HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$300+ 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.
SAO — MDW
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Sao Paulo to Midway 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 Sao Paulo to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Sao Paulo (SAO) to Midway (MDW). 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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$686
(Kiwi.com)

One-way from

$300
(Kiwi.com)

Popular in

November

Cheapest in

May

Average price

$793
Provider with most accurate pricing for Sao Paulo (SAO)-Chicago (CHI) flight deals.
Search Deals
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. 17% potential increase in price ($223 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($92 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find 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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/1311:45 pmGRU - MDW
2 stops25h 25mMultiple Airlines
Sun 11/306:00 amMDW - GRU
1 stop20h 40mMultiple Airlines
Deal found 10/28$686
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 11/1311:45 pmGRU - MDW
2 stops25h 25mMultiple Airlines
Wed 11/265:57 pmMDW - GRU
1 stop23h 03mMultiple Airlines
Deal found 10/27$767
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/209:15 pmGRU - MDW
1 stop15h 37mDelta
Sun 11/3010:47 amMDW - GRU
1 stop19h 48mDelta
Deal found 10/28$824
This Delta deal was found by Cheapflights users on 10/27. 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.
Thu 11/2710:40 pmGRU - MDW
2 stops20h 59mDelta
Fri 12/510:49 amMDW - GRU
2 stops15h 31mDelta
Deal found 10/27$825
This Delta deal was found by Cheapflights users on 10/28. 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.
Tue 11/1811:45 pmGRU - MDW
2 stops15h 49mDelta
Tue 11/2512:47 pmMDW - GRU
1 stop13h 53mDelta
Deal found 10/28$826
This LATAM Airlines deal was found by Cheapflights users on 10/28. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2011:45 pmGRU - MDW
1 stop15h 07mLATAM Airlines
Fri 11/285:34 pmMDW - GRU
1 stop13h 01mLATAM Airlines
Deal found 10/28$833
This Gurufare deal was found by Cheapflights users on 10/27. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1511:45 pmGRU - MDW
1 stop15h 10mLATAM Airlines
Wed 1/145:31 pmMDW - GRU
1 stop13h 04mLATAM Airlines
Deal found 10/27$903
This Gurufare deal was found by Cheapflights users on 10/27. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1911:45 pmGRU - MDW
1 stop25h 37mLATAM Airlines
Mon 1/126:45 amMDW - GRU
1 stop19h 55mLATAM Airlines
Deal found 10/27$911
This Delta deal was found by Cheapflights users on 10/28. 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.
Sun 12/1411:20 amGRU - MDW
2 stops15h 27mDelta
Tue 1/131:28 pmMDW - GRU
2 stops17h 27mDelta
Deal found 10/28$921
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 12/119:15 pmGRU - MDW
2 stops18h 19mDelta
Fri 2/139:30 amMDW - GRU
2 stops17h 10mDelta
Deal found 10/29$922
This LATAM Airlines deal was found by Cheapflights users on 10/27. 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 LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/18:15 amGRU - MDW
2 stops18h 25mLATAM Airlines
Wed 12/105:29 pmMDW - GRU
1 stop13h 06mLATAM Airlines
Deal found 10/27$930

Cheapflights Fare Finder

 
Customize your flight search to find flights from Sao Paulo to Midway 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 October 29, 2025.
Use the filters below to find and compare flights from Sao Paulo to Chicago Midway Airport that are best for you.

Fly from

Sao Paulo

Fly to

Midway

Route

Depart

Return

Price

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 11/21

11:45 pm-3:43 pm

1 stop18h 58m

Chicago Midway

Sun 11/30

12:47 pm-5:40 am

1 stop13h 53m

$824

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 4/10

10:45 pm-12:35 pm

2 stops15h 50m

Chicago Midway

Mon 4/27

9:30 am-5:40 am

2 stops18h 10m

$824

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 4/23

11:05 pm-11:56 am

2 stops14h 51m

Chicago Midway

Tue 5/12

10:35 am-5:40 am

2 stops17h 05m

$824

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 3/11

10:55 pm-12:35 pm

2 stops15h 40m

Chicago Midway

Tue 3/31

1:00 pm-5:40 am

2 stops14h 40m

$824

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 4/21

11:05 pm-11:56 am

2 stops14h 51m

Chicago Midway

Thu 4/30

1:00 pm-5:40 am

2 stops14h 40m

$824

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 2/5

6:00 am-7:50 pm

2 stops40h 50m

$300

Sao PauloChicago

CGH - MDW

CGHMDW

Sao Paulo Congonhas

Thu 2/5

6:05 am-7:50 pm

2 stops40h 45m

$306

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 12/12

11:59 pm-10:30 pm

2 stops25h 31m

$315

Sao PauloChicago

CGH - MDW

CGHMDW

Sao Paulo Congonhas

Sat 1/31

8:55 am-11:25 pm

3 stops41h 30m

$350

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 11/3

5:25 am-11:55 pm

3 stops45h 30m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 19 results
1
2

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

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?

    For as low as $824, Delta can have you in Chicago Midway Airport from Sao Paulo in 18h 58m. 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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 Sao Paulo to Midway

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