$327 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 10/22. 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

Tue, Sep 29 - Tue, Oct 20
Copa Airlines Logo
12:22 pm - 1:59 pm
SCL
-
ORD
27h 37m
1 stop
Copa Airlines Logo
8:01 am - 6:10 am
ORD
-
SCL
20h 09m
1 stop
$623Copa Airlines
Tue, Sep 1 - Sun, Sep 27
Delta Logo
8:40 pm - 4:51 pm
SCL
-
ORD
21h 11m
1 stop
Delta Logo
5:30 am - 8:15 am
ORD
-
SCL
24h 45m
1 stop
$624Delta
Mon, Aug 10 - Mon, Aug 31
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
$625Avianca
Tue, Aug 11 - Mon, Aug 24
Delta Logo
10:55 pm - 5:01 pm
SCL
-
ORD
19h 06m
1 stop
Delta Logo
1:50 pm - 7:15 am
ORD
-
SCL
16h 25m
1 stop
$626Delta
Tue, Aug 11 - Mon, Aug 31
Delta Logo
10:55 pm - 6:33 pm
SCL
-
MDW
20h 38m
2 stops
Delta Logo
10:54 am - 6:55 am
MDW
-
SCL
19h 01m
2 stops
$626Delta
Thu, Jul 23 - Thu, Oct 22
Copa Airlines Logo
11:22 am - 4:00 am
SCL
-
ORD
17h 38m
1 stop
Copa Airlines Logo
8:01 am - 12:22 am
ORD
-
SCL
14h 21m
1 stop
$627Copa Airlines
Tue, Aug 11 - Wed, Aug 19
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
$629Avianca
Wed, Oct 28 - Wed, Nov 4
United Airlines Logo
9:45 pm - 7:53 pm
SCL
-
ORD
24h 08m
1 stop
United Airlines Logo
6:00 am - 8:50 am
ORD
-
SCL
23h 50m
1 stop
$632United Airlines
Mon, Aug 17 - Mon, Aug 31
LATAM Airlines Logo
11:05 pm - 9:59 am
SCL
-
MDW
35h 54m
2 stops
LATAM Airlines Logo
4:39 pm - 7:15 am
MDW
-
SCL
13h 36m
1 stop
$635LATAM Airlines
Thu, Aug 20 - Wed, Sep 2
LATAM Airlines Logo
11:00 pm - 10:10 am
SCL
-
MDW
36h 10m
2 stops
LATAM Airlines Logo
10:54 am - 7:15 am
MDW
-
SCL
19h 21m
1 stop
$636LATAM 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 24% 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$327
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 8% 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 36,940 direct flights from within Chile to Chicago. The most common day for departures is Sunday, with 16% 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 8455 reviews
7.2Food
8.5Crew
7.8Comfort
7.8Entertainment
8.1Boarding
Airline reviews

It was as good as it could be. Flying is not a pleasant experience these days.

8.0 ExcellentMark, Jun 2026
LAX - ORD
Read more Delta reviews

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

stood in line to check in luggage for nearly an hour. very poor service and not excusable

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.

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.

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

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

horrible service, food was an embarrassment, no charging for cellphones, stay away

I would like a glass of wine or some kind of alcoholic drink.

Very long delay but we just made the connection. The requested wheel chairs were not there so I had to assist/carry BOTH of my parents to the gate while carrying their bags so we could make the connection. The plane had no entertainment system and NO WIFI, legroom zero. Restrooms on ALL of flights were dirty and one restroom did not even work properly. I was surprised to see COPA like this since my flight with them in 2013 was incredible, the seats were amazing and the food options were spectacular. Of course, I see this kind of service on many airlines now, with services and hospitality at an all time low. The worse part of the trip was seeing my 90 year old parents go through hell on these flights and having to try and rush to a gate to make the next flight. Never again

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.

The plane broke down at the Lima stopover and they offered to put me on a flight the be t day but I had to be back in LA that morning and so I had to buy another ticket from Avianca and United for $2k I asked LATAM for compensation and received none. Very bad experience

Everything was good except the check in. Could not do it online neither on the machines in the airport. Needed special assistance from the airline desk clerk

Great customer service, very accommodating. (Check in) Smooth flight, thank you Pilots. Only negative was one working bathroom in first class. Atlanta Base flight attendants were wonderful. Thank you for your smiling faces Delta..

The seats are getting smaller and smaller. Very uncomfortable trip. More than in other airlines

I do not speak Spanish or read in Spanish When asking for help, people were hard to find they spoke quickly and pointed a lot directions for where to go and what to do we’re unclear. Which made my traveling uneasy.

Flight was great Customer service was questionable until we found someone at checkin to help us. One young lady took all our passports disappeared for 15 minutes, came back with nothing done, handed to someone else and left for lunch. Very complacent. Baggage was very expensive until we went to the service counter and a separate person helped us. Even with platinum status they wouldn’t allow free bags. We will continue to fly Delta as our preferred carrier but will avoid checking in with Latam. Dr. Armand Radke

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.