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Cheap flights from Chicago Midway Airport to Sao Paulo from $343

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 8/9. 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
6:05 am - 5:40 am
MDW
-
GRU
21h 35m
1 stop
LATAM Airlines Logo
1:10 pm - 9:50 am
GRU
-
MDW
22h 40m
2 stops
$642LATAM Airlines
Sun, Sep 20 - Mon, Sep 21
LATAM Airlines Logo
6:05 am - 5:00 am
MDW
-
GRU
20h 55m
2 stops
LATAM Airlines Logo
1:10 pm - 9:50 am
GRU
-
MDW
22h 40m
2 stops
$646LATAM Airlines
Sun, Sep 20 - Mon, Sep 21
LATAM Airlines Logo
10:35 am - 6:50 am
MDW
-
GRU
17h 15m
2 stops
LATAM Airlines Logo
5:20 pm - 9:52 am
GRU
-
MDW
19h 32m
2 stops
$754LATAM Airlines
Sun, Dec 13 - Mon, Dec 14
Multiple Airlines Logo
8:49 pm - 9:20 am
MDW
-
GRU
34h 31m
3 stops
Multiple Airlines Logo
11:10 am - 9:45 am
GRU
-
MDW
24h 35m
2 stops
$905Multiple Airlines
Tue, Aug 11 - Tue, Aug 25
Multiple Airlines Logo
8:23 pm - 3:08 am
MDW
-
GRU
28h 45m
3 stops
Multiple Airlines Logo
4:08 am - 11:00 am
GRU
-
MDW
32h 52m
3 stops
$933Multiple Airlines
Fri, Aug 28 - Sun, Sep 6
Multiple Airlines Logo
8:49 pm - 4:20 am
MDW
-
GRU
29h 31m
3 stops
Multiple Airlines Logo
1:00 am - 9:45 am
GRU
-
MDW
34h 45m
2 stops
$939Multiple Airlines
Sat, Aug 8 - Wed, Aug 12
LATAM Airlines Logo
10:35 am - 6:50 am
MDW
-
GRU
17h 15m
2 stops
LATAM Airlines Logo
5:20 pm - 11:56 am
GRU
-
MDW
21h 36m
2 stops
$941LATAM Airlines
Thu, Nov 19 - Wed, Nov 25
LATAM Airlines Logo
6:05 am - 5:40 am
MDW
-
GRU
21h 35m
1 stop
LATAM Airlines Logo
8:00 am - 11:51 am
GRU
-
MDW
29h 51m
2 stops
$973LATAM Airlines
Tue, Aug 4 - Mon, Aug 17
Multiple Airlines Logo
8:23 pm - 2:50 am
MDW
-
GRU
28h 27m
3 stops
Multiple Airlines Logo
9:35 pm - 11:00 am
GRU
-
MDW
15h 25m
1 stop
$977Multiple Airlines
Mon, Aug 31 - Mon, Sep 21
LATAM Airlines Logo
10:54 am - 6:10 am
MDW
-
GRU
17h 16m
2 stops
LATAM Airlines Logo
8:00 am - 11:51 am
GRU
-
MDW
29h 51m
2 stops
$984LATAM Airlines
Tue, Aug 4 - Mon, Aug 17

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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
Sep 20
MDW6:05 amChicago Midway
21h 35m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Sep 21
GRU1:10 pmSao Paulo Guarulhos Intl
22h 40m
2 stops
MDW9:50 amChicago Midway
$642
LATAM Airlines
Sep 20
MDW6:05 amChicago Midway
20h 55m
2 stops
GRU5:00 amSao Paulo Guarulhos Intl
Sep 21
GRU1:10 pmSao Paulo Guarulhos Intl
22h 40m
2 stops
MDW9:50 amChicago Midway
$646
LATAM Airlines
Dec 13
MDW10:35 amChicago Midway
17h 15m
2 stops
GRU6:50 amSao Paulo Guarulhos Intl
Dec 14
GRU5:20 pmSao Paulo Guarulhos Intl
19h 32m
2 stops
MDW9:52 amChicago Midway
$754

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
Jul 27
MDW12:41 pmChicago Midway
14h 59m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Jul 30
GRU10:50 pmSao Paulo Guarulhos Intl
19h 25m
1 stop
MDW4:15 pmChicago Midway
$2,433
Delta
Jul 27
MDW6:00 amChicago Midway
21h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Jul 30
GRU8:30 pmSao Paulo Guarulhos Intl
18h 39m
2 stops
MDW1:09 pmChicago Midway
$2,437
Delta
Jul 29
MDW1:18 pmChicago Midway
17h 32m
2 stops
GRU8:50 amSao Paulo Guarulhos Intl
Aug 1
GRU8:30 pmSao Paulo Guarulhos Intl
18h 08m
2 stops
MDW12:38 pmChicago Midway
$2,477

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 July 15, 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

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 9/20

6:05 am-5:40 am

1 stop21h 35m

Sao Paulo Guarulhos Intl

Mon 9/21

1:10 pm-9:50 am

2 stops22h 40m

$642

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 9/20

6:05 am-5:00 am

2 stops20h 55m

Sao Paulo Guarulhos Intl

Mon 9/21

1:10 pm-9:50 am

2 stops22h 40m

$646
Quickest round-trip

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 12/13

10:35 am-6:50 am

2 stops17h 15m

Sao Paulo Guarulhos Intl

Mon 12/14

5:20 pm-9:52 am

2 stops19h 32m

$754

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 8/11

8:49 pm-9:20 am

3 stops34h 31m

Sao Paulo Guarulhos Intl

Tue 8/25

11:10 am-9:45 am

2 stops24h 35m

$905

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 8/28

8:23 pm-3:08 am

3 stops28h 45m

Sao Paulo Guarulhos Intl

Sun 9/6

4:08 am-11:00 am

3 stops32h 52m

$933

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 8/8

8:49 pm-4:20 am

3 stops29h 31m

Sao Paulo Guarulhos Intl

Wed 8/12

1:00 am-9:45 am

2 stops34h 45m

$939

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 11/19

10:35 am-6:50 am

2 stops17h 15m

Sao Paulo Guarulhos Intl

Wed 11/25

5:20 pm-11:56 am

2 stops21h 36m

$941

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 8/4

6:05 am-5:40 am

1 stop21h 35m

Sao Paulo Guarulhos Intl

Mon 8/17

8:00 am-11:51 am

2 stops29h 51m

$973

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 8/31

8:23 pm-2:50 am

3 stops28h 27m

Sao Paulo Guarulhos Intl

Mon 9/21

9:35 pm-11:00 am

1 stop15h 25m

$977

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 8/4

10:54 am-6:10 am

2 stops17h 16m

Sao Paulo Guarulhos Intl

Mon 8/17

8:00 am-11:51 am

2 stops29h 51m

$984

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Sao Paulo from

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 $951. 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 $1,193.

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 in the afternoon. Our users have found flights to Sao Paulo Guarulhos Intl Airport in the afternoon for as low as $1,001. Flights in the evening are often more expensive with an average ticket price of $1,098.

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

17h 10m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sao Paulo Guarulhos Intl Airport takes 17h 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 17h 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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