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Midway

$340+ Cheap flights from Sao Paulo, Brazil (SAO) to Midway (MDW)

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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
SAO — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Sao Paulo to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Sao Paulo (SAO) to Midway (MDW). 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 September 17, 2025.

Round-trip from

$604
(Cheapflightsfares)

One-way from

$340
(Kiwi.com)

Popular in

November

Cheapest in

March

Average price

$871
From Sao Paulo (SAO) to Chicago Midway
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One-way flight from Sao Paulo (SAO) to Chicago Midway
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Highest demand for flights based on searches. 19% potential increase in price ($248 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($95 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Sao Paulo to Midway

Cheapest flights from Sao Paulo to Midway
Explore the most affordable flight options available from Sao Paulo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:00 amGRU - MDW
2 stops22h 32mLATAM Airlines
Sat 2/710:35 amMDW - GRU
2 stops16h 40mLATAM Airlines
Deal found 9/17$604
This MaxMilhas deal was found by Cheapflights users on 9/16. 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 MaxMilhas is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:20 amGRU - MDW
2 stops25h 34mLATAM Airlines
Fri 1/166:00 amMDW - GRU
2 stops23h 50mLATAM Airlines
Deal found 9/16$606
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1010:35 amGRU - MDW
2 stops30h 51mLATAM Airlines
Thu 10/3010:40 amMDW - GRU
1 stop20h 55mLATAM Airlines
Deal found 9/16$607
This Expedia deal was found by Cheapflights users on 9/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/139:15 pmGRU - MDW
1 stop15h 39mLATAM Airlines
Sat 1/314:30 pmMDW - GRU
1 stop14h 05mLATAM Airlines
Deal found 9/16$623
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:20 amGRU - MDW
2 stops15h 12mDelta
Mon 3/91:05 pmMDW - GRU
2 stops14h 15mDelta
Deal found 9/17$683
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:45 pmGRU - MDW
2 stops15h 49mDelta
Fri 2/131:05 pmMDW - GRU
1 stop13h 35mDelta
Deal found 9/16$691
This SmartFares deal was found by Cheapflights users on 9/15. 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.
Sat 11/1511:45 pmGRU - MDW
1 stop15h 07mLATAM Airlines
Sat 2/146:00 amMDW - GRU
1 stop20h 40mLATAM Airlines
Deal found 9/15$726
This LATAM Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 10/279:15 pmGRU - MDW
1 stop14h 25mLATAM Airlines
Mon 11/105:34 pmMDW - GRU
2 stops19h 56mLATAM Airlines
Deal found 9/16$768
This LATAM Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 12/24:00 amGRU - MDW
2 stops22h 32mLATAM Airlines
Tue 1/610:35 amMDW - GRU
2 stops16h 40mLATAM Airlines
Deal found 9/17$770
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1511:20 amGRU - MDW
2 stops15h 12mDelta
Wed 1/76:00 amMDW - GRU
1 stop20h 40mDelta
Deal found 9/16$778
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/810:50 pmGRU - MDW
2 stops15h 38mDelta
Wed 10/156:00 amMDW - GRU
1 stop21h 40mDelta
Deal found 9/17$780

Cheapflights Fare Finder

 
Customize your flight search to find flights from Sao Paulo to Midway 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 September 17, 2025.
Use the filters below to find and compare flights from Sao Paulo to Chicago Midway Airport that are best for you.

Fly from

Sao Paulo

Fly to

Midway

Route

Depart

Return

Price

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 2/3

9:15 pm-12:35 pm

2 stops18h 20m

Chicago Midway

Sun 2/15

9:30 am-5:40 am

2 stops17h 10m

$681

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 12/11

9:15 pm-9:54 am

1 stop15h 39m

Chicago Midway

Fri 2/13

1:05 pm-5:40 am

1 stop13h 35m

$691

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 10/11

10:05 am-10:14 pm

1 stop14h 09m

Chicago Midway

Fri 10/24

1:08 pm-8:50 am

2 stops17h 42m

$780

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 10/8

10:50 pm-4:09 pm

1 stop19h 19m

Chicago Midway

Wed 10/15

6:00 am-5:40 am

1 stop21h 40m

$788

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 12/13

9:15 pm-12:34 pm

2 stops18h 19m

Chicago Midway

Sat 1/31

10:35 am-5:40 am

1 stop16h 05m

$788

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/7

11:05 pm-4:09 pm

2 stops19h 04m

Chicago Midway

Tue 10/14

10:35 am-9:00 am

1 stop20h 25m

$792

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 10/8

10:50 pm-4:09 pm

1 stop19h 19m

Chicago Midway

Wed 10/22

6:00 am-5:40 am

1 stop21h 40m

$792

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 9/28

11:10 am-7:23 am

2 stops22h 13m

$347

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 10/9

11:10 am-11:27 am

2 stops26h 17m

$385

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 11/15

9:45 pm-3:20 pm

2 stops20h 35m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 14 results
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Best time to book a flight from Sao Paulo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sao Paulo 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 Sao Paulo to Chicago Midway Airport
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 Sao Paulo to Midway. 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 Sao Paulo to Chicago Midway Airport?

    For as low as $681, Delta can have you in Chicago Midway Airport from Sao Paulo in 18h 20m. Airlines will cover a distance of 5218 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Sao Paulo to Midway 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 Sao Paulo to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Sao Paulo to Chicago Midway Airport (average of $160). Flying from Sao Paulo to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Sao Paulo to Midway

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