$157 Find Cheap Flights from Chicago Midway Airport to South America

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to South America departing on 2/15. 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

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Cheap Flights from Midway to South America

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Lima
Lima1 stop$490
Bogotá
Bogotá1 stop$327
Santiago
Santiago1 stop$597
Cartagena
Cartagena1 stop$415
Quito
Quito1 stop$404
Belo Horizonte
Belo Horizonte2 stops$785
Lima
Lima1 stop$490
Bogotá
Bogotá1 stop$327
Santiago
Santiago1 stop$597
Cartagena
Cartagena1 stop$415
Quito
Quito1 stop$404
Belo Horizonte
Belo Horizonte2 stops$785

Book Cheap Midway to South America Plane Tickets

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

Sat, Apr 11 - Sun, Apr 19
LATAM Airlines Logo
6:25 am - 2:25 pm
MDW
-
BOG
8h 00m1 stop
LATAM Airlines Logo
9:00 am - 10:29 pm
BOG
-
MDW
13h 29m1 stop
$327LATAM Airlines
Fri, Feb 6 - Sat, Feb 7
LATAM Airlines Logo
10:48 am - 7:30 pm
MDW
-
BOG
7h 42m1 stop
LATAM Airlines Logo
5:00 am - 10:22 pm
BOG
-
MDW
18h 22m2 stops
$343LATAM Airlines
Sat, Jan 24 - Tue, Jan 27
LATAM Airlines Logo
6:25 am - 7:30 pm
MDW
-
BOG
12h 05m1 stop
LATAM Airlines Logo
10:55 am - 10:22 pm
BOG
-
MDW
12h 27m2 stops
$359LATAM Airlines
Mon, Jan 19 - Sat, Apr 11
LATAM Airlines Logo
6:00 am - 7:30 pm
MDW
-
BOG
12h 30m1 stop
LATAM Airlines Logo
3:55 pm - 9:56 am
BOG
-
MDW
18h 01m1 stop
$362LATAM Airlines
Tue, Jan 20 - Tue, Apr 7
Delta Logo
12:48 pm - 12:05 pm
MDW
-
BOG
22h 17m2 stops
Delta Logo
3:55 pm - 9:56 am
BOG
-
MDW
18h 01m1 stop
$364Delta
Mon, Jan 19 - Wed, Jan 21
LATAM Airlines Logo
6:00 am - 7:30 pm
MDW
-
BOG
12h 30m1 stop
LATAM Airlines Logo
3:55 pm - 9:53 am
BOG
-
MDW
18h 58m1 stop
$366LATAM Airlines
Mon, Jan 19 - Tue, Apr 7
Delta Logo
6:00 am - 7:30 pm
MDW
-
BOG
12h 30m1 stop
Delta Logo
11:00 am - 10:31 pm
BOG
-
MDW
11h 31m2 stops
$369Delta
Sun, Jan 18 - Sat, Apr 11
Delta Logo
5:59 pm - 7:30 pm
MDW
-
BOG
24h 31m1 stop
Delta Logo
3:55 pm - 9:56 am
BOG
-
MDW
18h 01m1 stop
$371Delta
Sun, Mar 15 - Tue, Mar 17
LATAM Airlines Logo
6:25 am - 5:50 pm
MDW
-
BOG
11h 25m2 stops
LATAM Airlines Logo
8:35 am - 10:31 pm
BOG
-
MDW
13h 56m2 stops
$375LATAM Airlines
Thu, Mar 5 - Sun, Mar 8
Multiple Airlines Logo
6:15 am - 6:55 pm
MDW
-
MDE
11h 40m2 stops
Multiple Airlines Logo
11:50 pm - 1:41 pm
MDE
-
MDW
13h 51m1 stop
$407Multiple Airlines
Booking Insights

KAYAK's insights & trends for Midway to South America flights

Get data-powered insights and trends into flights from Midway to South America to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between Chicago Midway Airport and South America?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago Midway Airport to South America.

There is just one airline that flies from Chicago Midway Airport to South America direct and that is LATAM Airlines. The best round-trip deal found from LATAM Airlines for the route is to Cartagena (CTG) and costs $419.

Which airlines provide the cheapest flights from Chicago Midway Airport to South America?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to South America were found on Delta ($364) and LATAM Airlines ($364).

Find deals

Good to know

Cheapest flight$157
Flight from Chicago Midway Airport to Medellín

FAQs - booking South America flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to South America?

    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 Midway Airport to South America.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to South America 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 Midway Airport to South America?

    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 from Chicago Midway Airport to South America 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 from Chicago Midway Airport to South America?

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

Reviews of the top airline flying from Midway to South America

 
Need help choosing which airline to fly with from Midway to South America? 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 1898 reviews
7.6Boarding
6.7Food
8.1Crew
7.0Entertainment
7.3Comfort
Airline reviews

We traveled with two young children, and it was not possible for our family to be seated together. No one offered help or assistance to organize seating so we could sit with our kids. In the end, we managed to find two seats in Economy so I could at least sit with one of them, even though I had originally paid for Comfort+. In summary, I had to downgrade my seat just to be able to sit with one of my children, which was very disappointing

2.0 MediocreAnonymous, Dec 2025
JFK - EZE
Read more LATAM Airlines reviews

We traveled with two young children, and it was not possible for our family to be seated together. No one offered help or assistance to organize seating so we could sit with our kids. In the end, we managed to find two seats in Economy so I could at least sit with one of them, even though I had originally paid for Comfort+. In summary, I had to downgrade my seat just to be able to sit with one of my children, which was very disappointing

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

The assistance we received and the flight itself was wonderful. We will fly with LATAM airlines again, in the future.

Latam may be the worst airline in the world, far worse than even the lowest of low cost airlines in the USA. I wasted hours trying to PAY THEM TO CHECK A BAG! Then they misled me at the terminal, sent me through the wrong security line, the list goes on and on... Just absolutely terrible in every way. Avoid at all costs.

Poor, the airline was not able to help me move flights.

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

Just to drop my already labeled bag it took 50 minutes inline. Completely disappointed with Latam operation at GRU

I’m entitled to a refund per LATAM due to the mid flight itinerary change and being stuck in São Paulo for 24 hours and needing to get a hotel. The airline was dismissive and of no help.

The flight was late. Please do not delay next time.

I couldn't travel, now I can't get a refund and to change the date I have to pay an absurd fine.

Everything you need to know for your flight to South America

Information on your arrival and departure airports

Chicago Midway Airport (MDW)