$221 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 2/5. 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 Midway Airport

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$351
LATAM Airlines
Sun 2/22Wed 2/25
MDE - MDW • 2 stops
Cheapest one-way
$221
Multiple Airlines
Thu 2/5
BOG - MDW • 2 stops
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
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

Sun, Feb 22 - Wed, Feb 25
LATAM Airlines Logo
7:10 pm - 5:45 pm
MDE
-
MDW
23h 35m2 stops
LATAM Airlines Logo
10:49 am - 7:45 am
MDW
-
MDE
19h 56m2 stops
$351LATAM Airlines
Mon, Mar 2 - Sat, Mar 7
LATAM Airlines Logo
12:30 pm - 9:54 am
MDE
-
MDW
22h 24m2 stops
LATAM Airlines Logo
11:06 am - 8:55 am
MDW
-
MDE
20h 49m2 stops
$352LATAM Airlines
Thu, Feb 12 - Thu, Feb 19
Multiple Airlines Logo
1:45 pm - 2:26 pm
BOG
-
MDW
25h 41m1 stop
Multiple Airlines Logo
7:30 am - 12:47 pm
MDW
-
BOG
28h 17m1 stop
$364Multiple Airlines
Fri, Feb 13 - Sat, Feb 21
Delta Logo
9:00 am - 5:45 pm
BOG
-
MDW
9h 45m1 stop
Delta Logo
11:06 am - 7:30 pm
MDW
-
BOG
7h 24m1 stop
$368Delta
Wed, Jan 21 - Sun, Jan 25
LATAM Airlines Logo
3:55 pm - 9:53 am
BOG
-
MDW
18h 58m1 stop
LATAM Airlines Logo
10:48 am - 7:30 pm
MDW
-
BOG
7h 42m1 stop
$374LATAM Airlines
Fri, Mar 20 - Tue, Mar 31
LATAM Airlines Logo
3:55 pm - 9:56 am
BOG
-
MDW
18h 01m1 stop
LATAM Airlines Logo
10:45 am - 7:30 pm
MDW
-
BOG
8h 45m1 stop
$377LATAM Airlines
Wed, Jan 21 - Sun, Jan 25
LATAM Airlines Logo
3:55 pm - 9:53 am
BOG
-
MDW
18h 58m1 stop
LATAM Airlines Logo
10:48 am - 7:30 pm
MDW
-
BOG
7h 42m1 stop
$378LATAM Airlines
Fri, Feb 13 - Tue, Feb 17
Delta Logo
11:45 pm - 12:46 pm
UIO
-
MDW
14h 01m2 stops
Delta Logo
12:45 pm - 5:17 am
MDW
-
UIO
15h 32m2 stops
$448Delta
Thu, Jan 15 - Mon, Jan 19
Delta Logo
11:45 pm - 12:48 pm
UIO
-
MDW
14h 03m2 stops
Delta Logo
1:26 pm - 5:17 am
MDW
-
UIO
14h 51m2 stops
$520Delta
Mon, May 4 - Mon, May 18
Delta Logo
10:55 pm - 5:54 pm
SCL
-
MDW
19h 59m2 stops
Delta Logo
1:00 pm - 6:50 am
MDW
-
SCL
16h 50m2 stops
$645Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$221
Best time to beat the crowds but there is an average 63% increase in price.
Most popular time to fly and prices are also 22% 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 8012 reviews
7.8Entertainment
8.1Boarding
7.2Food
7.9Comfort
8.5Crew
Airline reviews

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.

6.0 GoodDorothy, Dec 2025
DTW - DCA
Read more Delta reviews

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.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

I went to washroom twice and once there was no toilet seat cover and the other no toilet paper at all. I don't think it was ever replenished or checked before we boarded as it was very early on in the flight.

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

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