$178 Find Cheap Flights from Chicago Midway Airport to Central America

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Central America departing on 6/20. 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 Midway to Central America

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
San Salvador
San Salvador2 stops$528
San José
San José1 stop$438
Guatemala City
Guatemala City1 stop$403
Panama City
Panama City1 stop$692
Liberia
Liberia1 stop$494
Managua
Managua3 stops$1,120
San Pedro Sula
San Pedro Sula2 stops$509
San Salvador
San Salvador2 stops$528
San José
San José1 stop$438
Guatemala City
Guatemala City1 stop$403
Panama City
Panama City1 stop$692
Liberia
Liberia1 stop$494
Managua
Managua3 stops$1,120
San Pedro Sula
San Pedro Sula2 stops$509

Book Cheap Midway to Central America Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Central America 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 Midway to Central America

Tue, Sep 1 - Wed, Sep 30
Delta Logo
6:00 am - 11:28 am
MDW
-
GUA
6h 28m
1 stop
Delta Logo
1:05 pm - 9:46 pm
GUA
-
MDW
7h 41m
1 stop
$403Delta
Tue, Sep 1 - Wed, Sep 30
Delta Logo
6:00 am - 11:28 am
MDW
-
GUA
6h 28m
1 stop
Delta Logo
1:05 pm - 9:46 pm
GUA
-
MDW
7h 41m
1 stop
$423Delta
Sat, Sep 26 - Sat, Oct 24
Delta Logo
5:59 pm - 11:30 am
MDW
-
GUA
18h 31m
2 stops
Delta Logo
2:15 pm - 8:45 am
GUA
-
MDW
17h 30m
2 stops
$427Delta
Wed, May 27 - Thu, Jun 4
Frontier Logo
3:07 pm - 8:19 am
MDW
-
SJO
18h 12m
2 stops
Frontier Logo
9:35 am - 10:02 pm
SJO
-
MDW
11h 27m
2 stops
$449Frontier
Sat, Jun 13 - Sat, Jul 11
Frontier Logo
6:00 am - 2:42 pm
MDW
-
GUA
33h 42m
2 stops
Frontier Logo
3:47 pm - 2:27 pm
GUA
-
MDW
21h 40m
2 stops
$457Frontier
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
6:15 am - 12:45 pm
MDW
-
SJO
7h 30m
1 stop
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$476Southwest
Mon, Sep 21 - Fri, Sep 25
Southwest Logo
9:20 am - 6:40 pm
MDW
-
SJO
10h 20m
2 stops
Southwest Logo
9:00 am - 9:00 pm
SJO
-
MDW
11h 00m
2 stops
$480Southwest
Thu, Jun 25 - Tue, Jun 30
Multiple Airlines Logo
4:10 pm - 10:00 am
MDW
-
SAL
18h 50m
1 stop
Multiple Airlines Logo
10:10 pm - 11:12 am
SAL
-
MDW
36h 02m
2 stops
$547Multiple Airlines
Thu, Jun 25 - Thu, Jul 2
Multiple Airlines Logo
4:10 pm - 10:00 am
MDW
-
SAL
18h 50m
1 stop
Multiple Airlines Logo
10:10 pm - 11:04 am
SAL
-
MDW
35h 54m
2 stops
$549Multiple Airlines
Thu, Sep 24 - Sat, Sep 26
KLM Logo
10:35 am - 12:56 pm
MDW
-
PTY
26h 21m
1 stop
KLM Logo
2:21 pm - 11:54 am
PTY
-
MDW
21h 33m
1 stop
$692KLM
Booking Insights

KAYAK's insights & trends for Midway to Central America flights

Get data-powered insights and trends into flights from Midway to Central America to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Central America?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Central America, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Central America is January, when tickets cost $0 (return) on average. On the other hand, the most expensive months are October and May, when the average cost of round-trip tickets is $985 and $908 respectively.

Good to know

Cheapest flight$178
Flight from Chicago Midway Airport to San José

FAQs - booking Central America flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Central America?

    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 Chicago Midway Airport to Central America.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Central America?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to 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 Chicago Midway Airport to Central America?

    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 from Chicago Midway Airport to Central America with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Central America?

    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 from Chicago Midway Airport to 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 Midway to Central America

 
Need help choosing which airline to fly with from Midway to Central America? 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 4317 reviews
7.5Entertainment
8.1Boarding
8.6Crew
8.0Comfort
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.

Everything you need to know for your flight to Central America

Information on your arrival and departure airports