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South America

$117+ Cheap flights from Midway (MDW) to South America

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOG
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Midway to South America

Keep the following information in mind while searching for Midway to South America flight deals. Data was last updated October 28, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$347
(Kiwi.com)

One-way from

$117
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$796
Provider with most accurate pricing for Chicago (CHI)-Sao Paulo (SAO) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Sao Paulo (SAO) flights.
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From Chicago Midway to South America
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One-way flight from Chicago Midway to South America
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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Midway to South America

Cheapest flights from Midway to South America
Explore the most affordable flight options available from Midway to South America. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/111:56 pmMDW - MDE
2 stops10h 01mMultiple Airlines
Fri 11/212:57 pmMDE - MDW
1 stop9h 32mMultiple Airlines
Deal found 10/26$347
This SmartFares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:00 amMDW - BOG
1 stop7h 25mDelta
Thu 11/203:55 pmBOG - MDW
1 stop8h 45mDelta
Deal found 10/26$347
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/105:34 pmMDW - BOG
1 stop19h 51mDelta
Mon 11/173:55 pmBOG - MDW
1 stop8h 45mDelta
Deal found 10/27$355
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:00 amMDW - BOG
1 stop12h 30mDelta
Thu 11/133:55 pmBOG - MDW
1 stop8h 45mDelta
Deal found 10/28$363
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:16 pmMDW - MDE
2 stops28h 09mMultiple Airlines
Mon 12/1511:50 amMDE - MDW
1 stop11h 08mMultiple Airlines
Deal found 10/27$365
This LATAM Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:00 amMDW - BOG
1 stop7h 25mLATAM Airlines
Fri 11/1410:55 amBOG - MDW
2 stops13h 45mLATAM Airlines
Deal found 10/27$365
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/299:35 amMDW - BOG
2 stops9h 55mDelta
Sat 11/810:55 amBOG - MDW
2 stops12h 19mDelta
Deal found 10/26$368
This Kiwi.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:37 pmMDW - MDE
1 stop15h 18mMultiple Airlines
Thu 12/2511:50 amMDE - MDW
1 stop11h 08mMultiple Airlines
Deal found 10/28$370
This LATAM Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1610:47 amMDW - BOG
1 stop7h 43mLATAM Airlines
Mon 11/1710:55 amBOG - MDW
2 stops13h 45mLATAM Airlines
Deal found 10/27$378
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:00 amMDW - BOG
1 stop8h 25mDelta
Wed 11/59:00 amBOG - MDW
1 stop14h 14mDelta
Deal found 10/27$379
This LATAM Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure LATAM Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/14:23 pmMDW - BOG
2 stops24h 22mMultiple Airlines
Sat 11/83:55 pmBOG - MDW
1 stop18h 57mMultiple Airlines
Deal found 10/25$382
This Orbitz deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:00 amMDW - BOG
1 stop13h 30mLATAM Airlines
Fri 10/319:00 amBOG - MDW
1 stop13h 14mLATAM Airlines
Deal found 10/26$383

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to South America that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to South America that are best for you.

Fly from

Midway

Fly to

South America

Route

Depart

Return

Price

ChicagoBogotá

MDW - BOG

MDWBOG

Chicago Midway

Fri 10/31

6:00 am-7:30 pm

1 stop13h 30m

Bogotá El Dorado

Sun 11/2

9:00 am-10:14 pm

1 stop14h 14m

$363

ChicagoBogotá

MDW - BOG

MDWBOG

Chicago Midway

Fri 11/7

6:00 am-7:30 pm

1 stop12h 30m

Bogotá El Dorado

Thu 11/13

3:55 pm-11:40 pm

1 stop8h 45m

$363

ChicagoBogotá

MDW - BOG

MDWBOG

Chicago Midway

Wed 11/26

10:47 am-7:30 pm

1 stop7h 43m

Bogotá El Dorado

Wed 12/3

5:00 am-11:47 pm

2 stops19h 47m

$363

ChicagoBogotá

MDW - BOG

MDWBOG

Chicago Midway

Thu 11/13

6:00 am-7:30 pm

1 stop12h 30m

Bogotá El Dorado

Tue 12/2

9:00 am-11:47 pm

1 stop15h 47m

$363

ChicagoBogotá

MDW - BOG

MDWBOG

Chicago Midway

Fri 11/14

6:00 am-7:30 pm

1 stop12h 30m

Bogotá El Dorado

Tue 12/2

9:00 am-11:47 pm

1 stop15h 47m

$363

ChicagoBogotá

MDW - BOG

MDWBOG

Chicago Midway

Sun 11/9

6:00 am-7:30 pm

1 stop12h 30m

Bogotá El Dorado

Wed 11/12

10:55 am-11:40 pm

2 stops13h 45m

$368

ChicagoQuito

MDW - UIO

MDWUIO

Chicago Midway

Wed 11/26

10:47 am-11:00 pm

2 stops11h 13m

Quito Mariscal Sucr

Wed 12/3

11:45 pm-9:54 am

1 stop11h 09m

$417

ChicagoQuito

MDW - UIO

MDWUIO

Chicago Midway

Sun 11/23

6:48 pm-7:05 pm

2 stops23h 17m

Quito Mariscal Sucr

Wed 12/3

11:45 pm-9:54 am

1 stop11h 09m

$421

ChicagoQuito

MDW - UIO

MDWUIO

Chicago Midway

Thu 1/22

1:28 pm-5:17 am

2 stops14h 49m

Quito Mariscal Sucr

Fri 1/30

7:00 pm-10:01 am

2 stops16h 01m

$421

ChicagoQuito

MDW - UIO

MDWUIO

Chicago Midway

Sun 11/23

6:48 pm-7:05 pm

2 stops23h 17m

Quito Mariscal Sucr

Tue 12/2

11:45 pm-11:55 am

1 stop13h 10m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 60 results
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Best time to book a flight from Midway to South America

Have a flexible travel schedule? Discover the best time to fly to South America from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to South America

What is the cheapest time of day to fly from MDW to SA?

Find hourly flight availability from Midway to South America. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to South America is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 44% on airfare.

Reviews of airlines servicing South America

Get insights into the airlines that provide service to South America. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to South America. Reviews last updated October 28, 2025.
Read reviews from past customers who have flown Delta and LATAM Airlines from Chicago Midway Airport to South America. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,995 reviews

Overall

7.9

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,995 reviews
Delta
7.9
Good
7,995 reviews

Overall

7.9

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
LATAM Airlines
7.5
Good
1,871 reviews
Delta
7.9
Good
7,995 reviews

Overall

7.9

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Midway to South America. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to South America?

    A quick flight from Chicago Midway Airport to South America can take about 11h 13m. Delta provides one of the quickest options available for as low as $417. The distance from Chicago Midway Airport to South America is about 2952 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago Midway Airport to South America?

    While some choose either Chicago Midway - Medellín Jose Maria Cordova Intl or Chicago Midway - Sao Paulo Guarulhos Intl, Chicago Midway - Lima J Chavez Intl is the most popular route from Chicago Midway Airport to South America.

  • Can I find deals for flights from Midway to South America that include hotel bookings?

    Yes. In addition to deals on Midway to South America flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to South America?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to South America.

  • Can I find deals for business class flights from Midway to South America?

    Yes. Cheapflights offers flight deals from Midway to South America by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Midway to South America

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Midway to South America

Discover the top 2 airlines that operate flights from Midway to South America. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
LATAM AirlinesCheapest$348Average$614FlexibilityNo cancel feeOn-time81%
DeltaCheapest$374Average$649FlexibilityNo cancel feeOn-timeN/A

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