How long is the flight from Sao Paulo to Chicago Midway Airport?

For as low as $800, Delta can have you in Chicago Midway Airport from Sao Paulo in 18h 46m. Airlines will cover a distance of 5218 mi.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July 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 January, when temperatures are typically at their lowest (around 23.0 F).

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

When flying from Sao Paulo to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Can I find deals for flights from Sao Paulo to Midway that include hotel bookings?

Yes. In addition to deals on Sao Paulo to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

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

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sao Paulo to Midway.

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

Yes. Cheapflights offers flight deals from Sao Paulo to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$319+ Flights from Sao Paulo, Brazil to Chicago Midway Airport

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Cheap flight deals from Sao Paulo to Midway

Cheapest flights from Sao Paulo to Midway
Explore the most affordable flight options available from Sao Paulo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

Wed 12/3110:40 amGRU - MDW

1 stop25h 25mLATAM Airlines

Sat 1/1011:21 amMDW - GRU

1 stop19h 14mLATAM Airlines

Deal found 12/9

$1,400

Thu 12/2510:40 amGRU - MDW

1 stop14h 42mDelta

Tue 1/61:28 pmMDW - GRU

2 stops17h 27mDelta

Deal found 12/11

$1,455

Thu 12/2510:55 pmGRU - MDW

2 stops20h 25mDelta

Thu 1/85:31 pmMDW - GRU

1 stop13h 04mDelta

Deal found 12/10

$1,456

Wed 12/314:35 pmGRU - MDW

2 stops19h 30mDelta

Sat 1/1011:21 amMDW - GRU

1 stop19h 14mDelta

Deal found 12/9

$1,489

Fri 12/2611:45 pmGRU - MDW

1 stop18h 43mDelta

Wed 1/79:32 amMDW - GRU

2 stops17h 08mDelta

Deal found 12/11

$1,495

Fri 12/2610:40 amGRU - MDW

1 stop14h 42mDelta

Mon 1/59:32 amMDW - GRU

2 stops17h 08mDelta

Deal found 12/10

$1,497

Fri 12/2611:45 pmGRU - MDW

1 stop18h 43mDelta

Sat 1/105:31 pmMDW - GRU

1 stop13h 04mDelta

Deal found 12/11

$1,535

Fri 12/2611:45 pmGRU - MDW

1 stop18h 43mDelta

Fri 1/212:45 pmMDW - GRU

1 stop13h 55mDelta

Deal found 12/10

$1,537

Thu 12/2510:40 amGRU - MDW

1 stop14h 42mLATAM Airlines

Tue 1/611:21 amMDW - GRU

1 stop15h 19mLATAM Airlines

Deal found 12/11

$1,865

Sat 12/2712:55 pmGRU - MDW

2 stops26h 03mLATAM Airlines

Thu 1/2912:48 pmMDW - GRU

2 stops19h 32mLATAM Airlines

Deal found 12/10

$1,941

Best flights from Sao Paulo to Midway
Discover carefully curated flight deals from Sao Paulo to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.

Sat 1/319:00 pmGRU - MDW

2 stops18h 46mDelta

Sun 2/810:48 amMDW - GRU

1 stop19h 47mDelta

Deal found 12/11

$800

Tue 2/109:15 pmGRU - MDW

2 stops18h 31mDelta

Wed 2/1810:53 amMDW - GRU

1 stop19h 42mDelta

Deal found 12/11

$800

Sun 3/111:45 pmGRU - MDW

1 stop15h 14mDelta

Sun 3/1512:47 pmMDW - GRU

1 stop14h 53mDelta

Deal found 12/11

$800

Wed 2/119:15 pmGRU - MDW

2 stops18h 31mDelta

Thu 2/1910:53 amMDW - GRU

1 stop15h 47mDelta

Deal found 12/11

$800

Sun 3/110:55 pmGRU - MDW

2 stops16h 51mDelta

Mon 3/165:38 pmMDW - GRU

1 stop13h 57mDelta

Deal found 12/11

$800

Tue 2/1011:45 pmGRU - MDW

2 stops21h 10mDelta

Tue 2/1710:53 amMDW - GRU

1 stop19h 42mDelta

Deal found 12/11

$800

Tue 2/39:00 pmGRU - MDW

2 stops18h 51mDelta

Tue 2/1710:53 amMDW - GRU

1 stop19h 42mDelta

Deal found 12/10

$801

Thu 3/510:55 pmGRU - MDW

2 stops16h 51mDelta

Tue 3/3112:47 pmMDW - GRU

1 stop14h 53mDelta

Deal found 12/10

$801

Last-minute flights from Sao Paulo to Midway
Discover last-minute flight deals from Sao Paulo to Midway. Data last updated December 12, 2025 and is based on user searches.

Mon 1/194:30 pmGRU - MDW

2 stops27h 59mLATAM Airlines

Mon 1/2612:48 pmMDW - GRU

1 stop17h 47mLATAM Airlines

Deal found 12/10

$860

Mon 1/194:30 pmGRU - MDW

2 stops27h 59mLATAM Airlines

Tue 1/2710:48 amMDW - GRU

2 stops20h 07mLATAM Airlines

Deal found 12/10

$864

Mon 1/199:15 pmGRU - MDW

1 stop17h 44mDelta

Mon 1/261:26 pmMDW - GRU

2 stops17h 09mDelta

Deal found 12/10

$925

Thu 1/229:15 pmGRU - MDW

2 stops18h 31mDelta

Wed 2/41:31 pmMDW - GRU

2 stops17h 24mDelta

Deal found 12/10

$733

Sat 1/243:55 amGRU - MDW

2 stops21h 27mLATAM Airlines

Sun 2/16:00 amMDW - GRU

1 stop20h 40mLATAM Airlines

Deal found 12/11

$741

Sun 1/259:00 pmGRU - MDW

2 stops18h 46mDelta

Sun 2/11:26 pmMDW - GRU

2 stops17h 29mDelta

Deal found 12/11

$855

Mon 1/269:15 pmGRU - MDW

1 stop17h 44mLATAM Airlines

Thu 2/2612:46 pmMDW - GRU

1 stop13h 54mLATAM Airlines

Deal found 12/10

$809

Fri 1/309:15 pmGRU - MDW

1 stop15h 38mDelta

Thu 7/3010:35 amMDW - GRU

2 stops16h 25mDelta

Deal found 12/11

$1,059

Sat 1/3111:45 pmGRU - MDW

1 stop15h 14mDelta

Sun 2/810:48 amMDW - GRU

1 stop19h 47mDelta

Deal found 12/11

$800

One-way flights from Sao Paulo to Midway
Search for one-way flight options from Sao Paulo to Midway. Find affordable one-way fares based on user searches. Data last updated December 12, 2025.

Thu 2/54:05 amGRU - MDW

3 stops31h 38mMultiple Airlines

Deal found 12/10

$319

Sat 2/79:35 pmGRU - MDW

3 stops27h 47mMultiple Airlines

Deal found 12/10

$334

Sun 2/85:40 pmCGH - MDW

2 stops26h 49mMultiple Airlines

Deal found 12/10

$334

Sun 2/85:45 pmGRU - MDW

2 stops26h 44mLATAM Airlines

Deal found 12/10

$347

Fri 2/63:25 pmCGH - MDW

2 stops21h 28mMultiple Airlines

Deal found 12/10

$348

Tue 2/1710:40 pmGRU - MDW

2 stops42h 16mMultiple Airlines

Deal found 12/10

$353

Thu 2/127:45 pmGRU - MDW

2 stops46h 10mMultiple Airlines

Deal found 12/11

$370

Sun 2/86:05 pmGRU - MDW

3 stops20h 40mMultiple Airlines

Deal found 12/10

$384

Thu 2/126:05 amCGH - MDW

3 stops30h 51mMultiple Airlines

Deal found 12/11

$439

Sat 2/77:20 pmCGH - MDW

3 stops19h 25mMultiple Airlines

Deal found 12/10

$490

Tue 2/176:30 amCGH - MDW

3 stops55h 57mMultiple Airlines

Deal found 12/10

$501

Sat 1/39:05 pmCGH - MDW

3 stops44h 00mMultiple Airlines

Deal found 12/11

$1,055

Find flight deals from Sao Paulo to Midway

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$733 (Delta)
One-way from	$319 (Kiwi.com)
Popular in	January
Cheapest in	July
Average price	$944

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

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

Search Deals

From Sao Paulo (SAO) to Chicago Midway

Search Deals

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

Search Deals

Highest demand for flights based on searches. 7% potential increase in price ($63 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($14 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 Sao Paulo to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 1/31

9:00 pm-12:46 pm

2 stops18h 46m

Chicago Midway

Sun 2/8

10:48 am-9:35 am

1 stop19h 47m

$800

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 2/10

9:15 pm-12:46 pm

2 stops18h 31m

Chicago Midway

Wed 2/18

10:53 am-9:35 am

1 stop19h 42m

$800

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 3/1

11:45 pm-11:59 am

1 stop15h 14m

Chicago Midway

Sun 3/15

12:47 pm-5:40 am

1 stop14h 53m

$800

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 2/11

9:15 pm-12:46 pm

2 stops18h 31m

Chicago Midway

Thu 2/19

10:53 am-5:40 am

1 stop15h 47m

$800

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 3/1

10:55 pm-12:46 pm

2 stops16h 51m

Chicago Midway

Mon 3/16

5:38 pm-9:35 am

1 stop13h 57m

$800

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 2/10

11:45 pm-5:55 pm

2 stops21h 10m

Chicago Midway

Tue 2/17

10:53 am-9:35 am

1 stop19h 42m

$800

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 2/3

9:00 pm-12:51 pm

2 stops18h 51m

Chicago Midway

Tue 2/17

10:53 am-9:35 am

1 stop19h 42m

$801

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 3/5

10:55 pm-12:46 pm

2 stops16h 51m

Chicago Midway

Tue 3/31

12:47 pm-5:40 am

1 stop14h 53m

$801

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 2/5

4:05 am-8:43 am

3 stops31h 38m

$319

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 2/7

9:35 pm-10:22 pm

3 stops27h 47m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 23 results

Best time to book a flight from Sao Paulo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sao Paulo 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 Sao Paulo to Chicago Midway Airport

No data available for this route at this time. Please check back soon.

Related info for your journey

How long is the flight from Sao Paulo to Chicago Midway Airport?
For as low as $800, Delta can have you in Chicago Midway Airport from Sao Paulo in 18h 46m. Airlines will cover a distance of 5218 mi.
Can I find deals for flights from Sao Paulo to Midway that include hotel bookings?
Yes. In addition to deals on Sao Paulo to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Sao Paulo to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sao Paulo to Midway.
Can I find deals for business class flights from Sao Paulo to Midway?
Yes. Cheapflights offers flight deals from Sao Paulo to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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$319+ Cheap flights from Sao Paulo, Brazil (SAO) to Midway (MDW)

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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Sao Paulo to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Sao Paulo to Midway

Cheapest flights from Sao Paulo to MidwayExplore the most affordable flight options available from Sao Paulo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

Explore the most affordable flight options available from Sao Paulo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

Find flight deals from Sao Paulo to Midway

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 Sao Paulo to Chicago Midway Airport that are best for you.

Best time to book a flight from Sao Paulo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Sao Paulo with our price prediction graph.

Cheapflights Insights

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

Related info for your journey

Find useful and relevant information for your journey from Sao Paulo to Midway. 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 Sao Paulo to Chicago Midway Airport?

Can I find deals for flights from Sao Paulo to Midway that include hotel bookings?

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

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

Traveling to a place near Chicago Midway Airport?

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Cheapest flights from Sao Paulo to Midway
Explore the most affordable flight options available from Sao Paulo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.