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Cheap flights from Sao Paulo Guarulhos Intl Airport to Chicago from $406

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 8/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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.
Multiple Airlines Logo
11:50 am - 9:40 am
GRU
-
MDW
23h 50m
2 stops
Multiple Airlines Logo
3:15 pm - 10:25 pm
MDW
-
GRU
29h 10m
3 stops
$832Multiple Airlines
Thu, Jul 16 - Tue, Aug 18
Multiple Airlines Logo
11:50 am - 9:40 am
GRU
-
MDW
23h 50m
2 stops
Multiple Airlines Logo
10:25 am - 9:50 am
MDW
-
GRU
21h 25m
2 stops
$836Multiple Airlines
Thu, Jul 16 - Tue, Aug 18
Multiple Airlines Logo
11:50 am - 9:40 am
GRU
-
MDW
23h 50m
2 stops
Multiple Airlines Logo
8:23 pm - 8:40 am
MDW
-
GRU
34h 17m
3 stops
$839Multiple Airlines
Thu, Jul 16 - Sun, Aug 9
Multiple Airlines Logo
11:50 am - 9:40 am
GRU
-
MDW
23h 50m
2 stops
Multiple Airlines Logo
8:49 pm - 7:30 am
MDW
-
GRU
32h 41m
3 stops
$912Multiple Airlines
Thu, Jul 16 - Thu, Aug 6
Multiple Airlines Logo
11:50 am - 9:40 am
GRU
-
MDW
23h 50m
2 stops
Multiple Airlines Logo
3:15 pm - 9:05 am
MDW
-
GRU
15h 50m
1 stop
$930Multiple Airlines
Thu, Jul 16 - Tue, Aug 18
Multiple Airlines Logo
11:50 am - 9:13 am
GRU
-
MDW
23h 23m
3 stops
Multiple Airlines Logo
8:23 pm - 8:40 am
MDW
-
GRU
34h 17m
3 stops
$993Multiple Airlines
Thu, Jul 16 - Sun, Aug 9
Multiple Airlines Logo
11:50 am - 9:40 am
GRU
-
MDW
23h 50m
2 stops
Multiple Airlines Logo
10:20 am - 9:50 am
MDW
-
GRU
21h 30m
2 stops
$1,025Multiple Airlines
Thu, Jul 16 - Sun, Aug 9
LATAM Airlines Logo
10:50 pm - 11:51 am
GRU
-
MDW
15h 01m
1 stop
LATAM Airlines Logo
10:54 am - 5:40 am
MDW
-
GRU
16h 46m
1 stop
$1,173LATAM Airlines
Tue, Aug 18 - Tue, Sep 1
LATAM Airlines Logo
10:50 pm - 9:53 am
GRU
-
MDW
13h 03m
1 stop
LATAM Airlines Logo
11:25 am - 5:40 am
MDW
-
GRU
16h 15m
1 stop
$1,177LATAM Airlines
Thu, Sep 17 - Sat, Sep 26
LATAM Airlines Logo
10:50 pm - 9:59 am
GRU
-
MDW
13h 09m
1 stop
LATAM Airlines Logo
10:54 am - 5:40 am
MDW
-
GRU
16h 46m
1 stop
$1,181LATAM Airlines
Wed, Aug 19 - Wed, Sep 2

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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
Jul 14
GRU10:50 pmSao Paulo Guarulhos Intl
13h 15m
1 stop
MDW10:05 amChicago Midway
Aug 11
MDW12:46 pmChicago Midway
14h 54m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$1,198
Delta
Sep 17
GRU8:30 pmSao Paulo Guarulhos Intl
18h 09m
2 stops
MDW12:39 pmChicago Midway
Sep 26
MDW11:35 amChicago Midway
15h 30m
2 stops
GRU5:05 amSao Paulo Guarulhos Intl
$1,199
Delta
Sep 17
GRU10:50 pmSao Paulo Guarulhos Intl
15h 05m
1 stop
MDW11:55 amChicago Midway
Sep 26
MDW6:05 amChicago Midway
21h 35m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$1,231

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
Aug 18
GRU10:50 pmSao Paulo Guarulhos Intl
15h 01m
1 stop
MDW11:51 amChicago Midway
Sep 1
MDW10:54 amChicago Midway
16h 46m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$1,173
LATAM Airlines
Sep 17
GRU10:50 pmSao Paulo Guarulhos Intl
13h 03m
1 stop
MDW9:53 amChicago Midway
Sep 26
MDW11:25 amChicago Midway
16h 15m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$1,177
LATAM Airlines
Aug 19
GRU10:50 pmSao Paulo Guarulhos Intl
13h 09m
1 stop
MDW9:59 amChicago Midway
Sep 2
MDW10:54 amChicago Midway
16h 46m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$1,181

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 June 23, 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

Thu 7/16

11:50 am-9:40 am

2 stops23h 50m

Chicago Midway

Tue 8/18

3:15 pm-10:25 pm

3 stops29h 10m

$832

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 7/16

11:50 am-9:40 am

2 stops23h 50m

Chicago Midway

Tue 8/18

10:25 am-9:50 am

2 stops21h 25m

$836

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 7/16

11:50 am-9:40 am

2 stops23h 50m

Chicago Midway

Sun 8/9

8:23 pm-8:40 am

3 stops34h 17m

$839

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 7/16

11:50 am-9:40 am

2 stops23h 50m

Chicago Midway

Thu 8/6

8:49 pm-7:30 am

3 stops32h 41m

$912

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 7/16

11:50 am-9:40 am

2 stops23h 50m

Chicago Midway

Tue 8/18

3:15 pm-9:05 am

1 stop15h 50m

$930

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 7/16

11:50 am-9:13 am

3 stops23h 23m

Chicago Midway

Sun 8/9

8:23 pm-8:40 am

3 stops34h 17m

$993

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 7/16

11:50 am-9:40 am

2 stops23h 50m

Chicago Midway

Sun 8/9

10:20 am-9:50 am

2 stops21h 30m

$1,025

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 8/18

10:50 pm-11:51 am

1 stop15h 01m

Chicago Midway

Tue 9/1

10:54 am-5:40 am

1 stop16h 46m

$1,173
Quickest round-trip

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 9/17

10:50 pm-9:53 am

1 stop13h 03m

Chicago Midway

Sat 9/26

11:25 am-5:40 am

1 stop16h 15m

$1,177

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 8/19

10:50 pm-9:59 am

1 stop13h 09m

Chicago Midway

Wed 9/2

10:54 am-5:40 am

1 stop16h 46m

$1,181

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?

LATAM Airlines and Delta are the most popular carriers 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

14h 56m

Direct flights

None
The fastest flight from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport takes 14h 56m
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 14h 56m, 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
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Munster
Crown Point
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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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