CHI - GRU

$218 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 2/11. 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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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

Wed, Nov 26 - Fri, Dec 5
Copa Airlines Logo
6:56 am - 12:15 amORD-GRU
14h 19m1 stop
Copa Airlines Logo
1:40 am - 12:52 pmGRU-ORD
14h 12m1 stop
$448Copa Airlines
Find Deal
Tue, Nov 18 - Tue, Nov 25
Copa Airlines Logo
6:56 am - 12:10 amORD-GRU
14h 14m1 stop
Copa Airlines Logo
1:30 am - 12:46 pmGRU-ORD
14h 16m1 stop
$454Copa Airlines
Find Deal
Wed, Nov 26 - Sun, Dec 7
Avianca Logo
10:20 pm - 4:15 pmORD-GRU
14h 55m1 stop
Avianca Logo
2:40 am - 8:20 pmGRU-ORD
20h 40m1 stop
$478Avianca
Find Deal
Thu, Nov 13 - Sun, Nov 16
Avianca Logo
10:20 pm - 10:40 pmORD-GRU
21h 20m1 stop
Avianca Logo
2:40 am - 8:20 pmGRU-ORD
20h 40m1 stop
$485Avianca
Find Deal
Thu, Feb 12 - Wed, Feb 18
GOL Logo
2:05 pm - 10:40 pmORD-GRU
29h 35m1 stop
GOL Logo
1:20 am - 12:15 pmGRU-ORD
13h 55m1 stop
$486GOL
Find Deal
Wed, Nov 12 - Fri, Nov 14
GOL Logo
10:20 pm - 10:40 pmORD-GRU
21h 20m1 stop
GOL Logo
2:40 am - 8:20 pmGRU-ORD
20h 40m1 stop
$503GOL
Find Deal
Mon, Nov 17 - Wed, Nov 26
Delta Logo
5:34 pm - 9:35 amMDW-GRU
13h 01m1 stop
Delta Logo
9:15 pm - 9:52 amGRU-MDW
15h 37m1 stop
$600Delta
Find Deal
Sat, Apr 11 - Sat, Apr 25
Delta Logo
10:35 am - 5:40 amMDW-GRU
17h 05m2 stops
Delta Logo
11:05 pm - 11:56 amGRU-MDW
14h 51m2 stops
$605Delta
Find Deal
Fri, Mar 13 - Sat, Mar 21
LATAM Airlines Logo
10:35 am - 5:40 amMDW-GRU
17h 05m1 stop
LATAM Airlines Logo
11:45 pm - 12:01 pmGRU-MDW
14h 16m1 stop
$620LATAM Airlines
Find Deal
Mon, Dec 1 - Sat, Dec 6
LATAM Airlines Logo
12:47 pm - 5:40 amMDW-GRU
13h 53m1 stop
LATAM Airlines Logo
11:45 pm - 11:55 amGRU-MDW
15h 10m1 stop
$622LATAM Airlines
Find Deal

Everything you should know

Top airlines
Copa Airlines
Cheapest • from $448 (round-trip)
Copa Airlines
Best reviews • 7.6 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 48% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 23% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$448
Overall average: $906
Copa Airlines
Wed 11/26Fri 12/5
ORD - GRU • 1 stop
Cheapest non-stop
$656
Typical prices: $754-$1,334
United Airlines
Fri 11/28Tue 12/9
ORD - GRU • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Sao Paulo!
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 November.

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 $485 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 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 $646 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $1,045 and $1,005 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 $567 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 48% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$218
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 24% 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 $218 for a one-way ticket and $448 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, SkyTeam, 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 $687 and an overall rating of 7.6.

  • 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 $303 or less one-way and $778 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.
7.6
Copa AirlinesOverall score based on 1563 reviews
7.8Boarding
6.8Entertainment
8.1Crew
7.4Comfort
6.8Food
Airline reviews

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

6.0 GoodZach, Oct 2025DEN - PTY
Read more Copa Airlines reviews

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.

Cops Airlines is fantastic! The level of care and professionalism provided by the entire crew was top rate.

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.

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.

Boarding was confusing with a delayed flight because there was no English translation

My biggest complaint is the comfort. I am not tall and there was no legroom. It was very uncomfortable. During my transfer in Sao Paola, the flight was slightly delayed so boarding was confusing because there were no instructions in English.

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

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Allow me to book extra bag check in as free though I packed in 1 luggage but that was 7 LBS overweight so make another bag to free check in.

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

My seat was one of those that couldn't recline, but the problem was that it was abnormally upright, so the headrest actually made the seat concave, which was uncomfortable and hard on my lower back. I had to ball my jacket up and use it as lumbar support. goodness I had it with me.

Boarding was so so after zone 3 was called all other zones went in

I liked a lot , the flight attendant so nice ,the seat very comfortable I enjoyed the flight , I will do it again with Air Canada,

Plane left an hour late, I missed my connection and my bow case was never even loaded on the plane in VA. I deal with this type of nonsense everytime I fly air canada.

For goodness sake, board from the back of the plane to the front and assign overhead space. It would fix everything. Seriously.

Elderly female flight attendant was not customer friendly. There were only about 12 people on a regional jet that had about 60 seats. There were 8 exit row seats and none of them were taken. We attempted to sit in those seats and the flight attendant gave the standard " you didn't pay for those" so she would not allow us to move. What harm would that have caused ? They assigned seats to 5 of the 12 people in 2 rows, row 20 and 21. A simple friendly customer experience gesture of allowing us to sit in exit rows would have gone a long way in me having a very favorable impression on Air Canada. After that I have very poor impression of Air Canada and will not fly with them when I can avoid it.

It was a smooth flight both in the sky and landing!

Horrible experience. Flight cancelled. Arrived at destination 12 hs later. No one gave us an answer or any information. Very very poor service. We won’t ever travel again with Avianca

Did not fly with Pakistan International Airlines. Have never flown with Pakistan International Airlines.

Boarding, crew were excellent, food was ok and entertainment need to improve

Luggage lost and nowhere to be found, no response from either airline regarding my bag

The seats were uncomfortable and barely reclined at all. Very little leg room despite being business class. The crew was friendly and the food was good. Had to use my own phone for in-flight entertainment.

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.

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