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$279+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAO
dic. 12 — dic. 191
vie. 12/12
vie. 12/19
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 noviembre 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$599
(LATAM Airlines)

One-way from

$279
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$716
Provider with most accurate pricing for Chicago Midway-Sao Paulo (SAO) flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Sao Paulo (SAO) flights.
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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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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 12, 2025.

This Delta deal was found by Cheapflights users on 11/12. 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.
mié. 11/2612:47 pmMDW - GRU
1 stop13h 53mDelta
lun. 12/89:15 pmGRU - MDW
1 stop15h 39mDelta
Deal found 11/12$600
This FlightHub deal was found by Cheapflights users on 11/12. 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.
jue. 11/2710:47 amMDW - GRU
1 stop15h 53mLATAM Airlines
mié. 12/311:45 pmGRU - MDW
1 stop15h 10mLATAM Airlines
Deal found 11/12$601
This KAYAK deal was found by Cheapflights users on 11/12. 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.
dom. 11/236:00 amMDW - GRU
1 stop20h 40mLATAM Airlines
mar. 12/211:45 pmGRU - MDW
1 stop15h 10mLATAM Airlines
Deal found 11/12$611
This Delta deal was found by Cheapflights users on 11/12. 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.
dom. 11/239:34 amMDW - GRU
2 stops17h 06mDelta
mar. 12/211:45 pmGRU - MDW
2 stops15h 49mDelta
Deal found 11/12$615
This Delta deal was found by Cheapflights users on 11/10. 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.
mié. 11/1210:47 amMDW - GRU
1 stop15h 53mDelta
mar. 11/189:15 pmGRU - MDW
1 stop15h 37mDelta
Deal found 11/10$620
This Delta deal was found by Cheapflights users on 11/10. 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.
sáb. 11/159:32 amMDW - GRU
2 stops16h 48mDelta
lun. 11/1711:45 pmGRU - MDW
1 stop15h 07mDelta
Deal found 11/10$625
This SmartFares deal was found by Cheapflights users on 11/10. 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.
sáb. 11/1510:47 amMDW - GRU
1 stop15h 53mLATAM Airlines
sáb. 11/2211:45 pmGRU - MDW
1 stop15h 07mLATAM Airlines
Deal found 11/10$642
This Expedia deal was found by Cheapflights users on 11/10. 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.
mar. 11/1810:47 amMDW - GRU
1 stop15h 53mLATAM Airlines
dom. 11/2310:20 amGRU - MDW
2 stops16h 20mLATAM Airlines
Deal found 11/10$650
This LATAM Airlines deal was found by Cheapflights users on 11/10. 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.
mar. 12/2312:45 pmMDW - GRU
1 stop13h 55mLATAM Airlines
lun. 1/129:15 pmGRU - MDW
1 stop16h 19mLATAM Airlines
Deal found 11/10$653
This Gurufare deal was found by Cheapflights users on 11/9. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/309:50 amMDW - GRU
1 stop16h 50mLATAM Airlines
mié. 12/3110:40 amGRU - MDW
1 stop14h 42mLATAM Airlines
Deal found 11/9$657
This Gurufare deal was found by Cheapflights users on 11/12. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/275:34 pmMDW - GRU
1 stop13h 01mLATAM Airlines
dom. 11/3011:45 pmGRU - MDW
1 stop26h 55mLATAM Airlines
Deal found 11/12$665
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
vie. 11/143:27 pmMDW - VCP
1 stop14h 13mMultiple Airlines
dom. 11/1611:20 pmVCP - MDW
2 stops28h 10mMultiple Airlines
Deal found 11/10$996

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 noviembre 12, 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

dom. 3/8

10:35 am-5:40 am

1 stop17h 05m

Sao Paulo Guarulhos Intl

mar. 3/17

11:45 pm-12:01 pm

1 stop14h 16m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mar. 2/3

10:53 am-9:35 am

1 stop19h 42m

Sao Paulo Guarulhos Intl

lun. 2/9

9:15 pm-12:01 pm

1 stop17h 46m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 3/11

5:25 pm-9:35 am

1 stop14h 10m

Sao Paulo Guarulhos Intl

mié. 3/18

11:45 pm-4:25 pm

1 stop18h 40m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

jue. 11/27

10:47 am-5:40 am

1 stop15h 53m

Sao Paulo Guarulhos Intl

mié. 12/3

9:15 pm-9:54 am

1 stop15h 39m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

jue. 2/12

6:00 am-5:40 am

1 stop20h 40m

Sao Paulo Guarulhos Intl

dom. 3/1

11:45 pm-12:01 pm

1 stop15h 16m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

dom. 3/8

10:35 am-5:40 am

1 stop17h 05m

Sao Paulo Guarulhos Intl

dom. 3/15

11:45 pm-4:25 pm

1 stop18h 40m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 2/4

10:46 am-9:35 am

1 stop19h 49m

Sao Paulo Guarulhos Intl

mié. 2/11

9:15 pm-12:01 pm

1 stop17h 46m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

vie. 2/27

10:53 am-5:40 am

1 stop15h 47m

Sao Paulo Guarulhos Intl

sáb. 3/7

11:45 pm-11:01 am

1 stop14h 16m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mar. 2/3

10:53 am-9:35 am

1 stop19h 42m

Sao Paulo Guarulhos Intl

mar. 2/10

11:45 pm-12:01 pm

1 stop15h 16m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mar. 2/10

10:53 am-5:40 am

1 stop15h 47m

Sao Paulo Guarulhos Intl

vie. 2/27

11:45 pm-3:23 pm

1 stop18h 38m

$600

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 43 results
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Compare providers for flights from Midway to Sao Paulo

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Sao Paulo in November.
ProviderPrice AccuracyTrust Score*
AranGrantPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Sao Paulo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Sao Paulo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Sao Paulo flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Sao Paulo flights, Cheapflights users trust AranGrant the most. AranGrant has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Sao Paulo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 17h 05m. Fly via LATAM Airlines or Delta to get the fastest option. Airlines will cover a distance of 5218 mi. This flight may include one or multiple stops.

  • 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.

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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