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Cheap flights from Sao Paulo to Chicago from $379

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 6/16. 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 Sao Paulo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:50 pm - 4:16 pm
GRU
-
MDW
19h 26m
1 stop
Delta Logo
11:05 am - 5:20 am
MDW
-
GRU
16h 15m
2 stops
$928Delta
Sun, Jun 7 - Mon, Jun 15
Delta Logo
11:00 pm - 9:45 pm
GRU
-
MDW
24h 45m
2 stops
Delta Logo
6:00 am - 5:40 am
MDW
-
GRU
20h 40m
1 stop
$929Delta
Sun, Oct 11 - Tue, Nov 3
Delta Logo
11:00 pm - 11:54 am
GRU
-
MDW
14h 54m
2 stops
Delta Logo
9:30 am - 5:40 am
MDW
-
GRU
18h 10m
2 stops
$930Delta
Wed, Aug 19 - Sun, Aug 30
Delta Logo
10:50 pm - 4:12 pm
GRU
-
MDW
19h 22m
1 stop
Delta Logo
6:05 am - 5:40 am
MDW
-
GRU
21h 35m
1 stop
$931Delta
Tue, May 19 - Sat, Jun 27
Delta Logo
10:50 pm - 4:12 pm
GRU
-
MDW
19h 22m
1 stop
Delta Logo
6:05 am - 5:40 am
MDW
-
GRU
21h 35m
1 stop
$932Delta
Tue, May 19 - Sat, Jun 27
Delta Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
Delta Logo
12:45 pm - 5:40 am
MDW
-
GRU
14h 55m
1 stop
$933Delta
Tue, May 19 - Wed, Jun 24
Delta Logo
10:50 pm - 4:12 pm
GRU
-
MDW
19h 22m
1 stop
Delta Logo
1:16 pm - 7:50 am
MDW
-
GRU
16h 34m
2 stops
$934Delta
Mon, Jun 1 - Sun, Jun 21
LATAM Airlines Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
LATAM Airlines Logo
12:45 pm - 5:40 am
MDW
-
GRU
14h 55m
1 stop
$937LATAM Airlines
Tue, Jun 2 - Wed, Jun 10
LATAM Airlines Logo
7:15 pm - 11:54 am
GRU
-
MDW
18h 39m
2 stops
LATAM Airlines Logo
5:25 pm - 4:15 pm
MDW
-
GRU
20h 50m
2 stops
$940LATAM Airlines
Wed, Sep 2 - Wed, Sep 23
LATAM Airlines Logo
8:15 am - 9:50 am
GRU
-
MDW
27h 35m
2 stops
LATAM Airlines Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
$941LATAM Airlines
Sat, Aug 22 - Mon, Sep 7

Delta flights from Sao Paulo to Chicago Midway Airport

Our best Delta deals on Sao Paulo to Chicago Midway Airport flight tickets
Delta
Jun 7
GRU7:15 pmSao Paulo Guarulhos Intl
18h 45m
2 stops
MDW12:00 pmChicago Midway
Jun 15
MDW11:05 amChicago Midway
16h 15m
2 stops
GRU5:20 amSao Paulo Guarulhos Intl
$928
Delta
Oct 11
GRU11:00 pmSao Paulo Guarulhos Intl
24h 45m
2 stops
MDW9:45 pmChicago Midway
Nov 3
MDW6:00 amChicago Midway
20h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$929
Delta
Aug 19
GRU11:00 pmSao Paulo Guarulhos Intl
14h 54m
2 stops
MDW11:54 amChicago Midway
Aug 30
MDW9:30 amChicago Midway
18h 10m
2 stops
GRU5:40 amSao Paulo Guarulhos Intl
$930

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
Jun 2
GRU10:50 pmSao Paulo Guarulhos Intl
15h 06m
1 stop
MDW11:56 amChicago Midway
Jun 10
MDW12:45 pmChicago Midway
14h 55m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$937
LATAM Airlines
Sep 2
GRU7:15 pmSao Paulo Guarulhos Intl
18h 39m
2 stops
MDW11:54 amChicago Midway
Sep 23
MDW5:25 pmChicago Midway
20h 50m
2 stops
GRU4:15 pmSao Paulo Guarulhos Intl
$940
LATAM Airlines
Aug 22
GRU8:15 amSao Paulo Guarulhos Intl
27h 35m
2 stops
MDW9:50 amChicago Midway
Sep 7
MDW6:00 amChicago Midway
21h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$941

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 April 17, 2026.
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

Cheapest round-trip

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 6/7

10:50 pm-4:16 pm

1 stop19h 26m

Chicago Midway

Mon 6/15

11:05 am-5:20 am

2 stops16h 15m

$928

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 10/11

11:00 pm-9:45 pm

2 stops24h 45m

Chicago Midway

Tue 11/3

6:00 am-5:40 am

1 stop20h 40m

$929

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 8/19

11:00 pm-11:54 am

2 stops14h 54m

Chicago Midway

Sun 8/30

9:30 am-5:40 am

2 stops18h 10m

$930

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 5/19

10:50 pm-4:12 pm

1 stop19h 22m

Chicago Midway

Sat 6/27

6:05 am-5:40 am

1 stop21h 35m

$931

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 5/19

10:50 pm-4:12 pm

1 stop19h 22m

Chicago Midway

Sat 6/27

6:05 am-5:40 am

1 stop21h 35m

$932
Quickest round-trip

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 5/19

10:50 pm-11:56 am

1 stop15h 06m

Chicago Midway

Wed 6/24

12:45 pm-5:40 am

1 stop14h 55m

$933

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 6/1

10:50 pm-4:12 pm

1 stop19h 22m

Chicago Midway

Sun 6/21

1:16 pm-7:50 am

2 stops16h 34m

$934

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 6/2

10:50 pm-11:56 am

1 stop15h 06m

Chicago Midway

Wed 6/10

12:45 pm-5:40 am

1 stop14h 55m

$937

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 9/2

7:15 pm-11:54 am

2 stops18h 39m

Chicago Midway

Wed 9/23

5:25 pm-4:15 pm

2 stops20h 50m

$940

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 8/22

8:15 am-9:50 am

2 stops27h 35m

Chicago Midway

Mon 9/7

6:00 am-5:40 am

1 stop21h 40m

$941

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

Fastest flight time

14h 54m

Direct flights

None
The fastest flight from Sao Paulo to Chicago Midway Airport takes 14h 54m
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.
Search flight deals

Frequently asked questions about flying from Sao Paulo to Chicago Midway Airport

  • 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 54m, 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
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.

An easier way to manage your Chicago Midway Airport trip

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