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Cheap flights from Chicago Midway Airport to Sao Paulo from $258

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 10/24. 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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Find the cheapest flights from Chicago Midway Airport to Sao Paulo

Cheap round-trip flights

Logo
9:45 am - 4:15 pmMDW-GRU
28h 30m2 stops
Logo
2:40 am - 12:30 amGRU-MDW
24h 50m2 stops
$502
Find Deal
Mon, Oct 27 - Sat, Nov 8
LATAM Airlines Logo
6:00 am - 6:15 amMDW-GRU
21h 15m2 stops
LATAM Airlines Logo
3:20 pm - 9:56 amGRU-MDW
21h 36m2 stops
$606LATAM Airlines
Find Deal
Mon, Mar 2 - Fri, Mar 6
Logo
9:00 am - 12:30 amMDW-GRU
37h 30m2 stops
Logo
11:05 pm - 11:17 amGRU-MDW
14h 12m1 stop
$653
Find Deal
Mon, Oct 13 - Sun, Oct 26
Logo
12:18 pm - 5:40 amMDW-GRU
15h 22m1 stop
Logo
11:59 pm - 9:22 pmGRU-MDW
23h 23m2 stops
$659
Find Deal
Fri, Oct 24 - Fri, Oct 31
Logo
4:24 pm - 2:57 amMDW-GRU
32h 33m2 stops
Logo
10:50 pm - 11:17 amGRU-MDW
14h 27m1 stop
$686
Find Deal
Mon, Oct 13 - Sun, Oct 26
LATAM Airlines Logo
6:00 am - 5:45 amMDW-GRU
20h 45m2 stops
LATAM Airlines Logo
1:35 pm - 9:56 amGRU-MDW
23h 21m2 stops
$691LATAM Airlines
Find Deal
Mon, Mar 2 - Fri, Mar 6
LATAM Airlines Logo
5:25 pm - 5:40 amMDW-GRU
33h 15m1 stop
LATAM Airlines Logo
3:20 pm - 12:01 pmGRU-MDW
23h 41m2 stops
$693LATAM Airlines
Find Deal
Tue, Feb 10 - Tue, Feb 17
Delta Logo
10:35 am - 5:40 amMDW-GRU
16h 05m1 stop
Delta Logo
11:45 pm - 4:25 pmGRU-MDW
18h 40m1 stop
$1,060Delta
Find Deal
Wed, Feb 18 - Thu, Mar 19
Delta Logo
1:00 pm - 9:55 amMDW-GRU
17h 55m2 stops
Delta Logo
9:30 pm - 12:01 pmGRU-MDW
17h 31m1 stop
$1,064Delta
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Mon, Jan 5 - Sun, Jan 18
Delta Logo
10:35 am - 9:35 amMDW-GRU
21h 00m1 stop
Delta Logo
9:15 pm - 9:52 amGRU-MDW
15h 37m1 stop
$1,086Delta
Find Deal
Mon, Oct 27 - Mon, Nov 10

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 2
MDW6:00 amChicago Midway
21h 15m
2 stops
GRU6:15 amSao Paulo Guarulhos Intl
Mar 6
GRU3:20 pmSao Paulo Guarulhos Intl
21h 36m
2 stops
MDW9:56 amChicago Midway
$606
Find similar
LATAM Airlines
Mar 2
MDW6:00 amChicago Midway
20h 45m
2 stops
GRU5:45 amSao Paulo Guarulhos Intl
Mar 6
GRU1:35 pmSao Paulo Guarulhos Intl
23h 21m
2 stops
MDW9:56 amChicago Midway
$691
Find similar
LATAM Airlines
Feb 10
MDW5:25 pmChicago Midway
33h 15m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Feb 17
GRU3:20 pmSao Paulo Guarulhos Intl
23h 41m
2 stops
MDW12:01 pmChicago Midway
$693
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
Feb 18
MDW10:35 amChicago Midway
16h 05m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Mar 19
GRU11:45 pmSao Paulo Guarulhos Intl
18h 40m
1 stop
MDW4:25 pmChicago Midway
$1,060
Find similar
Delta
Jan 5
MDW1:00 pmChicago Midway
17h 55m
2 stops
GRU9:55 amSao Paulo Guarulhos Intl
Jan 18
GRU9:30 pmSao Paulo Guarulhos Intl
17h 31m
1 stop
MDW12:01 pmChicago Midway
$1,064
Find similar
Delta
Oct 27
MDW10:35 amChicago Midway
21h 00m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Nov 10
GRU9:15 pmSao Paulo Guarulhos Intl
15h 37m
1 stop
MDW9:52 amChicago Midway
$1,086
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 September 11, 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 10/27

9:45 am-4:15 pm

2 stops28h 30m

Sao Paulo Guarulhos Intl

Sat 11/8

2:40 am-12:30 am

2 stops24h 50m

$502

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/2

6:00 am-6:15 am

2 stops21h 15m

Sao Paulo Guarulhos Intl

Fri 3/6

3:20 pm-9:56 am

2 stops21h 36m

$606

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 10/13

9:00 am-12:30 am

2 stops37h 30m

Sao Paulo Guarulhos Intl

Sun 10/26

11:05 pm-11:17 am

1 stop14h 12m

$653

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 10/24

12:18 pm-5:40 am

1 stop15h 22m

Sao Paulo Guarulhos Intl

Fri 10/31

11:59 pm-9:22 pm

2 stops23h 23m

$659

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 10/13

4:24 pm-2:57 am

2 stops32h 33m

Sao Paulo Guarulhos Intl

Sun 10/26

10:50 pm-11:17 am

1 stop14h 27m

$686

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/2

6:00 am-5:45 am

2 stops20h 45m

Sao Paulo Guarulhos Intl

Fri 3/6

1:35 pm-9:56 am

2 stops23h 21m

$691

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 2/10

5:25 pm-5:40 am

1 stop33h 15m

Sao Paulo Guarulhos Intl

Tue 2/17

3:20 pm-12:01 pm

2 stops23h 41m

$693

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 2/18

10:35 am-5:40 am

1 stop16h 05m

Sao Paulo Guarulhos Intl

Thu 3/19

11:45 pm-4:25 pm

1 stop18h 40m

$1,060

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 1/5

1:00 pm-9:55 am

2 stops17h 55m

Sao Paulo Guarulhos Intl

Sun 1/18

9:30 pm-12:01 pm

1 stop17h 31m

$1,064

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 10/27

10:35 am-9:35 am

1 stop21h 00m

Sao Paulo Guarulhos Intl

Mon 11/10

9:15 pm-9:52 am

1 stop15h 37m

$1,086

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 $1,004. 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 $1,193.

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 $1,100.

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.
Search flight deals

  • 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 10m.

  • 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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