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

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Sao Paulo (average of $691). 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.

How far in advance should I book a flight from Chicago Midway Airport to Sao Paulo?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 56 days in advance, which can save you up to 61% on flights from Chicago Midway Airport to Sao Paulo compared to booking the week you need them. Waiting 56 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $463. For sooner than that we have options available in the next 3 days from $911.

What is the cheapest month to fly from Chicago Midway Airport to Sao Paulo?

Flights from Chicago Midway Airport to Sao Paulo lean towards being more expensive in December. Prices are generally better when you fly from Chicago Midway Airport to Sao Paulo in March, with the cheapest ticket starting at $412.

What is the cheapest time of day to fly from MDW to SAO?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Sao Paulo as you normally would.

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 FlightHub the most. FlightHub 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.

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.

$301+ Flights from Chicago Midway Airport to Sao Paulo, Brazil

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Cheap flight deals from Midway to Sao Paulo

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 2 stars
Round-trip from	$711 (Mytrip)
One-way from	$318 (Mytrip)
Popular in	December
Cheapest in	March
Average price	$873

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)

Search Deals

Highest demand for flights based on searches. 1% potential increase in price ($20 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($24 potential savings vs. average RT price).

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Average for round-trip flights in April 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 April 17, 2025.

Fri 5/235:50 pmMDW - GRU

2 stops30h 25mMultiple Airlines

Mon 6/28:55 pmGRU - MDW

2 stops21h 29mMultiple Airlines

Deal found 4/17

$711

Wed 6/1810:26 amMDW - GRU

2 stops17h 49mLATAM Airlines

Mon 6/234:45 pmGRU - MDW

2 stops21h 14mLATAM Airlines

Deal found 4/17

$900

Sun 6/14:15 pmMDW - GRU

1 stop14h 45mDelta

Sun 6/810:50 pmGRU - MDW

1 stop21h 12mDelta

Deal found 4/17

$1,212

Best flights from Midway to Sao Paulo
Discover carefully curated flight deals from Midway to Sao Paulo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2025.

Fri 5/235:50 pmMDW - GRU

2 stops30h 25mMultiple Airlines

Mon 6/28:55 pmGRU - MDW

2 stops21h 29mMultiple Airlines

Deal found 4/17

$711

Wed 6/184:26 pmMDW - GRU

1 stop14h 34mLATAM Airlines

Mon 6/234:45 pmGRU - MDW

2 stops18h 56mLATAM Airlines

Deal found 4/17

$900

Sun 6/110:25 amMDW - GRU

1 stop17h 15mDelta

Sun 6/810:50 pmGRU - MDW

1 stop21h 12mDelta

Deal found 4/17

$1,212

Last-minute flights from Midway to Sao Paulo
Discover last-minute flight deals from Midway to Sao Paulo. Data last updated April 17, 2025 and is based on user searches.

Sat 4/196:45 pmMDW - GRU

1 stop12h 15mLATAM Airlines

Mon 4/211:30 pmGRU - MDW

2 stops21h 37mLATAM Airlines

Deal found 4/16

$1,060

Sun 4/2010:19 amMDW - VCP

1 stop17h 16mMultiple Airlines

Tue 4/228:10 pmVCP - MDW

2 stops42h 21mMultiple Airlines

Deal found 4/16

$1,184

Wed 4/236:04 amMDW - GRU

2 stops22h 11mLATAM Airlines

Tue 4/293:40 amGRU - MDW

2 stops31h 27mLATAM Airlines

Deal found 4/16

$1,500

Thu 4/2412:48 pmMDW - GRU

2 stops14h 52mDelta

Thu 5/110:05 amGRU - MDW

1 stop14h 17mDelta

Deal found 4/16

$2,563

Fri 4/2511:15 amMDW - GRU

1 stop20h 00mMultiple Airlines

Mon 5/58:55 pmGRU - MDW

2 stops21h 29mMultiple Airlines

Deal found 4/17

$1,091

Fri 5/235:50 pmMDW - GRU

2 stops30h 25mMultiple Airlines

Mon 6/28:55 pmGRU - MDW

2 stops21h 29mMultiple Airlines

Deal found 4/17

$711

Sat 5/3110:25 amMDW - GRU

1 stop17h 15mDelta

Sat 6/710:50 pmGRU - MDW

1 stop18h 51mDelta

Deal found 4/17

$1,212

One-way flights from Midway to Sao Paulo
Search for one-way flight options from Midway to Sao Paulo. Find affordable one-way fares based on user searches. Data last updated April 17, 2025.

Mon 5/55:50 pmMDW - GRU

2 stops30h 25mMultiple Airlines

Deal found 4/17

$318

Sun 5/1110:55 amMDW - VCP

3 stops25h 40mMultiple Airlines

Deal found 4/17

$409

Mon 9/83:40 pmMDW - GRU

2 stops22h 45mLATAM Airlines

Deal found 4/17

$754

Tue 4/2912:48 pmMDW - GRU

1 stop18h 12mDelta

Deal found 4/17

$1,318

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Sao Paulo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 5/23

5:50 pm-2:15 am

2 stops30h 25m

Sao Paulo Guarulhos Intl

Mon 6/2

8:55 pm-4:24 pm

2 stops21h 29m

$711

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 6/18

10:26 am-6:15 am

2 stops17h 49m

Sao Paulo Guarulhos Intl

Mon 6/23

4:45 pm-11:59 am

2 stops21h 14m

$900

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 6/1

12:48 pm-9:00 am

1 stop18h 12m

Sao Paulo Guarulhos Intl

Sun 6/8

10:50 pm-11:59 am

1 stop15h 09m

$1,212

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 5/12

5:20 pm-2:15 am

2 stops30h 55m

$301

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Sun 5/11

10:55 am-2:35 pm

3 stops25h 40m

$409

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 5/24

4:15 pm-4:25 pm

2 stops22h 10m

$767

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 5/14

4:15 pm-9:00 am

1 stop14h 45m

$1,318

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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 FlightHub the most. FlightHub 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

Rainfall in Sao Paulo by month

In terms of precipitation, rainfall in Sao Paulo ranges from 0.8 - 9.4 inches per month. January is typically the wettest month, when rainfall can reach 9.4 in. July is typically the driest time to visit Sao Paulo when rainfall is around 0.8 in.

Temperature in Sao Paulo by month

If weather is an important factor for your trip to Sao Paulo, use this chart to help with planning. For those seeking warmer temperatures, January is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of June, when temperatures are typically at their lowest (around 62.6 F).

Reviews of airlines servicing Sao Paulo

See what other customers who have flown with Delta and LATAM Airlines from Chicago to Sao Paulo have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,917 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

LATAM Airlines

7.5

Good

1,761 reviews

Delta

8.0

Very good

7,917 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Sao Paulo (average of $691). 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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$301+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Sao Paulo with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Sao Paulo

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Midway to Sao Paulo

Cheapest flights from Midway to Sao PauloExplore 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 April 17, 2025.

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 April 17, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Sao Paulo that are best for you.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Sao Paulo

Rainfall in Sao Paulo by month

Plan your trip to Sao Paulo by taking into account the average rainfall totals by month.

Temperature in Sao Paulo by month

Plan your trip to Sao Paulo by taking into account the average temperature totals by month.

Reviews of airlines servicing Sao Paulo

See what other customers who have flown with Delta and LATAM Airlines from Chicago to Sao Paulo have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

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?

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

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

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

Traveling to a place near Chicago Midway Airport?

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Alternative routes for Midway to Sao Paulo

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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 April 17, 2025.