$309 Find Cheap Flights from Chile to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/5. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Chile to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chile to Chicago 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 Chile to Chicago

Wed, Oct 7 - Wed, Oct 14
LATAM Airlines Logo
10:55 pm - 5:34 pm
SCL
-
ORD
20h 39m
1 stop
LATAM Airlines Logo
1:15 pm - 6:55 am
ORD
-
SCL
15h 40m
2 stops
$620LATAM Airlines
Thu, Aug 20 - Wed, Sep 2
LATAM Airlines Logo
10:55 pm - 5:41 pm
SCL
-
ORD
19h 46m
1 stop
LATAM Airlines Logo
1:15 pm - 6:55 am
ORD
-
SCL
16h 40m
2 stops
$621LATAM Airlines
Thu, Jul 30 - Wed, Aug 19
LATAM Airlines Logo
10:55 pm - 5:45 pm
SCL
-
ORD
19h 50m
1 stop
LATAM Airlines Logo
1:15 pm - 6:55 am
ORD
-
SCL
16h 40m
2 stops
$622LATAM Airlines
Thu, Oct 8 - Tue, Oct 13
LATAM Airlines Logo
10:55 pm - 5:34 pm
SCL
-
ORD
20h 39m
1 stop
LATAM Airlines Logo
10:40 am - 5:35 am
ORD
-
SCL
16h 55m
2 stops
$625LATAM Airlines
Thu, Oct 8 - Tue, Oct 13
LATAM Airlines Logo
10:55 pm - 5:34 pm
SCL
-
ORD
20h 39m
1 stop
LATAM Airlines Logo
1:30 pm - 6:25 am
ORD
-
SCL
14h 55m
1 stop
$628LATAM Airlines
Mon, Aug 10 - Mon, Aug 24
LATAM Airlines Logo
10:55 pm - 5:41 pm
SCL
-
ORD
19h 46m
1 stop
LATAM Airlines Logo
1:15 pm - 6:55 am
ORD
-
SCL
16h 40m
2 stops
$629LATAM Airlines
Wed, May 27 - Wed, Dec 2
LATAM Airlines Logo
10:55 pm - 5:54 pm
SCL
-
ORD
19h 59m
1 stop
LATAM Airlines Logo
1:15 pm - 7:40 am
ORD
-
SCL
15h 25m
1 stop
$631LATAM Airlines
Mon, Oct 5 - Sun, Oct 11
LATAM Airlines Logo
11:00 pm - 2:13 pm
SCL
-
ORD
17h 13m
2 stops
LATAM Airlines Logo
1:15 pm - 6:55 am
ORD
-
SCL
15h 40m
2 stops
$633LATAM Airlines
Thu, Aug 20 - Wed, Sep 2
Delta Logo
11:00 pm - 4:27 pm
SCL
-
MDW
18h 27m
2 stops
Delta Logo
1:00 pm - 7:15 am
MDW
-
SCL
17h 15m
2 stops
$646Delta
Tue, Sep 1 - Thu, Sep 17
Delta Logo
8:40 pm - 9:50 am
SCL
-
MDW
14h 10m
1 stop
Delta Logo
6:00 am - 8:15 am
MDW
-
SCL
24h 15m
1 stop
$647Delta
Booking Insights

KAYAK's insights & trends for flights to Chicago

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

What is the cheapest flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Santiago, at $620 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $120 in the last 3 days.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, 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 to Chicago is March, where tickets cost $645 on average for return flights. On the other hand, the most expensive months are January and May, where the average cost of tickets from Chile is $1,118 and $808 respectively. For one-way flights, the best month to travel is March with an average price of $645.

How far in advance should I book a flight to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, 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, you should book around 8 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $179.

Good to know

Low seasonMarch
Cheapest flight$309
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Santiago to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Santiago, at $620 return. The most popular connection is from New York to Chicago and KAYAK users have found round-trip deals for as low as $120 in the last 3 days.

  • Which Chicago airport is closest to central Chicago?

    There are 3 airports in Chicago. The closest airport to Chicago’s city center is Chicago Midway Airport (9 miles). Chicago O'Hare Airport and Chicago Greater Rockford are respectively 16 miles and 79 miles from the center of Chicago.

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

    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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 to Chicago?

    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 Chicago with an airline and back with another airline.

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

    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 Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago are there each week?

    Each week there are around 13,219 direct flights from within Chile to Chicago. The most common day for departures is Thursday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top 5 airlines serving from Chile to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Chile to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? 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.
7.9
DeltaOverall score based on 8404 reviews
7.2Food
8.1Boarding
8.5Crew
7.9Comfort
7.8Entertainment
Airline reviews

The tray table was broken and the food was terrible.

4.0 OkayJeremy, Apr 2026
BNA - BOS
Read more Delta reviews

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

Boarding was confusing from staff telling going to preboard and than to group 1 Airplane was not cooling at the beginning

Avoid at all costs. My wife had to stay back on a connecting flight as her parents flight was delayed. 10 days later on the way back they cancelled all our flights. We had to rebook all four of us on the next days flight.

Do not book it’s a scam! They stole $1200 from me

Flight got delayed; had to go through security three times.

A lot things happened in this trip.The fly should be less stress.

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

Some of the Air hostesses are not that friendly. Need improvement

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

They were super friendly bumped me up to exit row free of charge, All flight legs were on time

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

Nothing I like, I missed this connection b/c of an earlier flight delay. I had to stay one more night and I paid out my own pocket. LATAM failed to send me to a safe and decent hotel.

It was delayed for 2 hours. Then when we arrived they took us on a very uncomfortable bus and left us there. The bus driver wouldn't let us out because no one from Latam was there. Everything was disaster.

LATAM is a great airline who takes care of there guests. They consistently walk around and see if you need water in addition to taking care of all the passengers. The chicken in process is really easy and I’m always offered a chance for an upgrade which I appreciate.

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

Latam wouldn’t tell me how much checked luggage would until I was at the airport and they charged me the highest price possible. Besides that, it was okay.

Comfort in exit seat was excellent. FLight crew and flight were excellent. However exit seat tray table was broken so could not use it. Entertainment monitor did not work at all despite attempts to reset it.

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

Wish the seats were a little more comfortable.. it was a 6 hrs nonstop trip. But the crew was courteous and w a smile

I like this airline a lot no problems at all, except being forced to check a carry-on bag ., Overall very good airline

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

After boarding, there was a small issue with the aircraft which caused a delay of about 45 minutes. During boarding and while passengers were being seated, the plane was being refueled. There were also a lot of unusual noises during the flight, which was not very reassuring. In addition, there was no WiFi or entertainment available.

Overall, the flight went well and the service was good. However, there was a very frightening moment during landing in Bogotá. Just as the plane was about to touch down, it suddenly went back up into the air. The aircraft was not descending straight and seemed to move left and right, which made the situation feel unstable. This was quite scary. After going back up, the plane circled for about 15 minutes before attempting to land again. Although I understand that safety always comes first and situations like this can happen, it was still a shocking experience for passengers.

Seating was tight. Seats don't recline. Initial flight was cancelled. Lost two days of vacation.

Horrible experience with Avianca, they delayed their flight and when we arrived to NYC, AVIANCA took 1 hr y 30 mins to park the airplane and all passenger get off the plane, it made me lost all my trains to get back home and I came back to my place at 3 am instead of 12 am. On the top of that their plane seat are so uncomfortable and is not enough space and killed my legs and knees, Avianca used to be good when it was a Colombian company, now after Brasilian company bought them, their service quality is bad and their flights are delayed and oversold.

It was delayed and I lost my connection flight to Cali and I missed my Mom's funeral

only a bag of chips and a bottle of water in business class was served

We found the chairs to be really uncomfortable. It’s also really unacceptable that no form of food or drink is included in a 6+ hour flight

The flight attendant smashed her beverage cart into my knee, causing significant amount of pain. The seats were extremely uncomfortable. No food or drink is offered unless you want to pay the ridiculous prices for it. The schedule of flying in the overnight hours is also very uncomfortable.

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

I handed in my suitcase in perfect condition at SAL Airport. And in MIA Airport I received it with one corner broken and the wheels bent.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
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Lansing
Valparaiso
Chesterton
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Munster
Porter
Monticello
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Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.