Cheap flights from Chicago Midway Airport to Sao Paulo from $265

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 10/6. 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

LATAM Airlines Logo
10:35 am - 9:35 amMDW-GRU
20h 00m1 stop
LATAM Airlines Logo
3:20 pm - 9:56 amGRU-MDW
21h 36m2 stops
$606LATAM Airlines
Find Deal
Mon, Mar 2 - Fri, Mar 6
LATAM Airlines Logo
10:35 am - 5:40 amMDW-GRU
16h 05m1 stop
LATAM Airlines Logo
3:20 pm - 3:25 pmGRU-MDW
27h 05m2 stops
$607LATAM Airlines
Find Deal
Mon, Mar 2 - Fri, Mar 6
LATAM Airlines Logo
5:04 pm - 9:35 amMDW-GRU
14h 31m1 stop
LATAM Airlines Logo
3:20 pm - 9:35 amGRU-MDW
21h 15m2 stops
$616LATAM Airlines
Find Deal
Wed, Oct 29 - Sun, Nov 2
LATAM Airlines Logo
12:48 pm - 5:40 amMDW-GRU
14h 52m1 stop
LATAM Airlines Logo
4:35 pm - 11:53 amGRU-MDW
21h 18m2 stops
$617LATAM Airlines
Find Deal
Wed, Oct 8 - Tue, Oct 14
Multiple Airlines Logo
9:45 am - 4:15 pmMDW-GRU
28h 30m2 stops
Multiple Airlines Logo
2:40 am - 12:30 amGRU-MDW
24h 50m2 stops
$625Multiple Airlines
Find Deal
Mon, Oct 27 - Sat, Nov 8
Multiple Airlines Logo
10:13 am - 8:05 amMDW-GRU
19h 52m1 stop
Multiple Airlines Logo
4:23 am - 11:46 pmGRU-MDW
21h 23m2 stops
$656Multiple Airlines
Find Deal
Sun, Sep 28 - Mon, Oct 13
Delta Logo
12:48 pm - 9:00 amMDW-GRU
18h 12m1 stop
Delta Logo
10:50 pm - 11:53 amGRU-MDW
15h 03m1 stop
$660Delta
Find Deal
Tue, Oct 7 - Tue, Oct 21
Delta Logo
1:08 pm - 6:50 amMDW-GRU
15h 42m2 stops
Delta Logo
10:50 pm - 11:53 amGRU-MDW
15h 03m1 stop
$665Delta
Find Deal
Tue, Oct 7 - Tue, Oct 14
LATAM Airlines Logo
5:34 pm - 9:35 amMDW-GRU
13h 01m1 stop
LATAM Airlines Logo
4:00 am - 11:32 pmGRU-MDW
22h 32m2 stops
$670LATAM Airlines
Find Deal
Mon, Dec 1 - Sat, Dec 13
Delta Logo
5:32 pm - 9:35 amMDW-GRU
13h 03m1 stop
Delta Logo
7:35 am - 10:16 pmGRU-MDW
17h 41m2 stops
$967Delta
Find Deal
Mon, Dec 15 - Sun, Dec 28

Delta flights from Chicago Midway Airport to Sao Paulo

Our best Delta deals on Chicago Midway Airport to Sao Paulo flight tickets
Delta
Oct 7
MDW12:48 pmChicago Midway
18h 12m
1 stop
GRU9:00 amSao Paulo Guarulhos Intl
Oct 21
GRU10:50 pmSao Paulo Guarulhos Intl
15h 03m
1 stop
MDW11:53 amChicago Midway
Delta
Oct 7
MDW1:08 pmChicago Midway
15h 42m
2 stops
GRU6:50 amSao Paulo Guarulhos Intl
Oct 14
GRU10:50 pmSao Paulo Guarulhos Intl
15h 03m
1 stop
MDW11:53 amChicago Midway
Delta
Dec 15
MDW5:32 pmChicago Midway
13h 03m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Dec 28
GRU7:35 amSao Paulo Guarulhos Intl
17h 41m
2 stops
MDW10:16 pmChicago Midway

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
20h 00m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Mar 6
GRU3:20 pmSao Paulo Guarulhos Intl
21h 36m
2 stops
MDW9:56 amChicago Midway
LATAM Airlines
Mar 2
MDW10:35 amChicago Midway
16h 05m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
Mar 6
GRU3:20 pmSao Paulo Guarulhos Intl
27h 05m
2 stops
MDW3:25 pmChicago Midway
LATAM Airlines
Oct 29
MDW5:04 pmChicago Midway
14h 31m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Nov 2
GRU3:20 pmSao Paulo Guarulhos Intl
21h 15m
2 stops
MDW9:35 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 17, 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-9:35 am

1 stop20h 00m

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 3/2

10:35 am-5:40 am

1 stop16h 05m

Sao Paulo Guarulhos Intl

Fri 3/6

3:20 pm-3:25 pm

2 stops27h 05m

$607

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 10/29

5:04 pm-9:35 am

1 stop14h 31m

Sao Paulo Guarulhos Intl

Sun 11/2

3:20 pm-9:35 am

2 stops21h 15m

$616

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 10/8

12:48 pm-5:40 am

1 stop14h 52m

Sao Paulo Guarulhos Intl

Tue 10/14

4:35 pm-11:53 am

2 stops21h 18m

$617

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

$625

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 9/28

10:13 am-8:05 am

1 stop19h 52m

Sao Paulo Guarulhos Intl

Mon 10/13

4:23 am-11:46 pm

2 stops21h 23m

$656

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 10/7

12:48 pm-9:00 am

1 stop18h 12m

Sao Paulo Guarulhos Intl

Tue 10/21

10:50 pm-11:53 am

1 stop15h 03m

$660

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 10/7

1:08 pm-6:50 am

2 stops15h 42m

Sao Paulo Guarulhos Intl

Tue 10/14

10:50 pm-11:53 am

1 stop15h 03m

$665

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 12/1

5:34 pm-9:35 am

1 stop13h 01m

Sao Paulo Guarulhos Intl

Sat 12/13

4:00 am-11:32 pm

2 stops22h 32m

$670

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 12/15

5:32 pm-9:35 am

1 stop13h 03m

Sao Paulo Guarulhos Intl

Sun 12/28

7:35 am-10:16 pm

2 stops17h 41m

$967

Flights are sorted by cheapest round-trip flights 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 $1,007. 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 $1,192.

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 $1,082. 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 13h 01m.

  • 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
Fri 10/17
Fri 10/24

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