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Cheap flights from Sao Paulo Guarulhos Intl Airport to Chicago from $296

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 10/6. 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

LATAM Airlines Logo
4:30 pm - 9:54 amGRU-MDW
20h 24m2 stops
LATAM Airlines Logo
6:00 am - 5:40 amMDW-GRU
20h 40m1 stop
$653LATAM Airlines
Find Deal
Sat, Dec 6 - Sat, Feb 7
Delta Logo
9:15 pm - 12:34 pmGRU-MDW
18h 19m2 stops
Delta Logo
1:05 pm - 5:40 amMDW-GRU
13h 35m1 stop
$692Delta
Find Deal
Thu, Dec 11 - Fri, Feb 13
Delta Logo
9:00 pm - 12:34 pmGRU-MDW
18h 34m2 stops
Delta Logo
1:05 pm - 5:40 amMDW-GRU
13h 35m1 stop
$695Delta
Find Deal
Thu, Dec 11 - Fri, Feb 13
LATAM Airlines Logo
4:00 am - 10:14 pmGRU-MDW
21h 14m2 stops
LATAM Airlines Logo
10:47 am - 5:45 amMDW-GRU
15h 58m2 stops
$785LATAM Airlines
Find Deal
Sun, Nov 2 - Wed, Nov 19
Delta Logo
11:05 pm - 6:25 pmGRU-MDW
21h 20m2 stops
Delta Logo
5:09 pm - 9:35 amMDW-GRU
13h 26m1 stop
$789Delta
Find Deal
Sat, Oct 18 - Mon, Nov 3
Delta Logo
11:05 pm - 12:28 pmGRU-MDW
15h 23m2 stops
Delta Logo
1:08 pm - 9:35 amMDW-GRU
17h 27m2 stops
$792Delta
Find Deal
Sat, Oct 18 - Tue, Nov 4
Delta Logo
10:50 pm - 5:20 pmGRU-MDW
21h 30m2 stops
Delta Logo
9:30 am - 5:40 amMDW-GRU
17h 10m2 stops
$795Delta
Find Deal
Wed, Dec 31 - Sat, Jan 17
Delta Logo
9:15 pm - 9:54 amGRU-MDW
15h 39m1 stop
Delta Logo
6:00 am - 5:40 amMDW-GRU
20h 40m1 stop
$799Delta
Find Deal
Fri, Dec 12 - Thu, Jan 8
LATAM Airlines Logo
4:30 pm - 11:55 amGRU-MDW
22h 25m2 stops
LATAM Airlines Logo
9:54 am - 9:35 amMDW-GRU
20h 41m1 stop
$801LATAM Airlines
Find Deal
Wed, Dec 17 - Thu, Jan 1
LATAM Airlines Logo
10:05 am - 10:14 pmGRU-MDW
14h 09m1 stop
LATAM Airlines Logo
10:40 am - 9:35 amMDW-GRU
19h 55m1 stop
$804LATAM Airlines
Find Deal
Sat, Oct 18 - Thu, Nov 6

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
Dec 11
GRU9:15 pmSao Paulo Guarulhos Intl
18h 19m
2 stops
MDW12:34 pmChicago Midway
Feb 13
MDW1:05 pmChicago Midway
13h 35m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$692
Find similar
Delta
Dec 11
GRU9:00 pmSao Paulo Guarulhos Intl
18h 34m
2 stops
MDW12:34 pmChicago Midway
Feb 13
MDW1:05 pmChicago Midway
13h 35m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$695
Find similar
Delta
Oct 18
GRU11:05 pmSao Paulo Guarulhos Intl
21h 20m
2 stops
MDW6:25 pmChicago Midway
Nov 3
MDW5:09 pmChicago Midway
13h 26m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$789
Find similar

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
Dec 6
GRU4:30 pmSao Paulo Guarulhos Intl
20h 24m
2 stops
MDW9:54 amChicago Midway
Feb 7
MDW6:00 amChicago Midway
20h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$653
Find similar
LATAM Airlines
Nov 2
GRU4:00 amSao Paulo Guarulhos Intl
21h 14m
2 stops
MDW10:14 pmChicago Midway
Nov 19
MDW10:47 amChicago Midway
15h 58m
2 stops
GRU5:45 amSao Paulo Guarulhos Intl
$785
Find similar
LATAM Airlines
Dec 17
GRU4:30 pmSao Paulo Guarulhos Intl
22h 25m
2 stops
MDW11:55 amChicago Midway
Jan 1
MDW9:54 amChicago Midway
20h 41m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$801
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 September 15, 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

Sat 12/6

4:30 pm-9:54 am

2 stops20h 24m

Chicago Midway

Sat 2/7

6:00 am-5:40 am

1 stop20h 40m

$653

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 12/11

9:15 pm-12:34 pm

2 stops18h 19m

Chicago Midway

Fri 2/13

1:05 pm-5:40 am

1 stop13h 35m

$692

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 12/11

9:00 pm-12:34 pm

2 stops18h 34m

Chicago Midway

Fri 2/13

1:05 pm-5:40 am

1 stop13h 35m

$695

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 11/2

4:00 am-10:14 pm

2 stops21h 14m

Chicago Midway

Wed 11/19

10:47 am-5:45 am

2 stops15h 58m

$785

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 10/18

11:05 pm-6:25 pm

2 stops21h 20m

Chicago Midway

Mon 11/3

5:09 pm-9:35 am

1 stop13h 26m

$789

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 10/18

11:05 pm-12:28 pm

2 stops15h 23m

Chicago Midway

Tue 11/4

1:08 pm-9:35 am

2 stops17h 27m

$792

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 12/31

10:50 pm-5:20 pm

2 stops21h 30m

Chicago Midway

Sat 1/17

9:30 am-5:40 am

2 stops17h 10m

$795

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 12/12

9:15 pm-9:54 am

1 stop15h 39m

Chicago Midway

Thu 1/8

6:00 am-5:40 am

1 stop20h 40m

$799

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 12/17

4:30 pm-11:55 am

2 stops22h 25m

Chicago Midway

Thu 1/1

9:54 am-9:35 am

1 stop20h 41m

$801

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 10/18

10:05 am-10:14 pm

1 stop14h 09m

Chicago Midway

Thu 11/6

10:40 am-9:35 am

1 stop19h 55m

$804

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 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 09m, 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
Lansing
Portage
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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