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Sao Paulo

$271+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAO
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$637
(FlightHub)

One-way from

$271
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$995
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. 8% potential increase in price ($82 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This FlightHub deal was found by Cheapflights users on 6/30. 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 9/1710:35 amMDW - GRU
1 stop17h 05mLATAM Airlines
Tue 9/235:45 pmGRU - MDW
2 stops17h 55mLATAM Airlines
Deal found 6/30$637
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Thu 8/149:12 pmMDW - VCP
1 stop30h 23mMultiple Airlines
Thu 8/2112:45 pmVCP - MDW
1 stop21h 37mMultiple Airlines
Deal found 6/30$652
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Thu 8/149:12 pmMDW - GRU
2 stops28h 38mMultiple Airlines
Thu 8/2111:55 amGRU - MDW
1 stop22h 27mMultiple Airlines
Deal found 7/1$709

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 July 1, 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 9/17

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

$637

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Thu 8/14

9:12 pm-5:35 am

1 stop30h 23m

Sao Paulo Viracopos

Thu 8/21

12:45 pm-8:22 am

1 stop21h 37m

$652

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 8/14

9:12 pm-3:50 am

2 stops28h 38m

Sao Paulo Guarulhos Intl

Thu 8/21

11:55 am-8:22 am

1 stop22h 27m

$709

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 12/8

1:05 pm-5:40 am

1 stop13h 35m

Sao Paulo Guarulhos Intl

Mon 12/22

7:30 pm-9:21 am

2 stops16h 51m

$1,059

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 8/22

9:17 am-3:50 am

2 stops16h 33m

$271

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Fri 8/22

9:17 am-5:35 am

1 stop18h 18m

$282

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 11/15

10:35 am-5:45 am

2 stops16h 10m

$665

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 9/8

10:31 am-5:40 am

1 stop17h 09m

$1,312

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

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.

Reviews of airlines servicing Sao Paulo

Get insights into the airlines that provide service to Sao Paulo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Sao Paulo. Reviews last updated July 1, 2025.
Read reviews from past customers who have flown Delta and LATAM Airlines from Chicago Midway Airport to Sao Paulo. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,974 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,974 reviews
Delta
8.0
Very good
7,974 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
LATAM Airlines
7.5
Good
1,805 reviews
Delta
8.0
Very good
7,974 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport to Sao Paulo (average of $686). 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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