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MDW - GRU

Find cheap flights from Chicago Midway Airport to Sao Paulo from $331

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Guarulhos Intl departing on 5/22. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Tue 5/28
Tue 6/4

Search hundreds of travel sites at once for deals on flights to Sao Paulo

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sao Paulo, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sao Paulo, as well as popular online travel agencies
In the last 7 days travelers have searched 43,219,010 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Midway to Guarulhos Intl (MDW-GRU)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Guarulhos Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:23 pm - 12:20 amMDW-GRU
26h 57m2 stops
10:35 am - 9:57 pmGRU-MDW
13h 22m1 stop
$695
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Wed, May 29 - Thu, Jun 6
7:23 pm - 12:20 amMDW-GRU
26h 57m2 stops
10:35 am - 7:32 amGRU-MDW
22h 57m1 stop
$711
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Mon, May 27 - Tue, Jun 4
7:23 pm - 12:20 amMDW-GRU
26h 57m2 stops
10:35 am - 9:57 pmGRU-MDW
13h 22m1 stop
$721
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Sun, May 26 - Thu, Jun 6
7:23 pm - 12:20 amMDW-GRU
26h 57m2 stops
10:35 am - 8:36 amGRU-MDW
24h 01m1 stop
$735
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Sun, May 26 - Fri, Jun 7
3:45 pm - 4:10 pmMDW-GRU
22h 25m2 stops
10:05 am - 9:44 pmGRU-MDW
13h 39m1 stop
$956LATAM Airlines
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Sun, Oct 6 - Sat, Oct 12
6:50 pm - 2:05 pmMDW-GRU
41h 15m3 stops
9:55 am - 9:44 pmGRU-MDW
13h 49m1 stop
$973LATAM Airlines
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Sun, Oct 20 - Sun, Oct 27
3:45 pm - 2:05 pmMDW-GRU
20h 20m3 stops
10:05 am - 9:44 pmGRU-MDW
13h 39m1 stop
$1,037LATAM Airlines
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Sun, Oct 6 - Sat, Oct 12
1:05 pm - 5:40 amMDW-GRU
14h 35m1 stop
10:50 pm - 11:53 amGRU-MDW
15h 03m1 stop
$1,548Delta
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Wed, Aug 7 - Mon, Aug 19
12:45 pm - 8:50 amMDW-GRU
18h 05m1 stop
10:50 pm - 5:04 pmGRU-MDW
20h 14m2 stops
$1,552Delta
Find Deal
Thu, Jun 20 - Thu, Jun 27
3:45 pm - 8:50 amMDW-GRU
15h 05m1 stop
10:50 pm - 5:59 pmGRU-MDW
21h 09m1 stop
$1,588Delta
Find Deal
Fri, Aug 9 - Tue, Aug 20

Flights from Midway to Guarulhos Intl - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Guarulhos Intl to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport is January, where tickets cost $832 on average. On the other hand, the most expensive months are December and July, where the average cost of tickets is $1,586 and $1,444 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport, you should book around 3 days before departure. For the absolute cheapest price, our data suggests you should book 27 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Sao Paulo?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, LATAM Airlines offered the best one-way deal for that route, at $717. KAYAK users also found Chicago Midway Airport to Sao Paulo round-trip flights on LATAM Airlines from $956 and on Delta from $1,548.

Good to know

Cheapest flight

$331
Flight from Chicago Midway Airport to Sao Paulo

When to book flights from Midway to Guarulhos Intl

Are your dates flexible? Find out the best times to travel from Midway to Guarulhos Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Sao Paulo flights

  • What is the cheapest flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport was $331 for a one-way ticket and $695 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Sao Paulo?

    Yes

  • Which airports will I be using when flying from Chicago Midway Airport to Sao Paulo?

    On your way to Sao Paulo, you’ll fly out from Chicago Midway. You’ll be landing at Sao Paulo Guarulhos Intl.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Sao Paulo?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Sao Paulo?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Sao Paulo.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Sao Paulo?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Sao Paulo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Sao Paulo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Sao Paulo from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Sao Paulo?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Sao Paulo with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and GRU can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Sao Paulo?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Sao Paulo from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from Chicago to Sao Paulo

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Sao Paulo found on KAYAK in the last 72 hours.
5/22Wed
2 stops
26h 57mMDW-GRU
$331
9/2Mon
2 stops
26h 07mMDW-GRU
$351
6/3Mon
2 stops
26h 57mMDW-GRU
$357
6/3Mon
3 stops
30h 12mMDW-GRU
$384
6/4Tue
2 stopsLATAM Airlines
18h 55mMDW-GRU
$717
6/28Fri
2 stopsLATAM Airlines
21h 40mMDW-GRU
$774
5/25Sat
2 stopsLATAM Airlines
16h 39mMDW-GRU
$814
6/17Mon
1 stopDelta
18h 05mMDW-GRU
$1,312
8/18Sun
2 stopsDelta
17h 40mMDW-GRU
$1,352
5/22Wed
1 stopDelta
14h 58mMDW-GRU
$6,202

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Last minute flights from Midway to Guarulhos Intl

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Sao Paulo that are departing in the next 10 days.
5/2Thu
multi-stop
34h 04mMDW-GRU
5/9Thu
multi-stop
21h 22mGRU-MDW
$1,098
5/3Fri
multi-stop
34h 53mMDW-GRU
5/5Sun
multi-stop
23h 02mGRU-MDW
$1,267
5/2Thu
multi-stop
32h 02mMDW-GRU
5/8Wed
multi-stop
17h 25mGRU-MDW
$1,336
5/3Fri
multi-stop
23h 18mMDW-GRU
5/5Sun
multi-stop
32h 52mGRU-MDW
$1,348
5/2Thu
multi-stopLATAM Airlines
21h 40mMDW-GRU
5/4Sat
multi-stopLATAM Airlines
27h 34mGRU-MDW
$1,517
4/29Mon
multi-stopLATAM Airlines
32h 53mMDW-GRU
5/7Tue
multi-stopLATAM Airlines
31h 31mGRU-MDW
$1,531
5/2Thu
multi-stopLATAM Airlines
17h 40mMDW-GRU
5/8Wed
multi-stopLATAM Airlines
30h 25mGRU-MDW
$1,551
5/2Thu
multi-stopDelta
17h 40mMDW-GRU
5/6Mon
multi-stopDelta
15h 02mGRU-MDW
$2,798
5/3Fri
multi-stopDelta
17h 40mMDW-GRU
5/5Sun
multi-stopDelta
14h 45mGRU-MDW
$2,878
4/29Mon
multi-stopDelta
17h 40mMDW-GRU
5/7Tue
multi-stopDelta
15h 02mGRU-MDW
$3,098

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Chicago Midway Airport - Sao Paulo Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Sao Paulo (GRU)Brazil

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