$186 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 10/7. 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

Wed, Sep 23 - Mon, Sep 28
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
2 stops
$378Southwest
Wed, Oct 7 - Mon, Oct 12
Southwest Logo
9:00 am - 7:20 pm
SJO
-
MDW
9h 20m
1 stop
Southwest Logo
8:50 pm - 11:40 am
MDW
-
SJO
15h 50m
2 stops
$379Southwest
Thu, Sep 17 - Tue, Sep 22
Southwest Logo
1:40 pm - 10:15 pm
SJO
-
MDW
7h 35m
1 stop
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$383Southwest
Sat, Sep 5 - Tue, Sep 8
Southwest Logo
1:15 pm - 10:00 pm
SJO
-
MDW
7h 45m
1 stop
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
$405Southwest
Sat, Sep 19 - Fri, Oct 2
Delta Logo
12:41 pm - 10:45 pm
SAP
-
MDW
9h 04m
1 stop
Delta Logo
6:05 am - 11:16 am
MDW
-
SAP
6h 11m
1 stop
$424Delta
Fri, Sep 25 - Tue, Sep 29
Delta Logo
1:57 pm - 10:45 pm
SAL
-
MDW
7h 48m
1 stop
Delta Logo
6:05 am - 12:31 pm
MDW
-
SAL
7h 26m
1 stop
$456Delta
Wed, Jul 15 - Wed, Aug 12
Frontier Logo
2:47 pm - 10:03 pm
GUA
-
MDW
30h 16m
2 stops
Frontier Logo
4:45 pm - 10:05 am
MDW
-
GUA
18h 20m
1 stop
$483Frontier
Tue, Aug 4 - Wed, Aug 12
Frontier Logo
2:31 pm - 10:03 pm
GUA
-
MDW
30h 32m
2 stops
Frontier Logo
4:45 pm - 10:05 am
MDW
-
GUA
18h 20m
1 stop
$495Frontier
Tue, Oct 6 - Sun, Oct 11
Multiple Airlines Logo
9:33 pm - 10:58 am
PTY
-
MDW
13h 25m
2 stops
Multiple Airlines Logo
6:40 am - 8:34 pm
MDW
-
PTY
13h 54m
1 stop
$781Multiple Airlines
Sun, Nov 1 - Tue, Nov 10
Multiple Airlines Logo
4:00 pm - 10:58 am
PTY
-
MDW
19h 58m
2 stops
Multiple Airlines Logo
7:25 am - 8:34 pm
MDW
-
PTY
12h 09m
1 stop
$793Multiple Airlines
Useful Info

Good to know

Low seasonNovember
Cheapest flight$186
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from San José 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 4246 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

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

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

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

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

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