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Sao Paulo

$329+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAO
mar. 16 — mar. 231
lun. 3/16
lun. 3/23
1 adult, Economy
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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 febrero 14, 2026.

This KAYAK deal was found by Cheapflights users on 2/13. 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. 3/312:45 pm
MDW
-
GRU
1 stop13h 55m
LATAM Airlines
lun. 3/93:20 pm
GRU
-
MDW
2 stops22h 42m
LATAM Airlines
Deal found 2/13$608
This Ovago deal was found by Cheapflights users on 2/10. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/86:07 pm
MDW
-
GRU
1 stop13h 28m
LATAM Airlines
dom. 3/1511:45 pm
GRU
-
MDW
1 stop19h 37m
LATAM Airlines
Deal found 2/10$648
This FlightHub deal was found by Cheapflights users on 2/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/1212:51 pm
MDW
-
GRU
1 stop14h 49m
LATAM Airlines
jue. 5/2110:50 pm
GRU
-
MDW
1 stop15h 06m
LATAM Airlines
Deal found 2/10$701
This LATAM Airlines deal was found by Cheapflights users on 2/10. 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.
vie. 3/2710:45 am
MDW
-
GRU
2 stops16h 35m
LATAM Airlines
jue. 4/23:40 am
GRU
-
MDW
2 stops32h 16m
LATAM Airlines
Deal found 2/10$703
This Delta deal was found by Cheapflights users on 2/10. 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.
dom. 3/89:35 am
MDW
-
GRU
2 stops18h 05m
Delta
dom. 3/1511:45 pm
GRU
-
MDW
2 stops20h 09m
Delta
Deal found 2/10$705
This Kiwi.com deal was found by Cheapflights users on 2/12. 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. 3/56:15 am
MDW
-
GRU
1 stop20h 05m
Multiple Airlines
mar. 3/172:40 am
GRU
-
MDW
2 stops17h 33m
Multiple Airlines
Deal found 2/12$723
This Orbitz deal was found by Cheapflights users on 2/11. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/1910:45 am
MDW
-
GRU
2 stops18h 40m
LATAM Airlines
jue. 3/2610:40 am
GRU
-
MDW
1 stop13h 51m
LATAM Airlines
Deal found 2/11$726
This KAYAK deal was found by Cheapflights users on 2/13. 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.
mié. 3/410:49 am
MDW
-
GRU
2 stops17h 36m
LATAM Airlines
mar. 3/103:20 pm
GRU
-
MDW
2 stops20h 36m
LATAM Airlines
Deal found 2/13$737
This SmartFares deal was found by Cheapflights users on 2/10. 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. 5/1212:51 pm
MDW
-
GRU
1 stop14h 49m
LATAM Airlines
mar. 5/2610:50 pm
GRU
-
MDW
1 stop24h 19m
LATAM Airlines
Deal found 2/10$738
This SmartFares deal was found by Cheapflights users on 2/9. 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.
vie. 5/16:00 am
MDW
-
GRU
2 stops36h 20m
LATAM Airlines
dom. 5/3110:50 pm
GRU
-
MDW
1 stop15h 06m
LATAM Airlines
Deal found 2/9$741
This KAYAK deal was found by Cheapflights users on 2/11. 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.
vie. 3/66:00 am
MDW
-
GRU
2 stops21h 55m
LATAM Airlines
lun. 3/94:40 pm
GRU
-
MDW
2 stops21h 22m
LATAM Airlines
Deal found 2/11$742
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/206:00 am
MDW
-
GRU
2 stops23h 30m
LATAM Airlines
sáb. 3/288:15 am
GRU
-
MDW
2 stops27h 41m
LATAM Airlines
Deal found 2/10$747

Find 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 febrero 14, 2026.

Most accurate provider

AranGrant
2 stars

Most trusted provider

AranGrant
2 stars

Round-trip from

$608
(KAYAK)

One-way from

$329
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$685
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, 0% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 febrero 14, 2026.
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. 5/13

6:30 am-5:40 am

1 stop21h 10m

Sao Paulo Guarulhos Intl

vie. 5/22

10:50 pm-3:26 pm

1 stop18h 36m

$701

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

sáb. 4/11

10:45 am-5:40 am

1 stop16h 55m

Sao Paulo Guarulhos Intl

sáb. 4/25

11:00 pm-12:07 pm

2 stops15h 07m

$705

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

dom. 3/8

9:35 am-5:40 am

2 stops18h 05m

Sao Paulo Guarulhos Intl

dom. 3/15

11:45 pm-5:54 pm

2 stops20h 09m

$705

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 5/13

1:22 pm-6:45 am

2 stops15h 23m

Sao Paulo Guarulhos Intl

vie. 5/22

8:30 pm-3:26 pm

2 stops20h 56m

$705

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

jue. 3/19

10:45 am-7:25 am

2 stops18h 40m

Sao Paulo Guarulhos Intl

jue. 3/26

10:40 am-10:31 pm

1 stop13h 51m

$726

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mar. 5/12

12:51 pm-5:40 am

1 stop14h 49m

Sao Paulo Guarulhos Intl

mar. 5/26

10:50 pm-9:09 pm

1 stop24h 19m

$738

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

sáb. 5/16

4:30 pm-11:55 pm

2 stops29h 25m

Sao Paulo Guarulhos Intl

sáb. 5/30

10:50 pm-9:09 pm

1 stop24h 19m

$741

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

vie. 3/13

6:07 pm-5:40 am

1 stop33h 33m

Sao Paulo Guarulhos Intl

dom. 3/22

7:35 am-9:56 am

2 stops28h 21m

$768

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

mié. 2/25

7:00 am-7:20 pm

2 stops33h 20m

Sao Paulo Viracopos

sáb. 2/28

10:10 am-2:26 pm

1 stop31h 16m

$898

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mar. 2/24

6:10 am-9:15 am

3 stops48h 05m

$376

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 24 results
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  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Sao Paulo flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-Sao Paulo flight deals on Cheapflights vs. AranGrant 90-95% 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 16h 55m. Fly via LATAM Airlines or Delta to get the fastest option. Airlines will cover a distance of 5218 mi. This flight may include one or multiple stops.

  • 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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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
Midway to Guarulhos Intl flights
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