$183 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 5/28. 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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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, Apr 9 - Sun, Apr 12
Frontier Logo
6:38 pm - 2:01 pm
GUA
-
MDW
18h 23m
1 stop
Frontier Logo
4:46 pm - 8:30 am
MDW
-
GUA
16h 44m
1 stop
$320Frontier
Fri, Apr 17 - Fri, Apr 24
Frontier Logo
1:37 pm - 6:37 pm
SAL
-
MDW
28h 00m
1 stop
Frontier Logo
6:00 am - 12:31 pm
MDW
-
SAL
7h 31m
1 stop
$331Frontier
Thu, Apr 30 - Tue, May 5
Multiple Airlines Logo
10:55 am - 10:28 am
SAP
-
MDW
22h 33m
1 stop
Multiple Airlines Logo
2:20 pm - 10:00 am
MDW
-
SAP
20h 40m
2 stops
$332Multiple Airlines
Mon, Apr 6 - Fri, Apr 10
Frontier Logo
2:09 pm - 8:07 pm
GUA
-
MDW
28h 58m
1 stop
Frontier Logo
5:11 pm - 9:35 am
MDW
-
GUA
17h 24m
1 stop
$349Frontier
Thu, Apr 16 - Mon, Apr 27
Southwest Logo
1:10 pm - 9:55 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$356Southwest
Thu, Apr 16 - Mon, Apr 20
Southwest Logo
9:00 am - 7:00 pm
SJO
-
MDW
9h 00m
1 stop
Southwest Logo
12:10 pm - 7:00 pm
MDW
-
SJO
7h 50m
1 stop
$383Southwest
Thu, Apr 16 - Thu, Apr 23
Multiple Airlines Logo
10:55 am - 7:59 am
SAP
-
MDW
20h 04m
1 stop
Multiple Airlines Logo
4:15 pm - 10:00 am
MDW
-
SAP
18h 45m
2 stops
$385Multiple Airlines
Fri, Apr 24 - Tue, Apr 28
Delta Logo
1:14 pm - 10:28 pm
GUA
-
MDW
8h 14m
1 stop
Delta Logo
6:00 am - 11:46 am
MDW
-
GUA
6h 46m
1 stop
$405Delta
Wed, Apr 29 - Mon, May 4
Delta Logo
2:04 pm - 10:28 pm
SAL
-
MDW
7h 24m
1 stop
Delta Logo
6:00 am - 12:39 pm
MDW
-
SAL
7h 39m
1 stop
$416Delta
Sat, Apr 18 - Tue, May 5
LATAM Airlines Logo
12:35 pm - 10:28 pm
SAP
-
MDW
8h 53m
1 stop
LATAM Airlines Logo
1:24 pm - 11:20 am
MDW
-
SAP
22h 56m
2 stops
$577LATAM Airlines
Useful Info

Good to know

Low seasonNovember
Cheapest flight$173
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Guatemala City to Chicago Midway Airport

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 4309 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
Airline reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

4.0 OkayEmma, Mar 2026
LAX - PHX
Read more Southwest reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Great plane, great attendants,great flight crew,on time. Wonderful flight home..

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

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
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports