$135 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 8/31. 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 Salvador1 stop$447
San José
San José1 stop$462
Guatemala City
Guatemala City1 stop$456
Panama City
Panama City3 stops$603
Liberia
Liberia1 stop$410
Managua
Managua2 stops$1,130
San Pedro Sula
San Pedro Sula1 stop$503
Coxen Hole
Coxen Hole1 stop$781
San Salvador
San Salvador1 stop$447
San José
San José1 stop$462
Guatemala City
Guatemala City1 stop$456
Panama City
Panama City3 stops$603
Liberia
Liberia1 stop$410
Managua
Managua2 stops$1,130
San Pedro Sula
San Pedro Sula1 stop$503
Coxen Hole
Coxen Hole1 stop$781

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

Sun, Sep 20 - Tue, Sep 29
Delta Logo
6:05 am - 12:00 pm
MDW
-
LIR
6h 55m
1 stop
Delta Logo
1:25 pm - 10:25 pm
LIR
-
MDW
8h 00m
1 stop
$410Delta
Sun, Sep 20 - Thu, Oct 1
Delta Logo
6:51 pm - 12:00 pm
MDW
-
LIR
18h 09m
2 stops
Delta Logo
1:25 pm - 10:25 pm
LIR
-
MDW
8h 00m
1 stop
$415Delta
Wed, Aug 12 - Sun, Aug 16
Frontier Logo
4:45 pm - 10:05 am
MDW
-
GUA
18h 20m
1 stop
Frontier Logo
2:47 pm - 10:03 pm
GUA
-
MDW
30h 16m
2 stops
$456Frontier
Sat, Sep 19 - Wed, Sep 23
Southwest Logo
10:25 am - 6:00 pm
MDW
-
SJO
8h 35m
1 stop
Southwest Logo
1:40 pm - 11:10 pm
SJO
-
MDW
8h 30m
1 stop
$462Southwest
Tue, Sep 8 - Wed, Sep 23
Southwest Logo
9:05 am - 6:40 pm
MDW
-
SJO
10h 35m
2 stops
Southwest Logo
9:00 am - 9:50 pm
SJO
-
MDW
11h 50m
2 stops
$466Southwest
Wed, Aug 12 - Sat, Aug 22
Frontier Logo
4:45 pm - 10:05 am
MDW
-
GUA
18h 20m
1 stop
Frontier Logo
3:47 pm - 10:11 pm
GUA
-
MDW
29h 24m
2 stops
$488Frontier
Wed, Aug 19 - Sun, Aug 23
Multiple Airlines Logo
6:00 am - 9:15 am
MDW
-
PTY
27h 15m
3 stops
Multiple Airlines Logo
3:10 pm - 2:07 pm
PTY
-
MDW
22h 57m
3 stops
$603Multiple Airlines
Sat, Oct 24 - Mon, Nov 16
Multiple Airlines Logo
6:40 am - 8:34 pm
MDW
-
PTY
13h 54m
1 stop
Multiple Airlines Logo
9:31 pm - 10:58 am
PTY
-
MDW
14h 27m
2 stops
$778Multiple Airlines
Sat, Nov 21 - Sun, Nov 29
WestJet Logo
6:45 pm - 2:50 pm
MDW
-
RTB
20h 05m
2 stops
WestJet Logo
3:35 pm - 12:33 pm
RTB
-
MDW
20h 58m
2 stops
$2,907WestJet
Sat, Nov 21 - Sun, Nov 29
WestJet Logo
10:35 am - 2:50 pm
MDW
-
RTB
28h 15m
2 stops
WestJet Logo
3:35 pm - 4:25 pm
RTB
-
MDW
24h 50m
2 stops
$3,679WestJet
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.

Which airlines provide the cheapest flights from Chicago Midway Airport to Central America?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to Central America were found on Delta ($447) and Southwest ($462).

Good to know

Cheapest flight$135
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.
7.9
SouthwestOverall score based on 4235 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

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.

2.0 MediocreAngie, Jun 2026
CLE - DEN
Read more Southwest reviews

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

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

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

Everything you need to know for your flight to Central America

Information on your arrival and departure airports