HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Sao Paulo

$287+ 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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAO
dic. 26 — ene. 21
vie. 12/26
vie. 1/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Sao Paulo with Cheapflights

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”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 noviembre 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$600
(Delta)

One-way from

$287
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$697
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
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 noviembre 26, 2025.

This KAYAK deal was found by Cheapflights users on 11/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/110:47 amMDW - GRU
1 stop15h 53mLATAM Airlines
dom. 12/75:50 pmGRU - MDW
2 stops21h 05mLATAM Airlines
Deal found 11/23$872
This KAYAK deal was found by Cheapflights users on 11/25. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/212:50 pmMDW - GRU
2 stops20h 50mLATAM Airlines
mar. 12/911:45 pmGRU - MDW
1 stop15h 10mLATAM Airlines
Deal found 11/25$996
This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
jue. 12/42:16 pmMDW - GRU
2 stops31h 24mMultiple Airlines
dom. 12/710:20 amGRU - MDW
1 stop15h 10mMultiple Airlines
Deal found 11/23$999
This Travelocity deal was found by Cheapflights users on 11/24. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/259:50 amMDW - GRU
1 stop16h 50mLATAM Airlines
lun. 1/512:55 pmGRU - MDW
2 stops36h 12mLATAM Airlines
Deal found 11/24$1,029
This KAYAK deal was found by Cheapflights users on 11/25. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/309:50 amMDW - GRU
1 stop16h 50mLATAM Airlines
mié. 1/145:45 pmGRU - MDW
2 stops19h 42mLATAM Airlines
Deal found 11/25$1,173
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
jue. 12/112:16 pmMDW - GRU
2 stops23h 14mMultiple Airlines
lun. 12/1510:50 pmGRU - MDW
1 stop17h 11mMultiple Airlines
Deal found 11/25$1,175
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/309:29 amMDW - GRU
2 stops17h 11mDelta
mié. 1/149:15 pmGRU - MDW
2 stops18h 33mDelta
Deal found 11/25$1,186
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/235:05 pmMDW - GRU
1 stop33h 35mDelta
vie. 1/911:20 amGRU - MDW
2 stops26h 12mDelta
Deal found 11/25$1,205
This SmartFares deal was found by Cheapflights users on 11/25. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/235:05 pmMDW - GRU
1 stop33h 35mLATAM Airlines
mar. 12/3010:40 amGRU - MDW
1 stop14h 42mLATAM Airlines
Deal found 11/25$1,212
This SmartFares deal was found by Cheapflights users on 11/23. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/235:05 pmMDW - GRU
1 stop33h 35mLATAM Airlines
sáb. 2/289:15 pmGRU - MDW
1 stop15h 41mLATAM Airlines
Deal found 11/23$1,214
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
mar. 12/233:10 pmMDW - VCP
2 stops40h 35mMultiple Airlines
vie. 1/910:00 amVCP - MDW
1 stop16h 09mMultiple Airlines
Deal found 11/25$1,308
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
jue. 12/113:10 pmMDW - VCP
2 stops22h 00mMultiple Airlines
lun. 12/1510:00 amVCP - MDW
1 stop14h 58mMultiple Airlines
Deal found 11/25$1,356

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 noviembre 26, 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

mié. 2/4

6:00 am-5:40 am

1 stop20h 40m

Sao Paulo Guarulhos Intl

sáb. 2/14

11:45 pm-10:06 am

1 stop13h 21m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

dom. 2/8

10:48 am-5:40 am

1 stop15h 52m

Sao Paulo Guarulhos Intl

dom. 2/15

9:15 pm-9:56 am

1 stop15h 41m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 2/4

10:46 am-5:40 am

1 stop15h 54m

Sao Paulo Guarulhos Intl

dom. 2/15

11:45 pm-11:59 am

1 stop15h 14m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 2/4

12:48 pm-5:40 am

1 stop13h 52m

Sao Paulo Guarulhos Intl

lun. 2/16

11:45 pm-11:59 am

1 stop15h 14m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mar. 2/17

10:53 am-9:35 am

1 stop19h 42m

Sao Paulo Guarulhos Intl

mar. 3/3

9:15 pm-9:56 am

1 stop15h 41m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

dom. 2/8

10:48 am-5:40 am

1 stop15h 52m

Sao Paulo Guarulhos Intl

lun. 2/16

11:45 pm-5:45 pm

1 stop21h 00m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

jue. 2/5

6:00 am-9:35 am

1 stop24h 35m

Sao Paulo Guarulhos Intl

dom. 2/15

9:15 pm-9:56 am

1 stop15h 41m

$683

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

dom. 2/15

4:13 pm-9:35 am

1 stop14h 22m

Sao Paulo Guarulhos Intl

dom. 2/22

4:00 am-10:42 pm

2 stops21h 42m

$940

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

vie. 1/23

10:48 am-9:35 am

1 stop19h 47m

Sao Paulo Guarulhos Intl

mar. 3/17

11:45 pm-12:02 pm

1 stop14h 17m

$940

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 1/21

12:48 pm-9:35 am

1 stop17h 47m

Sao Paulo Guarulhos Intl

mar. 2/3

11:45 pm-5:29 pm

1 stop20h 44m

$940

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 35 results
1
2
3
4

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 November.
ProviderPrice AccuracyTrust Score*
AranGrantPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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

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?

    There are many flights that can get you from Chicago Midway Airport to Sao Paulo in 20h 40m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Sao Paulo

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Guarulhos Intl flights
O'Hare Intl to Viracopos flights
Midway to Guarulhos Intl flights
O'Hare Intl to Congonhas flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.