Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago Midway Airport to Sao Paulo from $268

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 11/15. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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
12:46 pm - 4:30 pmMDW-GRU
24h 44m2 stops
LATAM Airlines Logo
5:45 pm - 10:15 amGRU-MDW
19h 30m2 stops
$607LATAM Airlines
Find Deal
Mon, Mar 2 - Fri, Mar 6
LATAM Airlines Logo
10:53 am - 9:55 amMDW-GRU
20h 02m2 stops
LATAM Airlines Logo
5:45 pm - 10:15 amGRU-MDW
19h 30m2 stops
$611LATAM Airlines
Find Deal
Mon, Mar 2 - Fri, Mar 6
Delta Logo
1:05 pm - 5:40 amMDW-GRU
14h 35m1 stop
Delta Logo
10:50 pm - 4:25 pmGRU-MDW
19h 35m1 stop
$620Delta
Find Deal
Tue, May 5 - Tue, May 19
Delta Logo
12:47 pm - 9:35 amMDW-GRU
17h 48m1 stop
Delta Logo
10:20 am - 11:47 pmGRU-MDW
16h 27m2 stops
$625Delta
Find Deal
Wed, Nov 26 - Mon, Dec 8
LATAM Airlines Logo
6:00 am - 5:40 amMDW-GRU
20h 40m1 stop
LATAM Airlines Logo
11:45 pm - 9:46 pmGRU-MDW
24h 01m1 stop
$628LATAM Airlines
Find Deal
Sat, Feb 28 - Sat, Mar 14
LATAM Airlines Logo
6:00 am - 5:40 amMDW-GRU
20h 40m1 stop
LATAM Airlines Logo
11:45 pm - 5:45 pmGRU-MDW
21h 00m1 stop
$642LATAM Airlines
Find Deal
Thu, Feb 12 - Sun, Feb 22
LATAM Airlines Logo
6:00 am - 9:35 amMDW-GRU
24h 35m1 stop
LATAM Airlines Logo
9:30 pm - 12:01 pmGRU-MDW
17h 31m1 stop
$648LATAM Airlines
Find Deal
Thu, Feb 12 - Mon, Feb 23
LATAM Airlines Logo
6:00 am - 9:35 amMDW-GRU
24h 35m1 stop
LATAM Airlines Logo
11:45 pm - 5:45 pmGRU-MDW
21h 00m1 stop
$650LATAM Airlines
Find Deal
Thu, Feb 12 - Sun, Feb 22
Multiple Airlines Logo
2:16 pm - 8:00 pmMDW-GRU
26h 44m1 stop
Multiple Airlines Logo
3:10 am - 9:53 pmGRU-MDW
21h 43m2 stops
$686Multiple Airlines
Find Deal
Thu, Dec 4 - Wed, Dec 10
Delta Logo
9:34 am - 5:40 amMDW-GRU
17h 06m2 stops
Delta Logo
9:15 pm - 9:54 amGRU-MDW
15h 39m1 stop
$725Delta
Find Deal
Sun, Nov 23 - Tue, Dec 2

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
Mar 2
MDW12:46 pmChicago Midway
24h 44m
2 stops
GRU4:30 pmSao Paulo Guarulhos Intl
Mar 6
GRU5:45 pmSao Paulo Guarulhos Intl
19h 30m
2 stops
MDW10:15 amChicago Midway
$607
Find similar
LATAM Airlines
Mar 2
MDW10:53 amChicago Midway
20h 02m
2 stops
GRU9:55 amSao Paulo Guarulhos Intl
Mar 6
GRU5:45 pmSao Paulo Guarulhos Intl
19h 30m
2 stops
MDW10:15 amChicago Midway
$611
Find similar
LATAM Airlines
Nov 16
MDW10:47 amChicago Midway
17h 38m
2 stops
GRU7:25 amSao Paulo Guarulhos Intl
Nov 24
GRU9:15 pmSao Paulo Guarulhos Intl
17h 37m
1 stop
MDW11:52 amChicago Midway
$620
Find similar

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
May 5
MDW1:05 pmChicago Midway
14h 35m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
May 19
GRU10:50 pmSao Paulo Guarulhos Intl
19h 35m
1 stop
MDW4:25 pmChicago Midway
$620
Find similar
Delta
Nov 26
MDW12:47 pmChicago Midway
17h 48m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Dec 8
GRU10:20 amSao Paulo Guarulhos Intl
16h 27m
2 stops
MDW11:47 pmChicago Midway
$625
Find similar
Delta
Nov 15
MDW10:47 amChicago Midway
19h 48m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
Nov 22
GRU11:45 pmSao Paulo Guarulhos Intl
19h 53m
1 stop
MDW4:38 pmChicago Midway
$720
Find similar

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 November 6, 2025.
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

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/2

12:46 pm-4:30 pm

2 stops24h 44m

Sao Paulo Guarulhos Intl

Fri 3/6

5:45 pm-10:15 am

2 stops19h 30m

$607

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Mon 3/2

10:53 am-9:55 am

2 stops20h 02m

Sao Paulo Guarulhos Intl

Fri 3/6

5:45 pm-10:15 am

2 stops19h 30m

$611

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Tue 5/5

1:05 pm-5:40 am

1 stop14h 35m

Sao Paulo Guarulhos Intl

Tue 5/19

10:50 pm-4:25 pm

1 stop19h 35m

$620

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Wed 11/26

12:47 pm-9:35 am

1 stop17h 48m

Sao Paulo Guarulhos Intl

Mon 12/8

10:20 am-11:47 pm

2 stops16h 27m

$625

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sat 2/28

6:00 am-5:40 am

1 stop20h 40m

Sao Paulo Guarulhos Intl

Sat 3/14

11:45 pm-9:46 pm

1 stop24h 01m

$628

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/12

6:00 am-5:40 am

1 stop20h 40m

Sao Paulo Guarulhos Intl

Sun 2/22

11:45 pm-5:45 pm

1 stop21h 00m

$642

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/12

6:00 am-9:35 am

1 stop24h 35m

Sao Paulo Guarulhos Intl

Mon 2/23

9:30 pm-12:01 pm

1 stop17h 31m

$648

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 2/12

6:00 am-9:35 am

1 stop24h 35m

Sao Paulo Guarulhos Intl

Sun 2/22

11:45 pm-5:45 pm

1 stop21h 00m

$650

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Thu 12/4

2:16 pm-8:00 pm

1 stop26h 44m

Sao Paulo Guarulhos Intl

Wed 12/10

3:10 am-9:53 pm

2 stops21h 43m

$686

ChicagoSao Paulo

MDW - GRU

MDWGRU

Chicago Midway

Sun 11/23

9:34 am-5:40 am

2 stops17h 06m

Sao Paulo Guarulhos Intl

Tue 12/2

9:15 pm-9:54 am

1 stop15h 39m

$725

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 Thursday. momondo users have found tickets for Thursday departures for as low as $948. 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 $1,097.

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 at noon. Our users have found flights to Sao Paulo Guarulhos Intl Airport at noon for as low as $956. Flights in the afternoon are often more expensive with an average ticket price of $1,045.

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

Direct flights

None
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

  • 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 01m.

  • 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.

An easier way to manage your Sao Paulo Guarulhos Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 12/6
Sat 12/13
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Sao Paulo

Popular cities in Brazil

Popular flights according to clicks in the last 7 days on momondo
Flights to Sao Paulo Viracopos Airportfrom $396
Flights to Sao Paulo Congonhas Airportfrom $421
Flights to Rio de Janeiro–Galeão Intl Airportfrom $436
Flights to Rio de Janeiro Santos Dumont Airportfrom $436