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Cheap flights from Chicago Midway Airport to Sao Paulo from $385

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 9/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Sao Paulo

Cheap round-trip flights

Enter your travel dates to find the best prices.
LATAM Airlines Logo
1:00 pm - 5:40 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
14h 40m1 stop Atlanta Hartsfield-Jackson
LATAM Airlines Logo
5:45 pm - 11:50 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
20h 05m2 stops Rio de Janeiro–Galeão Intl Atlanta Hartsfield-Jackson
$692LATAM Airlines
Fri, Oct 2 - Mon, Oct 5
LATAM Airlines Logo
12:45 pm - 5:40 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
14h 55m1 stop Atlanta Hartsfield-Jackson
LATAM Airlines Logo
3:50 pm - 10:03 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
20h 13m2 stops Rio de Janeiro–Galeão Intl Atlanta Hartsfield-Jackson
$780LATAM Airlines
Wed, Oct 21 - Sun, Oct 25
Multiple Airlines Logo
8:23 pm - 2:50 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
28h 27m3 stops Guadalajara Miguel Hidal Cancun Punta Cana
Multiple Airlines Logo
11:50 am - 2:35 pmGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
28h 45m3 stops Punta Cana Montreal Pierre Elliott Trudeau Intl Toronto Island
$882Multiple Airlines
Mon, Sep 14 - Thu, Sep 24
LATAM Airlines Logo
12:46 pm - 5:40 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
14h 54m1 stop Atlanta Hartsfield-Jackson
LATAM Airlines Logo
1:05 pm - 9:59 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
22h 54m2 stops Buenos Aires Ministro Pistarini Atlanta Hartsfield-Jackson
$913LATAM Airlines
Sun, Aug 23 - Wed, Aug 26
LATAM Airlines Logo
5:15 pm - 4:15 pmMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
21h 00m2 stops Atlanta Hartsfield-Jackson Lima J Chavez Intl
LATAM Airlines Logo
3:50 pm - 10:03 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
20h 13m2 stops Rio de Janeiro–Galeão Intl Atlanta Hartsfield-Jackson
$916LATAM Airlines
Wed, Oct 21 - Sun, Oct 25
LATAM Airlines Logo
10:54 am - 5:00 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
16h 06m2 stops Atlanta Hartsfield-Jackson Miami
LATAM Airlines Logo
1:05 pm - 9:59 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
22h 54m2 stops Buenos Aires Ministro Pistarini Atlanta Hartsfield-Jackson
$918LATAM Airlines
Sun, Aug 23 - Wed, Aug 26
Multiple Airlines Logo
8:23 pm - 2:50 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
28h 27m3 stops Guadalajara Miguel Hidal Cancun Punta Cana
Multiple Airlines Logo
11:10 am - 11:00 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
25h 50m3 stops Punta Cana Montreal Pierre Elliott Trudeau Intl Toronto Island
$927Multiple Airlines
Mon, Sep 28 - Tue, Oct 13
LATAM Airlines Logo
10:59 am - 5:30 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
16h 31m2 stops Atlanta Hartsfield-Jackson Bogotá El Dorado
LATAM Airlines Logo
3:50 pm - 10:03 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
20h 13m2 stops Rio de Janeiro–Galeão Intl Atlanta Hartsfield-Jackson
$966LATAM Airlines
Mon, Oct 19 - Sun, Oct 25
Multiple Airlines Logo
8:23 pm - 2:50 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
28h 27m3 stops Guadalajara Miguel Hidal Cancun Punta Cana
Multiple Airlines Logo
10:45 pm - 2:35 pmGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
17h 50m2 stops Boston Logan Intl Toronto Island
$973Multiple Airlines
Mon, Sep 14 - Thu, Sep 24
Multiple Airlines Logo
3:20 pm - 10:30 pmMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
29h 10m3 stops Toronto Island Montreal Pierre Elliott Trudeau Intl Punta Cana
Multiple Airlines Logo
7:35 am - 2:35 pmGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
33h 00m2 stops Bogotá El Dorado Toronto Pearson Intl
$975Multiple Airlines
Thu, Sep 3 - Sat, Sep 26

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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
Oct 2
MDW1:00 pmChicago Midway
14h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Oct 5
GRU5:45 pmSao Paulo Guarulhos Intl
20h 05m
2 stops
MDW11:50 amChicago Midway
$692
LATAM Airlines
Oct 21
MDW12:45 pmChicago Midway
14h 55m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Oct 25
GRU3:50 pmSao Paulo Guarulhos Intl
20h 13m
2 stops
MDW10:03 amChicago Midway
$780
LATAM Airlines
Aug 23
MDW12:46 pmChicago Midway
14h 54m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Aug 26
GRU1:05 pmSao Paulo Guarulhos Intl
22h 54m
2 stops
MDW9:59 amChicago Midway
$913

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
Jan 4
MDW10:35 amChicago Midway
16h 05m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Jan 18
GRU9:30 pmSao Paulo Guarulhos Intl
15h 22m
1 stop
MDW9:52 amChicago Midway
$1,234
Delta
Oct 1
MDW1:00 pmChicago Midway
14h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Oct 14
GRU10:50 pmSao Paulo Guarulhos Intl
15h 57m
2 stops
MDW12:47 pmChicago Midway
$1,238
Delta
Aug 19
MDW10:54 amChicago Midway
16h 46m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Sep 1
GRU10:50 pmSao Paulo Guarulhos Intl
18h 54m
1 stop
MDW3:44 pmChicago Midway
$2,734

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 August 13, 2026.
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

Cheapest round-trip
Quickest round-trip

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Fri 10/2

1:00 pm-5:40 am

1 stop14h 40m

Sao Paulo Guarulhos Intl

Mon 10/5

5:45 pm-11:50 am

2 stops20h 05m

$692

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Wed 10/21

12:45 pm-5:40 am

1 stop14h 55m

Sao Paulo Guarulhos Intl

Sun 10/25

3:50 pm-10:03 am

2 stops20h 13m

$780

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Mon 9/14

8:23 pm-2:50 am

3 stops28h 27m

Sao Paulo Guarulhos Intl

Thu 9/24

11:50 am-2:35 pm

3 stops28h 45m

$882

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Sun 8/23

12:46 pm-5:40 am

1 stop14h 54m

Sao Paulo Guarulhos Intl

Wed 8/26

1:05 pm-9:59 am

2 stops22h 54m

$913

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Wed 10/21

5:15 pm-4:15 pm

2 stops21h 00m

Sao Paulo Guarulhos Intl

Sun 10/25

3:50 pm-10:03 am

2 stops20h 13m

$916

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Sun 8/23

10:54 am-5:00 am

2 stops16h 06m

Sao Paulo Guarulhos Intl

Wed 8/26

1:05 pm-9:59 am

2 stops22h 54m

$918

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Mon 9/28

8:23 pm-2:50 am

3 stops28h 27m

Sao Paulo Guarulhos Intl

Tue 10/13

11:10 am-11:00 am

3 stops25h 50m

$927

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Mon 10/19

10:59 am-5:30 am

2 stops16h 31m

Sao Paulo Guarulhos Intl

Sun 10/25

3:50 pm-10:03 am

2 stops20h 13m

$966

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Mon 9/14

8:23 pm-2:50 am

3 stops28h 27m

Sao Paulo Guarulhos Intl

Thu 9/24

10:45 pm-2:35 pm

2 stops17h 50m

$973

ChicagoSao Paulo

MDW Chicago Midway - GRU Sao Paulo Guarulhos Intl

MDWGRU

Chicago Midway

Thu 9/3

3:20 pm-10:30 pm

3 stops29h 10m

Sao Paulo Guarulhos Intl

Sat 9/26

7:35 am-2:35 pm

2 stops33h 00m

$975

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 Monday. momondo users have found tickets for Monday departures for as low as $992. 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 $1,196.

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 in the afternoon. Our users have found flights to Sao Paulo Guarulhos Intl Airport in the afternoon for as low as $1,021. Flights in the evening 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

Fastest flight time

13h 10m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport takes 13h 10m
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

Frequently asked questions about flying from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport

  • 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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