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Midway

$150+ Cheap flights from Central America to Midway (MDW)

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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Central America to Midway

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

Round-trip from

$262
(Kiwi.com)

One-way from

$150
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$334
From Central America to Chicago Midway
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One-way flight from Central America to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 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 Central America to Midway

Cheapest flights from Central America to Midway
Explore the most affordable flight options available from Central America to Midway. 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 10/27. 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.
Wed 11/192:55 pmGUA - MDW
1 stop25h 35mMultiple Airlines
Thu 11/274:00 pmMDW - GUA
1 stop18h 15mMultiple Airlines
Deal found 10/27$262
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.
Thu 12/412:20 pmGUA - MDW
1 stop9h 38mMultiple Airlines
Sun 12/76:37 pmMDW - GUA
1 stop19h 28mMultiple Airlines
Deal found 10/26$270
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.
Fri 12/52:28 pmGUA - MDW
1 stop7h 00mMultiple Airlines
Sun 12/76:37 pmMDW - GUA
1 stop19h 28mMultiple Airlines
Deal found 10/26$277
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.
Fri 12/52:28 pmGUA - MDW
1 stop7h 00mMultiple Airlines
Mon 12/88:42 pmMDW - GUA
2 stops16h 41mMultiple Airlines
Deal found 10/26$283
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 12/412:39 pmSJO - MDW
1 stop9h 19mMultiple Airlines
Sun 12/76:37 pmMDW - SJO
1 stop17h 05mMultiple Airlines
Deal found 10/27$294
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.
Wed 12/32:55 pmGUA - MDW
1 stop31h 03mMultiple Airlines
Sun 12/76:37 pmMDW - GUA
1 stop16h 46mMultiple Airlines
Deal found 10/26$298
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1011:19 pmSAL - MDW
1 stop24h 36mMultiple Airlines
Fri 11/146:15 amMDW - SAL
1 stop6h 54mMultiple Airlines
Deal found 10/26$306
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.
Thu 12/47:35 amSAL - MDW
1 stop14h 18mMultiple Airlines
Sun 12/76:15 amMDW - SAL
2 stops32h 33mMultiple Airlines
Deal found 10/26$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.
Fri 11/2111:24 amSJO - MDW
1 stop12h 05mMultiple Airlines
Mon 11/245:47 pmMDW - SJO
1 stop16h 32mMultiple Airlines
Deal found 10/27$323
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/311:19 pmSAL - MDW
1 stop24h 36mMultiple Airlines
Fri 11/76:15 amMDW - SAL
1 stop6h 54mMultiple Airlines
Deal found 10/26$329
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 12/52:31 pmSJO - MDW
1 stop9h 16mDelta
Tue 12/99:34 amMDW - SJO
2 stops12h 46mDelta
Deal found 10/28$339
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.
Wed 12/3111:25 amSAP - MDW
2 stops10h 47mMultiple Airlines
Mon 1/53:10 pmMDW - SAP
1 stop19h 51mMultiple Airlines
Deal found 10/28$343

Cheapflights Fare Finder

 
Customize your flight search to find flights from Central America to Midway 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 Central America to Chicago Midway Airport that are best for you.

Fly from

Central America

Fly to

Midway

Route

Depart

Return

Price

San SalvadorChicago

SAL - MDW

SALMDW

San Salvador El Salvador Intl

Thu 12/4

7:35 am-9:53 pm

1 stop14h 18m

Chicago Midway

Sun 12/7

6:15 am-2:48 pm

2 stops32h 33m

$322

Guatemala CityChicago

GUA - MDW

GUAMDW

Guatemala City La Aurora

Wed 11/19

2:55 pm-4:30 pm

1 stop25h 35m

Chicago Midway

Sun 11/30

5:30 pm-11:19 am

1 stop17h 49m

$326

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 12/5

7:00 am-4:18 pm

1 stop9h 18m

Chicago Midway

Tue 12/9

9:34 am-10:20 pm

2 stops12h 46m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 11/24

7:00 am-6:08 pm

2 stops11h 08m

Chicago Midway

Mon 12/1

12:47 pm-10:07 pm

1 stop9h 20m

$339

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 11/23

2:31 pm-11:40 pm

1 stop9h 09m

Chicago Midway

Thu 11/27

9:34 am-10:07 pm

2 stops12h 33m

$339

San Pedro SulaChicago

SAP - MDW

SAPMDW

San Pedro Sula Ramon Villeda

Wed 12/31

11:25 am-10:12 pm

2 stops10h 47m

Chicago Midway

Mon 1/5

3:10 pm-11:01 am

1 stop19h 51m

$343

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/17

7:00 am-4:31 pm

1 stop9h 31m

Chicago Midway

Sat 1/24

9:34 am-10:15 pm

2 stops12h 41m

$343

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/24

2:31 pm-10:26 pm

1 stop7h 55m

Chicago Midway

Wed 1/28

9:34 am-10:15 pm

2 stops12h 41m

$343

San JoséChicago

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/17

7:00 am-10:09 pm

1 stop15h 09m

Chicago Midway

Fri 1/23

10:53 am-10:15 pm

1 stop11h 22m

$343

Guatemala CityChicago

GUA - MDW

GUAMDW

Guatemala City La Aurora

Sat 12/27

2:09 pm-10:22 pm

1 stop8h 13m

Chicago Midway

Thu 1/1

6:00 am-12:44 pm

1 stop6h 44m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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

Have a flexible travel schedule? Discover the best time to fly to Midway from Central America 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 Central America to Chicago Midway Airport

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

Currently, July is the cheapest month in which you can book a flight from Central America to Chicago Midway Airport (average of $220). Flying from Central America to Chicago Midway Airport in February is currently the most expensive (average of $795). 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 CA to MDW?

Find hourly flight availability from Central America to Midway. 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 Central America to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 75% on airfare.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated October 28, 2025.
See what other customers who have flown with Southwest from Central America to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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 Central America to Midway. 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 Central America to Chicago Midway Airport?

    Departing from Central America to Chicago Midway Airport will take you 7h 47m. There are 1958 mi between Central America and Chicago Midway Airport. This flight may include one or multiple stops.

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

    The most popular route from Central America to Chicago Midway Airport is Guatemala City La Aurora - Chicago Midway. You may also consider San José Juan Santamaria Intl - Chicago Midway or San Salvador El Salvador Intl - Chicago Midway.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Central America to Midway 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 Central America to Chicago Midway Airport?

    Currently, July is the cheapest month in which you can book a flight from Central America to Chicago Midway Airport (average of $220). Flying from Central America to Chicago Midway Airport in February is currently the most expensive (average of $795). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Central America to Midway

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

Discover the top airline that operate flights from Central America to Midway. 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
SouthwestCheapest$463Average$646FlexibilityNo cancel feeOn-time63%

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