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Cheap flights from Chicago Midway Airport to Sao Paulo from $320

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 12/24. 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
1:05 pm - 4:30 pmMDW-GRU
25h 25m2 stops
LATAM Airlines Logo
11:55 pm - 9:46 pmGRU-MDW
23h 51m2 stops
$607LATAM Airlines
Find Deal
Mon, Mar 9 - Wed, Mar 11
Multiple Airlines Logo
5:25 pm - 9:35 amMDW-GRU
14h 10m1 stop
Multiple Airlines Logo
1:00 am - 9:58 pmGRU-MDW
22h 58m2 stops
$683Multiple Airlines
Find Deal
Mon, Mar 16 - Mon, Mar 30
LATAM Airlines Logo
6:00 am - 4:30 pmMDW-GRU
32h 30m2 stops
LATAM Airlines Logo
3:20 pm - 12:01 pmGRU-MDW
22h 41m2 stops
$736LATAM Airlines
Find Deal
Mon, Mar 9 - Wed, Mar 11
Multiple Airlines Logo
4:30 pm - 9:35 amMDW-GRU
15h 05m1 stop
Multiple Airlines Logo
10:40 pm - 3:33 pmGRU-MDW
42h 53m2 stops
$772Multiple Airlines
Find Deal
Sat, Mar 14 - Sat, Mar 21
Multiple Airlines Logo
4:13 pm - 9:35 amMDW-GRU
14h 22m1 stop
Multiple Airlines Logo
2:40 am - 5:11 pmGRU-MDW
17h 31m2 stops
$803Multiple Airlines
Find Deal
Sat, Feb 14 - Fri, Feb 20
Multiple Airlines Logo
5:25 pm - 9:35 amMDW-GRU
14h 10m1 stop
Multiple Airlines Logo
5:25 am - 9:58 pmGRU-MDW
18h 33m2 stops
$806Multiple Airlines
Find Deal
Mon, Mar 16 - Tue, Mar 31
LATAM Airlines Logo
12:46 pm - 9:35 amMDW-GRU
17h 49m1 stop
LATAM Airlines Logo
3:20 pm - 9:58 amGRU-MDW
21h 38m2 stops
$815LATAM Airlines
Find Deal
Thu, Feb 12 - Tue, Feb 17
Multiple Airlines Logo
10:35 am - 5:40 amMDW-GRU
17h 05m1 stop
Multiple Airlines Logo
1:55 pm - 9:58 pmGRU-MDW
34h 03m2 stops
$827Multiple Airlines
Find Deal
Sat, Mar 21 - Sat, Mar 28
LATAM Airlines Logo
12:46 pm - 5:40 amMDW-GRU
13h 54m1 stop
LATAM Airlines Logo
5:45 pm - 8:56 amGRU-MDW
18h 11m2 stops
$852LATAM Airlines
Find Deal
Fri, Feb 27 - Sat, Mar 7
Multiple Airlines Logo
3:10 pm - 7:50 amMDW-GRU
14h 40m1 stop
Multiple Airlines Logo
1:00 am - 9:58 pmGRU-MDW
22h 58m2 stops
$856Multiple Airlines
Find Deal
Wed, Mar 18 - Mon, Mar 30

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
Mar 9
MDW1:05 pmChicago Midway
25h 25m
2 stops
GRU4:30 pmSao Paulo Guarulhos Intl
Mar 11
GRU11:55 pmSao Paulo Guarulhos Intl
23h 51m
2 stops
MDW9:46 pmChicago Midway
$607
Find similar
LATAM Airlines
Mar 9
MDW6:00 amChicago Midway
32h 30m
2 stops
GRU4:30 pmSao Paulo Guarulhos Intl
Mar 11
GRU3:20 pmSao Paulo Guarulhos Intl
22h 41m
2 stops
MDW12:01 pmChicago Midway
$736
Find similar
LATAM Airlines
Feb 12
MDW12:46 pmChicago Midway
17h 49m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Feb 17
GRU3:20 pmSao Paulo Guarulhos Intl
21h 38m
2 stops
MDW9:58 amChicago Midway
$815
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
Mar 3
MDW10:53 amChicago Midway
15h 47m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Mar 19
GRU11:45 pmSao Paulo Guarulhos Intl
14h 16m
1 stop
MDW12:01 pmChicago Midway
$940
Find similar
Delta
Feb 18
MDW12:46 pmChicago Midway
17h 49m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Mar 19
GRU9:00 pmSao Paulo Guarulhos Intl
18h 23m
2 stops
MDW1:23 pmChicago Midway
$945
Find similar
Delta
Jan 9
MDW6:45 amChicago Midway
19h 55m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Jan 22
GRU9:15 pmSao Paulo Guarulhos Intl
17h 44m
1 stop
MDW11:59 amChicago Midway
$1,181
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 November 23, 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

Mon 3/9

1:05 pm-4:30 pm

2 stops25h 25m

Sao Paulo Guarulhos Intl

Wed 3/11

11:55 pm-9:46 pm

2 stops23h 51m

$607

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/16

5:25 pm-9:35 am

1 stop14h 10m

Sao Paulo Guarulhos Intl

Mon 3/30

1:00 am-9:58 pm

2 stops22h 58m

$683

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/9

6:00 am-4:30 pm

2 stops32h 30m

Sao Paulo Guarulhos Intl

Wed 3/11

3:20 pm-12:01 pm

2 stops22h 41m

$736

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 3/14

4:30 pm-9:35 am

1 stop15h 05m

Sao Paulo Guarulhos Intl

Sat 3/21

10:40 pm-3:33 pm

2 stops42h 53m

$772

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 2/14

4:13 pm-9:35 am

1 stop14h 22m

Sao Paulo Guarulhos Intl

Fri 2/20

2:40 am-5:11 pm

2 stops17h 31m

$803

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/16

5:25 pm-9:35 am

1 stop14h 10m

Sao Paulo Guarulhos Intl

Tue 3/31

5:25 am-9:58 pm

2 stops18h 33m

$806

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/12

12:46 pm-9:35 am

1 stop17h 49m

Sao Paulo Guarulhos Intl

Tue 2/17

3:20 pm-9:58 am

2 stops21h 38m

$815

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 3/21

10:35 am-5:40 am

1 stop17h 05m

Sao Paulo Guarulhos Intl

Sat 3/28

1:55 pm-9:58 pm

2 stops34h 03m

$827

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 2/27

12:46 pm-5:40 am

1 stop13h 54m

Sao Paulo Guarulhos Intl

Sat 3/7

5:45 pm-8:56 am

2 stops18h 11m

$852

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 3/18

3:10 pm-7:50 am

1 stop14h 40m

Sao Paulo Guarulhos Intl

Mon 3/30

1:00 am-9:58 pm

2 stops22h 58m

$856

Flights are sorted by cheapest round-trip flights 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 $948. 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 Tuesday, with ticket prices averaging around $1,097.

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 $1,045.

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 04m.

  • 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
Guarujá
Campinas
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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