$101 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 12/20. 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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Everything you should know

Cheapest round-trip
$238
Frontier
Thu 12/25Wed 12/31
SAP - MDW • 1 stop
Cheapest one-way
$101
Frontier
Sat 12/20
SJO - MDW • 1 stop
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We hope you love your trip to Midway!
Flight Deals
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Flight Deals

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

Thu, Dec 25 - Wed, Dec 31
Frontier Logo
12:35 pm - 10:12 pmSAP-MDW
9h 37m1 stop
Frontier Logo
8:15 am - 11:20 amMDW-SAP
27h 05m1 stop
$238Frontier
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Sat, Dec 6 - Mon, Jan 19
Multiple Airlines Logo
2:38 pm - 8:45 pmGUA-MDW
30h 07m1 stop
Multiple Airlines Logo
4:19 pm - 1:03 pmMDW-GUA
20h 44m1 stop
$247Multiple Airlines
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Tue, Dec 30 - Fri, Jan 9
Multiple Airlines Logo
2:38 pm - 8:45 pmGUA-MDW
30h 07m1 stop
Multiple Airlines Logo
3:01 pm - 10:03 amMDW-GUA
19h 02m1 stop
$255Multiple Airlines
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Sat, Dec 20 - Sun, Jan 11
Frontier Logo
10:36 am - 9:04 pmSJO-MDW
10h 28m1 stop
Frontier Logo
12:41 pm - 1:36 pmMDW-SJO
24h 55m1 stop
$270Frontier
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Sat, Dec 6 - Mon, Jan 19
Multiple Airlines Logo
2:38 pm - 8:45 pmGUA-MDW
30h 07m1 stop
Multiple Airlines Logo
4:19 pm - 12:24 pmMDW-GUA
20h 05m2 stops
$270Multiple Airlines
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Wed, Dec 24 - Wed, Dec 31
Frontier Logo
2:52 pm - 5:38 pmSJO-MDW
26h 46m1 stop
Frontier Logo
6:12 am - 1:42 pmMDW-SJO
7h 30m1 stop
$287Frontier
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Fri, Jan 16 - Mon, Jan 26
Delta Logo
2:35 pm - 10:07 pmSAL-MDW
7h 32m1 stop
Delta Logo
6:00 am - 1:10 pmMDW-SAL
7h 10m1 stop
$337Delta
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Thu, Jan 22 - Mon, Jan 26
Delta Logo
1:45 pm - 10:22 pmSAP-MDW
8h 37m1 stop
Delta Logo
6:00 am - 12:30 pmMDW-SAP
6h 30m1 stop
$352Delta
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Mon, Dec 15 - Tue, Dec 16
Southwest Logo
2:55 pm - 10:10 pmBZE-MDW
7h 15m1 stop
Southwest Logo
8:20 pm - 2:00 pmMDW-BZE
17h 40m2 stops
$565Southwest
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Mon, Dec 15 - Sat, Jan 3
Southwest Logo
2:55 pm - 10:10 pmBZE-MDW
7h 15m1 stop
Southwest Logo
5:15 am - 2:50 pmMDW-BZE
9h 35m1 stop
$614Southwest
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Useful Info

Good to know

Low seasonFebruary
Cheapest flight$101
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 9% lower on average.
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 airline 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 4251 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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

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