CHI - GRU

$201 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 5/25. 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
$626
Overall average: $742
Avianca
Tue 3/31Tue 4/7
ORD - GRU • 1 stop
Cheapest non-stop
$676
Typical prices: $825-$1,045
Multiple Airlines
Wed 3/18Wed 3/25
ORD - GRU • Non-stop
Top airlines
Avianca
Cheapest • from $626 (round-trip)
LATAM Airlines
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD
-
GRU
Cheapest
ORD
-
GRU
Most popular
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 59% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 24% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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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

Tue, Mar 31 - Tue, Apr 7
Avianca Logo
11:20 pm - 1:10 am
ORD
-
GRU
23h 50m
1 stop
Avianca Logo
5:15 pm - 9:20 pm
GRU
-
ORD
30h 05m
1 stop
$626Avianca
Sun, Mar 8 - Fri, Sep 4
Multiple Airlines Logo
11:20 pm - 4:15 pm
ORD
-
GRU
14h 55m
1 stop
Multiple Airlines Logo
10:37 pm - 9:57 am
GRU
-
ORD
13h 20m
1 stop
$628Multiple Airlines
Mon, Feb 16 - Sun, Mar 1
Multiple Airlines Logo
5:45 am - 10:20 pm
ORD
-
GRU
13h 35m
1 stop
Multiple Airlines Logo
5:25 pm - 8:20 pm
GRU
-
ORD
29h 55m
1 stop
$629Multiple Airlines
Sat, Mar 21 - Sun, Mar 29
Multiple Airlines Logo
11:27 am - 3:10 am
ORD
-
GRU
13h 43m
1 stop
Multiple Airlines Logo
2:20 am - 9:20 pm
GRU
-
ORD
21h 00m
1 stop
$630Multiple Airlines
Sun, Mar 8 - Wed, Sep 2
Multiple Airlines Logo
11:20 pm - 4:15 pm
ORD
-
GRU
14h 55m
1 stop
Multiple Airlines Logo
1:00 am - 6:15 pm
GRU
-
ORD
19h 15m
2 stops
$631Multiple Airlines
Sun, Feb 22 - Thu, Feb 26
Copa Airlines Logo
2:22 pm - 3:50 am
ORD
-
GRU
34h 28m
1 stop
Copa Airlines Logo
3:10 am - 12:31 pm
GRU
-
ORD
36h 21m
1 stop
$636Copa Airlines
Tue, Feb 24 - Sat, Mar 21
LATAM Airlines Logo
12:45 pm - 12:45 pm
MDW
-
GRU
21h 00m
2 stops
LATAM Airlines Logo
11:55 pm - 5:22 pm
GRU
-
MDW
19h 27m
2 stops
$699LATAM Airlines
Fri, Mar 13 - Fri, Mar 20
Delta Logo
10:45 am - 5:40 am
MDW
-
GRU
16h 55m
1 stop
Delta Logo
10:40 am - 10:31 pm
GRU
-
MDW
13h 51m
1 stop
$700Delta
Wed, Mar 18 - Wed, Mar 25
LATAM Airlines Logo
6:07 pm - 9:35 am
MDW
-
GRU
13h 28m
1 stop
LATAM Airlines Logo
11:45 pm - 12:02 pm
GRU
-
MDW
14h 17m
1 stop
$701LATAM Airlines
Fri, Mar 13 - Fri, Mar 20
Delta Logo
1:10 pm - 5:55 am
MDW
-
GRU
14h 45m
2 stops
Delta Logo
10:40 am - 10:31 pm
GRU
-
MDW
13h 51m
1 stop
$705Delta
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.

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 $685 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 Monday, 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 Sunday and avoiding Fridays 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 $604 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $1,094 and $987 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 1 stop layover the cheapest option at $793 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 59% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$201
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 38% 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 $201 for a one-way ticket and $626 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, Delta or Copa Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Sao Paulo are Delta and Copa Airlines. With an average price for the route of $748 and an overall rating of 7.9, Delta is the most popular choice. Copa Airlines is also a great choice for the route, with an average price of $706 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 $770 or less one-way and $893 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 1918 reviews
7.5Boarding
7.3Comfort
7.0Entertainment
6.7Food
8.0Crew
Airline reviews

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.

2.0 MediocreJess, Jan 2026
BSB - GRU
Read more LATAM Airlines reviews

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

I’m entitled to a refund per LATAM due to the mid flight itinerary change and being stuck in São Paulo for 24 hours and needing to get a hotel. The airline was dismissive and of no help.

The flight was late. Please do not delay next time.

I couldn't travel, now I can't get a refund and to change the date I have to pay an absurd fine.

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

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)

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

The movies offered were great. Staff were very pleasant and very efficient.

The plane was delayed substantially due to a mechanical problem, that being said, the airline was very fair with providing a meal coupon for us. I would rather arrive late on a mechanically sound plane than the alternative. The food served in the plane was just awful, however and I recommend a new catering company.

I waiting for 2 hrs to retrieve my luggage. Didn't get home till 3am.

The flight left late and I didn’t get a glass of bubbly upon boarding (which I’m used to when booking business class on other flights), but otherwise it was a pleasant flight with lovely, helpful crew members and I enjoyed my meal.

Flight cancellations, delays, mass confusion and disorganization! That’s Air Canada for you, nothing new. I would have chosen a different airline if it were an option, and Air Canada continues to prove they don’t care about their customers.

everything was fine. but paying for 1 piece of check-in luggage and denying passengers to board with carry-on luggage which by air line's standards does not fit is not acceptable. when one travels for a longer time one needs to have some essentials

Couldn't fit knees, only 1 toilet working, didn't get anything to drink cause the stewards were not able to get to us

Flight was canceled for a reason they knew hours before but did not mention. Next the gate chnage from 37 to 38 at least 10 times. Ridiculous.

The flight from SFO to YVR was delayed and my bag did not make it to my next flight from YVR to SYD. It took almost 3 days after I landed to get my bag and when I got it, it was filled with dust

Our biggest complaint about Air Canada is that if you don’t like your seat during check-in, there’s a fee to move elsewhere. On our flight from YUL to FFL, we were charged to change seats—just regular seats. What’s maddening is that the plane wasn’t even full; there were even a few people sleeping in the middle row sections (entire rows, completely empty), using them as beds. In my opinion, charging passengers for seat changes is a cash grab by Air Canada. They are definitely not the airline they were back in the day. I suppose they need to gouge the consumer now that they pay their attendants while on ground. One out of 10.

Nothing specific. Cabin temperature was too high for some reason.

Boarding was late due to the company’s that cleaned the aircraft (very poorly done) and the catering company. The entertainment system was not working for this six hour flight, uncomfortable seats in business (barely any cushion or recline). The airline staff is very good but the planes are horrible and not well maintained.

Deplaning was a mess, I sat in business (seats are horrible) and the front door had a problem so we had to deplane from the rear exit. The stairs were not tall enough to reach so there was a large step down from the plane to the top of the stairs.

Staff are the rudest in the industry … awful customer service … will never fly Avianca again

Pros: we leave and arrive on time Cons: the most uncomfortable seats ever. You cant recline at all your seats. No entertainment No TVs flight attendants didn't provide even a glass of water. You have to go to back of the airplane and ask for one. I am Colombian and I remember seeing the flight attendants very neat, elegants which is or was a staple of Avianca.it was one with tennis shoes, no male up, the hair was messy... that was really odd.

Here we have another airline flying to Guatemala but doesn't have a plus or a less, just in the middle. Why? Well, first we don't have even free water Movie selection is poor Seats don't recline in some places Food selection is carb based Forgot to mention, customer service on the web is the worst. Good things; Very reliable on schedule Kind crew

Last seat of Bussines Class it does recline but passenger seating behind kept pushing since they did not have space once my seat was reclined

We waited for one hour to deboard the plane after landing. That could be better

I like the crew they're very friendly. I don't like. on five hour flight they not offered snacks. Any drink. Not even coffee

Not even water is offered on the flight. You cannot lean back on the seats and the seats are so narrow you can’t avoid rubbing elbows with the person next to you.

I couldnt recline the seat. Other than that crew was very attentive and helpful. Thsnk you

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

Information on your arrival and departure airports