$242 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 7/9. 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

Tue, Sep 15 - Fri, Sep 25
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
10:05 am - 6:40 pm
MDW
-
SJO
9h 35m
1 stop
$404Southwest
Mon, Sep 28 - Thu, Oct 1
Southwest Logo
9:00 am - 10:20 pm
SJO
-
MDW
12h 20m
2 stops
Southwest Logo
5:05 am - 12:00 pm
MDW
-
SJO
7h 55m
1 stop
$408Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
Southwest Logo
5:00 am - 12:45 pm
MDW
-
SJO
8h 45m
1 stop
$414Southwest
Tue, Sep 15 - Sun, Sep 20
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
7:10 am - 6:40 pm
MDW
-
SJO
12h 30m
2 stops
$415Southwest
Fri, Sep 25 - Tue, Sep 29
Delta Logo
1:37 pm - 10:25 pm
SAL
-
MDW
7h 48m
1 stop
Delta Logo
6:05 am - 12:22 pm
MDW
-
SAL
7h 17m
1 stop
$451Delta
Sun, Sep 13 - Thu, Sep 17
Delta Logo
12:09 pm - 9:46 pm
SAP
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 10:52 am
MDW
-
SAP
5h 47m
1 stop
$452Delta
Thu, Jul 9 - Mon, Sep 7
Frontier Logo
11:10 am - 8:32 pm
GUA
-
MDW
8h 22m
1 stop
Frontier Logo
6:00 am - 2:42 pm
MDW
-
GUA
33h 42m
2 stops
$517Frontier
Thu, Jul 9 - Wed, Aug 26
Frontier Logo
11:10 am - 8:32 pm
GUA
-
MDW
8h 22m
1 stop
Frontier Logo
6:00 am - 2:42 pm
MDW
-
GUA
33h 42m
2 stops
$529Frontier
Tue, Jul 14 - Tue, Jul 28
Multiple Airlines Logo
6:34 pm - 10:03 pm
PTY
-
MDW
27h 29m
2 stops
Multiple Airlines Logo
12:11 pm - 8:34 pm
MDW
-
PTY
8h 23m
1 stop
$776Multiple Airlines
Tue, Nov 3 - Mon, Nov 9
Multiple Airlines Logo
9:31 pm - 10:58 am
PTY
-
MDW
14h 27m
2 stops
Multiple Airlines Logo
7:25 am - 8:34 pm
MDW
-
PTY
12h 09m
1 stop
$789Multiple Airlines
Useful Info

Good to know

Low seasonNovember
Cheapest flight$242
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 29% increase in price.
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 airlines 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.
7.9
SouthwestOverall score based on 4236 reviews
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

In flight from Miami to Anchorage, we were all on board ready to take off. Pilot decided to take on more fuel causing a delay. Once fueled, the pilot came back over the radio stating more delay due to VIP. These delays caused me to miss my connecting flight. I went to the Alaska Air counter for information. They flat out stated that it was ATCs fault that I missed my flight and booked me a flight the next day about 1300 . I believe if we had the fuel prior to getting on board we would not of been delayed and I would have taken off on time. Pilot was taken out of the equation. I think they should’ve taken responsibility for their pilots decision to top off his aircraft instead of waiting til the last moment. Enough said…

We liked the way we were treated by the sraff at lima airport counter and the the flight attendants. We did not like the fact that the kiosks at airport rebooted after we entered our information and then told us that there was an issueand we needed to go to the counter. Such a waste of time for a group of 6. Once we got our boarding passes there was no assigned gate so we did not know where to go.

Honestly first time flying with delta and it was pretty good. All the process very smooth and crew was always nice and attentive.

Nothing I like, I missed this connection b/c of an earlier flight delay. I had to stay one more night and I paid out my own pocket. LATAM failed to send me to a safe and decent hotel.

It was delayed for 2 hours. Then when we arrived they took us on a very uncomfortable bus and left us there. The bus driver wouldn't let us out because no one from Latam was there. Everything was disaster.

LATAM is a great airline who takes care of there guests. They consistently walk around and see if you need water in addition to taking care of all the passengers. The chicken in process is really easy and I’m always offered a chance for an upgrade which I appreciate.

Deleted flight made me loose my connection flight now stuck in Atlanta for a day

Comfort in exit seat was excellent. FLight crew and flight were excellent. However exit seat tray table was broken so could not use it. Entertainment monitor did not work at all despite attempts to reset it.

I booked a flight through Kayak to Brazil I have traveled to Brazil several times before Kayak Delta or LATAM never mentioned during the booking or in the pre flight process that the visa requirements to visit Brazil have changed earlier this year. I was unaware of this change and as such never got a visa and was unable to fly from JFK to Sao Paulo Add to this that Delta allowed me to fly from Boston to JFK which they should not have as I didn’t have a visa. It has been a terrible experience and a huge loss of money

Wish the seats were a little more comfortable.. it was a 6 hrs nonstop trip. But the crew was courteous and w a smile

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
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on your arrival and departure airports