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Central America

$94+ Cheap flights from Midway (MDW) to Central 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
nov. 27 — déc. 41
jeu. 11/27
jeu. 12/4
1 adult, Economy
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Cheap flight deals from Midway to Central America

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$276
(Kiwi.com)

One-way from

$94
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$435
Provider with most accurate pricing for Chicago (CHI)-San Salvador El Salvador Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San Salvador El Salvador Intl flights.
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From Chicago Midway to Central America
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One-way flight from Chicago Midway to Central America
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Highest demand for flights based on searches. 21% potential increase in price ($120 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($26 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 Central America

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

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.
jeu. 12/47:23 pmMDW - GUA
2 stops18h 00mMultiple Airlines
lun. 12/82:38 pmGUA - MDW
1 stop7h 40mMultiple Airlines
Deal found 10/28$276
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.
mer. 12/246:12 amMDW - GUA
2 stops31h 11mMultiple Airlines
sam. 1/103:10 pmGUA - MDW
1 stop29h 35mMultiple Airlines
Deal found 10/27$291
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.
dim. 11/166:30 amMDW - GUA
1 stop28h 36mMultiple Airlines
ven. 11/212:55 pmGUA - MDW
1 stop8h 34mMultiple Airlines
Deal found 10/27$292
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.
jeu. 11/205:30 pmMDW - GUA
1 stop17h 49mMultiple Airlines
ven. 11/212:55 pmGUA - MDW
1 stop8h 34mMultiple Airlines
Deal found 10/26$298
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.
mer. 12/246:12 amMDW - GUA
2 stops31h 11mMultiple Airlines
jeu. 1/812:11 pmGUA - MDW
1 stop21h 02mMultiple Airlines
Deal found 10/27$309
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.
mer. 12/246:12 amMDW - SAP
2 stops32h 01mMultiple Airlines
jeu. 1/811:48 amSAP - MDW
1 stop21h 25mMultiple Airlines
Deal found 10/27$315
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.
lun. 11/173:40 pmMDW - SAP
2 stops22h 30mMultiple Airlines
ven. 11/2111:48 amSAP - MDW
1 stop11h 41mMultiple Airlines
Deal found 10/28$320
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.
lun. 11/106:00 amMDW - SAP
1 stop5h 59mDelta
jeu. 11/131:14 pmSAP - MDW
1 stop10h 26mDelta
Deal found 10/28$322
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.
jeu. 11/275:30 pmMDW - SJO
1 stop16h 49mMultiple Airlines
jeu. 12/412:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Deal found 10/27$322
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.
mar. 12/306:14 amMDW - SJO
2 stops30h 11mMultiple Airlines
sam. 1/1012:22 pmSJO - MDW
1 stop20h 51mMultiple Airlines
Deal found 10/26$327
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.
ven. 11/284:46 pmMDW - SJO
1 stop17h 33mMultiple Airlines
jeu. 12/412:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Deal found 10/28$328
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.
mer. 12/313:10 pmMDW - SJO
1 stop20h 32mMultiple Airlines
sam. 1/101:19 pmSJO - MDW
2 stops31h 26mMultiple Airlines
Deal found 10/26$333

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Central 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 octobre 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Central America that are best for you.

Fly from

Midway

Fly to

Central America

Route

Depart

Return

Price

ChicagoGuatemala City

MDW - GUA

MDWGUA

Chicago Midway

jeu. 12/4

7:23 pm-1:23 pm

2 stops18h 00m

Guatemala City La Aurora

lun. 12/8

2:38 pm-10:18 pm

1 stop7h 40m

$276

ChicagoSan Pedro Sula

MDW - SAP

MDWSAP

Chicago Midway

mar. 3/10

6:00 am-11:15 am

1 stop6h 15m

San Pedro Sula Ramon Villeda

mer. 3/11

12:35 pm-9:46 pm

1 stop8h 11m

$322

ChicagoSan Pedro Sula

MDW - SAP

MDWSAP

Chicago Midway

lun. 11/10

6:00 am-11:59 am

1 stop5h 59m

San Pedro Sula Ramon Villeda

jeu. 11/13

1:14 pm-11:40 pm

1 stop10h 26m

$322

ChicagoSan Salvador

MDW - SAL

MDWSAL

Chicago Midway

mar. 12/30

6:14 am-11:56 am

1 stop29h 42m

San Salvador El Salvador Intl

ven. 1/30

8:45 am-7:50 pm

1 stop11h 05m

$340

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mer. 11/19

10:47 am-10:07 pm

1 stop11h 20m

San José Juan Santamaria Intl

mar. 11/25

7:00 am-4:38 pm

1 stop9h 38m

$342

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

mar. 12/9

9:34 am-10:20 pm

2 stops12h 46m

San José Juan Santamaria Intl

lun. 12/15

7:00 am-4:34 pm

1 stop9h 34m

$346

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

sam. 1/24

6:00 am-1:00 pm

1 stop7h 00m

San José Juan Santamaria Intl

mar. 2/3

7:00 am-5:32 pm

1 stop10h 32m

$346

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

jeu. 12/4

9:34 am-10:20 pm

2 stops12h 46m

San José Juan Santamaria Intl

lun. 12/8

7:00 am-6:00 pm

2 stops11h 00m

$346

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

sam. 12/6

11:05 am-10:20 pm

1 stop11h 15m

San José Juan Santamaria Intl

mer. 12/10

7:00 am-6:00 pm

2 stops11h 00m

$346

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

jeu. 11/27

9:34 am-10:07 pm

2 stops12h 33m

San José Juan Santamaria Intl

mar. 12/2

2:31 pm-11:47 pm

1 stop9h 16m

$346

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 Central America

Have a flexible travel schedule? Discover the best time to fly to Central 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 Central America

What is the cheapest month to book a flight from Chicago Midway Airport to Central America?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Central America (average of $394). Flying from Chicago Midway Airport to Central America in March is currently the most expensive (average of $637). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

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

Unlike at noon, when flights are generally more expensive, you can save up to 42% on flights from Chicago Midway Airport to Central America by exploring options for tickets in the evening.

Reviews of airlines servicing Central America

Get insights into the airlines that provide service to Central 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 Central America. Reviews last updated octobre 28, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Central America, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Central 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 Central America?

    Departing from Chicago Midway Airport to Central America will take you 6h 15m. The distance from Chicago Midway Airport to Central America is about 1818 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Most travelers choose Chicago Midway - San José Juan Santamaria Intl, Chicago Midway - Guatemala City La Aurora or Chicago Midway - Panama City Tocumen Intl when deciding on the best route from Chicago Midway Airport to Central America.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Central 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Central America?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Central America (average of $394). Flying from Chicago Midway Airport to Central America in March is currently the most expensive (average of $637). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Central America

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

Discover the top airline that operate flights from Midway to Central 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 octobre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$394Average$689FlexibilityNo cancel feeOn-time63%

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