Cheap flights from Sao Paulo to Chicago from $332

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 9/10. 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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Cheap round-trip flights

Delta Logo
10:05 am - 9:26 pmGRU-MDW
13h 21m1 stop
Delta Logo
1:08 pm - 8:50 amMDW-GRU
17h 42m2 stops
$887Delta
Find Deal
Mon, Sep 8 - Mon, Sep 22
Delta Logo
10:50 pm - 12:28 pmGRU-MDW
15h 38m2 stops
Delta Logo
9:35 am - 5:40 amMDW-GRU
18h 05m2 stops
$978Delta
Find Deal
Tue, Oct 7 - Fri, Oct 17
Delta Logo
10:50 pm - 12:28 pmGRU-MDW
15h 38m2 stops
Delta Logo
4:25 pm - 9:00 amMDW-GRU
14h 35m1 stop
$980Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
Delta Logo
10:50 pm - 11:53 amGRU-MDW
15h 03m1 stop
Delta Logo
5:04 pm - 9:00 amMDW-GRU
13h 56m1 stop
$983Delta
Find Deal
Tue, Oct 7 - Thu, Oct 16
Delta Logo
10:50 pm - 11:48 amGRU-MDW
14h 58m1 stop
Delta Logo
9:30 am - 5:40 amMDW-GRU
18h 10m2 stops
$985Delta
Find Deal
Thu, Aug 21 - Wed, Sep 3
Delta Logo
11:05 pm - 11:53 amGRU-MDW
14h 48m2 stops
Delta Logo
1:08 pm - 6:50 amMDW-GRU
15h 42m2 stops
$986Delta
Find Deal
Tue, Oct 7 - Mon, Oct 20
LATAM Airlines Logo
11:45 pm - 9:44 pmGRU-MDW
23h 59m2 stops
LATAM Airlines Logo
4:23 pm - 4:30 pmMDW-GRU
22h 07m2 stops
$987LATAM Airlines
Find Deal
Tue, Aug 19 - Sat, Oct 25
LATAM Airlines Logo
8:30 pm - 1:36 pmGRU-MDW
19h 06m2 stops
LATAM Airlines Logo
4:25 pm - 1:20 pmMDW-GRU
18h 55m2 stops
$991LATAM Airlines
Find Deal
Tue, Aug 26 - Tue, Sep 2
LATAM Airlines Logo
10:50 pm - 11:53 amGRU-MDW
15h 03m1 stop
LATAM Airlines Logo
6:00 am - 5:40 amMDW-GRU
21h 40m1 stop
$992LATAM Airlines
Find Deal
Tue, Oct 7 - Fri, Oct 17
 Logo
7:20 am - 1:03 pmGRU-MDW
31h 43m3 stops
 Logo
9:15 am - 3:20 pmMDW-GRU
28h 05m3 stops
$1,129
Find Deal
Wed, Sep 3 - Wed, Sep 10

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
Aug 19
GRU11:45 pmSao Paulo Guarulhos Intl
23h 59m
2 stops
MDW9:44 pmChicago Midway
Oct 25
MDW4:23 pmChicago Midway
22h 07m
2 stops
GRU4:30 pmSao Paulo Guarulhos Intl
LATAM Airlines
Aug 26
GRU8:30 pmSao Paulo Guarulhos Intl
19h 06m
2 stops
MDW1:36 pmChicago Midway
Sep 2
MDW4:25 pmChicago Midway
18h 55m
2 stops
GRU1:20 pmSao Paulo Guarulhos Intl
LATAM Airlines
Oct 7
GRU10:50 pmSao Paulo Guarulhos Intl
15h 03m
1 stop
MDW11:53 amChicago Midway
Oct 17
MDW6:00 amChicago Midway
21h 40m
1 stop
GRU5:40 amSao Paulo Guarulhos Intl

Delta flights from Sao Paulo to Chicago Midway Airport

Our best Delta deals on Sao Paulo to Chicago Midway Airport flight tickets
Delta
Sep 8
GRU10:05 amSao Paulo Guarulhos Intl
13h 21m
1 stop
MDW9:26 pmChicago Midway
Sep 22
MDW1:08 pmChicago Midway
17h 42m
2 stops
GRU8:50 amSao Paulo Guarulhos Intl
Delta
Oct 7
GRU10:50 pmSao Paulo Guarulhos Intl
15h 38m
2 stops
MDW12:28 pmChicago Midway
Oct 17
MDW9:35 amChicago Midway
18h 05m
2 stops
GRU5:40 amSao Paulo Guarulhos Intl
Delta
Aug 30
GRU10:50 pmSao Paulo Guarulhos Intl
15h 38m
2 stops
MDW12:28 pmChicago Midway
Sep 6
MDW4:25 pmChicago Midway
14h 35m
1 stop
GRU9:00 amSao Paulo Guarulhos Intl

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 July 31, 2025.
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

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Mon 9/8

10:05 am-9:26 pm

1 stop13h 21m

Chicago Midway

Mon 9/22

1:08 pm-8:50 am

2 stops17h 42m

$887

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/7

10:50 pm-12:28 pm

2 stops15h 38m

Chicago Midway

Fri 10/17

9:35 am-5:40 am

2 stops18h 05m

$978

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Sat 8/30

10:50 pm-12:28 pm

2 stops15h 38m

Chicago Midway

Sat 9/6

4:25 pm-9:00 am

1 stop14h 35m

$980

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/7

10:50 pm-11:53 am

1 stop15h 03m

Chicago Midway

Thu 10/16

5:04 pm-9:00 am

1 stop13h 56m

$983

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Thu 8/21

10:50 pm-11:48 am

1 stop14h 58m

Chicago Midway

Wed 9/3

9:30 am-5:40 am

2 stops18h 10m

$985

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/7

11:05 pm-11:53 am

2 stops14h 48m

Chicago Midway

Mon 10/20

1:08 pm-6:50 am

2 stops15h 42m

$986

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 8/19

11:45 pm-9:44 pm

2 stops23h 59m

Chicago Midway

Sat 10/25

4:23 pm-4:30 pm

2 stops22h 07m

$987

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 8/26

8:30 pm-1:36 pm

2 stops19h 06m

Chicago Midway

Tue 9/2

4:25 pm-1:20 pm

2 stops18h 55m

$991

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Tue 10/7

10:50 pm-11:53 am

1 stop15h 03m

Chicago Midway

Fri 10/17

6:00 am-5:40 am

1 stop21h 40m

$992

Sao PauloChicago

GRU - MDW

GRUMDW

Sao Paulo Guarulhos Intl

Wed 9/3

7:20 am-1:03 pm

3 stops31h 43m

Chicago Midway

Wed 9/10

9:15 am-3:20 pm

3 stops28h 05m

$1,129

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 typical price of a round-trip flight between Sao Paulo and Chicago Midway Airport?


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

Best Price Found

$332

Fastest flight time

13h 18m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Sao Paulo in the past 72 hours is $332. The best round-trip flight deal from Sao Paulo to Chicago Midway Airport found on momondo in the last 72 hours is $887.
The fastest flight from Sao Paulo to Chicago Midway Airport takes 13h 18m
There are no direct flights from Sao Paulo to Chicago Midway Airport. Popular non-direct routes for this connection are Sao Paulo Guarulhos Intl Airport - Chicago Midway Airport and Sao Paulo Congonhas Airport - 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 21m, 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
Benton Harbor
Saint Joseph
Portage
Lansing
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?

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.


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Tue 8/5
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