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$268+ Cheap flights from Midway (MDW) to Sao Paulo, Brazil (SAO)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAO
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Midway to Sao Paulo

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Sao Paulo (SAO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 20, 2025.

Round-trip from

$568
(KAYAK)

One-way from

$268
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$773
From Chicago Midway to Sao Paulo (SAO)
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One-way flight from Chicago Midway to Sao Paulo (SAO)
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Highest demand for flights based on searches. 9% potential increase in price ($96 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Midway to Sao Paulo

Cheapest flights from Midway to Sao Paulo
Explore the most affordable flight options available from Midway to Sao Paulo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This KAYAK deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:30 pmMDW - GRU
2 stops18h 25mLATAM Airlines
Tue 10/74:10 pmGRU - MDW
2 stops19h 30mLATAM Airlines
Deal found 8/18$568
This SmartFares deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/294:40 pmMDW - GRU
1 stop35h 00mLATAM Airlines
Mon 9/14:40 pmGRU - MDW
2 stops18h 56mLATAM Airlines
Deal found 8/17$600
This FlightHub deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1712:43 pmMDW - GRU
1 stop14h 57mLATAM Airlines
Tue 9/235:45 pmGRU - MDW
2 stops20h 03mLATAM Airlines
Deal found 8/19$638
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/228:05 amMDW - VCP
2 stops19h 30mMultiple Airlines
Wed 10/2910:00 amVCP - MDW
1 stop25h 12mMultiple Airlines
Deal found 8/19$718
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:32 pmMDW - VCP
1 stop14h 03mMultiple Airlines
Sun 11/161:10 pmVCP - MDW
1 stop22h 22mMultiple Airlines
Deal found 8/19$726
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/34:25 pmMDW - GRU
1 stop14h 35mLATAM Airlines
Tue 9/97:00 amGRU - MDW
2 stops28h 34mLATAM Airlines
Deal found 8/20$742
This Mytrip deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1512:50 pmMDW - VCP
2 stops26h 55mMultiple Airlines
Thu 9/2510:50 pmVCP - MDW
2 stops22h 10mMultiple Airlines
Deal found 8/18$753
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:32 amMDW - VCP
1 stop20h 03mMultiple Airlines
Sun 11/301:10 pmVCP - MDW
2 stops47h 55mMultiple Airlines
Deal found 8/19$758
This Trip.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/134:24 pmMDW - GRU
1 stop13h 56mMultiple Airlines
Sun 10/266:00 amGRU - MDW
2 stops31h 17mMultiple Airlines
Deal found 8/18$785
This LATAM Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2012:43 pmMDW - GRU
1 stop14h 57mLATAM Airlines
Tue 8/264:35 pmGRU - MDW
2 stops23h 01mLATAM Airlines
Deal found 8/17$794
This FlightHub deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:30 pmMDW - GRU
1 stop12h 30mLATAM Airlines
Thu 9/2510:50 pmGRU - MDW
1 stop14h 58mLATAM Airlines
Deal found 8/19$813
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1810:35 amMDW - GRU
1 stop17h 05mLATAM Airlines
Sat 11/1511:05 pmGRU - MDW
2 stops15h 50mLATAM Airlines
Deal found 8/20$817

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated August 20, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Sao Paulo that are best for you.

Fly from

Midway

Fly to

Sao Paulo

Route

Depart

Return

Price

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 9/3

4:25 pm-9:00 am

1 stop14h 35m

Sao Paulo Guarulhos Intl

Tue 9/9

4:40 pm-1:36 pm

2 stops22h 56m

$568

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 10/1

6:30 pm-2:55 pm

2 stops18h 25m

Sao Paulo Guarulhos Intl

Tue 10/7

10:50 pm-11:58 am

1 stop15h 08m

$568

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 1/28

10:35 am-9:35 am

1 stop20h 00m

Sao Paulo Guarulhos Intl

Mon 2/2

5:45 pm-9:56 am

2 stops19h 11m

$593

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 9/17

10:35 am-5:40 am

1 stop17h 05m

Sao Paulo Guarulhos Intl

Tue 9/23

5:45 pm-9:40 am

2 stops17h 55m

$638

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 8/31

4:25 pm-9:00 am

1 stop14h 35m

Sao Paulo Guarulhos Intl

Wed 9/3

8:15 pm-1:36 pm

2 stops43h 21m

$638

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Wed 10/22

8:05 am-5:35 am

2 stops19h 30m

Sao Paulo Viracopos

Wed 10/29

10:00 am-9:12 am

1 stop25h 12m

$718

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Fri 11/7

3:32 pm-8:35 am

1 stop14h 03m

Sao Paulo Viracopos

Sun 11/16

1:10 pm-8:32 am

1 stop22h 22m

$726

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Mon 9/15

12:50 pm-5:45 pm

2 stops26h 55m

Sao Paulo Viracopos

Thu 9/25

10:50 pm-7:00 pm

2 stops22h 10m

$753

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Mon 11/17

9:32 am-8:35 am

1 stop20h 03m

Sao Paulo Viracopos

Sun 11/30

1:10 pm-10:05 am

2 stops47h 55m

$758

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Thu 11/20

2:11 pm-8:35 am

1 stop15h 24m

Sao Paulo Viracopos

Thu 11/27

10:50 pm-10:05 am

2 stops38h 15m

$928

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 32 results
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Best time to book a flight from Midway to Sao Paulo

Have a flexible travel schedule? Discover the best time to fly to Sao Paulo from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Sao Paulo
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Midway to Sao Paulo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Sao Paulo?

    There are many flights that can get you from Chicago Midway Airport to Sao Paulo in 14h 35m. Fly via LATAM Airlines to get the fastest option. Airlines will cover a distance of 5218 mi.

  • Can I find deals for flights from Midway to Sao Paulo that include hotel bookings?

    Yes. In addition to deals on Midway to Sao Paulo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Sao Paulo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Sao Paulo.

  • Can I find deals for business class flights from Midway to Sao Paulo?

    Yes. Cheapflights offers flight deals from Midway to Sao Paulo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Sao Paulo?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Sao Paulo (average of $672). Flying from Chicago Midway Airport to Sao Paulo in December is currently the most expensive (average of $1,209). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Sao Paulo

See prices for flight routes from nearby airports that may be better suited for you.
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