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Cheap flights from Sao Paulo Guarulhos Intl Airport to Chicago from $312

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 Guarulhos Intl Airport to Chicago departing on 11/16. 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 Guarulhos Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:15 pm - 12:28 pmGRU-MDW
18h 13m2 stops
Delta Logo
5:34 pm - 9:35 amMDW-GRU
13h 01m1 stop
$814Delta
Find Deal
Tue, Nov 4 - Mon, Nov 17
Delta Logo
9:15 pm - 12:34 pmGRU-MDW
18h 19m2 stops
Delta Logo
5:34 pm - 9:35 amMDW-GRU
13h 01m1 stop
$818Delta
Find Deal
Tue, Nov 18 - Tue, Nov 25
Delta Logo
11:45 pm - 4:38 pmGRU-MDW
19h 53m1 stop
Delta Logo
12:47 pm - 5:40 amMDW-GRU
13h 53m1 stop
$821Delta
Find Deal
Thu, Nov 20 - Sat, Nov 29
Delta Logo
9:15 pm - 3:26 pmGRU-MDW
21h 11m1 stop
Delta Logo
6:00 am - 5:40 amMDW-GRU
20h 40m1 stop
$822Delta
Find Deal
Fri, Nov 7 - Wed, Nov 19
Delta Logo
11:45 pm - 12:28 pmGRU-MDW
15h 43m2 stops
Delta Logo
10:47 am - 5:40 amMDW-GRU
15h 53m1 stop
$823Delta
Find Deal
Thu, Nov 6 - Mon, Nov 17
Delta Logo
11:45 pm - 12:34 pmGRU-MDW
15h 49m2 stops
Delta Logo
12:47 pm - 5:40 amMDW-GRU
13h 53m1 stop
$829Delta
Find Deal
Thu, Nov 20 - Sun, Nov 30
LATAM Airlines Logo
2:20 pm - 9:52 amGRU-MDW
22h 32m2 stops
LATAM Airlines Logo
6:00 am - 5:40 amMDW-GRU
20h 40m1 stop
$838LATAM Airlines
Find Deal
Thu, Nov 27 - Thu, Dec 4
LATAM Airlines Logo
10:40 pm - 4:39 pmGRU-MDW
20h 59m2 stops
LATAM Airlines Logo
5:13 pm - 9:35 amMDW-GRU
13h 22m1 stop
$842LATAM Airlines
Find Deal
Thu, Nov 27 - Sun, Dec 7
LATAM Airlines Logo
11:45 pm - 11:55 amGRU-MDW
15h 10m1 stop
LATAM Airlines Logo
10:49 am - 5:45 amMDW-GRU
15h 56m2 stops
$846LATAM Airlines
Find Deal
Mon, Dec 1 - Tue, Dec 9
Multiple Airlines Logo
7:35 am - 10:05 amGRU-MDW
28h 30m2 stops
Multiple Airlines Logo
8:00 am - 5:20 amMDW-GRU
19h 20m1 stop
$878Multiple Airlines
Find Deal
Tue, Mar 10 - Fri, Mar 13

LATAM Airlines flights from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport

Our best LATAM Airlines deals on Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport flight tickets
LATAM Airlines
Nov 27
GRU2:20 pmSao Paulo Guarulhos Intl
22h 32m
2 stops
MDW9:52 amChicago Midway
Dec 4
MDW6:00 amChicago Midway
20h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$838
Find similar
LATAM Airlines
Nov 27
GRU10:40 pmSao Paulo Guarulhos Intl
20h 59m
2 stops
MDW4:39 pmChicago Midway
Dec 7
MDW5:13 pmChicago Midway
13h 22m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$842
Find similar
LATAM Airlines
Dec 1
GRU11:45 pmSao Paulo Guarulhos Intl
15h 10m
1 stop
MDW11:55 amChicago Midway
Dec 9
MDW10:49 amChicago Midway
15h 56m
2 stops
GRU5:45 amSao Paulo Guarulhos Intl
$846
Find similar

Delta flights from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport

Our best Delta deals on Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport flight tickets
Delta
Nov 4
GRU9:15 pmSao Paulo Guarulhos Intl
18h 13m
2 stops
MDW12:28 pmChicago Midway
Nov 17
MDW5:34 pmChicago Midway
13h 01m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$814
Find similar
Delta
Nov 18
GRU9:15 pmSao Paulo Guarulhos Intl
18h 19m
2 stops
MDW12:34 pmChicago Midway
Nov 25
MDW5:34 pmChicago Midway
13h 01m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$818
Find similar
Delta
Nov 20
GRU11:45 pmSao Paulo Guarulhos Intl
19h 53m
1 stop
MDW4:38 pmChicago Midway
Nov 29
MDW12:47 pmChicago Midway
13h 53m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$821
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Sao Paulo Guarulhos Intl Airport 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 October 16, 2025.
Use the filters below to find and compare flights from Sao Paulo Guarulhos Intl Airport 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

Tue 11/4

9:15 pm-12:28 pm

2 stops18h 13m

Chicago Midway

Mon 11/17

5:34 pm-9:35 am

1 stop13h 01m

$814

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 11/18

9:15 pm-12:34 pm

2 stops18h 19m

Chicago Midway

Tue 11/25

5:34 pm-9:35 am

1 stop13h 01m

$818

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 11/20

11:45 pm-4:38 pm

1 stop19h 53m

Chicago Midway

Sat 11/29

12:47 pm-5:40 am

1 stop13h 53m

$821

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 11/7

9:15 pm-3:26 pm

1 stop21h 11m

Chicago Midway

Wed 11/19

6:00 am-5:40 am

1 stop20h 40m

$822

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 11/6

11:45 pm-12:28 pm

2 stops15h 43m

Chicago Midway

Mon 11/17

10:47 am-5:40 am

1 stop15h 53m

$823

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 11/20

11:45 pm-12:34 pm

2 stops15h 49m

Chicago Midway

Sun 11/30

12:47 pm-5:40 am

1 stop13h 53m

$829

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 11/27

2:20 pm-9:52 am

2 stops22h 32m

Chicago Midway

Thu 12/4

6:00 am-5:40 am

1 stop20h 40m

$838

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 11/27

10:40 pm-4:39 pm

2 stops20h 59m

Chicago Midway

Sun 12/7

5:13 pm-9:35 am

1 stop13h 22m

$842

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 12/1

11:45 pm-11:55 am

1 stop15h 10m

Chicago Midway

Tue 12/9

10:49 am-5:45 am

2 stops15h 56m

$846

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 3/10

7:35 am-10:05 am

2 stops28h 30m

Chicago Midway

Fri 3/13

8:00 am-5:20 am

1 stop19h 20m

$878

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Sao Paulo Guarulhos Intl Airport 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 Guarulhos Intl to Chicago Midway?

LATAM Airlines is the most popular carrier operating from Sao Paulo Guarulhos Intl to Chicago Midway

When to book flights from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Sao Paulo Guarulhos Intl Airport 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 Guarulhos Intl Airport to Chicago Midway Airport (GRU to MDW) flight deals and tips

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

Direct flights

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

    Chicago Midway is 5217.7 mi away from Sao Paulo Guarulhos Intl. 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 Guarulhos Intl Airport to Chicago Midway Airport?

    Prices for flights from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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?

All flight searches from Sao Paulo to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search for Sao Paulo to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Sao Paulo to Chicago 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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