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Cheap flights from Sao Paulo to Chicago from $286

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sao Paulo to Chicago departing on 12/11. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:25 am - 9:58 pmGRU-MDW
18h 33m2 stops
Multiple Airlines Logo
1:05 pm - 5:40 amMDW-GRU
14h 35m1 stop
$820Multiple Airlines
Find Deal
Fri, Apr 10 - Fri, Apr 17
Multiple Airlines Logo
12:55 pm - 4:30 pmGRU-MDW
30h 35m1 stop
Multiple Airlines Logo
10:49 am - 5:40 amMDW-GRU
15h 51m1 stop
$837Multiple Airlines
Find Deal
Sat, Nov 22 - Fri, Dec 5
Delta Logo
11:45 pm - 11:55 amGRU-MDW
15h 10m1 stop
Delta Logo
6:00 am - 5:40 amMDW-GRU
20h 40m1 stop
$926Delta
Find Deal
Sat, Dec 6 - Tue, Jan 20
Delta Logo
9:15 pm - 12:01 pmGRU-MDW
17h 46m1 stop
Delta Logo
12:46 pm - 9:35 amMDW-GRU
17h 49m1 stop
$927Delta
Find Deal
Tue, Feb 10 - Tue, Feb 17
LATAM Airlines Logo
7:35 am - 10:26 pmGRU-MDW
17h 51m2 stops
LATAM Airlines Logo
6:00 am - 6:15 amMDW-GRU
21h 15m2 stops
$936LATAM Airlines
Find Deal
Fri, Jan 30 - Sun, Feb 8
LATAM Airlines Logo
9:00 pm - 4:44 pmGRU-MDW
22h 44m2 stops
LATAM Airlines Logo
12:48 pm - 4:30 pmMDW-GRU
24h 42m2 stops
$940LATAM Airlines
Find Deal
Mon, Dec 15 - Fri, Feb 6
Delta Logo
9:15 pm - 9:54 amGRU-MDW
15h 39m1 stop
Delta Logo
5:29 pm - 9:35 amMDW-GRU
13h 06m1 stop
$976Delta
Find Deal
Mon, Dec 1 - Tue, Dec 9
Delta Logo
9:15 pm - 9:54 amGRU-MDW
15h 39m1 stop
Delta Logo
1:14 pm - 9:55 amMDW-GRU
17h 41m2 stops
$977Delta
Find Deal
Mon, Dec 1 - Tue, Dec 9
LATAM Airlines Logo
8:15 am - 11:40 pmGRU-MDW
18h 25m2 stops
LATAM Airlines Logo
6:00 am - 5:45 amMDW-GRU
20h 45m2 stops
$985LATAM Airlines
Find Deal
Mon, Dec 1 - Mon, Dec 8
LATAM Airlines Logo
11:45 pm - 4:31 pmGRU-MDW
19h 46m1 stop
LATAM Airlines Logo
10:46 am - 5:40 amMDW-GRU
15h 54m1 stop
$986LATAM Airlines
Find Deal
Fri, Jan 16 - Mon, Jan 26

Delta flights from Sao Paulo to Chicago Midway Airport

Our best Delta deals on Sao Paulo to Chicago Midway Airport flight tickets
Delta
Dec 6
GRU11:45 pmSao Paulo Guarulhos Intl
15h 10m
1 stop
MDW11:55 amChicago Midway
Jan 20
MDW6:00 amChicago Midway
20h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$926
Find similar
Delta
Feb 10
GRU9:15 pmSao Paulo Guarulhos Intl
17h 46m
1 stop
MDW12:01 pmChicago Midway
Feb 17
MDW12:46 pmChicago Midway
17h 49m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$927
Find similar
Delta
Dec 1
GRU9:15 pmSao Paulo Guarulhos Intl
15h 39m
1 stop
MDW9:54 amChicago Midway
Dec 9
MDW5:29 pmChicago Midway
13h 06m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$976
Find similar

LATAM Airlines flights from Sao Paulo to Chicago Midway Airport

Our best LATAM Airlines deals on Sao Paulo to Chicago Midway Airport flight tickets
LATAM Airlines
Jan 30
GRU7:35 amSao Paulo Guarulhos Intl
17h 51m
2 stops
MDW10:26 pmChicago Midway
Feb 8
MDW6:00 amChicago Midway
21h 15m
2 stops
GRU6:15 amSao Paulo Guarulhos Intl
$936
Find similar
LATAM Airlines
Dec 15
GRU9:00 pmSao Paulo Guarulhos Intl
22h 44m
2 stops
MDW4:44 pmChicago Midway
Feb 6
MDW12:48 pmChicago Midway
24h 42m
2 stops
GRU4:30 pmSao Paulo Guarulhos Intl
$940
Find similar
LATAM Airlines
Dec 1
GRU8:15 amSao Paulo Guarulhos Intl
18h 25m
2 stops
MDW11:40 pmChicago Midway
Dec 8
MDW6:00 amChicago Midway
20h 45m
2 stops
GRU5:45 amSao Paulo Guarulhos Intl
$985
Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 4/10

5:25 am-9:58 pm

2 stops18h 33m

Chicago Midway

Fri 4/17

1:05 pm-5:40 am

1 stop14h 35m

$820

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 11/22

12:55 pm-4:30 pm

1 stop30h 35m

Chicago Midway

Fri 12/5

10:49 am-5:40 am

1 stop15h 51m

$837

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 12/6

11:45 pm-11:55 am

1 stop15h 10m

Chicago Midway

Tue 1/20

6:00 am-5:40 am

1 stop20h 40m

$926

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 2/10

9:15 pm-12:01 pm

1 stop17h 46m

Chicago Midway

Tue 2/17

12:46 pm-9:35 am

1 stop17h 49m

$927

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 1/30

7:35 am-10:26 pm

2 stops17h 51m

Chicago Midway

Sun 2/8

6:00 am-6:15 am

2 stops21h 15m

$936

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 12/15

9:00 pm-4:44 pm

2 stops22h 44m

Chicago Midway

Fri 2/6

12:48 pm-4:30 pm

2 stops24h 42m

$940

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 12/1

9:15 pm-9:54 am

1 stop15h 39m

Chicago Midway

Tue 12/9

5:29 pm-9:35 am

1 stop13h 06m

$976

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 12/1

9:15 pm-9:54 am

1 stop15h 39m

Chicago Midway

Tue 12/9

1:14 pm-9:55 am

2 stops17h 41m

$977

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 12/1

8:15 am-11:40 pm

2 stops18h 25m

Chicago Midway

Mon 12/8

6:00 am-5:45 am

2 stops20h 45m

$985

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 1/16

11:45 pm-4:31 pm

1 stop19h 46m

Chicago Midway

Mon 1/26

10:46 am-5:40 am

1 stop15h 54m

$986

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 Chicago from

How to get the cheapest flight ticket from Sao Paulo to Chicago Midway 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 airline that flies from Sao Paulo to Chicago Midway?

LATAM Airlines and Delta are the most popular carriers operating from Sao Paulo to Chicago Midway

When to book flights from Sao Paulo to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Sao Paulo to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Sao Paulo to Chicago Midway Airport (SAO to MDW) flight deals and tips

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

Direct flights

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

    The distance between Sao Paulo and Chicago Midway is about 5219.4 mi. Flights usually cover this in 14h 42m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Sao Paulo to Chicago Midway Airport are refreshed on a daily basis.

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

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway 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 Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

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 Chicago from Sao Paulo.

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

Yes. momondo enables you to select and highlight flights to Chicago from Sao Paulo with this policy.

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

momondo helps you find the best flight between Sao Paulo and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Sao Paulo and alert you when they change.

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