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 19h 49m. Fly via Delta to get the fastest option. Airlines will cover a distance of 5218 mi.

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.

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).

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 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.

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.

$377+ Flights from Chicago Midway Airport to Sao Paulo, Brazil

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheap 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 December 26, 2025.

Wed 12/243:29 pmMDW - GRU

2 stops18h 11mLATAM Airlines

Sun 12/2810:40 amGRU - MDW

1 stop14h 42mLATAM Airlines

Deal found 12/23

$735

Sat 12/274:25 pmMDW - GRU

2 stops20h 45mLATAM Airlines

Mon 12/2910:40 amGRU - MDW

1 stop14h 42mLATAM Airlines

Deal found 12/25

$1,472

Mon 12/295:05 pmMDW - GRU

2 stops16h 35mLATAM Airlines

Wed 12/3110:40 amGRU - MDW

1 stop14h 42mLATAM Airlines

Deal found 12/26

$1,548

Mon 12/293:10 pmMDW - GRU

1 stop14h 40mMultiple Airlines

Wed 12/3111:59 pmGRU - MDW

2 stops20h 39mMultiple Airlines

Deal found 12/25

$1,686

Fri 12/266:00 amMDW - GRU

2 stops20h 45mLATAM Airlines

Tue 1/68:15 amGRU - MDW

2 stops29h 12mLATAM Airlines

Deal found 12/25

$2,203

Thu 12/259:50 amMDW - GRU

2 stops16h 55mLATAM Airlines

Sun 1/45:45 pmGRU - MDW

2 stops19h 42mLATAM Airlines

Deal found 12/24

$3,094

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 December 26, 2025.

Thu 2/266:15 amMDW - GRU

2 stops17h 25mMultiple Airlines

Sun 3/811:55 amGRU - MDW

1 stop27h 13mMultiple Airlines

Deal found 12/25

$682

Wed 1/2110:46 amMDW - GRU

1 stop19h 49mDelta

Wed 1/289:15 pmGRU - MDW

1 stop15h 38mDelta

Deal found 12/24

$912

Thu 3/510:49 amMDW - GRU

1 stop15h 51mLATAM Airlines

Mon 3/1610:40 amGRU - MDW

1 stop13h 51mLATAM Airlines

Deal found 12/25

$912

Thu 1/2210:48 amMDW - GRU

1 stop15h 52mDelta

Thu 1/299:15 pmGRU - MDW

1 stop17h 44mDelta

Deal found 12/24

$912

Tue 3/2410:45 amMDW - GRU

1 stop16h 55mDelta

Sun 4/510:50 pmGRU - MDW

1 stop20h 05mDelta

Deal found 12/25

$912

Thu 2/1212:45 pmMDW - GRU

1 stop13h 55mDelta

Tue 2/247:30 amGRU - MDW

2 stops18h 03mDelta

Deal found 12/25

$912

Mon 3/2310:45 amMDW - GRU

1 stop16h 55mDelta

Sun 4/510:50 pmGRU - MDW

1 stop20h 05mDelta

Deal found 12/25

$912

Thu 2/2610:49 amMDW - GRU

1 stop15h 51mDelta

Sat 3/79:15 pmGRU - MDW

1 stop21h 40mDelta

Deal found 12/25

$912

Wed 1/2110:46 amMDW - GRU

2 stops16h 29mDelta

Thu 1/299:15 pmGRU - MDW

1 stop17h 44mDelta

Deal found 12/24

$912

Wed 3/255:40 pmMDW - GRU

1 stop13h 55mDelta

Sun 4/510:50 pmGRU - MDW

1 stop20h 05mDelta

Deal found 12/25

$912

Wed 3/2511:19 amMDW - VCP

1 stop16h 21mMultiple Airlines

Sun 4/510:10 amVCP - MDW

1 stop13h 48mMultiple Airlines

Deal found 12/25

$1,671

Last-minute flights from Midway to Sao Paulo
Discover last-minute flight deals from Midway to Sao Paulo. Data last updated December 26, 2025 and is based on user searches.

Wed 12/243:29 pmMDW - GRU

2 stops18h 11mLATAM Airlines

Sun 12/2810:40 amGRU - MDW

1 stop14h 42mLATAM Airlines

Deal found 12/23

$735

Fri 1/96:54 pmMDW - VCP

3 stops35h 06mMultiple Airlines

Fri 1/1611:10 amVCP - MDW

2 stops27h 40mMultiple Airlines

Deal found 12/26

$1,820

Wed 1/149:32 amMDW - GRU

2 stops17h 08mDelta

Thu 1/2211:45 pmGRU - MDW

1 stop20h 44mDelta

Deal found 12/24

$944

Thu 1/158:19 pmMDW - GRU

1 stop30h 01mMultiple Airlines

Thu 1/225:25 pmGRU - MDW

2 stops19h 28mMultiple Airlines

Deal found 12/25

$748

Thu 1/159:32 amMDW - GRU

2 stops17h 08mDelta

Thu 1/229:15 pmGRU - MDW

2 stops18h 31mDelta

Deal found 12/25

$945

Fri 1/168:04 pmMDW - GRU

1 stop30h 16mMultiple Airlines

Fri 1/2312:55 pmGRU - MDW

2 stops22h 48mMultiple Airlines

Deal found 12/24

$853

Sun 1/185:59 pmMDW - GRU

1 stop12h 36mDelta

Mon 1/2611:45 pmGRU - MDW

1 stop15h 14mDelta

Deal found 12/24

$940

Wed 1/2112:48 pmMDW - GRU

1 stop13h 52mLATAM Airlines

Wed 1/289:15 pmGRU - MDW

1 stop15h 38mLATAM Airlines

Deal found 12/24

$825

Wed 1/2112:48 pmMDW - GRU

2 stops19h 32mLATAM Airlines

Mon 1/267:35 amGRU - MDW

2 stops17h 47mLATAM Airlines

Deal found 12/24

$871

Wed 1/2112:48 pmMDW - GRU

1 stop13h 52mDelta

Thu 1/2911:45 pmGRU - MDW

1 stop20h 44mDelta

Deal found 12/24

$912

Wed 1/2110:46 amMDW - GRU

2 stops15h 34mDelta

Wed 1/2811:45 pmGRU - MDW

1 stop15h 14mDelta

Deal found 12/24

$916

Sat 1/314:30 pmMDW - GRU

2 stops21h 00mLATAM Airlines

Thu 2/123:15 pmGRU - MDW

3 stops21h 39mLATAM Airlines

Deal found 12/25

$922

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 December 26, 2025.

Thu 1/156:45 amMDW - VCP

2 stops40h 40mMultiple Airlines

Deal found 12/25

$377

Thu 1/158:19 pmMDW - GRU

1 stop30h 01mMultiple Airlines

Deal found 12/25

$400

Thu 1/156:45 amMDW - GRU

2 stops26h 55mLATAM Airlines

Deal found 12/25

$439

Tue 6/165:59 pmMDW - GRU

3 stops26h 26mMultiple Airlines

Deal found 12/25

$496

Thu 6/185:59 pmMDW - GRU

3 stops25h 38mMultiple Airlines

Deal found 12/25

$759

Wed 3/1810:45 amMDW - GRU

2 stops17h 30mLATAM Airlines

Deal found 12/25

$993

Mon 6/110:35 amMDW - GRU

2 stops16h 55mLATAM Airlines

Deal found 12/25

$994

Thu 6/1810:35 amMDW - GRU

2 stops16h 55mLATAM Airlines

Deal found 12/25

$1,026

Sat 1/2410:46 amMDW - GRU

2 stops17h 44mLATAM Airlines

Deal found 12/25

$1,067

Tue 5/265:25 pmMDW - GRU

2 stops25h 55mLATAM Airlines

Deal found 12/23

$1,141

Tue 6/1610:35 amMDW - GRU

2 stops18h 45mLATAM Airlines

Deal found 12/25

$1,217

Find flight deals from Midway to Sao Paulo

Most accurate provider	FlightHub 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$682 (Kiwi.com)
One-way from	$377 (Kiwi.com)
Popular in	December
Cheapest in	January
Average price	$1,121

Provider with most accurate pricing for Chicago Midway-Sao Paulo (SAO) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Chicago Midway-Sao Paulo (SAO) flights.

Search Deals

From Chicago Midway to Sao Paulo (SAO)

Search Deals

One-way flight from Chicago Midway to Sao Paulo (SAO)

Search Deals

Highest demand for flights based on searches. 2% potential increase in price ($17 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

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

Thu 2/26

6:15 am-2:40 am

2 stops17h 25m

Sao Paulo Guarulhos Intl

Sun 3/8

11:55 am-1:08 pm

1 stop27h 13m

$682

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 1/21

10:46 am-9:35 am

1 stop19h 49m

Sao Paulo Guarulhos Intl

Wed 1/28

9:15 pm-9:53 am

1 stop15h 38m

$912

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 3/5

10:49 am-5:40 am

1 stop15h 51m

Sao Paulo Guarulhos Intl

Mon 3/16

10:40 am-10:31 pm

1 stop13h 51m

$912

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 1/22

10:48 am-5:40 am

1 stop15h 52m

Sao Paulo Guarulhos Intl

Thu 1/29

9:15 pm-11:59 am

1 stop17h 44m

$912

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 3/24

10:45 am-5:40 am

1 stop16h 55m

Sao Paulo Guarulhos Intl

Sun 4/5

10:50 pm-4:55 pm

1 stop20h 05m

$912

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/12

12:45 pm-5:40 am

1 stop13h 55m

Sao Paulo Guarulhos Intl

Tue 2/24

7:30 am-10:33 pm

2 stops18h 03m

$912

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/23

10:45 am-5:40 am

1 stop16h 55m

Sao Paulo Guarulhos Intl

Sun 4/5

10:50 pm-4:55 pm

1 stop20h 05m

$912

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/26

10:49 am-5:40 am

1 stop15h 51m

Sao Paulo Guarulhos Intl

Sat 3/7

9:15 pm-3:55 pm

1 stop21h 40m

$912

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 1/21

10:46 am-6:15 am

2 stops16h 29m

Sao Paulo Guarulhos Intl

Thu 1/29

9:15 pm-11:59 am

1 stop17h 44m

$912

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 3/25

5:40 pm-9:35 am

1 stop13h 55m

Sao Paulo Guarulhos Intl

Sun 4/5

10:50 pm-4:55 pm

1 stop20h 05m

$912

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 20 results

Compare providers for flights from Midway to Sao Paulo

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 December.

Provider	Price Accuracy	Trust Score*
AranGrant	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust 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

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 19h 49m. Fly via Delta 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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$377+ 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 1/15. 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

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 December 26, 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 December 26, 2025.

Find 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

Cheapflights Fare Finder

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

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 December.

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

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?

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?

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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 December 26, 2025.