Cheap flights from Chicago Midway Airport to Sao Paulo from $276

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 10/3. 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 (MDW-SAO)

Cheap round-trip flights

LATAM Airlines Logo
10:35 am - 5:45 amMDW-GRU
16h 10m2 stops
LATAM Airlines Logo
1:35 pm - 12:01 pmGRU-MDW
25h 26m2 stops
$606LATAM Airlines
Find Deal
Mon, Mar 2 - Fri, Mar 6
 Logo
12:17 pm - 5:20 amMDW-GRU
15h 03m1 stop
 Logo
4:10 am - 8:32 amGRU-MDW
31h 22m2 stops
Mon, Oct 27 - Sat, Nov 8
LATAM Airlines Logo
10:35 am - 5:40 amMDW-GRU
17h 05m1 stop
LATAM Airlines Logo
5:45 pm - 9:40 amGRU-MDW
17h 55m2 stops
$641LATAM Airlines
Find Deal
Wed, Sep 17 - Tue, Sep 23
 Logo
9:45 am - 4:15 pmMDW-GRU
28h 30m2 stops
 Logo
2:40 am - 12:30 amGRU-MDW
24h 50m2 stops
Mon, Oct 27 - Sat, Nov 8
 Logo
8:19 am - 3:50 amMDW-GRU
17h 31m2 stops
 Logo
10:35 am - 9:33 amGRU-MDW
24h 58m1 stop
Mon, Oct 6 - Sun, Oct 19
 Logo
12:50 pm - 5:45 pmMDW-VCP
26h 55m2 stops
 Logo
10:50 pm - 7:00 pmVCP-MDW
22h 10m2 stops
Mon, Sep 15 - Thu, Sep 25
Delta Logo
12:48 pm - 9:00 amMDW-GRU
18h 12m1 stop
Delta Logo
10:50 pm - 11:53 amGRU-MDW
15h 03m1 stop
$820Delta
Find Deal
Thu, Oct 16 - Thu, Oct 23
Delta Logo
12:48 pm - 9:00 amMDW-GRU
18h 12m1 stop
Delta Logo
10:50 pm - 12:28 pmGRU-MDW
15h 38m2 stops
$824Delta
Find Deal
Thu, Oct 16 - Thu, Oct 23
LATAM Airlines Logo
10:35 am - 5:45 amMDW-GRU
16h 10m2 stops
LATAM Airlines Logo
3:20 pm - 9:56 amGRU-MDW
21h 36m2 stops
$833LATAM Airlines
Find Deal
Thu, Feb 19 - Sun, Feb 22
Delta Logo
9:35 am - 5:40 amMDW-GRU
17h 05m2 stops
Delta Logo
11:45 pm - 11:52 amGRU-MDW
15h 07m1 stop
$944Delta
Find Deal
Fri, Nov 7 - Sun, Nov 30

LATAM Airlines flights from Chicago Midway Airport to Sao Paulo

Our best LATAM Airlines deals on Chicago Midway Airport to Sao Paulo flight tickets
LATAM Airlines
Mar 2
MDW10:35 amChicago Midway
16h 10m
2 stops
GRU5:45 amSao Paulo Guarulhos Intl
Mar 6
GRU1:35 pmSao Paulo Guarulhos Intl
25h 26m
2 stops
MDW12:01 pmChicago Midway
LATAM Airlines
Sep 17
MDW10:35 amChicago Midway
17h 05m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Sep 23
GRU5:45 pmSao Paulo Guarulhos Intl
17h 55m
2 stops
MDW9:40 amChicago Midway
LATAM Airlines
Sep 12
MDW10:35 amChicago Midway
17h 05m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Sep 16
GRU5:45 pmSao Paulo Guarulhos Intl
17h 55m
2 stops
MDW9:40 amChicago Midway

Delta flights from Chicago Midway Airport to Sao Paulo

Our best Delta deals on Chicago Midway Airport to Sao Paulo flight tickets
Delta
Oct 16
MDW12:48 pmChicago Midway
18h 12m
1 stop
GRU9:00 amSao Paulo Guarulhos Intl
Oct 23
GRU10:50 pmSao Paulo Guarulhos Intl
15h 03m
1 stop
MDW11:53 amChicago Midway
Delta
Oct 16
MDW12:48 pmChicago Midway
18h 12m
1 stop
GRU9:00 amSao Paulo Guarulhos Intl
Oct 23
GRU10:50 pmSao Paulo Guarulhos Intl
15h 38m
2 stops
MDW12:28 pmChicago Midway
Delta
Nov 7
MDW9:35 amChicago Midway
17h 05m
2 stops
GRU5:40 amSao Paulo Guarulhos Intl
Nov 30
GRU11:45 pmSao Paulo Guarulhos Intl
15h 07m
1 stop
MDW11:52 amChicago Midway

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Sao Paulo 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 3, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Sao Paulo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/2

10:35 am-5:45 am

2 stops16h 10m

Sao Paulo Guarulhos Intl

Fri 3/6

1:35 pm-12:01 pm

2 stops25h 26m

$606

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 10/27

12:17 pm-5:20 am

1 stop15h 03m

Sao Paulo Guarulhos Intl

Sat 11/8

4:10 am-8:32 am

2 stops31h 22m

$636

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 9/17

10:35 am-5:40 am

1 stop17h 05m

Sao Paulo Guarulhos Intl

Tue 9/23

5:45 pm-9:40 am

2 stops17h 55m

$641

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

$649

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 10/6

8:19 am-3:50 am

2 stops17h 31m

Sao Paulo Guarulhos Intl

Sun 10/19

10:35 am-9:33 am

1 stop24h 58m

$679

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Mon 9/15

12:50 pm-5:45 pm

2 stops26h 55m

Sao Paulo Viracopos

Thu 9/25

10:50 pm-7:00 pm

2 stops22h 10m

$697

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 10/16

12:48 pm-9:00 am

1 stop18h 12m

Sao Paulo Guarulhos Intl

Thu 10/23

10:50 pm-11:53 am

1 stop15h 03m

$820

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 10/16

12:48 pm-9:00 am

1 stop18h 12m

Sao Paulo Guarulhos Intl

Thu 10/23

10:50 pm-12:28 pm

2 stops15h 38m

$824

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/19

10:35 am-5:45 am

2 stops16h 10m

Sao Paulo Guarulhos Intl

Sun 2/22

3:20 pm-9:56 am

2 stops21h 36m

$833

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 11/7

9:35 am-5:40 am

2 stops17h 05m

Sao Paulo Guarulhos Intl

Sun 11/30

11:45 pm-11:52 am

1 stop15h 07m

$944

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

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?

The cheapest day to depart on your flight to Sao Paulo is on a Thursday when prices can be found for as low as $996. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,193.

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

At noon is the cheapest time of day to fly from Chicago Midway Airport to Sao Paulo when you can find flight prices for as low as $916. Flying to Sao Paulo at noon is an ideal time because this is during off-peak travel hours. Flights to Sao Paulo are more costly in the afternoon, with an average ticket price of $1,103. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from Chicago Midway Airport to Sao Paulo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Sao Paulo 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 (MDW to SAO) flight deals and tips

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

Direct flights

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

    The distance between Chicago Midway and Sao Paulo is about 5219.4 mi. A reasonable flight in good conditions will take 12h 30m.

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

    Prices for flights from Chicago Midway Airport to Sao Paulo are updated daily.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Sao Paulo.

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

    The necessary travel and health documents for your Sao Paulo trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Sao Paulo?

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

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Sao Paulo from Chicago.

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

Flights from Chicago to Sao Paulo with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Chicago to Sao Paulo flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Chicago to Sao Paulo flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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1 adult
Mon 9/8
Mon 9/15

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