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Cheap flights from Sao Paulo to Chicago from $429

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 to Chicago departing on 6/17. 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 to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:00 pm - 11:55 am
GRU
-
MDW
14h 55m
2 stops
Delta Logo
6:05 am - 5:40 am
MDW
-
GRU
21h 35m
1 stop
$945Delta
Thu, Sep 17 - Sat, Sep 26
Delta Logo
10:50 pm - 9:59 am
GRU
-
MDW
13h 09m
1 stop
Delta Logo
10:35 am - 5:05 am
MDW
-
GRU
16h 30m
2 stops
$949Delta
Tue, Aug 18 - Tue, Sep 8
Delta Logo
10:50 pm - 12:33 pm
GRU
-
MDW
15h 43m
2 stops
Delta Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
$950Delta
Tue, Oct 6 - Tue, Oct 13
Delta Logo
10:50 pm - 9:53 am
GRU
-
MDW
13h 03m
1 stop
Delta Logo
1:14 pm - 5:40 am
MDW
-
GRU
14h 26m
2 stops
$951Delta
Thu, Sep 17 - Sat, Sep 26
Delta Logo
10:50 pm - 10:09 am
GRU
-
MDW
13h 19m
1 stop
Delta Logo
12:46 pm - 5:05 am
MDW
-
GRU
14h 19m
2 stops
$952Delta
Tue, Jun 23 - Mon, Aug 10
LATAM Airlines Logo
12:05 pm - 10:09 am
GRU
-
MDW
24h 04m
2 stops
LATAM Airlines Logo
11:05 am - 8:40 am
MDW
-
GRU
19h 35m
2 stops
$959LATAM Airlines
Sun, Jul 5 - Wed, Jul 15
LATAM Airlines Logo
10:50 pm - 12:05 pm
GRU
-
MDW
15h 15m
1 stop
LATAM Airlines Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
$960LATAM Airlines
Tue, Jun 23 - Thu, Jul 2
LATAM Airlines Logo
10:50 pm - 11:56 am
GRU
-
MDW
15h 06m
1 stop
LATAM Airlines Logo
10:35 am - 5:40 am
MDW
-
GRU
17h 05m
1 stop
$961LATAM Airlines
Mon, Oct 5 - Sun, Oct 25
LATAM Airlines Logo
11:00 pm - 10:36 pm
GRU
-
MDW
25h 36m
2 stops
LATAM Airlines Logo
11:25 am - 5:40 am
MDW
-
GRU
16h 15m
1 stop
$963LATAM Airlines
Thu, Aug 20 - Sat, Sep 26
LATAM Airlines Logo
10:55 pm - 3:40 pm
GRU
-
MDW
18h 45m
2 stops
LATAM Airlines Logo
6:00 am - 5:40 am
MDW
-
GRU
21h 40m
1 stop
$964LATAM Airlines
Tue, Jun 30 - Fri, Jul 10

Delta flights from Sao Paulo to Chicago Midway Airport

Our best Delta deals on Sao Paulo to Chicago Midway Airport flight tickets
Delta
Aug 18
GRU10:50 pmSao Paulo Guarulhos Intl
13h 09m
1 stop
MDW9:59 amChicago Midway
Sep 8
MDW10:35 amChicago Midway
17h 05m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$949
Delta
Sep 17
GRU10:50 pmSao Paulo Guarulhos Intl
13h 03m
1 stop
MDW9:53 amChicago Midway
Sep 26
MDW1:14 pmChicago Midway
14h 26m
2 stops
GRU5:40 amSao Paulo Guarulhos Intl
$951
Delta
Jun 23
GRU10:50 pmSao Paulo Guarulhos Intl
13h 19m
1 stop
MDW10:09 amChicago Midway
Aug 10
MDW12:46 pmChicago Midway
14h 19m
2 stops
GRU5:05 amSao Paulo Guarulhos Intl
$952

LATAM Airlines flights from Sao Paulo to Chicago Midway Airport

Our best LATAM Airlines deals on Sao Paulo to Chicago Midway Airport flight tickets
LATAM Airlines
Jul 5
GRU12:05 pmSao Paulo Guarulhos Intl
24h 04m
2 stops
MDW10:09 amChicago Midway
Jul 15
MDW11:05 amChicago Midway
19h 35m
2 stops
GRU8:40 amSao Paulo Guarulhos Intl
$959
LATAM Airlines
Jun 23
GRU10:50 pmSao Paulo Guarulhos Intl
15h 15m
1 stop
MDW12:05 pmChicago Midway
Jul 2
MDW6:00 amChicago Midway
21h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$960
LATAM Airlines
Aug 25
GRU10:50 pmSao Paulo Guarulhos Intl
15h 01m
1 stop
MDW11:51 amChicago Midway
Sep 2
MDW6:05 amChicago Midway
21h 35m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl
$961

momondo Fare Finder

 
Customize your flight search to find flights from Sao Paulo 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 2, 2026.
Use the filters below to find and compare flights from Sao Paulo 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 9/17

11:00 pm-11:55 am

2 stops14h 55m

Chicago Midway

Sat 9/26

6:05 am-5:40 am

1 stop21h 35m

$945

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 8/18

10:50 pm-9:59 am

1 stop13h 09m

Chicago Midway

Tue 9/8

10:35 am-5:05 am

2 stops16h 30m

$949

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/6

10:50 pm-12:33 pm

2 stops15h 43m

Chicago Midway

Tue 10/13

6:00 am-5:40 am

1 stop21h 40m

$950
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

1:14 pm-5:40 am

2 stops14h 26m

$951

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 6/23

10:50 pm-10:09 am

1 stop13h 19m

Chicago Midway

Mon 8/10

12:46 pm-5:05 am

2 stops14h 19m

$952

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sun 7/5

12:05 pm-10:09 am

2 stops24h 04m

Chicago Midway

Wed 7/15

11:05 am-8:40 am

2 stops19h 35m

$959

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 6/23

10:50 pm-12:05 pm

1 stop15h 15m

Chicago Midway

Thu 7/2

6:00 am-5:40 am

1 stop21h 40m

$960

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 10/5

10:50 pm-11:56 am

1 stop15h 06m

Chicago Midway

Sun 10/25

10:35 am-5:40 am

1 stop17h 05m

$961

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 8/20

11:00 pm-10:36 pm

2 stops25h 36m

Chicago Midway

Sat 9/26

11:25 am-5:40 am

1 stop16h 15m

$963

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 6/30

10:55 pm-3:40 pm

2 stops18h 45m

Chicago Midway

Fri 7/10

6:00 am-5:40 am

1 stop21h 40m

$964

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 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 to Chicago Midway?

LATAM Airlines and Delta are the most popular carriers operating from Sao Paulo to Chicago Midway

When to book flights from Sao Paulo to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Sao Paulo 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 to Chicago Midway Airport (SAO to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sao Paulo to Chicago Midway Airport

Fastest flight time

13h 19m

Direct flights

None
The fastest flight from Sao Paulo to Chicago Midway Airport takes 13h 19m
There are no direct flights from Sao Paulo to Chicago Midway Airport. There are no popular flight routes from Sao Paulo to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Sao Paulo to Chicago Midway Airport

  • How far is Sao Paulo to Chicago Midway by plane?

    The distance between Sao Paulo and Chicago Midway is about 5219.4 mi. Flights usually cover this in 13h 19m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Sao Paulo to Chicago Midway Airport?

    Prices for flights from Sao Paulo to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Sao Paulo to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Sao Paulo to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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?

Yes. momondo enables you to select and highlight flights to Chicago from Sao Paulo with this policy.

How can momondo help me find flights from Sao Paulo to Chicago?

momondo helps you find the best flight between Sao Paulo and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Sao Paulo to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Sao Paulo and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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