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Cheap flights from Sao Paulo Guarulhos Intl Airport to Chicago from $333

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 4/23. 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.
Multiple Airlines Logo
11:50 am - 9:40 am
GRU
-
MDW
23h 50m
3 stops
Multiple Airlines Logo
3:20 pm - 10:25 pm
MDW
-
GRU
29h 05m
3 stops
$783Multiple Airlines
Thu, May 28 - Tue, Jun 2
Delta Logo
11:00 pm - 4:12 pm
GRU
-
MDW
19h 12m
2 stops
Delta Logo
1:22 pm - 6:45 am
MDW
-
GRU
15h 23m
2 stops
$808Delta
Mon, May 25 - Mon, Jun 1
LATAM Airlines Logo
11:45 pm - 9:09 pm
GRU
-
MDW
23h 24m
2 stops
LATAM Airlines Logo
10:59 am - 6:05 am
MDW
-
GRU
17h 06m
2 stops
$817LATAM Airlines
Mon, May 25 - Wed, Jun 3
LATAM Airlines Logo
10:50 pm - 9:09 pm
GRU
-
MDW
24h 19m
1 stop
LATAM Airlines Logo
12:53 pm - 3:35 pm
MDW
-
GRU
24h 42m
2 stops
$818LATAM Airlines
Mon, May 25 - Thu, Jun 4
LATAM Airlines Logo
11:00 pm - 11:56 am
GRU
-
MDW
14h 56m
2 stops
LATAM Airlines Logo
10:59 am - 5:20 am
MDW
-
GRU
16h 21m
2 stops
$821LATAM Airlines
Tue, May 26 - Thu, Jun 4
LATAM Airlines Logo
7:15 pm - 4:29 pm
GRU
-
MDW
23h 14m
2 stops
LATAM Airlines Logo
11:18 am - 5:30 am
MDW
-
GRU
16h 12m
2 stops
$826LATAM Airlines
Fri, Apr 24 - Sat, May 2
LATAM Airlines Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
LATAM Airlines Logo
5:08 pm - 8:00 pm
MDW
-
GRU
24h 52m
2 stops
$830LATAM Airlines
Mon, May 11 - Mon, May 25
LATAM Airlines Logo
3:40 am - 9:56 am
GRU
-
MDW
32h 16m
2 stops
LATAM Airlines Logo
12:52 pm - 4:15 pm
MDW
-
GRU
25h 23m
2 stops
$867LATAM Airlines
Thu, Apr 23 - Sun, May 3
LATAM Airlines Logo
11:00 pm - 11:56 am
GRU
-
MDW
14h 56m
2 stops
LATAM Airlines Logo
5:10 pm - 8:40 pm
MDW
-
GRU
25h 30m
2 stops
$871LATAM Airlines
Tue, May 12 - Wed, May 20
LATAM Airlines Logo
2:50 pm - 9:56 am
GRU
-
MDW
21h 06m
2 stops
LATAM Airlines Logo
5:21 pm - 7:30 pm
MDW
-
GRU
24h 09m
2 stops
$876LATAM Airlines
Thu, Apr 23 - Mon, May 4

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 25
GRU11:00 pmSao Paulo Guarulhos Intl
19h 12m
2 stops
MDW4:12 pmChicago Midway
Jun 1
MDW1:22 pmChicago Midway
15h 23m
2 stops
GRU6:45 amSao Paulo Guarulhos Intl
$808
Delta
May 4
GRU10:50 pmSao Paulo Guarulhos Intl
21h 08m
2 stops
MDW5:58 pmChicago Midway
May 13
MDW9:22 amChicago Midway
18h 18m
2 stops
GRU5:40 amSao Paulo Guarulhos Intl
$819
Delta
Jun 7
GRU10:50 pmSao Paulo Guarulhos Intl
21h 41m
2 stops
MDW6:31 pmChicago Midway
Jun 15
MDW10:35 amChicago Midway
16h 45m
2 stops
GRU5:20 amSao Paulo Guarulhos Intl
$883

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 25
GRU11:45 pmSao Paulo Guarulhos Intl
23h 24m
2 stops
MDW9:09 pmChicago Midway
Jun 3
MDW10:59 amChicago Midway
17h 06m
2 stops
GRU6:05 amSao Paulo Guarulhos Intl
$817
LATAM Airlines
May 25
GRU10:50 pmSao Paulo Guarulhos Intl
24h 19m
1 stop
MDW9:09 pmChicago Midway
Jun 4
MDW12:53 pmChicago Midway
24h 42m
2 stops
GRU3:35 pmSao Paulo Guarulhos Intl
$818
LATAM Airlines
May 26
GRU11:00 pmSao Paulo Guarulhos Intl
14h 56m
2 stops
MDW11:56 amChicago Midway
Jun 4
MDW10:59 amChicago Midway
16h 21m
2 stops
GRU5:20 amSao Paulo Guarulhos Intl
$821

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 March 19, 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 5/28

11:50 am-9:40 am

3 stops23h 50m

Chicago Midway

Tue 6/2

3:20 pm-10:25 pm

3 stops29h 05m

$783

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 5/25

11:00 pm-4:12 pm

2 stops19h 12m

Chicago Midway

Mon 6/1

1:22 pm-6:45 am

2 stops15h 23m

$808

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 5/25

11:45 pm-9:09 pm

2 stops23h 24m

Chicago Midway

Wed 6/3

10:59 am-6:05 am

2 stops17h 06m

$817

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 5/25

10:50 pm-9:09 pm

1 stop24h 19m

Chicago Midway

Thu 6/4

12:53 pm-3:35 pm

2 stops24h 42m

$818
Quickest round-trip

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 5/26

11:00 pm-11:56 am

2 stops14h 56m

Chicago Midway

Thu 6/4

10:59 am-5:20 am

2 stops16h 21m

$821

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Fri 4/24

7:15 pm-4:29 pm

2 stops23h 14m

Chicago Midway

Sat 5/2

11:18 am-5:30 am

2 stops16h 12m

$826

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 5/11

10:50 pm-11:56 am

1 stop15h 06m

Chicago Midway

Mon 5/25

5:08 pm-8:00 pm

2 stops24h 52m

$830

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 4/23

3:40 am-9:56 am

2 stops32h 16m

Chicago Midway

Sun 5/3

12:52 pm-4:15 pm

2 stops25h 23m

$867

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 5/12

11:00 pm-11:56 am

2 stops14h 56m

Chicago Midway

Wed 5/20

5:10 pm-8:40 pm

2 stops25h 30m

$871

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 4/23

2:50 pm-9:56 am

2 stops21h 06m

Chicago Midway

Mon 5/4

5:21 pm-7:30 pm

2 stops24h 09m

$876

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

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.

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
Valparaiso
Schererville
Munster
Crown Point
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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