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Cheap flights from Sao Paulo Guarulhos Intl Airport to Chicago from $301

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 2/26. 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 - 11:56 am
GRU
-
MDW
15h 06m
1 stop
Delta Logo
10:35 am - 5:40 am
MDW
-
GRU
17h 05m
1 stop
$657Delta
Tue, May 26 - Mon, Jun 8
Delta Logo
11:45 pm - 5:37 pm
GRU
-
MDW
20h 52m
2 stops
Delta Logo
1:10 pm - 9:35 am
MDW
-
GRU
18h 25m
2 stops
$675Delta
Sun, Mar 1 - Sun, Mar 15
Delta Logo
9:15 pm - 9:54 am
GRU
-
MDW
15h 39m
1 stop
Delta Logo
9:35 am - 5:40 am
MDW
-
GRU
18h 05m
2 stops
$678Delta
Sun, Mar 1 - Mon, Mar 16
LATAM Airlines Logo
9:15 pm - 5:45 pm
GRU
-
MDW
23h 30m
1 stop
LATAM Airlines Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
$684LATAM Airlines
Sun, Mar 1 - Sun, Mar 15
LATAM Airlines Logo
9:15 pm - 9:54 am
GRU
-
MDW
15h 39m
1 stop
LATAM Airlines Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
$687LATAM Airlines
Sun, Mar 1 - Sun, Mar 15
Multiple Airlines Logo
12:45 pm - 2:26 pm
GRU
-
MDW
28h 41m
1 stop
Multiple Airlines Logo
11:19 am - 9:55 am
MDW
-
GRU
20h 36m
2 stops
$743Multiple Airlines
Wed, Feb 18 - Wed, Mar 11
Delta Logo
11:45 pm - 11:59 am
GRU
-
MDW
15h 14m
1 stop
Delta Logo
12:47 pm - 8:50 am
MDW
-
GRU
18h 03m
2 stops
$746Delta
Thu, Mar 5 - Tue, Mar 31
Delta Logo
11:45 pm - 12:02 pm
GRU
-
MDW
14h 17m
1 stop
Delta Logo
12:47 pm - 8:50 am
MDW
-
GRU
18h 03m
2 stops
$749Delta
Mon, Mar 16 - Tue, Mar 31
Delta Logo
10:50 pm - 12:07 pm
GRU
-
MDW
15h 17m
1 stop
Delta Logo
12:51 pm - 5:40 am
MDW
-
GRU
14h 49m
1 stop
$752Delta
Thu, Apr 23 - Tue, May 12
LATAM Airlines Logo
10:40 am - 10:31 pm
GRU
-
MDW
13h 51m
1 stop
LATAM Airlines Logo
12:47 pm - 5:40 am
MDW
-
GRU
14h 53m
1 stop
$758LATAM Airlines
Mon, Mar 16 - Tue, Mar 31

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
May 26
GRU10:50 pmSao Paulo Guarulhos Intl
15h 52m
2 stops
MDW12:42 pmChicago Midway
Jun 8
MDW10:35 amChicago Midway
17h 05m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$657
Delta
Mar 1
GRU11:45 pmSao Paulo Guarulhos Intl
21h 00m
1 stop
MDW5:45 pmChicago Midway
Mar 16
MDW1:10 pmChicago Midway
18h 45m
2 stops
GRU9:55 amSao Paulo Guarulhos Intl
$675
Delta
Mar 1
GRU9:15 pmSao Paulo Guarulhos Intl
15h 39m
1 stop
MDW9:54 amChicago Midway
Mar 15
MDW1:10 pmChicago Midway
18h 25m
2 stops
GRU9:35 amSao Paulo Guarulhos Intl
$678

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
Mar 1
GRU9:15 pmSao Paulo Guarulhos Intl
23h 30m
1 stop
MDW5:45 pmChicago Midway
Mar 15
MDW6:00 amChicago Midway
21h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$684
LATAM Airlines
Mar 1
GRU9:15 pmSao Paulo Guarulhos Intl
15h 39m
1 stop
MDW9:54 amChicago Midway
Mar 15
MDW6:00 amChicago Midway
21h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$687
LATAM Airlines
Mar 16
GRU10:40 amSao Paulo Guarulhos Intl
13h 51m
1 stop
MDW10:31 pmChicago Midway
Mar 31
MDW12:47 pmChicago Midway
14h 53m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$758

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 February 3, 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

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 5/26

10:50 pm-11:56 am

1 stop15h 06m

Chicago Midway

Mon 6/8

10:35 am-5:40 am

1 stop17h 05m

$657

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 3/1

11:45 pm-5:37 pm

2 stops20h 52m

Chicago Midway

Sun 3/15

1:10 pm-9:35 am

2 stops18h 25m

$675

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 3/1

9:15 pm-9:54 am

1 stop15h 39m

Chicago Midway

Mon 3/16

9:35 am-5:40 am

2 stops18h 05m

$678

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 3/1

9:15 pm-5:45 pm

1 stop23h 30m

Chicago Midway

Sun 3/15

6:00 am-5:40 am

1 stop21h 40m

$684

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 3/1

9:15 pm-9:54 am

1 stop15h 39m

Chicago Midway

Sun 3/15

6:00 am-5:40 am

1 stop21h 40m

$687

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 2/18

12:45 pm-2:26 pm

1 stop28h 41m

Chicago Midway

Wed 3/11

11:19 am-9:55 am

2 stops20h 36m

$743

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 3/5

11:45 pm-11:59 am

1 stop15h 14m

Chicago Midway

Tue 3/31

12:47 pm-8:50 am

2 stops18h 03m

$746

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 3/16

11:45 pm-12:02 pm

1 stop14h 17m

Chicago Midway

Tue 3/31

12:47 pm-8:50 am

2 stops18h 03m

$749

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 4/23

10:50 pm-12:07 pm

1 stop15h 17m

Chicago Midway

Tue 5/12

12:51 pm-5:40 am

1 stop14h 49m

$752

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 3/16

10:40 am-10:31 pm

1 stop13h 51m

Chicago Midway

Tue 3/31

12:47 pm-5:40 am

1 stop14h 53m

$758

Flights are sorted by cheapest round-trip flights first.

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

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

14h 17m

Direct flights

None
The fastest flight from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport takes 14h 17m
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

  • 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 17m, 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.

  • How do I get Price Alerts for flights from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport?

    Price Alerts will notify you by email when the price for flights to Chicago Midway Airport from Sao Paulo Guarulhos Intl Airport decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.

  • How can I save money on flights from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport with momondo?

    Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Valparaiso
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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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