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Cheap flights from Sao Paulo Guarulhos Intl Airport to Chicago from $386

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 9/29. 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
11:10 am - 11:00 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
25h 50m3 stops Punta Cana Montreal Pierre Elliott Trudeau Intl Toronto Island
Multiple Airlines Logo
3:20 pm - 10:25 pmMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
29h 05m3 stops Toronto Island Montreal Pierre Elliott Trudeau Intl Punta Cana
$1,128Multiple Airlines
Tue, Sep 8 - Tue, Sep 15
LATAM Airlines Logo
9:30 pm - 10:03 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
14h 33m1 stop Atlanta Hartsfield-Jackson
LATAM Airlines Logo
4:19 pm - 9:35 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
14h 16m1 stop Atlanta Hartsfield-Jackson
$1,202LATAM Airlines
Tue, Oct 27 - Thu, Nov 5
LATAM Airlines Logo
9:30 pm - 10:33 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
16h 03m1 stop Atlanta Hartsfield-Jackson
LATAM Airlines Logo
1:05 pm - 5:40 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
13h 35m1 stop Atlanta Hartsfield-Jackson
$1,217LATAM Airlines
Thu, Dec 3 - Tue, Feb 23
LATAM Airlines Logo
9:30 pm - 10:33 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
16h 03m1 stop Atlanta Hartsfield-Jackson
LATAM Airlines Logo
5:25 pm - 9:35 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
13h 10m1 stop Atlanta Hartsfield-Jackson
$1,217LATAM Airlines
Thu, Dec 3 - Wed, Jan 20
Delta Logo
9:30 pm - 11:50 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
16h 20m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:39 am - 5:40 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
15h 01m2 stops Atlanta Hartsfield-Jackson Miami
$1,219Delta
Tue, Oct 27 - Thu, Nov 5
Delta Logo
9:30 pm - 10:03 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
14h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 9:35 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
17h 35m1 stop Atlanta Hartsfield-Jackson
$1,221Delta
Tue, Oct 27 - Wed, Nov 11
Delta Logo
9:30 pm - 12:05 pmGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
17h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:09 pm - 9:35 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
13h 26m1 stop Atlanta Hartsfield-Jackson
$1,221Delta
Mon, Nov 23 - Mon, Nov 30
Delta Logo
11:00 pm - 11:50 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
14h 50m2 stops Miami Atlanta Hartsfield-Jackson
Delta Logo
12:45 pm - 5:05 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
14h 20m2 stops Atlanta Hartsfield-Jackson Miami
$1,221Delta
Tue, Oct 6 - Tue, Oct 13
Delta Logo
9:30 pm - 9:52 amGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
15h 22m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:00 pm - 9:35 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
17h 35m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$1,221Delta
Wed, Dec 23 - Tue, Jan 12
Delta Logo
9:30 pm - 12:47 pmGRU  Sao Paulo Guarulhos Intl-MDW Chicago Midway
17h 17m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
11:39 am - 5:40 amMDW  Chicago Midway-GRU Sao Paulo Guarulhos Intl
15h 01m1 stop Atlanta Hartsfield-Jackson
$1,221Delta
Tue, Oct 27 - Wed, Nov 4

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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
Oct 27
GRU9:30 pmSao Paulo Guarulhos Intl
16h 20m
1 stop
MDW11:50 amChicago Midway
Nov 5
MDW11:39 amChicago Midway
15h 01m
2 stops
GRU5:40 amSao Paulo Guarulhos Intl
$1,219
Delta
Dec 2
GRU11:45 pmSao Paulo Guarulhos Intl
13h 48m
1 stop
MDW10:33 amChicago Midway
Feb 23
MDW5:25 pmChicago Midway
13h 10m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$1,221
Delta
Jan 12
GRU11:45 pmSao Paulo Guarulhos Intl
15h 11m
1 stop
MDW11:56 amChicago Midway
Feb 1
MDW1:00 pmChicago Midway
17h 55m
2 stops
GRU9:55 amSao Paulo Guarulhos Intl
$1,222

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
Oct 27
GRU9:30 pmSao Paulo Guarulhos Intl
14h 33m
1 stop
MDW10:03 amChicago Midway
Nov 5
MDW4:19 pmChicago Midway
14h 16m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$1,202
LATAM Airlines
Dec 3
GRU9:30 pmSao Paulo Guarulhos Intl
16h 03m
1 stop
MDW10:33 amChicago Midway
Jan 20
MDW5:25 pmChicago Midway
13h 10m
1 stop
GRU9:35 amSao Paulo Guarulhos Intl
$1,217
LATAM Airlines
Sep 30
GRU11:45 pmSao Paulo Guarulhos Intl
24h 59m
2 stops
MDW10:44 pmChicago Midway
Oct 20
MDW10:59 amChicago Midway
16h 41m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$1,230

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 August 10, 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 Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Tue 9/8

11:10 am-11:00 am

3 stops25h 50m

Chicago Midway

Tue 9/15

3:20 pm-10:25 pm

3 stops29h 05m

$1,128
Quickest round-trip

Sao PauloChicago

GRU Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/27

9:30 pm-10:03 am

1 stop14h 33m

Chicago Midway

Thu 11/5

4:19 pm-9:35 am

1 stop14h 16m

$1,202

Sao PauloChicago

GRU Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Thu 12/3

9:30 pm-10:33 am

1 stop16h 03m

Chicago Midway

Tue 2/23

1:05 pm-5:40 am

1 stop13h 35m

$1,217

Sao PauloChicago

GRU Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Thu 12/3

9:30 pm-10:33 am

1 stop16h 03m

Chicago Midway

Wed 1/20

5:25 pm-9:35 am

1 stop13h 10m

$1,217

Sao PauloChicago

GRU Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/27

9:30 pm-11:50 am

1 stop16h 20m

Chicago Midway

Thu 11/5

11:39 am-5:40 am

2 stops15h 01m

$1,219

Sao PauloChicago

GRU Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/27

9:30 pm-10:03 am

1 stop14h 33m

Chicago Midway

Wed 11/11

1:00 pm-9:35 am

1 stop17h 35m

$1,221

Sao PauloChicago

GRU Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Mon 11/23

9:30 pm-12:05 pm

1 stop17h 35m

Chicago Midway

Mon 11/30

5:09 pm-9:35 am

1 stop13h 26m

$1,221

Sao PauloChicago

GRU Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/6

11:00 pm-11:50 am

2 stops14h 50m

Chicago Midway

Tue 10/13

12:45 pm-5:05 am

2 stops14h 20m

$1,221

Sao PauloChicago

GRU Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Wed 12/23

9:30 pm-9:52 am

1 stop15h 22m

Chicago Midway

Tue 1/12

1:00 pm-9:35 am

2 stops17h 35m

$1,221

Sao PauloChicago

GRU Sao Paulo Guarulhos Intl - MDW Chicago Midway

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/27

9:30 pm-12:47 pm

2 stops17h 17m

Chicago Midway

Wed 11/4

11:39 am-5:40 am

1 stop15h 01m

$1,221

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

13h 09m

Direct flights

None
The fastest flight from Sao Paulo Guarulhos Intl Airport to Chicago Midway Airport takes 13h 09m
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 13h 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
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Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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