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 Delta to get the fastest option. Airlines will cover a distance of 5218 mi.

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

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Sao Paulo (average of $677). 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.

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).

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 11 days in advance, which can save you up to 83% on flights from Chicago Midway Airport to Sao Paulo compared to booking the week you need them. Waiting 11 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 $373. For sooner than that we have options available in the next 3 days from $910.

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 January, with the cheapest ticket starting at $451.

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.

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.

$225+ Cheap Flights from Chicago Midway Airport to Sao Paulo, Brazil

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Cheap flight deals from Midway to Sao Paulo

Round-trip from	$606 (LATAM Airlines)
One-way from	$225 (Trip.com)
Popular in	December
Cheapest in	January
Average price	$1,097

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. 6% potential increase in price ($63 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($27 potential savings vs. average RT price).

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Average for round-trip flights in September 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 September 16, 2025.

Wed 10/295:04 pmMDW - GRU

1 stop14h 31mLATAM Airlines

Sun 11/23:20 pmGRU - MDW

2 stops21h 15mLATAM Airlines

Deal found 9/15

$616

Mon 10/279:45 amMDW - GRU

2 stops28h 30mMultiple Airlines

Sat 11/82:40 amGRU - MDW

2 stops24h 50mMultiple Airlines

Deal found 9/15

$625

Sun 9/2810:13 amMDW - GRU

1 stop19h 52mMultiple Airlines

Mon 10/134:23 amGRU - MDW

2 stops21h 23mMultiple Airlines

Deal found 9/16

$656

Mon 9/298:19 amMDW - GRU

1 stop21h 46mMultiple Airlines

Mon 10/134:23 amGRU - MDW

2 stops21h 23mMultiple Airlines

Deal found 9/16

$660

Fri 10/319:32 amMDW - VCP

2 stops23h 13mMultiple Airlines

Fri 11/141:00 pmVCP - MDW

1 stop24h 26mMultiple Airlines

Deal found 9/14

$663

Thu 11/1312:47 pmMDW - GRU

2 stops20h 53mLATAM Airlines

Wed 11/1911:45 pmGRU - MDW

1 stop15h 07mLATAM Airlines

Deal found 9/15

$701

Sun 9/2810:13 amMDW - GRU

1 stop19h 52mMultiple Airlines

Wed 10/110:50 pmGRU - MDW

2 stops39h 54mMultiple Airlines

Deal found 9/14

$724

Sat 9/2710:51 amMDW - GRU

1 stop17h 59mMultiple Airlines

Sun 10/56:10 amGRU - MDW

2 stops27h 13mMultiple Airlines

Deal found 9/15

$725

Sat 9/2710:51 amMDW - GRU

1 stop17h 59mMultiple Airlines

Tue 9/3012:50 pmGRU - MDW

2 stops22h 50mMultiple Airlines

Deal found 9/13

$726

Fri 9/2610:35 amMDW - GRU

1 stop17h 05mLATAM Airlines

Mon 9/295:45 pmGRU - MDW

2 stops17h 55mLATAM Airlines

Deal found 9/13

$727

Sat 9/2710:51 amMDW - GRU

1 stop17h 59mMultiple Airlines

Mon 10/134:23 amGRU - MDW

2 stops21h 23mMultiple Airlines

Deal found 9/16

$736

Sun 9/2810:13 amMDW - GRU

1 stop19h 52mMultiple Airlines

Sun 10/510:35 amGRU - MDW

2 stops22h 36mMultiple Airlines

Deal found 9/15

$767

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 September 16, 2025.

Sun 9/2810:13 amMDW - GRU

1 stop19h 52mMultiple Airlines

Mon 10/134:23 amGRU - MDW

2 stops21h 23mMultiple Airlines

Deal found 9/16

$656

Sun 3/810:35 amMDW - GRU

1 stop17h 05mDelta

Sun 3/1511:45 pmGRU - MDW

1 stop18h 40mDelta

Deal found 9/14

$1,060

Wed 11/265:34 pmMDW - GRU

1 stop13h 01mLATAM Airlines

Mon 12/811:45 pmGRU - MDW

1 stop15h 10mLATAM Airlines

Deal found 9/16

$1,060

Fri 10/319:32 amMDW - VCP

2 stops23h 13mMultiple Airlines

Fri 11/141:00 pmVCP - MDW

1 stop24h 26mMultiple Airlines

Deal found 9/14

$663

Mon 11/179:27 amMDW - VCP

2 stops22h 18mMultiple Airlines

Sun 11/301:00 pmVCP - MDW

1 stop30h 52mMultiple Airlines

Deal found 9/15

$930

Sat 12/611:05 amMDW - GRU

1 stop15h 35mDelta

Sat 12/1311:45 pmGRU - MDW

1 stop19h 51mDelta

Deal found 9/15

$1,060

Fri 10/319:32 amMDW - GRU

2 stops21h 18mMultiple Airlines

Fri 11/145:55 amGRU - MDW

2 stops19h 15mMultiple Airlines

Deal found 9/14

$968

Mon 1/265:25 pmMDW - GRU

1 stop13h 10mDelta

Sun 2/810:50 pmGRU - MDW

2 stops16h 11mDelta

Deal found 9/15

$1,065

Sat 2/149:30 amMDW - GRU

2 stops17h 10mDelta

Sun 2/229:30 pmGRU - MDW

1 stop15h 26mDelta

Deal found 9/14

$1,065

Sun 9/2810:13 amMDW - GRU

1 stop19h 52mMultiple Airlines

Sun 10/128:30 pmGRU - MDW

2 stops21h 58mMultiple Airlines

Deal found 9/16

$1,009

Wed 12/101:14 pmMDW - GRU

2 stops17h 21mDelta

Wed 12/2411:45 pmGRU - MDW

2 stops20h 35mDelta

Deal found 9/14

$1,065

Mon 11/171:14 pmMDW - GRU

2 stops17h 21mDelta

Sun 11/3011:45 pmGRU - MDW

1 stop15h 07mDelta

Deal found 9/15

$1,065

Last-minute flights from Midway to Sao Paulo
Discover last-minute flight deals from Midway to Sao Paulo. Data last updated September 16, 2025 and is based on user searches.

Fri 9/2610:35 amMDW - GRU

1 stop17h 05mLATAM Airlines

Mon 9/295:45 pmGRU - MDW

2 stops17h 55mLATAM Airlines

Deal found 9/13

$727

Fri 9/269:48 amMDW - GRU

1 stop20h 17mMultiple Airlines

Sun 9/283:10 amGRU - MDW

2 stops17h 33mMultiple Airlines

Deal found 9/13

$871

Sat 9/2710:51 amMDW - GRU

1 stop17h 59mMultiple Airlines

Sun 10/56:10 amGRU - MDW

2 stops27h 13mMultiple Airlines

Deal found 9/15

$725

Sat 9/2710:51 amMDW - GRU

1 stop17h 59mMultiple Airlines

Tue 9/3012:50 pmGRU - MDW

2 stops22h 50mMultiple Airlines

Deal found 9/13

$726

Sat 9/2710:51 amMDW - GRU

1 stop17h 59mMultiple Airlines

Mon 10/134:23 amGRU - MDW

2 stops21h 23mMultiple Airlines

Deal found 9/16

$736

Sun 9/2810:13 amMDW - GRU

1 stop19h 52mMultiple Airlines

Mon 10/134:23 amGRU - MDW

2 stops21h 23mMultiple Airlines

Deal found 9/16

$656

Sun 9/2810:13 amMDW - GRU

1 stop19h 52mMultiple Airlines

Wed 10/110:50 pmGRU - MDW

2 stops39h 54mMultiple Airlines

Deal found 9/14

$724

Sun 9/2810:13 amMDW - GRU

1 stop19h 52mMultiple Airlines

Sun 10/510:35 amGRU - MDW

2 stops22h 36mMultiple Airlines

Deal found 9/15

$767

Mon 9/298:19 amMDW - GRU

1 stop21h 46mMultiple Airlines

Mon 10/134:23 amGRU - MDW

2 stops21h 23mMultiple Airlines

Deal found 9/16

$660

Mon 10/279:45 amMDW - GRU

2 stops28h 30mMultiple Airlines

Sat 11/82:40 amGRU - MDW

2 stops24h 50mMultiple Airlines

Deal found 9/15

$625

Wed 10/295:04 pmMDW - GRU

1 stop14h 31mLATAM Airlines

Sun 11/23:20 pmGRU - MDW

2 stops21h 15mLATAM Airlines

Deal found 9/15

$616

Fri 10/319:32 amMDW - VCP

2 stops23h 13mMultiple Airlines

Fri 11/141:00 pmVCP - MDW

1 stop24h 26mMultiple Airlines

Deal found 9/14

$663

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 September 16, 2025.

Thu 11/1310:12 amMDW - VCP

1 stop19h 28mMultiple Airlines

Deal found 9/14

$225

Mon 10/68:19 amMDW - VCP

2 stops24h 21mMultiple Airlines

Deal found 9/15

$265

Sun 10/510:13 amMDW - GRU

2 stops36h 27mMultiple Airlines

Deal found 9/15

$274

Mon 10/68:19 amMDW - GRU

2 stops19h 16mMultiple Airlines

Deal found 9/15

$279

Mon 10/275:28 pmMDW - VCP

2 stops39h 17mMultiple Airlines

Deal found 9/15

$287

Mon 10/134:24 pmMDW - VCP

2 stops16h 16mMultiple Airlines

Deal found 9/15

$298

Mon 10/275:28 pmMDW - GRU

2 stops25h 22mMultiple Airlines

Deal found 9/15

$310

Wed 10/158:05 amMDW - GRU

3 stops40h 05mMultiple Airlines

Deal found 9/14

$317

Fri 10/2412:18 pmMDW - GRU

1 stop15h 22mMultiple Airlines

Deal found 9/14

$318

Wed 10/158:05 amMDW - VCP

3 stops24h 35mMultiple Airlines

Deal found 9/14

$319

Sat 9/2710:51 amMDW - GRU

1 stop17h 59mMultiple Airlines

Deal found 9/15

$321

Thu 11/1310:12 amMDW - GRU

1 stop19h 38mMultiple Airlines

Deal found 9/14

$373

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

Sun 9/28

10:13 am-8:05 am

1 stop19h 52m

Sao Paulo Guarulhos Intl

Mon 10/13

4:23 am-11:46 pm

2 stops21h 23m

$656

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Fri 10/31

9:32 am-10:45 am

2 stops23h 13m

Sao Paulo Viracopos

Fri 11/14

1:00 pm-10:26 am

1 stop24h 26m

$663

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Mon 11/17

9:27 am-10:45 am

2 stops22h 18m

Sao Paulo Viracopos

Sun 11/30

1:00 pm-4:52 pm

1 stop30h 52m

$930

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 10/31

9:32 am-8:50 am

2 stops21h 18m

Sao Paulo Guarulhos Intl

Fri 11/14

5:55 am-10:10 pm

2 stops19h 15m

$968

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 9/28

10:13 am-8:05 am

1 stop19h 52m

Sao Paulo Guarulhos Intl

Sun 10/12

8:30 pm-4:28 pm

2 stops21h 58m

$1,009

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 3/8

10:35 am-5:40 am

1 stop17h 05m

Sao Paulo Guarulhos Intl

Sun 3/15

11:45 pm-4:25 pm

1 stop18h 40m

$1,060

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 11/26

5:34 pm-9:35 am

1 stop13h 01m

Sao Paulo Guarulhos Intl

Mon 12/8

11:45 pm-11:55 am

1 stop15h 10m

$1,060

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 12/6

11:05 am-5:40 am

1 stop15h 35m

Sao Paulo Guarulhos Intl

Sat 12/13

11:45 pm-4:36 pm

1 stop19h 51m

$1,060

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 1/26

5:25 pm-9:35 am

1 stop13h 10m

Sao Paulo Guarulhos Intl

Sun 2/8

10:50 pm-12:01 pm

2 stops16h 11m

$1,065

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 2/14

9:30 am-5:40 am

2 stops17h 10m

Sao Paulo Guarulhos Intl

Sun 2/22

9:30 pm-9:56 am

1 stop15h 26m

$1,065

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 34 results

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 17h 05m. 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.
What is the cheapest month to book a flight from Chicago Midway Airport to Sao Paulo?
Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Sao Paulo (average of $677). 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.

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$225+ 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 11/13. 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

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2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Sao Paulo

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 September 16, 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 September 16, 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

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?

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

Browse thousands of different options on Cheapflights for your next trip

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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 September 16, 2025.