CHI - GRU

$257 Find Cheap Flights from Chicago to Sao Paulo

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Sao Paulo departing on 5/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Sao Paulo Guarulhos Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sao Paulo.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sao Paulo.
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Everything you should know

Cheapest round-trip
$642
Typical prices: $1,232-$675
Arajet
Mon 5/11Wed 5/13
ORD - GRU • 1 stop
Cheapest non-stop
$1,026
Typical prices: $1,121-$846
United Airlines
Mon 7/6Fri 8/21
ORD - GRU • Non-stop
Top airlines
Cheapest • from $651 (round-trip)
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 10h 10m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 54% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $583 (round-trip)
Shortest trip • 13h 05m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 36% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 63% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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We hope you love your trip to Sao Paulo!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Sao Paulo (CHI-GRU)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Sao Paulo that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Sao Paulo

Mon, May 11 - Wed, May 13
Multiple Airlines Logo
4:30 am - 10:25 pm
ORD
-
GRU
15h 55m
1 stop
Multiple Airlines Logo
1:00 am - 4:54 pm
GRU
-
ORD
17h 54m
2 stops
$642Multiple Airlines
Mon, May 11 - Fri, May 22
Arajet Logo
4:30 am - 10:25 pm
ORD
-
GRU
15h 55m
1 stop
Arajet Logo
11:55 pm - 11:12 am
GRU
-
ORD
13h 17m
1 stop
$651Arajet
Sat, Aug 22 - Thu, Sep 3
Arajet Logo
12:12 pm - 3:08 am
ORD
-
GRU
12h 56m
1 stop
Arajet Logo
11:50 am - 11:40 pm
GRU
-
ORD
13h 50m
1 stop
$655Arajet
Sat, Jul 11 - Wed, Aug 19
Multiple Airlines Logo
7:10 am - 3:08 am
ORD
-
GRU
17h 58m
2 stops
Multiple Airlines Logo
1:00 am - 11:40 pm
GRU
-
ORD
24h 40m
1 stop
$656Multiple Airlines
Mon, Jun 1 - Tue, Jun 23
Multiple Airlines Logo
4:30 am - 10:25 pm
ORD
-
GRU
15h 55m
1 stop
Multiple Airlines Logo
3:50 am - 12:03 pm
GRU
-
ORD
34h 13m
2 stops
$660Multiple Airlines
Sat, Aug 22 - Fri, Sep 4
Arajet Logo
12:12 pm - 3:08 am
ORD
-
GRU
12h 56m
1 stop
Arajet Logo
11:55 pm - 11:12 am
GRU
-
ORD
13h 17m
1 stop
$662Arajet
Wed, Jun 3 - Tue, Jun 9
LATAM Airlines Logo
10:59 am - 5:40 am
MDW
-
GRU
16h 41m
1 stop
LATAM Airlines Logo
9:45 am - 10:07 am
GRU
-
MDW
26h 22m
2 stops
$821LATAM Airlines
Tue, Jun 2 - Tue, Jun 9
LATAM Airlines Logo
5:15 pm - 5:40 am
MDW
-
GRU
34h 25m
1 stop
LATAM Airlines Logo
9:45 am - 10:07 am
GRU
-
MDW
26h 22m
2 stops
$829LATAM Airlines
Wed, Jun 10 - Sat, Jun 13
LATAM Airlines Logo
6:05 am - 5:40 am
MDW
-
GRU
21h 35m
1 stop
LATAM Airlines Logo
5:45 pm - 10:07 am
GRU
-
MDW
18h 22m
2 stops
$832LATAM Airlines
Thu, Jun 11 - Tue, Jun 16
LATAM Airlines Logo
11:05 am - 6:05 am
MDW
-
GRU
17h 00m
2 stops
LATAM Airlines Logo
5:45 pm - 10:07 am
GRU
-
MDW
18h 22m
2 stops
$867LATAM Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Sao Paulo flights

Get data-powered insights and trends into flights from Chicago to Sao Paulo to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Sao Paulo Guarulhos Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Sao Paulo Guarulhos Intl Airport departing in May.

What is the cheapest Chicago to Sao Paulo Guarulhos Intl Airport flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Sao Paulo Guarulhos Intl Airport costs $947 on the route between Chicago O'Hare Intl Airport (ORD) and Sao Paulo Guarulhos Intl Airport (GRU). It is also the most popular route.

What’s the cheapest day of the week to fly from Chicago to Sao Paulo?

The average price of all round-trip flights from Chicago to Sao Paulo Guarulhos Intl Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Sao Paulo on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Chicago to Sao Paulo. For your return ticket, we recommend flying on a Sunday and avoiding Saturdays for the best deals.

What is the cheapest month to fly from Chicago to Sao Paulo Guarulhos Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Sao Paulo Guarulhos Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Sao Paulo Guarulhos Intl Airport is December, where tickets cost $132 (return) on average. On the other hand, the most expensive months are August and October, where the average cost of round-trip tickets is $656 and $493 respectively.

Can I save money by flying with a layover from Chicago to Sao Paulo Guarulhos Intl Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $810, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Chicago to Sao Paulo Guarulhos Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Sao Paulo Guarulhos Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Sao Paulo Guarulhos Intl Airport, you should book around 5 weeks before departure, which saves you about 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$257
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Chicago O'Hare Airport to Sao Paulo Guarulhos Airport

When to book flights from Chicago to Sao Paulo

Are your dates flexible? Find out the best times to travel from Chicago to Sao Paulo based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Sao Paulo flights

  • What is the cheapest flight from Chicago to Sao Paulo Guarulhos Intl Airport?

    In the last 3 days, the lowest price for a flight from Chicago to Sao Paulo Guarulhos Intl Airport was $257 for a one-way ticket and $642 for a round-trip.

  • Do I need a passport to fly between Chicago and Sao Paulo?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Sao Paulo.

  • Which airports will I be using when flying from Chicago to Sao Paulo?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. Sao Paulo Guarulhos Intl is the only airport in Sao Paulo. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

  • Which aircraft models fly most regularly from Chicago to Sao Paulo?

    The Boeing 787-10 Dreamliner is the aircraft model that flies most regularly on the Chicago to Sao Paulo flight route.

  • Which airline alliances offer flights from Chicago to Sao Paulo?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Sao Paulo, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Sao Paulo?

    There are nonstop flights from Chicago to Sao Paulo on a daily basis.

  • Which is the best airline for flights from Chicago to Sao Paulo, Copa Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Sao Paulo are Copa Airlines and United Airlines. With an average price for the route of $748 and an overall rating of 7.5, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $1,031 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Sao Paulo?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Sao Paulo.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Sao Paulo?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Sao Paulo from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Sao Paulo?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Sao Paulo with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Sao Paulo?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Sao Paulo from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Sao Paulo Guarulhos Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $381 or less one-way and $1,052 or less round-trip.

Prefer to fly direct from Chicago to Sao Paulo?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Sao Paulo Guarulhos Intl.
Find which airlines fly direct from Chicago to Sao Paulo Guarulhos Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago to Sao Paulo Guarulhos Intl

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Sao Paulo Guarulhos Intl to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top 5 airlines serving from Chicago to Sao Paulo

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Sao Paulo. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Sao Paulo? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.5
Copa AirlinesOverall score based on 1578 reviews
7.8Boarding
6.8Entertainment
7.4Comfort
8.1Crew
6.8Food
Airline reviews

Friendly crew, good food options, food not the best and seats not as comfy but that’s typical.

10.0 ExcellentSasha, Mar 2026
ASU - PTY
Read more Copa Airlines reviews

Friendly crew, good food options, food not the best and seats not as comfy but that’s typical.

The food is terrible I ask for water never got transport my mother we’re late and my sister from Lima was the worst waiting to long for wheelchair

Copa staff at PTY and one particular crew member were unhelpful & rude.

Horrible. No TV or any type of entertainment on board. Passwnger listening to/watching stuff on their own phone with no headphones making it noise and uncomfortable for everyone else, little/tiny food portions, old seats, useless wifi (cant access anything). Horrible exlerience especially it was a lomg distance flight with kids.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

horrible service, food was an embarrassment, no charging for cellphones, stay away

Great experience with a crew always thinking in the passenger

Honestly first time flying with delta and it was pretty good. All the process very smooth and crew was always nice and attentive.

Deleted flight made me loose my connection flight now stuck in Atlanta for a day

Apart of Sky miles delta. And they go everywhere in Brazil

There was a mechanical issue with the plane that they had to work on before we could take off. That's fine, by all means, PLEASE make sure the mechanics are functioning properly. What was a problem was the fact that we sat on the tarmac for 4.5 hours without moving, without letting us off the plane, and without climate control and air running through the plane. There was no explanation as to what was going on; they just kept promising that it would be "15 minutes, then we are on our way." At one point, they even switched the entire crew out and told everyone we just needed to wait for new employees to show up. Then, as the 4 hours were not moving, an hour before the full refund, they made a big show about "the flight starting and the doors are locked, so you have to sit down." We didn't move for another 40 minutes; they were just trying to skirt around legalities that entitled us to restitution. When the flight finally was underway, the plane was gigantic but cramped in design, my entertainment screen kept freezing and glitching, and subtitles didn't work, and the crew was passive-aggressive. Terrible flight.

We traveled with two young children, and it was not possible for our family to be seated together. No one offered help or assistance to organize seating so we could sit with our kids. In the end, we managed to find two seats in Economy so I could at least sit with one of them, even though I had originally paid for Comfort+. In summary, I had to downgrade my seat just to be able to sit with one of my children, which was very disappointing

I booked a flight through Kayak to Brazil I have traveled to Brazil several times before Kayak Delta or LATAM never mentioned during the booking or in the pre flight process that the visa requirements to visit Brazil have changed earlier this year. I was unaware of this change and as such never got a visa and was unable to fly from JFK to Sao Paulo Add to this that Delta allowed me to fly from Boston to JFK which they should not have as I didn’t have a visa. It has been a terrible experience and a huge loss of money

Latam may be the worst airline in the world, far worse than even the lowest of low cost airlines in the USA. I wasted hours trying to PAY THEM TO CHECK A BAG! Then they misled me at the terminal, sent me through the wrong security line, the list goes on and on... Just absolutely terrible in every way. Avoid at all costs.

Poor, the airline was not able to help me move flights.

The way the Pilot made all announcements, specially the way he congratulated the entire crew as the best team ever, making a comment that due to them they were able to shorter the delay to the destination. Amazing flight .

Just to drop my already labeled bag it took 50 minutes inline. Completely disappointed with Latam operation at GRU

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

Was given all 3 boarding passes. Was refused boarding to Brasilia in Miami even though I had up to date Brazilian Visa and US passport. Had to return to Phoenix as trip was cancelled. Waiting for refund of the fare. Missed my son's birthday and visit with him and his wife.

The pilots landing and taking off was very bad on the first flight, the second one taking off was great but landing was also rough

The check in and on the ground experience is very poor. Their online check and trip management is the worst I have ever seen and they have long lines to check in at the airport, technology is glitchy/unusable and have exorbitant baggage fees. The flight itself is fine, although the food is about what you would expect and their was no functioning entertainment for an international flight.

My experience with this flight was extremely negative and resulted in serious financial and personal consequences. The flight departed with a significant delay, which caused me to miss my international connecting flight. As a direct result of this delay — which was entirely beyond my control — I was unable to reach my final destination on time, causing me to lose a previously scheduled hair transplant surgery that had been arranged months in advance. This was not a minor inconvenience. The surgery involved: • A reserved operating room • Medical and technical staff scheduled specifically for that date • Surgical instruments prepared in advance • Strict scheduling that does not allow for easy rescheduling Due to the airline’s delay and poor handling of the situation: • I lost already paid international flight tickets • I was forced to purchase new tickets, incurring duplicate expenses • I spent over six additional hours in airports, under stressful conditions • I incurred unexpected costs for meals and transportation • I lost a medical opportunity that cannot be easily recovered, along with the emotional distress associated with it Although the airline covered one night of hotel accommodation, this did not address the real impact of the delay, nor the significant damages caused by missing a critical medical procedure. The lack of punctuality, planning, and effective solutions reflects a serious lack of responsibility toward passengers, especially when international connections and time-sensitive medical commitments are involved. I do not recommend this airline for travelers with important schedules, medical appointments, or critical connections. In my case, the delay did not merely cause inconvenience — it resulted in the loss of a surgery and substantial financial damage.

I was not able to get on the flight due to delays out of Philadelphia. I arrived in MIA at 10:30pm and there was no one at the GOL Desk. Is there any flight credit available for this flight?

I have a hand injury and the flight attendant denied to help me with luggage, she said "she couldn't help me because I should manage my own way to put the luggage on the plane" SO RUDE

I had two around 6 hours flight and they did not even offer water to us.

Overall it was good. The food was not great quality and seats were very uncomfortable. But overall the staff was very friendly and helpful.

We flew with Avianca, some how they are not n sync, making the process a bit uncomfortable.

Unfortunately it was very disappointed experience. Our first flight our was delayed 2 hours, as a consequence we missed our connecting international flight. Customer server at Miami American Airlines was very disrespectful, gave us the worst replace itenarary for the next day that we had to spend 2 hours calling Gol to get a better itinerary otherwise we wouldn't make it on time to fulfill our trip purpose. We would have missed the reason to travel all the way to Brazil if we didn't change for a better itinerary. The worst thing is that our baggage was missing for 4 days. We had no cloths for all this time, plus the aggravation to locate our baggage. Nobody knew where our baggage was. We ended up picking it up at the airport when they said that they will bring them home. Unfortunately our experience was very dissatisfied.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

Everything you need to know for your flight from Chicago to Sao Paulo

Information on your arrival and departure airports