$208 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 5/18. 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 25 - Tue, Sep 29
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
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
$384Delta
Thu, Sep 10 - Wed, Sep 16
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, Sep 10 - Wed, Sep 16
Southwest Logo
9:00 am - 9:00 pm
SJO
-
MDW
11h 00m
2 stops
Southwest Logo
9:05 am - 6:40 pm
MDW
-
SJO
10h 35m
2 stops
$481Southwest
Sun, Aug 16 - Sat, Aug 29
Frontier Logo
3:47 pm - 11:12 am
GUA
-
MDW
42h 25m
2 stops
Frontier Logo
6:00 am - 2:42 pm
MDW
-
GUA
33h 42m
2 stops
$488Frontier
Mon, May 18 - Sun, May 24
Multiple Airlines Logo
7:00 am - 3:57 pm
SJO
-
MDW
7h 57m
1 stop
Multiple Airlines Logo
12:27 pm - 11:45 am
MDW
-
SJO
24h 18m
2 stops
$496Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
10:10 pm - 3:15 pm
SAL
-
MDW
16h 05m
2 stops
Multiple Airlines Logo
4:10 pm - 10:00 am
MDW
-
SAL
18h 50m
1 stop
$506Multiple Airlines
Wed, Jul 1 - Sat, Jul 18
JetBlue Logo
1:51 pm - 10:17 pm
SAL
-
MDW
7h 26m
1 stop
JetBlue Logo
6:05 am - 12:23 pm
MDW
-
SAL
7h 18m
1 stop
$523JetBlue
Wed, Aug 12 - Sun, Aug 16
JetBlue Logo
1:19 pm - 9:46 pm
SAL
-
MDW
7h 27m
1 stop
JetBlue Logo
6:00 am - 12:04 pm
MDW
-
SAL
7h 04m
1 stop
$534JetBlue
Tue, Jul 21 - Mon, Jul 27
Frontier Logo
9:30 am - 11:07 am
SAP
-
MDW
24h 37m
2 stops
Frontier Logo
6:00 am - 8:25 am
MDW
-
SAP
27h 25m
2 stops
$564Frontier
Useful Info

Good to know

Low seasonNovember
Cheapest flight$208
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 4314 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

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

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

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.

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

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

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