$224 Find Cheap Flights from South America to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 2/7. 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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Everything you should know

Cheapest round-trip
$346
LATAM Airlines
Wed 1/28Sat 2/7
MDE - MDW • 2 stops
Cheapest one-way
$224
Multiple Airlines
Sat 2/7
BOG - MDW • 2 stops
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from South America to Midway

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

Wed, Jan 28 - Sat, Feb 7
LATAM Airlines Logo
6:15 pm - 11:59 am
MDE
-
MDW
18h 44m2 stops
LATAM Airlines Logo
6:25 am - 6:35 am
MDW
-
MDE
23h 10m2 stops
$346LATAM Airlines
Sat, Feb 21 - Sat, Feb 28
LATAM Airlines Logo
5:30 am - 10:31 pm
MDE
-
MDW
18h 01m2 stops
LATAM Airlines Logo
6:00 am - 10:40 pm
MDW
-
MDE
15h 40m2 stops
$350LATAM Airlines
Fri, Jan 23 - Tue, Mar 10
LATAM Airlines Logo
10:45 am - 9:53 am
MDE
-
MDW
24h 08m2 stops
LATAM Airlines Logo
6:25 am - 7:20 pm
MDW
-
MDE
12h 55m2 stops
$353LATAM Airlines
Fri, Feb 20 - Wed, Feb 25
LATAM Airlines Logo
11:10 am - 10:21 am
MDE
-
MDW
24h 11m2 stops
LATAM Airlines Logo
10:49 am - 6:35 am
MDW
-
MDE
18h 46m2 stops
$355LATAM Airlines
Fri, Feb 13 - Sun, Feb 22
Delta Logo
7:00 am - 10:31 pm
BOG
-
MDW
16h 31m2 stops
Delta Logo
6:00 am - 7:30 pm
MDW
-
BOG
12h 30m1 stop
$370Delta
Tue, Feb 17 - Sun, Feb 22
Delta Logo
3:55 pm - 9:54 am
BOG
-
MDW
18h 59m1 stop
Delta Logo
10:49 am - 7:30 pm
MDW
-
BOG
7h 41m1 stop
$371Delta
Sun, Mar 1 - Mon, Mar 16
Delta Logo
3:55 pm - 5:45 pm
BOG
-
MDW
26h 50m1 stop
Delta Logo
6:25 am - 7:30 pm
MDW
-
BOG
13h 05m1 stop
$372Delta
Sun, Mar 22 - Tue, Mar 31
LATAM Airlines Logo
3:55 pm - 9:56 am
BOG
-
MDW
18h 01m1 stop
LATAM Airlines Logo
6:25 am - 7:30 pm
MDW
-
BOG
13h 05m1 stop
$377LATAM Airlines
Wed, Jan 21 - Mon, Jan 26
Delta Logo
11:45 pm - 9:53 am
UIO
-
MDW
11h 08m1 stop
Delta Logo
12:48 pm - 5:17 am
MDW
-
UIO
15h 29m2 stops
$449Delta
Fri, Jan 23 - Tue, Mar 10
Multiple Airlines Logo
6:35 am - 7:52 pm
MDE
-
MDW
14h 17m1 stop
Multiple Airlines Logo
6:00 am - 6:45 pm
MDW
-
MDE
12h 45m2 stops
$501Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$224
Best time to beat the crowds but there is an average 70% increase in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Bogotá to Chicago Midway Airport

FAQs for booking South America to Chicago Midway Airport flights

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

    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 South America to Chicago Midway Airport.

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

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

    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 Midway Airport with an airline and back to South America with another airline.

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

    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 Midway Airport from 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 airlines flying from South America to Midway

 
Need help choosing which airline to fly with from South America to Midway? 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 8029 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.2Food
7.9Comfort
Airline reviews

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

2.0 MediocreWilliam, Jan 2026
LGA - BOS
Read more Delta reviews

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

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 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

Really bad experience – delayed for 6 hours without any notice, no food or drinks provided, and stuck in the horrible Cartagena airport.

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

Boarding was confusing with a delayed flight because there was no English translation

Because the flight was late, we lost the connection to Brazil. You, Delta delayed, and you Delta anticipated the door closing in 15 min from Miami to GRU. Why? It caused a lot of stress! I almost could not see my mother in law alive because of your delay.

My entertainment did not work. I was very tired from the botched connection, and the poor sleep

It’s a delta flight operated by LATAM. The whole ticket sale is a mess, delta changed my flight but didn’t update it in LATAM system, I couldn’t get my boarding pass, it took me hours to resolve this issue with delta. I had to change my travel plan. No apology from Delta even though it’s their fault.

Traveling to a place near Midway?

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

Everything you need to know for your flight to Midway

Information on your arrival and departure airports