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Cheap flights from Chicago Midway Airport to Sao Paulo from $291

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 6/22. 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

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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
6:00 am - 7:15 am
MDW
-
GRU
23h 15m
2 stops
LATAM Airlines Logo
3:20 pm - 10:00 am
GRU
-
MDW
20h 40m
2 stops
$854LATAM Airlines
Wed, Apr 29 - Tue, May 26
LATAM Airlines Logo
10:59 am - 5:40 am
MDW
-
GRU
16h 41m
1 stop
LATAM Airlines Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
$859LATAM Airlines
Wed, May 13 - Wed, May 20
Delta Logo
12:52 pm - 5:40 am
MDW
-
GRU
14h 48m
1 stop
Delta Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
$861Delta
Wed, Apr 29 - Tue, May 26
LATAM Airlines Logo
12:53 pm - 8:50 am
MDW
-
GRU
17h 57m
2 stops
LATAM Airlines Logo
11:00 pm - 11:56 am
GRU
-
MDW
14h 56m
2 stops
$863LATAM Airlines
Wed, May 13 - Wed, May 20
LATAM Airlines Logo
12:53 pm - 5:40 am
MDW
-
GRU
14h 47m
1 stop
LATAM Airlines Logo
11:00 pm - 11:56 am
GRU
-
MDW
14h 56m
2 stops
$864LATAM Airlines
Thu, May 14 - Thu, May 21
Delta Logo
9:22 am - 5:40 am
MDW
-
GRU
18h 18m
2 stops
Delta Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
$865Delta
Wed, May 13 - Wed, May 20
LATAM Airlines Logo
5:10 pm - 5:40 am
MDW
-
GRU
34h 30m
1 stop
LATAM Airlines Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
$871LATAM Airlines
Fri, May 22 - Mon, Jun 1
LATAM Airlines Logo
5:21 pm - 6:25 pm
MDW
-
GRU
23h 04m
2 stops
LATAM Airlines Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
$874LATAM Airlines
Mon, May 4 - Wed, May 6
LATAM Airlines Logo
5:21 pm - 6:25 pm
MDW
-
GRU
23h 04m
2 stops
LATAM Airlines Logo
11:00 pm - 9:09 pm
GRU
-
MDW
24h 09m
2 stops
$879LATAM Airlines
Mon, May 4 - Wed, May 6
Multiple Airlines Logo
5:30 am - 10:45 am
MDW
-
VCP
27h 15m
2 stops
Multiple Airlines Logo
10:10 am - 7:59 am
VCP
-
MDW
23h 49m
1 stop
$992Multiple Airlines
Mon, Apr 13 - Thu, Apr 16

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
Apr 29
MDW6:00 amChicago Midway
23h 15m
2 stops
GRU7:15 amSao Paulo Guarulhos Intl
May 26
GRU3:20 pmSao Paulo Guarulhos Intl
20h 40m
2 stops
MDW10:00 amChicago Midway
$854
LATAM Airlines
May 13
MDW10:59 amChicago Midway
16h 41m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
May 20
GRU10:50 pmSao Paulo Guarulhos Intl
15h 06m
1 stop
MDW11:56 amChicago Midway
$859
LATAM Airlines
May 13
MDW12:53 pmChicago Midway
17h 57m
2 stops
GRU8:50 amSao Paulo Guarulhos Intl
May 20
GRU11:00 pmSao Paulo Guarulhos Intl
14h 56m
2 stops
MDW11:56 amChicago Midway
$863

Delta flights from Chicago Midway Airport to Sao Paulo

Our best Delta deals on Chicago Midway Airport to Sao Paulo flight tickets
Delta
Apr 29
MDW12:52 pmChicago Midway
14h 48m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
May 26
GRU10:50 pmSao Paulo Guarulhos Intl
15h 06m
1 stop
MDW11:56 amChicago Midway
$861
Delta
May 13
MDW9:22 amChicago Midway
18h 18m
2 stops
GRU5:40 amSao Paulo Guarulhos Intl
May 20
GRU10:50 pmSao Paulo Guarulhos Intl
15h 06m
1 stop
MDW11:56 amChicago Midway
$865
Delta
Jun 1
MDW12:53 pmChicago Midway
17h 57m
2 stops
GRU8:50 amSao Paulo Guarulhos Intl
Jul 31
GRU10:50 pmSao Paulo Guarulhos Intl
21h 12m
2 stops
MDW6:02 pmChicago Midway
$961

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 April 2, 2026.
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

Cheapest round-trip

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 4/29

6:00 am-7:15 am

2 stops23h 15m

Sao Paulo Guarulhos Intl

Tue 5/26

3:20 pm-10:00 am

2 stops20h 40m

$854

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 5/13

10:59 am-5:40 am

1 stop16h 41m

Sao Paulo Guarulhos Intl

Wed 5/20

10:50 pm-11:56 am

1 stop15h 06m

$859

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 4/29

12:52 pm-5:40 am

1 stop14h 48m

Sao Paulo Guarulhos Intl

Tue 5/26

10:50 pm-11:56 am

1 stop15h 06m

$861

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 5/13

12:53 pm-8:50 am

2 stops17h 57m

Sao Paulo Guarulhos Intl

Wed 5/20

11:00 pm-11:56 am

2 stops14h 56m

$863
Quickest round-trip

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 5/14

12:53 pm-5:40 am

1 stop14h 47m

Sao Paulo Guarulhos Intl

Thu 5/21

11:00 pm-11:56 am

2 stops14h 56m

$864

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 5/13

9:22 am-5:40 am

2 stops18h 18m

Sao Paulo Guarulhos Intl

Wed 5/20

10:50 pm-11:56 am

1 stop15h 06m

$865

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Fri 5/22

5:10 pm-5:40 am

1 stop34h 30m

Sao Paulo Guarulhos Intl

Mon 6/1

10:50 pm-11:56 am

1 stop15h 06m

$871

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 5/4

5:21 pm-6:25 pm

2 stops23h 04m

Sao Paulo Guarulhos Intl

Wed 5/6

10:50 pm-11:56 am

1 stop15h 06m

$874

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 5/4

5:21 pm-6:25 pm

2 stops23h 04m

Sao Paulo Guarulhos Intl

Wed 5/6

11:00 pm-9:09 pm

2 stops24h 09m

$879

ChicagoSao Paulo

MDW - VCP

MDWVCP

Chicago Midway

Mon 4/13

5:30 am-10:45 am

2 stops27h 15m

Sao Paulo Viracopos

Thu 4/16

10:10 am-7:59 am

1 stop23h 49m

$992

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 $946. This is often the case because there is less demand to fly during this day of the week. On the other hand, Tuesday 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 $1,098.

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

In the afternoon 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 $986. Flying to Sao Paulo in the afternoon is an ideal time because this is during off-peak travel hours. Flights to Sao Paulo are more costly in the evening, with an average ticket price of $1,073. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

Can stopping save me money on Chicago Midway Airport to Sao Paulo flights?

You could potentially save up to 59% on your flight if you consider stops on a Chicago Midway Airport to Sao Paulo flight.

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

Fastest flight time

14h 10m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sao Paulo takes 14h 10m
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.
Search flight deals

Frequently asked questions about flying 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 14h 10m.

  • 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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Find better results for your trip to Brazil

Fly into one of these airports located in Sao Paulo

Airports listed have a maximum distance of 48.9 mi from Sao Paulo
Sao Paulo Congonhas Airport
Sao Paulo Guarulhos Intl Airport
Sao Paulo Viracopos Airport