$328 Find Cheap Flights from Chile to Chicago - Compare and Save

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 9/23. 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, Aug 19 - Wed, Sep 2
Avianca Logo
12:30 am - 9:20 pm
SCL
-
ORD
21h 50m
1 stop
Avianca Logo
11:20 pm - 2:15 pm
ORD
-
SCL
13h 55m
1 stop
$627Avianca
Wed, Aug 19 - Wed, Sep 2
Avianca Logo
12:30 am - 9:20 pm
SCL
-
ORD
21h 50m
1 stop
Avianca Logo
11:20 pm - 2:15 pm
ORD
-
SCL
13h 55m
1 stop
$631Avianca
Mon, Sep 28 - Tue, Oct 20
Avianca Logo
1:30 am - 9:20 pm
SCL
-
ORD
21h 50m
1 stop
Avianca Logo
11:20 pm - 3:15 pm
ORD
-
SCL
13h 55m
1 stop
$632Avianca
Thu, Aug 6 - Thu, Aug 13
Delta Logo
8:40 pm - 4:51 pm
SCL
-
ORD
21h 11m
1 stop
Delta Logo
11:22 am - 6:55 am
ORD
-
SCL
18h 33m
2 stops
$634Delta
Sun, Aug 2 - Wed, Aug 12
Delta Logo
11:00 pm - 6:33 pm
SCL
-
MDW
20h 33m
2 stops
Delta Logo
5:10 pm - 7:15 am
MDW
-
SCL
13h 05m
1 stop
$634Delta
Mon, Aug 3 - Tue, Aug 18
Delta Logo
11:00 pm - 4:51 pm
SCL
-
ORD
18h 51m
2 stops
Delta Logo
3:25 pm - 6:55 am
ORD
-
SCL
14h 30m
2 stops
$635Delta
Tue, Aug 11 - Tue, Aug 18
Avianca Logo
6:40 am - 9:20 pm
SCL
-
ORD
15h 40m
1 stop
Avianca Logo
11:20 pm - 2:15 pm
ORD
-
SCL
13h 55m
1 stop
$637Avianca
Mon, Jul 6 - Tue, Jul 14
Copa Airlines Logo
12:43 am - 4:00 am
SCL
-
ORD
28h 17m
1 stop
Copa Airlines Logo
3:21 pm - 10:43 pm
ORD
-
SCL
30h 22m
1 stop
$639Copa Airlines
Thu, Jul 9 - Sat, Aug 15
LATAM Airlines Logo
7:50 am - 10:05 am
SCL
-
MDW
27h 15m
2 stops
LATAM Airlines Logo
10:56 am - 6:00 am
MDW
-
SCL
18h 04m
2 stops
$643LATAM Airlines
Tue, Jul 28 - Tue, Aug 4
LATAM Airlines Logo
3:20 pm - 11:56 am
SCL
-
MDW
21h 36m
2 stops
LATAM Airlines Logo
6:05 am - 1:35 pm
MDW
-
SCL
30h 30m
2 stops
$644LATAM Airlines
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 month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip 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 April, where tickets cost $253 on average for return flights. On the other hand, the most expensive months are August and January, where the average cost of tickets from Chile is $600 and $587 respectively. For one-way flights, the best month to travel is February with an average price of $223.

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 7 weeks before departure, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 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 $126.

Good to know

Low seasonMarch
Cheapest flight$328
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Santiago to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • 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 32,307 direct flights from within Chile to Chicago. The most common day for departures is Sunday, 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 3 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.
7.8
DeltaOverall score based on 8423 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.2Food
7.8Entertainment
Airline reviews

Very good flight. Crew was great. No issues and we even arrived early.

10.0 ExcellentAnonymous, Jun 2026
SAN - DTW
Read more Delta reviews

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Orderly boarding, priority for platinum members, courtesy drinks from business class even when we were seating in economy.

Same as the previous flight as far as comfort and food. Entertainment didn’t have a watchable screen so everything would need to be watched on your own device in which they didn’t have a charging port that accommodated my iPhone. Seats were very uncomfortable. Staff was very friendly.

They didn’t have any headphones for the entertainment screen and their USB port didn’t accommodate a USB-C for more modern phones. The food was just ok. The staff was friendly but the seats were very uncomfortable for a full flight.

I had to run from the end of terminal one to the end of terminal two to make the connecting flight....probably a kilometer. No electric carts were available. I'm 76 and literally had to run to make the connection at the last minute. The connecting time was absolutely unrealistic. When Last Call was announced, I tried to get other Copa gate staff to call Gate 221 to let them know I was on my way, but they said no. I came within 1 minute of missing the flight.

I was flying business class, and the French fellow passengers were super noisy. It was not a comfortable flight. And the crew was not helpful.

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

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.

In flight from Miami to Anchorage, we were all on board ready to take off. Pilot decided to take on more fuel causing a delay. Once fueled, the pilot came back over the radio stating more delay due to VIP. These delays caused me to miss my connecting flight. I went to the Alaska Air counter for information. They flat out stated that it was ATCs fault that I missed my flight and booked me a flight the next day about 1300 . I believe if we had the fuel prior to getting on board we would not of been delayed and I would have taken off on time. Pilot was taken out of the equation. I think they should’ve taken responsibility for their pilots decision to top off his aircraft instead of waiting til the last moment. Enough said…

We liked the way we were treated by the sraff at lima airport counter and the the flight attendants. We did not like the fact that the kiosks at airport rebooted after we entered our information and then told us that there was an issueand we needed to go to the counter. Such a waste of time for a group of 6. Once we got our boarding passes there was no assigned gate so we did not know where to go.

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

Traveling to a place near Chicago?

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

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.