CHI - GRU

$203 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 11/15. 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

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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Sao Paulo, as well as popular online travel agencies
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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, Nov 3 - Sat, Nov 15
 Logo
8:56 pm - 2:40 amORD-GRU
26h 44m3 stops
 Logo
4:10 am - 9:10 pmGRU-ORD
20h 00m1 stop
Sun, Jan 18 - Sat, Jan 31
Arajet Logo
3:30 am - 10:20 pmORD-GRU
15h 50m1 stop
Arajet Logo
4:10 am - 9:10 pmGRU-ORD
20h 00m1 stop
$542Arajet
Find Deal
Mon, Nov 10 - Sat, Nov 22
 Logo
6:05 am - 3:25 pmORD-GRU
30h 20m2 stops
 Logo
4:10 am - 9:10 pmGRU-ORD
20h 00m1 stop
Mon, Nov 3 - Sat, Nov 15
 Logo
7:00 pm - 2:40 amORD-GRU
28h 40m3 stops
 Logo
4:10 am - 9:10 pmGRU-ORD
20h 00m1 stop
Mon, Nov 10 - Sat, Nov 22
 Logo
7:30 pm - 2:40 amORD-GRU
28h 10m3 stops
 Logo
4:10 am - 9:10 pmGRU-ORD
20h 00m1 stop
Mon, Nov 10 - Sat, Nov 22
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7:30 pm - 2:40 amORD-GRU
28h 10m3 stops
 Logo
4:10 am - 9:10 pmGRU-ORD
20h 00m1 stop
Thu, Nov 13 - Mon, Nov 17
LATAM Airlines Logo
3:35 pm - 11:30 amORD-GRU
16h 55m2 stops
LATAM Airlines Logo
4:00 am - 11:53 pmGRU-ORD
22h 53m2 stops
$567LATAM Airlines
Find Deal
Thu, Aug 14 - Tue, Aug 19
LATAM Airlines Logo
10:31 am - 5:40 amMDW-GRU
17h 09m1 stop
LATAM Airlines Logo
5:40 pm - 11:48 amGRU-MDW
20h 08m2 stops
$567LATAM Airlines
Find Deal
Wed, Sep 24 - Thu, Oct 2
Delta Logo
10:35 am - 5:40 amMDW-GRU
17h 05m1 stop
Delta Logo
10:50 pm - 11:48 amGRU-MDW
14h 58m1 stop
$1,059Delta
Find Deal
Wed, Dec 24 - Wed, Jan 7
Delta Logo
10:08 am - 9:35 amMDW-GRU
20h 27m1 stop
Delta Logo
11:05 pm - 4:25 pmGRU-MDW
20h 20m2 stops
$1,063Delta
Find Deal
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?

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Sao Paulo Guarulhos Intl Airport.

Our data shows that the cheapest route for a return flight from Chicago to Sao Paulo Guarulhos Intl Airport cost $646 and was between Chicago O'Hare Intl Airport (ORD) and Sao Paulo Guarulhos Intl Airport (GRU). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $646.

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, Friday is the most expensive day to fly from Chicago to Sao Paulo. For your return ticket, we recommend flying on a Monday and avoiding Sundays 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 April, where tickets cost $646 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $1,403 and $1,034 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $1,844 on average.

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 2 weeks before departure, which saves you about 57% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$203
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly with an average 57% 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 $203 for a one-way ticket and $537 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?

    Star Alliance is the only airline alliance operating flights between Chicago and Sao Paulo.

  • 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, LATAM Airlines or Copa Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Sao Paulo are LATAM Airlines and Copa Airlines. With an average price for the route of $1,046 and an overall rating of 7.5, LATAM Airlines is the most popular choice. Copa Airlines is also a great choice for the route, with an average price of $693 and an overall rating of 7.5.

  • 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 $345 or less one-way and $804 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
LATAM AirlinesOverall score based on 1822 reviews
8.1Crew
7.6Boarding
7.0Entertainment
7.4Comfort
6.7Food
Airline reviews

Bought a ticket that included a bag and they still charged me to check it in, latam is the worst airline.

2.0 MediocreWertson, Jul 2025VIX - GRU
Read more LATAM Airlines reviews

Bought a ticket that included a bag and they still charged me to check it in, latam is the worst airline.

I never got this flight. You sent me to Chile!!! And from Chile I got the other flight to São Paulo... I've arrived 7h latter than I was supposed to arrive because of Delta delays.

Because the flight was late, we lost the connection to Brazil. You, Delta delayed, and you Delta anticipated the door closing in 15 min from Miami to GRU. Why? It caused a lot of stress! I almost could not see my mother in law alive because of your delay.

Lost ,y connection due to a mechanical delay, huge line to get new connection and vouchers

Boarding was done by woman who insisted on strict standing in line policy; food was ok; entertainment minimal

The boarding and new bag drop-off process was confusing and causing massive delays.

Wider seats, better seat cushions, (I felt like there was a board I was sitting on). I had the chicken to eat but It neither tasted nor looked like chicken. The fruit was good.

It was a very good flight, no entertainment is the reason for not checking that box.

I was in the last row and they sent me to check in my luggage last minute after boarding. I had to go through the crowd.

We didn’t have any entertainment. I tried to go online without success. The airplane was extremely cold and they didn’t have blankets.

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

Great experience with a crew always thinking in the passenger

I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.

Very happy with my flight. I would definitely recommend it.

Did upgrade, travel in business it was great (more room I could sleep)

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

It was ok. However, the food was quite poor since I don't eat pasta.

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

Terrible. Out flight was delayed for 21 (twenty one) hours. United is a joke.

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Both flights are delayed so I rate the whole experience as mediocre.

I booked my flight months ago, and checked-in online about 12 hours before the flight. I received an email confirmation of check-in. I had no subsequent communication from Air Canada after my original booking. After arriving at the airport three hours before the flight, as instructed, I waited 90 minutes for an agent to appear to check my bag. I was informed that my flight had been canceled many weeks before, and that flight was no longer being run!! I showed a copy of my check-in confirmation, but no explanation could be found. I was placed on standby for the next flight and the connection. Luckily, those flights were not full and I arrived at my destination. I double checked my email, but I received no update about the flight from Air Canada until the day of the flight.

I had a good experience. I liked being informed about the status of my luggage

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

I was forcefully re-routed to another destination and was delayed a total of 8hours. I have still not received my bags, no one is taking responsibility. The agents at the airport lied to me that I will get to my destination same time as my previous flight where I was forcefully re-routed from.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Our flight was canceled at the last minute. Someone on the flight said the exact same thing happened to her the day before. I will say they helped us book a flight on another airline so that we could still make our vacation with little delay.

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

We had a very long delay. First the inbound flight took a while, then maintenance, they “fixed it” to then do boarding and leave the gate, and waste a lot of time to have to go back to the gate and eventually deplane. Had to wait for a new aircraft, wait for a gate, and do the whole thing again. Instead of leaving at 9:50am we left until past 1. I could’ve not woken up at 5am, or spend some more time with my family if they gave more grace period of time between flights to give some time in case of any issues. But they have to make all and every dollar possible

Aircraft had technical issues. After 3 hours of trying to resolve, flight was cancelled. Was booked on a flight leaving 12 hours after intended departure. Now on 4 flights instead of 2 and a day late to my destination.

Boarding was excessively slow. They do it by groups in a way that it doesn’t make sense. After business class , ppl that need assistance and any other priority group they should have ppl board from the back to the front. First rows 20+. Then 15+. Then 10, etc. having ppl sitting in the back board last makes no sense. The libe backame long as soon as ppl on rows 10 or so where told to board. The line went all the way up the ramp and tunnel for 25 mins.

Seats are very tight even in Plus, no complimentary snacks or beverage

I receive a service for what I pay, so it is fair.

A few years ago long flights 6 hours or so used to have video screens and they offered ear phones. The food cart used to come and drinks. Now absolutely nothing. Avianca is as bad as Spirit Airlines. Avianca will now be my last choice when booking my next flight.

There isn't much space in-between seats and even water needs to be paid for during the flight.

We did not know about the bag fees until check in. They are way too high. It’s insane. We also had a huge delay and everything costed extra which was very annoying.

Boarding was somewhat confusing in that the wrong messages were being displayed at the gate. It was somewhat annoying that I got off one flight and straight onto another (from the same gate), but in between they re-checked my hand luggage and made me get rid of my water (which they charge for on the plane). I was sitting in their 'Plus' seating, but the leg room was still too small to be able to sit square. The food options on the flights are pretty cheap quality (but not price). They got me from 'A' to 'B' on-time and for a relatively good price, but the experience itself was below average.

Lounge for business was closed. Boarding was rush and stand by. Seat for business is just the middle seat blocked and some more leg room.

Flew with our two children. Paid $380 to check two bags (one was overweight). They then left the bags behind on Sunday, December 21st, with all our family’s clothes and family Christmas presents. When we arrived at our destination they told us the bags had not arrived, and they thought (but didn’t know) they were still in Boston, but that there’d be a flight the next day and the bags would arrive the next day. The next day we found out there was no flight, now we’re hoping we get our bags before we fly back out. Meanwhile, trying to get any engagement or accurate information is a waste of time. The folks at the call center are just gatekeepers, who can’t connect with any departments that actually do things to solve a problem. Getting information is made deliberately difficult. My biggest regret is that I’ve had a number of awful experiences with Avianca traveling between the US and Colombia, and still let myself get suckered into buying these tickets because the schedule was great. Never again.

We were not aware carry-on bags cost extra until we arrived at the airport so, we were charged $240.00 for two small carry- on bags! There was a substantial fee for drinks and snacks. No wifi, or other entertainment was available. Waiting areas were crowded and uncomfortable.

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