What is the cheapest airline that flies from Chicago Midway to Sao Paulo?

LATAM Airlines is the most popular carrier operating from Chicago Midway to Sao Paulo

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.

$265 Cheap Flights from Chicago Midway Airport to Sao Paulo in 2025/26

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Find the cheapest flights from Chicago Midway Airport to Sao Paulo

Round-trip

One-way

Last minute

Cheap round-trip flights

10:35 am - 9:35 amMDW-GRU

20h 00m1 stop

3:20 pm - 9:56 amGRU-MDW

21h 36m2 stops

$606LATAM Airlines

Find Deal

Mon, Mar 2 - Fri, Mar 6

10:35 am - 5:40 amMDW-GRU

16h 05m1 stop

3:20 pm - 3:25 pmGRU-MDW

27h 05m2 stops

$607LATAM Airlines

Find Deal

Mon, Mar 2 - Fri, Mar 6

5:04 pm - 9:35 amMDW-GRU

14h 31m1 stop

3:20 pm - 9:35 amGRU-MDW

21h 15m2 stops

$616LATAM Airlines

Find Deal

Wed, Oct 29 - Sun, Nov 2

12:48 pm - 5:40 amMDW-GRU

14h 52m1 stop

4:35 pm - 11:53 amGRU-MDW

21h 18m2 stops

$617LATAM Airlines

Find Deal

Wed, Oct 8 - Tue, Oct 14

9:45 am - 4:15 pmMDW-GRU

28h 30m2 stops

2:40 am - 12:30 amGRU-MDW

24h 50m2 stops

$625Multiple Airlines

Find Deal

Mon, Oct 27 - Sat, Nov 8

10:13 am - 8:05 amMDW-GRU

19h 52m1 stop

4:23 am - 11:46 pmGRU-MDW

21h 23m2 stops

$656Multiple Airlines

Find Deal

Sun, Sep 28 - Mon, Oct 13

12:48 pm - 9:00 amMDW-GRU

18h 12m1 stop

10:50 pm - 11:53 amGRU-MDW

15h 03m1 stop

$660Delta

Find Deal

Tue, Oct 7 - Tue, Oct 21

1:08 pm - 6:50 amMDW-GRU

15h 42m2 stops

10:50 pm - 11:53 amGRU-MDW

15h 03m1 stop

$665Delta

Find Deal

Tue, Oct 7 - Tue, Oct 14

5:34 pm - 9:35 amMDW-GRU

13h 01m1 stop

4:00 am - 11:32 pmGRU-MDW

22h 32m2 stops

$670LATAM Airlines

Find Deal

Mon, Dec 1 - Sat, Dec 13

5:32 pm - 9:35 amMDW-GRU

13h 03m1 stop

7:35 am - 10:16 pmGRU-MDW

17h 41m2 stops

$967Delta

Find Deal

Mon, Dec 15 - Sun, Dec 28

Delta flights from Chicago Midway Airport to Sao Paulo

Our best Delta deals on Chicago Midway Airport to Sao Paulo flight tickets

Delta

Oct 7

MDW12:48 pmChicago Midway

18h 12m

1 stop

GRU9:00 amSao Paulo Guarulhos Intl

Oct 21

GRU10:50 pmSao Paulo Guarulhos Intl

15h 03m

1 stop

MDW11:53 amChicago Midway

$660

Find similar

Delta

Oct 7

MDW1:08 pmChicago Midway

15h 42m

2 stops

GRU6:50 amSao Paulo Guarulhos Intl

Oct 14

GRU10:50 pmSao Paulo Guarulhos Intl

15h 03m

1 stop

MDW11:53 amChicago Midway

$665

Find similar

Delta

Dec 15

MDW5:32 pmChicago Midway

13h 03m

1 stop

GRU9:35 amSao Paulo Guarulhos Intl

Dec 28

GRU7:35 amSao Paulo Guarulhos Intl

17h 41m

2 stops

MDW10:16 pmChicago Midway

$967

Find similar

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

Mar 2

MDW10:35 amChicago Midway

20h 00m

1 stop

GRU9:35 amSao Paulo Guarulhos Intl

Mar 6

GRU3:20 pmSao Paulo Guarulhos Intl

21h 36m

2 stops

MDW9:56 amChicago Midway

$606

Find similar

LATAM Airlines

Mar 2

MDW10:35 amChicago Midway

16h 05m

1 stop

GRU5:40 amSao Paulo Guarulhos Intl

Mar 6

GRU3:20 pmSao Paulo Guarulhos Intl

27h 05m

2 stops

MDW3:25 pmChicago Midway

$607

Find similar

LATAM Airlines

Oct 29

MDW5:04 pmChicago Midway

14h 31m

1 stop

GRU9:35 amSao Paulo Guarulhos Intl

Nov 2

GRU3:20 pmSao Paulo Guarulhos Intl

21h 15m

2 stops

MDW9:35 amChicago Midway

$616

Find similar

momondo Fare Finder

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

Mon 3/2

10:35 am-9:35 am

1 stop20h 00m

Sao Paulo Guarulhos Intl

Fri 3/6

3:20 pm-9:56 am

2 stops21h 36m

$606

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/2

10:35 am-5:40 am

1 stop16h 05m

Sao Paulo Guarulhos Intl

Fri 3/6

3:20 pm-3:25 pm

2 stops27h 05m

$607

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 10/29

5:04 pm-9:35 am

1 stop14h 31m

Sao Paulo Guarulhos Intl

Sun 11/2

3:20 pm-9:35 am

2 stops21h 15m

$616

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 10/8

12:48 pm-5:40 am

1 stop14h 52m

Sao Paulo Guarulhos Intl

Tue 10/14

4:35 pm-11:53 am

2 stops21h 18m

$617

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 10/27

9:45 am-4:15 pm

2 stops28h 30m

Sao Paulo Guarulhos Intl

Sat 11/8

2:40 am-12:30 am

2 stops24h 50m

$625

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 9/28

10:13 am-8:05 am

1 stop19h 52m

Sao Paulo Guarulhos Intl

Mon 10/13

4:23 am-11:46 pm

2 stops21h 23m

$656

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 10/7

12:48 pm-9:00 am

1 stop18h 12m

Sao Paulo Guarulhos Intl

Tue 10/21

10:50 pm-11:53 am

1 stop15h 03m

$660

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 10/7

1:08 pm-6:50 am

2 stops15h 42m

Sao Paulo Guarulhos Intl

Tue 10/14

10:50 pm-11:53 am

1 stop15h 03m

$665

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 12/1

5:34 pm-9:35 am

1 stop13h 01m

Sao Paulo Guarulhos Intl

Sat 12/13

4:00 am-11:32 pm

2 stops22h 32m

$670

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 12/15

5:32 pm-9:35 am

1 stop13h 03m

Sao Paulo Guarulhos Intl

Sun 12/28

7:35 am-10:16 pm

2 stops17h 41m

$967

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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 $1,007. 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 $1,192.

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

At noon 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 $916. Flying to Sao Paulo at noon is an ideal time because this is during off-peak travel hours. Flights to Sao Paulo are more costly in the afternoon, with an average ticket price of $1,082. Departure times in the afternoon 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

Direct flights	None

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.

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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 01m.
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.

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.