9:45 am
GRU
-
MDW
24h 35m
3 stops
$1,083Multiple Airlines
Tue, Aug 11 - Tue, Aug 25
LATAM Airlines Logo
10:58 am - 5:40 am
MDW
-
GRU
16h 42m
1 stop
LATAM Airlines Logo
12:45 pm - 12:05 pm
GRU
-
MDW
25h 20m
2 stops
$1,102LATAM Airlines
Thu, Oct 8 - Wed, Oct 14
Multiple Airlines Logo
8:23 pm - 2:50 am
MDW
-
GRU
28h 27m
3 stops
Multiple Airlines Logo
4:08 am - 9:45 am
GRU
-
MDW
31h 37m
2 stops
$1,107Multiple Airlines
Wed, Jul 29 - Sun, Aug 9
LATAM Airlines Logo
10:54 am - 5:40 am
MDW
-
GRU
16h 46m
1 stop
LATAM Airlines Logo
5:45 pm - 9:53 am
GRU
-
MDW
18h 08m
2 stops
$1,110LATAM Airlines
Mon, Aug 31 - Mon, Sep 21
LATAM Airlines Logo
10:54 am - 5:30 am
MDW
-
GRU
16h 36m
2 stops
LATAM Airlines Logo
5:45 pm - 9:59 am
GRU
-
MDW
18h 14m
2 stops
$1,115LATAM Airlines
Tue, Aug 11 - Tue, Aug 25

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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 24
MDW10:54 amChicago Midway
17h 16m
2 stops
GRU6:10 amSao Paulo Guarulhos Intl
Aug 29
GRU5:45 pmSao Paulo Guarulhos Intl
18h 14m
2 stops
MDW9:59 amChicago Midway
$643
LATAM Airlines
Oct 23
MDW5:15 pmChicago Midway
25h 30m
2 stops
GRU8:45 pmSao Paulo Guarulhos Intl
Oct 29
GRU7:15 pmSao Paulo Guarulhos Intl
18h 50m
2 stops
MDW12:05 pmChicago Midway
$754
LATAM Airlines
Jul 31
MDW6:00 amChicago Midway
21h 30m
2 stops
GRU5:30 amSao Paulo Guarulhos Intl
Aug 6
GRU8:10 amSao Paulo Guarulhos Intl
27h 49m
2 stops
MDW9:59 amChicago Midway
$820

Delta flights from Chicago Midway Airport to Sao Paulo

Our best Delta deals on Chicago Midway Airport to Sao Paulo flight tickets
Delta
Nov 4
MDW1:05 pmChicago Midway
17h 30m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Nov 16
GRU9:30 pmSao Paulo Guarulhos Intl
15h 22m
1 stop
MDW9:52 amChicago Midway
$1,233
Delta
Aug 17
MDW9:24 amChicago Midway
17h 41m
2 stops
GRU5:05 amSao Paulo Guarulhos Intl
Aug 31
GRU10:50 pmSao Paulo Guarulhos Intl
13h 09m
1 stop
MDW9:59 amChicago Midway
$1,237
Delta
Sep 7
MDW9:24 amChicago Midway
17h 41m
2 stops
GRU5:05 amSao Paulo Guarulhos Intl
Sep 19
GRU11:00 pmSao Paulo Guarulhos Intl
19h 16m
2 stops
MDW4:16 pmChicago Midway
$1,261

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 1, 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

Mon 8/24

10:54 am-6:10 am

2 stops17h 16m

Sao Paulo Guarulhos Intl

Sat 8/29

5:45 pm-9:59 am

2 stops18h 14m

$643

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 10/23

5:15 pm-8:45 pm

2 stops25h 30m

Sao Paulo Guarulhos Intl

Thu 10/29

7:15 pm-12:05 pm

2 stops18h 50m

$754

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 8/11

8:49 pm-9:20 am

3 stops34h 31m

Sao Paulo Guarulhos Intl

Tue 8/25

11:10 am-9:45 am

3 stops24h 35m

$807

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 7/31

6:00 am-5:30 am

2 stops21h 30m

Sao Paulo Guarulhos Intl

Thu 8/6

8:10 am-9:59 am

2 stops27h 49m

$820

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 9/21

5:11 pm-4:10 pm

2 stops20h 59m

Sao Paulo Guarulhos Intl

Tue 9/22

10:50 pm-11:55 am

1 stop15h 05m

$1,019

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 8/11

10:25 am-9:50 am

2 stops21h 25m

Sao Paulo Guarulhos Intl

Tue 8/25

11:10 am-9:45 am

3 stops24h 35m

$1,083

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 10/8

10:58 am-5:40 am

1 stop16h 42m

Sao Paulo Guarulhos Intl

Wed 10/14

12:45 pm-12:05 pm

2 stops25h 20m

$1,102

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 7/29

8:23 pm-2:50 am

3 stops28h 27m

Sao Paulo Guarulhos Intl

Sun 8/9

4:08 am-9:45 am

2 stops31h 37m

$1,107

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 8/31

10:54 am-5:40 am

1 stop16h 46m

Sao Paulo Guarulhos Intl

Mon 9/21

5:45 pm-9:53 am

2 stops18h 08m

$1,110
Quickest round-trip

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 8/11

10:54 am-5:30 am

2 stops16h 36m

Sao Paulo Guarulhos Intl

Tue 8/25

5:45 pm-9:59 am

2 stops18h 14m

$1,115

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 $951. 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 $1,199.

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 $1,000. 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 $1,099. 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

13h 35m

Direct flights

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

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 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