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Cheap flights from Sao Paulo Guarulhos Intl Airport to Chicago from $341

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 5/26. 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
10:50 pm - 12:00 pm
GRU
-
MDW
15h 10m
1 stop
Delta Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
$930Delta
Sun, Jun 7 - Sat, Jun 20
Delta Logo
10:50 pm - 10:09 am
GRU
-
MDW
13h 19m
1 stop
Delta Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
$931Delta
Sun, Jun 7 - Sat, Jun 20
Delta Logo
8:30 pm - 1:19 pm
GRU
-
MDW
18h 49m
2 stops
Delta Logo
1:22 pm - 7:15 am
MDW
-
GRU
15h 53m
2 stops
$932Delta
Tue, May 26 - Fri, Jun 5
Delta Logo
7:15 pm - 11:56 am
GRU
-
MDW
18h 41m
2 stops
Delta Logo
6:00 am - 5:05 am
MDW
-
GRU
21h 05m
2 stops
$933Delta
Mon, May 25 - Fri, Jun 19
Delta Logo
11:00 pm - 4:25 pm
GRU
-
MDW
19h 25m
2 stops
Delta Logo
5:25 pm - 9:35 am
MDW
-
GRU
14h 10m
1 stop
$934Delta
Sun, Oct 18 - Mon, Oct 26
Delta Logo
7:15 pm - 11:56 am
GRU
-
MDW
18h 41m
2 stops
Delta Logo
11:05 am - 5:05 am
MDW
-
GRU
16h 00m
2 stops
$935Delta
Mon, Jun 1 - Sun, Jun 21
LATAM Airlines Logo
10:50 pm - 4:12 pm
GRU
-
MDW
19h 22m
1 stop
LATAM Airlines Logo
6:23 am - 5:40 am
MDW
-
GRU
21h 17m
1 stop
$939LATAM Airlines
Fri, May 29 - Sat, Jun 6
LATAM Airlines Logo
8:15 am - 9:52 am
GRU
-
MDW
27h 37m
2 stops
LATAM Airlines Logo
1:05 pm - 5:40 am
MDW
-
GRU
13h 35m
1 stop
$940LATAM Airlines
Sun, Oct 11 - Tue, Nov 3
LATAM Airlines Logo
2:10 pm - 10:00 am
GRU
-
MDW
21h 50m
2 stops
LATAM Airlines Logo
5:11 pm - 4:40 pm
MDW
-
GRU
21h 29m
2 stops
$942LATAM Airlines
Mon, Jun 1 - Mon, Jun 8
LATAM Airlines Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
LATAM Airlines Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
$944LATAM Airlines
Tue, Jun 2 - Wed, Jun 10

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
May 29
GRU10:50 pmSao Paulo Guarulhos Intl
19h 22m
1 stop
MDW4:12 pmChicago Midway
Jun 6
MDW6:23 amChicago Midway
21h 17m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$939
LATAM Airlines
Oct 11
GRU8:15 amSao Paulo Guarulhos Intl
27h 37m
2 stops
MDW9:52 amChicago Midway
Nov 3
MDW1:05 pmChicago Midway
13h 35m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$940
LATAM Airlines
Jun 1
GRU2:10 pmSao Paulo Guarulhos Intl
21h 50m
2 stops
MDW10:00 amChicago Midway
Jun 8
MDW5:11 pmChicago Midway
21h 29m
2 stops
GRU4:40 pmSao Paulo Guarulhos Intl
$942

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
Jun 7
GRU7:15 pmSao Paulo Guarulhos Intl
18h 45m
2 stops
MDW12:00 pmChicago Midway
Jun 20
MDW9:17 amChicago Midway
18h 03m
2 stops
GRU5:20 amSao Paulo Guarulhos Intl
$930
Delta
Jun 7
GRU10:50 pmSao Paulo Guarulhos Intl
13h 19m
1 stop
MDW10:09 amChicago Midway
Jun 20
MDW6:00 amChicago Midway
21h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$931
Delta
May 26
GRU10:50 pmSao Paulo Guarulhos Intl
19h 22m
1 stop
MDW4:12 pmChicago Midway
Jun 5
MDW1:22 pmChicago Midway
15h 53m
2 stops
GRU7:15 amSao Paulo Guarulhos Intl
$932

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 May 5, 2026.
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

Cheapest round-trip

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 6/7

10:50 pm-12:00 pm

1 stop15h 10m

Chicago Midway

Sat 6/20

6:00 am-5:40 am

1 stop21h 40m

$930

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 6/7

10:50 pm-10:09 am

1 stop13h 19m

Chicago Midway

Sat 6/20

6:00 am-5:40 am

1 stop21h 40m

$931

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 5/26

8:30 pm-1:19 pm

2 stops18h 49m

Chicago Midway

Fri 6/5

1:22 pm-7:15 am

2 stops15h 53m

$932

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 5/25

7:15 pm-11:56 am

2 stops18h 41m

Chicago Midway

Fri 6/19

6:00 am-5:05 am

2 stops21h 05m

$933
Quickest round-trip

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 10/18

11:00 pm-4:25 pm

2 stops19h 25m

Chicago Midway

Mon 10/26

5:25 pm-9:35 am

1 stop14h 10m

$934

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 6/1

7:15 pm-11:56 am

2 stops18h 41m

Chicago Midway

Sun 6/21

11:05 am-5:05 am

2 stops16h 00m

$935

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 5/29

10:50 pm-4:12 pm

1 stop19h 22m

Chicago Midway

Sat 6/6

6:23 am-5:40 am

1 stop21h 17m

$939

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 10/11

8:15 am-9:52 am

2 stops27h 37m

Chicago Midway

Tue 11/3

1:05 pm-5:40 am

1 stop13h 35m

$940

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 6/1

2:10 pm-10:00 am

2 stops21h 50m

Chicago Midway

Mon 6/8

5:11 pm-4:40 pm

2 stops21h 29m

$942

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

6:00 am-5:40 am

1 stop21h 40m

$944

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 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?

Delta 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

Fastest flight time

15h 04m

Direct flights

None
The fastest flight from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport takes 15h 04m
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.
Search flight deals

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

  • 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 15h 04m, 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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