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Cheap flights from Chicago Midway Airport to Sao Paulo from $297

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Sao Paulo departing on 11/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
LATAM Airlines Logo
12:47 pm - 5:40 amMDW-GRU
13h 53m1 stop
LATAM Airlines Logo
9:15 pm - 11:52 amGRU-MDW
17h 37m1 stop
$597LATAM Airlines
Find Deal
mié., nov. 12 - mié., nov. 19
Delta Logo
10:47 am - 5:40 amMDW-GRU
15h 53m1 stop
Delta Logo
11:45 pm - 11:52 amGRU-MDW
15h 07m1 stop
$600Delta
Find Deal
lun., nov. 10 - dom., nov. 23
Delta Logo
12:47 pm - 5:40 amMDW-GRU
13h 53m1 stop
Delta Logo
10:20 am - 11:40 pmGRU-MDW
16h 20m2 stops
$605Delta
Find Deal
dom., nov. 9 - mar., nov. 18
LATAM Airlines Logo
10:35 am - 5:45 amMDW-GRU
16h 10m2 stops
LATAM Airlines Logo
1:35 pm - 9:56 amGRU-MDW
23h 21m2 stops
$607LATAM Airlines
Find Deal
lun., mar. 2 - vie., mar. 6
LATAM Airlines Logo
6:00 am - 5:40 amMDW-GRU
20h 40m1 stop
LATAM Airlines Logo
9:15 pm - 9:52 amGRU-MDW
15h 37m1 stop
$622LATAM Airlines
Find Deal
dom., nov. 16 - mié., nov. 26
LATAM Airlines Logo
4:28 pm - 5:40 amMDW-GRU
34h 12m1 stop
LATAM Airlines Logo
9:15 pm - 11:52 amGRU-MDW
17h 37m1 stop
$629LATAM Airlines
Find Deal
sáb., nov. 15 - mar., nov. 25
LATAM Airlines Logo
10:47 am - 8:20 pmMDW-GRU
30h 33m2 stops
LATAM Airlines Logo
9:15 pm - 11:52 amGRU-MDW
17h 37m1 stop
$633LATAM Airlines
Find Deal
sáb., nov. 15 - mar., nov. 25
LATAM Airlines Logo
5:34 pm - 8:20 pmMDW-GRU
47h 46m2 stops
LATAM Airlines Logo
11:45 pm - 4:38 pmGRU-MDW
19h 53m1 stop
$640LATAM Airlines
Find Deal
vie., nov. 14 - lun., nov. 24
Multiple Airlines Logo
5:57 pm - 8:00 pmMDW-GRU
23h 03m1 stop
Multiple Airlines Logo
4:25 am - 2:05 pmGRU-MDW
36h 40m2 stops
$660Multiple Airlines
Find Deal
mié., nov. 26 - mar., dic. 2
Delta Logo
6:00 am - 5:40 amMDW-GRU
20h 40m1 stop
Delta Logo
11:45 pm - 11:55 amGRU-MDW
15h 10m1 stop
$843Delta
Find Deal
mié., nov. 19 - lun., dic. 1

LATAM Airlines flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Our best LATAM Airlines deals on Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport flight tickets
LATAM Airlines
Nov 12
MDW12:47 pmChicago Midway
13h 53m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Nov 19
GRU9:15 pmSao Paulo Guarulhos Intl
17h 37m
1 stop
MDW11:52 amChicago Midway
$597
Find similar
LATAM Airlines
Mar 2
MDW6:00 amChicago Midway
21h 15m
2 stops
GRU6:15 amSao Paulo Guarulhos Intl
Mar 6
GRU5:45 pmSao Paulo Guarulhos Intl
19h 11m
2 stops
MDW9:56 amChicago Midway
$607
Find similar
LATAM Airlines
Nov 16
MDW6:00 amChicago Midway
20h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Nov 26
GRU9:15 pmSao Paulo Guarulhos Intl
22h 24m
1 stop
MDW4:39 pmChicago Midway
$622
Find similar

Delta flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Our best Delta deals on Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport flight tickets
Delta
Nov 10
MDW10:47 amChicago Midway
15h 53m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Nov 23
GRU11:45 pmSao Paulo Guarulhos Intl
15h 07m
1 stop
MDW11:52 amChicago Midway
$600
Find similar
Delta
Nov 9
MDW12:47 pmChicago Midway
13h 53m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Nov 18
GRU10:20 amSao Paulo Guarulhos Intl
16h 20m
2 stops
MDW11:40 pmChicago Midway
$605
Find similar
Delta
Nov 19
MDW6:00 amChicago Midway
20h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Dec 1
GRU11:45 pmSao Paulo Guarulhos Intl
15h 10m
1 stop
MDW11:55 amChicago Midway
$843
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport 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, momondo users made 832,500 searches. Data last updated octubre 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 11/12

12:47 pm-5:40 am

1 stop13h 53m

Sao Paulo Guarulhos Intl

mié. 11/19

9:15 pm-11:52 am

1 stop17h 37m

$597

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

lun. 11/10

10:47 am-5:40 am

1 stop15h 53m

Sao Paulo Guarulhos Intl

dom. 11/23

11:45 pm-11:52 am

1 stop15h 07m

$600

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

dom. 11/9

12:47 pm-5:40 am

1 stop13h 53m

Sao Paulo Guarulhos Intl

mar. 11/18

10:20 am-11:40 pm

2 stops16h 20m

$605

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

lun. 3/2

10:35 am-5:45 am

2 stops16h 10m

Sao Paulo Guarulhos Intl

vie. 3/6

1:35 pm-9:56 am

2 stops23h 21m

$607

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

dom. 11/16

6:00 am-5:40 am

1 stop20h 40m

Sao Paulo Guarulhos Intl

mié. 11/26

9:15 pm-9:52 am

1 stop15h 37m

$622

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

sáb. 11/15

4:28 pm-5:40 am

1 stop34h 12m

Sao Paulo Guarulhos Intl

mar. 11/25

9:15 pm-11:52 am

1 stop17h 37m

$629

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

sáb. 11/15

10:47 am-8:20 pm

2 stops30h 33m

Sao Paulo Guarulhos Intl

mar. 11/25

9:15 pm-11:52 am

1 stop17h 37m

$633

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

vie. 11/14

5:34 pm-8:20 pm

2 stops47h 46m

Sao Paulo Guarulhos Intl

lun. 11/24

11:45 pm-4:38 pm

1 stop19h 53m

$640

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 11/26

5:57 pm-8:00 pm

1 stop23h 03m

Sao Paulo Guarulhos Intl

mar. 12/2

4:25 am-2:05 pm

2 stops36h 40m

$660

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

mié. 11/19

6:00 am-5:40 am

1 stop20h 40m

Sao Paulo Guarulhos Intl

lun. 12/1

11:45 pm-11:55 am

1 stop15h 10m

$843

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Sao Paulo Guarulhos Intl Airport?

On average, the least expensive day to fly to Sao Paulo Guarulhos Intl Airport from Chicago Midway Airport is on a Thursday. momondo users have found tickets for Thursday departures for as low as $970. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Sao Paulo Guarulhos Intl Airport is Friday, with ticket prices averaging around $1,098.

What is the cheapest time of day to depart on your flight to Sao Paulo Guarulhos Intl Airport?

Our data shows that the cheapest Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport flights are usually those with departure times at noon. Our users have found flights to Sao Paulo Guarulhos Intl Airport at noon for as low as $956. Flights in the afternoon are often more expensive with an average ticket price of $1,048.

When to book flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport (MDW to GRU) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

Direct flights

None
There are no direct flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport. There are no popular flight routes from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport.
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  • How far is Chicago Midway to Sao Paulo Guarulhos Intl by plane?

    A flight from Chicago Midway to Sao Paulo Guarulhos Intl will travel around 5217.7 mi. In terms of flight time, this usually takes a little over 13h 01m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport?

    Prices for flights from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport.

  • What documentation or ID do you need to fly to Sao Paulo Guarulhos Intl Airport?

    The travel and health documents required for your trip to Sao Paulo Guarulhos Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Sao Paulo Guarulhos Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Sao Paulo?

Book flights to Sao Paulo if you plan to visit one of these locations
Guarulhos
Santos
Campinas
Guarujá
Aparecida

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Sao Paulo?

Finding the right flight to Sao Paulo from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Sao Paulo quick and easy, saving you time and money.

Can I find flights from Chicago to Sao Paulo with flexible booking policies on momondo?

All flight searches from Chicago to Sao Paulo on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Sao Paulo?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Sao Paulo from Chicago.

I’m not ready to book a flight from Chicago to Sao Paulo right now. Can momondo alert me if prices change?

Price alerts on flights to Sao Paulo from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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