$292 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 4/22. 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

Fri, Apr 24 - Sun, May 3
Multiple Airlines Logo
12:55 am - 11:59 pm
SCL
-
ORD
24h 04m
2 stops
Multiple Airlines Logo
3:52 pm - 11:05 am
ORD
-
SCL
42h 13m
2 stops
$506Multiple Airlines
Fri, Apr 24 - Fri, May 8
Multiple Airlines Logo
11:35 am - 11:59 pm
SCL
-
ORD
37h 24m
2 stops
Multiple Airlines Logo
7:15 pm - 1:30 pm
ORD
-
SCL
41h 15m
2 stops
$523Multiple Airlines
Fri, Apr 24 - Fri, May 8
Multiple Airlines Logo
11:35 am - 11:59 pm
SCL
-
ORD
37h 24m
2 stops
Multiple Airlines Logo
7:15 pm - 5:30 am
ORD
-
SCL
33h 15m
2 stops
$528Multiple Airlines
Sun, Apr 26 - Tue, May 5
Delta Logo
8:40 pm - 9:56 am
SCL
-
MDW
14h 16m
1 stop
Delta Logo
5:21 pm - 7:15 am
MDW
-
SCL
12h 54m
1 stop
$577Delta
Tue, Mar 10 - Tue, Mar 31
Delta Logo
11:25 pm - 5:22 pm
SCL
-
MDW
19h 57m
2 stops
Delta Logo
10:45 am - 5:35 am
MDW
-
SCL
16h 50m
2 stops
$578Delta
Tue, Mar 10 - Sat, Mar 14
Delta Logo
10:25 pm - 9:56 am
SCL
-
MDW
13h 31m
1 stop
Delta Logo
6:34 pm - 7:40 am
MDW
-
SCL
35h 06m
2 stops
$579Delta
Tue, Apr 14 - Mon, Apr 27
LATAM Airlines Logo
6:45 pm - 12:07 pm
SCL
-
MDW
18h 22m
2 stops
LATAM Airlines Logo
12:52 pm - 6:55 am
MDW
-
SCL
17h 03m
2 stops
$581LATAM Airlines
Tue, Apr 14 - Mon, Apr 27
LATAM Airlines Logo
6:45 pm - 12:07 pm
SCL
-
MDW
18h 22m
2 stops
LATAM Airlines Logo
12:52 pm - 6:55 am
MDW
-
SCL
17h 03m
2 stops
$582LATAM Airlines
Tue, Apr 14 - Sat, Apr 25
LATAM Airlines Logo
7:55 pm - 12:07 pm
SCL
-
MDW
17h 12m
2 stops
LATAM Airlines Logo
10:41 am - 7:15 am
MDW
-
SCL
19h 34m
1 stop
$586LATAM Airlines
Wed, Apr 22 - Sun, Apr 26
LATAM Airlines Logo
11:05 pm - 10:28 pm
SCL
-
MDW
24h 23m
2 stops
LATAM Airlines Logo
5:21 pm - 2:05 pm
MDW
-
SCL
19h 44m
2 stops
$587LATAM 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 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 $513 on average for one-way flights. On the other hand, the most expensive months are January and July, where the average cost of tickets from Chile is $1,118 and $797 respectively. For return trips, the best month to travel is April with an average price of $513.

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 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 27 days 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, with an average flight price of $141.

Good to know

Low seasonJanuary
Cheapest flight$292
Best time to beat the crowds but there is an average 52% increase in price.
Most popular time to fly and prices are also 30% 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 11,872 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 4 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 8237 reviews
8.5Crew
7.8Entertainment
7.2Food
7.9Comfort
8.1Boarding
Airline reviews

alike schedule and times it’s very good for me, I will stay wad delta for ever

10.0 Excellentomar, Feb 2026
RAK - ATL
Read more Delta reviews

alike schedule and times it’s very good for me, I will stay wad delta for ever

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

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

Good check in process Poor information on payments at Lima airport

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

we were missing our luggage, trying to find someone to have any empathy was pretty much not happening....

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

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

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

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.

I like the crew members they're very friendly. Clean plane. The flight was on time. I dont like the comfort my car seat its better that the plane seats. They charge for everything. This airline was very good. Now it's a low cost airline

No free snacks nor drinks on very short 30min flight. Entertainment system is over wifi to your own phone or tablet, which is good but often a show or movie just stops and refuses to continue

I had to go to the boarding counter for them to enter my return flight as it’s not with Avianca. There was a long queue as there were lots of people being called to the counter.

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
Chesterton
Munster
Schererville
Porter
Monticello
Griffith
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.