$149 Find Cheap Flights from Central 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 1/28. 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

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Everything you should know

Cheapest round-trip
$278
Delta
Thu 2/26Mon 3/2
SAP - MDW • 1 stop
Cheapest one-way
$149
Frontier
Wed 1/28
SAL - MDW • 1 stop
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We hope you love your trip to Midway!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Central America to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Central 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 Central America to Midway

Thu, Feb 26 - Mon, Mar 2
Delta Logo
1:45 pm - 10:31 pm
SAP
-
MDW
8h 46m1 stop
Delta Logo
6:00 am - 12:30 pm
MDW
-
SAP
6h 30m1 stop
$278Delta
Wed, Apr 29 - Mon, May 4
Delta Logo
2:00 pm - 10:29 pm
SAL
-
MDW
7h 29m1 stop
Delta Logo
6:30 am - 12:35 pm
MDW
-
SAL
7h 05m1 stop
$279Delta
Mon, Jan 12 - Mon, Jan 26
Multiple Airlines Logo
11:46 am - 11:09 pm
SAP
-
MDW
11h 23m1 stop
Multiple Airlines Logo
1:00 pm - 10:50 am
MDW
-
SAP
21h 50m1 stop
$281Multiple Airlines
Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
5:10 am - 7:58 pm
GUA
-
MDW
14h 48m2 stops
Multiple Airlines Logo
1:00 pm - 11:20 am
MDW
-
GUA
22h 20m1 stop
$299Multiple Airlines
Thu, Feb 5 - Mon, Feb 9
Multiple Airlines Logo
2:11 pm - 7:52 pm
GUA
-
MDW
29h 41m2 stops
Multiple Airlines Logo
7:00 pm - 11:20 am
MDW
-
GUA
16h 20m1 stop
$300Multiple Airlines
Wed, Apr 15 - Wed, Apr 29
LATAM Airlines Logo
1:05 pm - 10:29 pm
GUA
-
MDW
8h 24m1 stop
LATAM Airlines Logo
6:30 am - 11:43 am
MDW
-
GUA
6h 13m1 stop
$305LATAM Airlines
Sat, Jan 10 - Sat, Jan 17
Frontier Logo
1:35 pm - 10:27 pm
SJO
-
MDW
8h 52m1 stop
Frontier Logo
6:10 am - 1:42 pm
MDW
-
SJO
7h 32m1 stop
$314Frontier
Thu, Feb 5 - Sun, Feb 8
Southwest Logo
1:45 pm - 10:25 pm
SJO
-
MDW
8h 40m1 stop
Southwest Logo
5:00 am - 12:50 pm
MDW
-
SJO
7h 50m1 stop
$355Southwest
Fri, May 1 - Sat, May 16
LATAM Airlines Logo
12:30 pm - 12:30 pm
SAP
-
MDW
23h 00m2 stops
LATAM Airlines Logo
1:00 pm - 11:10 am
MDW
-
SAP
23h 10m2 stops
$411LATAM Airlines
Fri, Feb 20 - Sun, Mar 1
Southwest Logo
1:55 pm - 12:20 am
BZE
-
MDW
10h 25m2 stops
Southwest Logo
9:35 pm - 1:00 pm
MDW
-
BZE
15h 25m2 stops
$552Southwest
Useful Info

Good to know

Low seasonMarch
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 5% lower on average.

FAQs for booking Central America to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Central 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 Central 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 Central 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 Central 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 Central 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 Central America with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Central 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 Central America up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Central America to Midway

 
Need help choosing which airline to fly with from Central 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.
8.0
SouthwestOverall score based on 4251 reviews
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

8.0 ExcellentMaggie, Dec 2025
BWI - LAS
Read more Southwest reviews

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

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
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Griffith

Everything you need to know for your flight to Midway

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