CHI - GRU

$267 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Chicago to Sao Paulo

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Sao Paulo.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
9:17 am - 12:40 amORD-GRU
37h 23m2 stops
 Logo
4:10 am - 12:36 amGRU-ORD
22h 26m2 stops
Sun, May 25 - Wed, Jun 4
 Logo
7:47 am - 3:20 pmORD-GRU
29h 33m2 stops
 Logo
4:10 am - 11:29 pmGRU-ORD
21h 19m2 stops
Tue, May 27 - Fri, Jun 6
Copa Airlines Logo
7:54 am - 12:10 amORD-GRU
14h 16m1 stop
Copa Airlines Logo
1:40 am - 1:47 pmGRU-ORD
14h 07m1 stop
$657Copa Airlines
Find Deal
Wed, Jun 4 - Tue, Jun 10
Copa Airlines Logo
3:07 pm - 6:30 amORD-GRU
13h 23m1 stop
Copa Airlines Logo
11:10 am - 12:34 amGRU-ORD
15h 24m1 stop
$676Copa Airlines
Find Deal
Fri, Jun 6 - Thu, Jun 19
Air Canada Logo
10:40 am - 9:45 amORD-GRU
21h 05m1 stop
Air Canada Logo
9:00 pm - 6:21 pmGRU-ORD
23h 21m1 stop
$689Air Canada
Find Deal
Sun, May 25 - Wed, Jun 4
Air Canada Logo
2:00 pm - 9:45 amORD-GRU
17h 45m2 stops
Air Canada Logo
9:00 pm - 2:47 pmGRU-ORD
19h 47m1 stop
$695Air Canada
Find Deal
Fri, May 23 - Mon, May 26
United Airlines Logo
9:20 pm - 9:30 amORD-GRU
10h 10mnonstop
United Airlines Logo
10:20 pm - 6:45 amGRU-ORD
10h 25mnonstop
$754United Airlines
Find Deal
Sat, Jun 14 - Wed, Jun 25
United Airlines Logo
1:55 pm - 9:30 amORD-GRU
17h 35m1 stop
United Airlines Logo
10:20 pm - 6:45 amGRU-ORD
10h 25mnonstop
$759United Airlines
Find Deal
Wed, Jun 4 - Tue, Jun 17
LATAM Airlines Logo
4:22 pm - 9:00 amMDW-GRU
14h 38m1 stop
LATAM Airlines Logo
6:40 pm - 9:41 amGRU-MDW
17h 01m2 stops
$905LATAM Airlines
Find Deal
Tue, Jul 8 - Mon, Jul 14
LATAM Airlines Logo
4:26 pm - 9:00 amMDW-GRU
14h 34m1 stop
LATAM Airlines Logo
5:45 pm - 9:41 amGRU-MDW
17h 56m2 stops
$910LATAM Airlines
Find Deal
Tue, Jun 17 - Mon, Jun 23
Useful Info

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?

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 $1,033 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 $1,033.

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, Wednesday is the most expensive day to fly from Chicago to Sao Paulo. For your return ticket, we recommend flying on a Tuesday 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 April, where tickets cost $676 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $1,473 and $1,193 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 $1,682 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. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonJanuary
High seasonDecember
Cheapest flight$267
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 44% 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 $267 for a one-way ticket and $495 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, Copa Airlines or LATAM Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Sao Paulo are Copa Airlines and LATAM Airlines. With an average price for the route of $811 and an overall rating of 7.5, Copa Airlines is the most popular choice. LATAM Airlines is also a great choice for the route, with an average price of $1,040 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 $1,197 or less round-trip.

Prefer to fly direct from Chicago to Sao Paulo?

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
See more direct flights

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 1767 reviews
6.7Food
7.4Comfort
8.1Crew
7.0Entertainment
7.6Boarding
Airline reviews

I travel often with LATAM, it never disappoints me. The service is great, nice crew, latest and some classic movies. I got 3 small meals, cannot complaint. I’ll definitely travel again with them.

10.0 ExcellentRita, Apr 2025LIM - JFK
Read more LATAM Airlines reviews

I travel often with LATAM, it never disappoints me. The service is great, nice crew, latest and some classic movies. I got 3 small meals, cannot complaint. I’ll definitely travel again with them.

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

It was good, however the airplane was really cold. We received snacks and the crew was friendly.

Delta has an outstanding service. They are courteous and punctual most of the time. The flight departed a half hour late but we arrived 15 minutes early.

Change of gate in Santiago devolved into half plus hour delay and a really tight connection in Lima

Although the flight is goof and the crew is good, the way the airline charges you for every service is ridiculous.

Plane never left the ground. Mech issues - entire trip was rerouted through united.

No entertainment but not expected. Unless you are referring to monitor that you can use. Then Al, was fine on all flights.

Friendly staff, It was the first flight out for our plane, so had to be deiced from the frost. Only delayed a few minutes,

We boarded so late it caused us to miss time at Foz. No real information was provided to the passengers waiting.

My flight delayed and i misss the connection they send me to orlando no to tampa i have to pay a uber to my house

It would have been better if they don't separate families in seating. We were seated in the aile row in the middle of a family of four. It would have been better if they they seat the family of four together than separated.

I upgraded myself to Business Class at the last minute so I had a DREAMS window seat. Seeing as I've never flown Business before everything was novel and fun for me and it made the 7 hour flight much more enjoyable for sure.

The flight was delayed about 4 hours without any explanation. No wifi or entertainment at all on planes. Had to pay for checked bags I was allowed according to reservations.

It was good, plane is a bit older so seats are somewhat flat

Copa stranded us ans then tried to charge us thousands to leave Panama.

Well the airline was fine. The only thing is I was charged for a checked in luggage. But when I reserved the ticket it showed a check in bag allowed. Who can I get in contact with for reimbursement.? The airline said I had to speak to whoever I booked ticket with.

Friendly flight team and seamless travel from one stop to next.

I loved my experience. Very safe, Very informative and very friendly.

At JFK the Security line was extremely long and few checkpoints open.

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

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

All was good except for the seats, not very comfy.

2.5 hour delay sitting in the plane on the tarmac, you tell me how the experience was

I hope these comments will find their way to AC customer experience team. Me and my spouse 50 years of aged coming back from 7 days perfect vacation... While boarding in FLL flight AC1621, one of the boarding agents (tall aged african american) man literelly yeld at my wife during the picture talking process. MAM ! STEP !! BACK !!! We are not illegal immegrants beying deported, nor are we in the millitary. We are customers returning home. This was unacceptable. While boarding in YYZ flight AC1154, one of the boarding agents (tall aged caucasian) man criticied with several complesant remarks my passport condition saying that I could not travel intl with it due to stain, decoloration, and BLOOD. My passport does not have blood on it! Yes it might be in less than perfect condition, but their are ways to talk to customer that does not imply not allow a boarding agent to be angry fathery like, or a custom agent looking at a suspicious individual. Both experience were less than acceptable for might I remind you a paying CUSTOMER returning home.

Short flight so no food or entertainment. Good landing at SFO and on time. We were told no carryon luggage yet lots of people were puting bags in overhead compartments. The rules need to be made more clear. I was on the first leg of an international flight and this is the first time I could not have carryon luggage.

This flight didn't happen for me because of overbooking.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Comfortable seats and movies entertainment available. Better experience than the flight from Toronto to Denver.

Poor air traffic controller staffing led to a 50%reduction on flights so we got to wait 4 hrs for our flight! Very disorganized at the gate Poor communication with customers

It was delayed by almost 90 minutes and that messed up our plans but it was beyond UA’s control that is what we heard

Terrible experience, flight was delayed both ways. Limited compensation for the 5+ hour delay. Will not be flying Air Canada Rouge, and don’t recommend you do either.

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

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.

COP 7,000 for a cup of mediocre coffee. I thought I was on Spirit Airlines for a minute. Otherwise the flight was fine. Nothing exceptional to report.

I enjoyed it! In that case, I should have been offered this choice. On my first trip to Miami, I was asked to pay $320 for my luggage just for getting it totally broken. I cannot accept this situation at all!!!!

Be very careful of the initial low price because Avianca wil bill you for a carryon of $120 or a checked bag for $120. Also, be careful with connections because the customs entry process is slow and the connecting terminal is not close.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.