$196 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 5/15. 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

Fri, Sep 11 - Tue, Sep 15
Delta Logo
1:37 pm - 9:46 pm
SAL
-
MDW
7h 09m
1 stop
Delta Logo
6:00 am - 12:22 pm
MDW
-
SAL
7h 22m
1 stop
$373Delta
Sat, Aug 29 - Mon, Aug 31
Delta Logo
12:53 pm - 9:46 pm
GUA
-
MDW
7h 53m
1 stop
Delta Logo
6:00 am - 11:28 am
MDW
-
GUA
6h 28m
1 stop
$405Delta
Tue, Jun 16 - Sat, Jun 20
Frontier Logo
3:47 pm - 10:11 pm
GUA
-
MDW
29h 24m
2 stops
Frontier Logo
11:59 am - 2:42 pm
MDW
-
GUA
27h 43m
2 stops
$438Frontier
Fri, May 29 - Thu, Jun 4
Frontier Logo
3:50 pm - 2:12 pm
SAL
-
MDW
21h 22m
1 stop
Frontier Logo
3:07 pm - 2:45 pm
MDW
-
SAL
24h 38m
1 stop
$454Frontier
Sat, May 2 - Sun, May 10
Delta Logo
2:04 pm - 10:28 pm
SAL
-
MDW
7h 24m
1 stop
Delta Logo
6:23 am - 12:26 pm
MDW
-
SAL
7h 03m
1 stop
$455Delta
Wed, May 13 - Mon, May 18
Multiple Airlines Logo
7:00 am - 10:02 pm
SJO
-
MDW
14h 02m
2 stops
Multiple Airlines Logo
4:52 pm - 3:18 pm
MDW
-
SJO
23h 26m
1 stop
$456Multiple Airlines
Sat, May 2 - Sun, May 10
Delta Logo
2:04 pm - 10:28 pm
SAL
-
MDW
7h 24m
1 stop
Delta Logo
6:23 am - 12:26 pm
MDW
-
SAL
7h 03m
1 stop
$461Delta
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
$468Southwest
Thu, Sep 24 - Wed, Sep 30
Southwest Logo
9:00 am - 9:30 pm
SJO
-
MDW
11h 30m
1 stop
Southwest Logo
10:10 am - 6:40 pm
MDW
-
SJO
9h 30m
2 stops
$477Southwest
Thu, May 14 - Mon, May 18
Multiple Airlines Logo
7:00 am - 10:02 pm
SJO
-
MDW
14h 02m
2 stops
Multiple Airlines Logo
4:52 pm - 3:18 pm
MDW
-
SJO
23h 26m
1 stop
$484Multiple Airlines
Useful Info

Good to know

Low seasonNovember
Cheapest flight$196
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly with an average 2% 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.
8.0
SouthwestOverall score based on 4331 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

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

The seat was not comfortable. 1D. My back was sore all night and the next day.

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

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

Terrible all around. Left prior review detailing massive delay/cancellation to then rebook travel. Topping on the cake was lost luggage even after travel to ultimate destination was secured on a new plane(s).

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

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

I like this airline a lot no problems at all, except being forced to check a carry-on bag ., Overall very good airline

The plane broke down at the Lima stopover and they offered to put me on a flight the be t day but I had to be back in LA that morning and so I had to buy another ticket from Avianca and United for $2k I asked LATAM for compensation and received none. Very bad experience

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