$106 Find Cheap Flights from Chicago Midway Airport to Central America

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 Central America departing on 9/1. 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

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Best Central America Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
San Salvador
San Salvador1 stop$260
San José
San José1 stop$383
Guatemala City
Guatemala City1 stop$282
Panama City
Panama City1 stop$672
Liberia
Liberia1 stop$453
Managua
Managua3 stops$940
San Pedro Sula
San Pedro Sula1 stop$354
Coxen Hole
Coxen Hole1 stop$661
San Salvador
San Salvador1 stop$260
San José
San José1 stop$383
Guatemala City
Guatemala City1 stop$282
Panama City
Panama City1 stop$672
Liberia
Liberia1 stop$453
Managua
Managua3 stops$940
San Pedro Sula
San Pedro Sula1 stop$354
Coxen Hole
Coxen Hole1 stop$661

Cheap Flights from Midway to Central America

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

Tue, Sep 2 - Wed, Sep 24
Delta Logo
6:00 am - 12:27 pmMDW-SAL
7h 27m1 stop
Delta Logo
1:34 pm - 9:44 pmSAL-MDW
7h 10m1 stop
$260Delta
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Thu, Sep 4 - Tue, Sep 16
Delta Logo
6:00 am - 12:27 pmMDW-SAL
7h 27m1 stop
Delta Logo
1:34 pm - 9:44 pmSAL-MDW
7h 10m1 stop
$270Delta
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Wed, Jul 16 - Wed, Jul 23
Frontier Logo
11:39 am - 10:38 pmMDW-GUA
11h 59m1 stop
Frontier Logo
11:43 pm - 1:47 pmGUA-MDW
13h 04m1 stop
$282Frontier
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Wed, Jul 9 - Wed, Jul 23
Frontier Logo
11:39 am - 10:38 pmMDW-GUA
11h 59m1 stop
Frontier Logo
11:43 pm - 1:47 pmGUA-MDW
13h 04m1 stop
$284Frontier
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Thu, Aug 28 - Thu, Sep 4
Southwest Logo
11:15 am - 6:55 pmMDW-SJO
8h 40m1 stop
Southwest Logo
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
$383Southwest
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Fri, Oct 24 - Mon, Oct 27
Southwest Logo
5:00 am - 12:00 pmMDW-SJO
8h 00m1 stop
Southwest Logo
1:30 pm - 12:45 amSJO-MDW
10h 15m1 stop
$403Southwest
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Sat, Jul 12 - Sat, Jul 19
 Logo
9:12 pm - 10:17 amMDW-GUA
14h 05m1 stop
 Logo
11:12 am - 8:22 pmGUA-MDW
8h 10m1 stop
Thu, Jul 31 - Thu, Aug 7
 Logo
9:12 pm - 11:24 amMDW-GUA
15h 12m2 stops
 Logo
11:12 am - 8:22 pmGUA-MDW
8h 10m1 stop
Thu, Sep 4 - Tue, Sep 16
Aeromexico Logo
10:11 am - 2:44 pmMDW-SAL
29h 33m2 stops
Aeromexico Logo
4:05 pm - 9:44 pmSAL-MDW
28h 39m2 stops
$975Aeromexico
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Tue, Aug 26 - Tue, Sep 2
Aeromexico Logo
6:00 am - 2:40 pmMDW-SAL
33h 40m2 stops
Aeromexico Logo
3:09 pm - 9:26 pmSAL-MDW
29h 17m2 stops
$1,035Aeromexico
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Useful Info

KAYAK's insights & trends for Midway to Central America flights

Get data-powered insights and trends into flights from Midway to Central America to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Chicago Midway Airport to Central America?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Central America were found on Delta ($260) and Frontier ($282).


Good to know

Low seasonMarch
High seasonJuly
Cheapest flight$106
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 25% lower on average.
Flight from Chicago Midway Airport to San Salvador

FAQs - booking Central America flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Central 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 Central 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 Central America?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to 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 Chicago Midway Airport to Central 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 from Chicago Midway Airport to Central America with an airline and back 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 Central 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 from Chicago Midway Airport to Central America up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Central America?

    The cheapest time of day to fly to Central America is generally in the afternoon, when round-trip flights cost $461 on average. The most expensive time of day to fly to Central America is generally in the morning, which is peak travel time and where the average cost of a ticket is $876.

Top airlines flying from Midway to Central America

 
Need help choosing which airline to fly with from Midway to Central 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
SouthwestOverall score based on 4278 reviews
7.1Food
8.6Crew
7.6Entertainment
8.2Boarding
8.0Comfort
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

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