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Find cheap flights from Chicago Midway Airport to South America from $135

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 5/14. 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
0 bags
Fri 6/7
Fri 6/14

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Best South America Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Lima
Lima1 stop$478
Bogotá
Bogotá1 stop$318
Cartagena
Cartagena1 stop$366
Santiago
Santiago2 stops$731
Quito
Quito1 stop$375
Belo Horizonte
Belo Horizonte3 stops$1,027

Good to know

Low season

May

High season

May

Cheapest flight

$135
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Chicago Midway Airport to Bogotá

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

See more FAQs

Top tips for finding cheap flights to South America

  • Morning departure is around 22% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top airlines 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.
8.0
DeltaOverall score based on 10789 reviews
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

They offered food. The crew passed by again offering water. I enjoyed the two seating section. I think is very comfortable instead of the three seat way, unless you seat in the middle; which it's not bad, but I wouldn't prefer. All and all, I think the lay out of the seating rows are better than other airlines so far( I haven't tried many anyways). The lay out makes the getting in and out to use the restroom less uncomfortable and cramped. First time flying with Latam. I will fly with them again

I didn't realize they didn't have bathrooms on the plane. Almost had a very bad situation.

Everything was as you would expect in coach - fine. Flight was close to on time.

It was confusing because I got a notification that my gate was changed when in reality it wasn’t

No air in the middle rows. Had a hard time breathing. Was dying of heat.

Horrific checkin procedure with neither Delta nor Latam figuring out how to check me in. 4 hrs on customer support with both and both airlines pointing to each other who should do checking. I was not checked in until morning of flight, which for international flight is concerning.

It was a good experience, the flight was a little too long & the food was ok

Liked check in process To improve: food and beverages. Not second round was offered and meal had no salad.

the flight from Boston to Curitiba was on time actually 30 minutes earlier. latam was not able to unload the luggage for custom checkup in Sao Paulo ii took two and half hours . i missed the flight to Curitiba spend the night in hotel and then flying in the morning to Curitiba

Tough flight with turbulence… I was told by a fellow passenger that it is common. Nonetheless, very stressful. Cordial staff.

Book cheap flights from Chicago to South America

Recent round-trip flight deals

10/1Tue
1 stopLATAM Airlines
7h 30mMDW-BOG
10/15Tue
1 stopLATAM Airlines
8h 59mBOG-MDW
$318
5/29Wed
2 stopsLATAM Airlines
14h 18mMDW-BOG
6/12Wed
2 stopsLATAM Airlines
14h 46mBOG-MDW
$322
9/7Sat
2 stopsLATAM Airlines
26h 02mMDW-BOG
9/21Sat
1 stopLATAM Airlines
8h 16mBOG-MDW
$323
6/21Fri
2 stopsLATAM Airlines
14h 19mMDW-BOG
6/25Tue
2 stopsLATAM Airlines
10h 59mBOG-MDW
$328
8/12Mon
2 stopsLATAM Airlines
21h 10mMDW-BOG
8/22Thu
2 stopsLATAM Airlines
9h 55mBOG-MDW
$332
8/6Tue
1 stop
22h 42mMDW-CTG
8/14Wed
1 stop
7h 43mCTG-MDW
$366
6/5Wed
1 stopDelta
15h 15mMDW-UIO
6/12Wed
2 stopsDelta
13h 23mUIO-MDW
$380
7/27Sat
2 stopsDelta
19h 25mMDW-BOG
8/3Sat
2 stopsDelta
17h 50mBOG-MDW
$393
7/9Tue
2 stopsDelta
16h 08mMDW-MDE
7/11Thu
2 stopsDelta
17h 23mMDE-MDW
$405
6/8Sat
2 stopsDelta
9h 56mMDW-BOG
6/9Sun
2 stopsDelta
17h 24mBOG-MDW
$423

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Recent one-way flight deals

5/14Tue
1 stop
21h 04mMDW-BOG
$135
5/14Tue
2 stops
21h 54mMDW-BOG
$136
5/14Tue
2 stops
28h 52mMDW-BOG
$137
5/13Mon
1 stopLATAM Airlines
15h 15mMDW-UIO
$144
5/13Mon
1 stopDelta
13h 45mMDW-BOG
$146
6/25Tue
2 stopsLATAM Airlines
10h 35mMDW-MDE
$146
5/13Mon
2 stopsLATAM Airlines
28h 12mMDW-UIO
$148
6/18Tue
1 stopDelta
13h 24mMDW-BOG
$206
6/9Sun
1 stopDelta
15h 20mMDW-UIO
$228
6/12Wed
2 stopsDelta
14h 18mMDW-BOG
$276

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Last minute flights from Midway to South America

Last minute flight, train and bus deals

5/12Sun
multi-stopLATAM Airlines
11h 00mMDW-BOG
5/26Sun
multi-stopLATAM Airlines
17h 15mBOG-MDW
$317
5/11Sat
multi-stop
7h 30mMDW-BOG
5/21Tue
multi-stop
17h 05mBOG-MDW
$318
5/11Sat
multi-stopLATAM Airlines
13h 45mMDW-BOG
5/21Tue
multi-stopLATAM Airlines
20h 55mBOG-MDW
$379
5/11Sat
multi-stopLATAM Airlines
13h 45mMDW-BOG
5/13Mon
multi-stopLATAM Airlines
24h 26mBOG-MDW
$383
5/12Sun
multi-stopLATAM Airlines
11h 32mMDW-BOG
5/26Sun
multi-stopLATAM Airlines
17h 15mBOG-MDW
$392
5/9Thu
multi-stop
28h 52mMDW-BOG
5/21Tue
multi-stop
18h 04mBOG-MDW
$493
5/12Sun
multi-stopDelta
15h 05mMDW-LIM
5/18Sat
multi-stopDelta
26h 55mLIM-MDW
$598
5/12Sun
multi-stopDelta
15h 00mMDW-LIM
5/18Sat
multi-stopDelta
26h 55mLIM-MDW
$603
5/12Sun
multi-stopDelta
15h 00mMDW-LIM
5/18Sat
multi-stopDelta
25h 25mLIM-MDW
$663
5/10Fri
multi-stopDelta
12h 30mMDW-UIO
5/14Tue
multi-stopDelta
8h 40mUIO-MDW
$961

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Chicago Midway Airport - South America Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

South America - Chicago Midway Airport

Cabin classes: