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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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAO
dic. 5 — dic. 121
vie. 12/5
vie. 12/12
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 5, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$607
(LATAM Airlines)

One-way from

$268
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$757
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. 3% potential price decrease ($31 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 5, 2025.

This KAYAK deal was found by Cheapflights users on 11/4. 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.
jue. 11/2710:47 amMDW - GRU
1 stop15h 53mLATAM Airlines
mié. 12/35:45 pmGRU - MDW
2 stops21h 10mLATAM Airlines
Deal found 11/4$607
This Delta deal was found by Cheapflights users on 11/4. 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.
jue. 11/2710:47 amMDW - GRU
1 stop15h 53mDelta
mié. 12/1011:45 pmGRU - MDW
1 stop19h 33mDelta
Deal found 11/4$620
This Delta deal was found by Cheapflights users on 11/5. 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. 12/89:00 pmGRU - MDW
2 stops18h 34mDelta
Deal found 11/5$625
This Travelocity deal was found by Cheapflights users on 11/5. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/1810:47 amMDW - GRU
1 stop19h 48mLATAM Airlines
mar. 12/1610:55 pmGRU - MDW
2 stops27h 52mLATAM Airlines
Deal found 11/5$657
This FlightHub deal was found by Cheapflights users on 11/5. 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.
lun. 12/1512:50 pmMDW - GRU
1 stop17h 45mLATAM Airlines
mar. 12/2310:40 amGRU - MDW
1 stop14h 42mLATAM Airlines
Deal found 11/5$676
This Justfly.com deal was found by Cheapflights users on 11/5. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/224:28 pmMDW - GRU
1 stop34h 12mLATAM Airlines
jue. 12/49:15 pmGRU - MDW
1 stop15h 39mLATAM Airlines
Deal found 11/5$677
This FlightHub deal was found by Cheapflights users on 11/5. 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.
lun. 11/1012:47 pmMDW - GRU
1 stop13h 53mLATAM Airlines
jue. 11/2011:45 pmGRU - MDW
1 stop15h 07mLATAM Airlines
Deal found 11/5$684
This Gurufare deal was found by Cheapflights users on 11/5. 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. 11/66:00 amMDW - GRU
1 stop24h 35mLATAM Airlines
jue. 11/139:15 pmGRU - MDW
1 stop22h 23mLATAM Airlines
Deal found 11/5$685
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
jue. 12/42:16 pmMDW - GRU
1 stop26h 44mMultiple Airlines
mié. 12/103:10 amGRU - MDW
2 stops21h 43mMultiple Airlines
Deal found 11/4$686
This Ovago deal was found by Cheapflights users on 11/4. 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 Ovago 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 11/4$689
This FlightHub deal was found by Cheapflights users on 11/5. 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.
sáb. 11/84:23 pmMDW - GRU
1 stop34h 17mLATAM Airlines
mar. 11/189:15 pmGRU - MDW
1 stop15h 37mLATAM Airlines
Deal found 11/5$692
This Ovago deal was found by Cheapflights users on 11/5. 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 Ovago 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
dom. 11/3011:45 pmGRU - MDW
1 stop26h 55mLATAM Airlines
Deal found 11/5$696

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 5, 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

mié. 11/26

12:47 pm-5:40 am

1 stop13h 53m

Sao Paulo Guarulhos Intl

vie. 12/5

9:15 pm-9:54 am

1 stop15h 39m

$620

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 11/26

12:47 pm-5:40 am

1 stop13h 53m

Sao Paulo Guarulhos Intl

mié. 12/3

11:45 pm-11:55 am

1 stop15h 10m

$620

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

9:30 pm-11:01 am

1 stop16h 31m

$620

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mar. 11/25

12:47 pm-5:40 am

1 stop13h 53m

Sao Paulo Guarulhos Intl

mar. 12/2

11:45 pm-11:55 am

1 stop15h 10m

$620

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

vie. 11/28

10:47 am-5:40 am

1 stop15h 53m

Sao Paulo Guarulhos Intl

mar. 12/2

9:15 pm-11:55 am

1 stop17h 40m

$620

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mar. 11/25

12:47 pm-5:40 am

1 stop13h 53m

Sao Paulo Guarulhos Intl

mié. 12/3

9:15 pm-9:54 am

1 stop15h 39m

$620

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

jue. 11/27

5:34 pm-9:35 am

1 stop13h 01m

Sao Paulo Guarulhos Intl

vie. 12/5

9:15 pm-9:54 am

1 stop15h 39m

$620

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mar. 2/10

1:28 pm-9:55 am

2 stops17h 27m

Sao Paulo Guarulhos Intl

mar. 2/17

11:45 pm-5:45 pm

1 stop21h 00m

$625

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

jue. 11/27

5:34 pm-9:35 am

1 stop13h 01m

Sao Paulo Guarulhos Intl

mié. 12/10

9:15 pm-12:34 pm

2 stops18h 19m

$625

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 11/26

9:34 am-5:40 am

2 stops17h 06m

Sao Paulo Guarulhos Intl

lun. 12/8

10:20 am-11:47 pm

2 stops16h 27m

$625

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 41 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 13h 53m. Fly via Delta or 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.

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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