$153 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 1/17. 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
$278
Delta
Sun 2/1Sun 2/8
SAP - MDW • 1 stop
Cheapest one-way
$153
Frontier
Sat 1/17
SJO - MDW • 1 stop
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Flight Deals
Useful Info
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

Sun, Feb 1 - Sun, Feb 8
Delta Logo
1:45 pm - 10:22 pm
SAP
-
MDW
8h 37m1 stop
Delta Logo
6:00 am - 12:30 pm
MDW
-
SAP
6h 30m1 stop
$278Delta
Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
10:09 am - 6:54 pm
SAL
-
MDW
8h 45m1 stop
Multiple Airlines Logo
8:28 am - 7:40 pm
MDW
-
SAL
11h 12m2 stops
$295Multiple Airlines
Thu, Jan 15 - Mon, Jan 19
Frontier Logo
10:56 am - 4:23 pm
SAL
-
MDW
29h 27m1 stop
Frontier Logo
6:10 am - 1:32 pm
MDW
-
SAL
7h 22m1 stop
$317Frontier
Fri, Jan 16 - Fri, Jan 23
Frontier Logo
10:09 am - 6:54 pm
SAL
-
MDW
8h 45m1 stop
Frontier Logo
5:01 pm - 10:05 am
MDW
-
SAL
17h 04m2 stops
$319Frontier
Thu, Jan 15 - Mon, Jan 19
Frontier Logo
10:56 am - 9:09 am
SAL
-
MDW
22h 13m2 stops
Frontier Logo
6:10 am - 1:32 pm
MDW
-
SAL
7h 22m1 stop
$323Frontier
Thu, Jan 29 - Wed, Feb 4
Southwest Logo
9:40 am - 10:55 pm
SJO
-
MDW
13h 15m1 stop
Southwest Logo
6:15 am - 7:30 pm
MDW
-
SJO
13h 15m1 stop
$354Southwest
Thu, Jan 22 - Tue, Jan 27
Southwest Logo
9:40 am - 10:55 pm
SJO
-
MDW
13h 15m1 stop
Southwest Logo
8:55 am - 7:30 pm
MDW
-
SJO
10h 35m1 stop
$376Southwest
Thu, Jan 15 - Thu, Jan 22
WestJet Logo
4:25 pm - 5:37 pm
BZE
-
MDW
25h 12m2 stops
WestJet Logo
1:26 pm - 2:09 pm
MDW
-
BZE
48h 43m2 stops
$1,147WestJet
Thu, Jan 1 - Mon, Jan 5
WestJet Logo
4:25 pm - 11:06 am
BZE
-
MDW
18h 41m2 stops
WestJet Logo
6:14 pm - 2:09 pm
MDW
-
BZE
43h 55m2 stops
$1,281WestJet
Fri, Feb 27 - Mon, Mar 2
Aeromexico Logo
12:30 pm - 3:21 pm
MGA
-
MDW
26h 51m2 stops
Aeromexico Logo
12:46 pm - 11:30 am
MDW
-
MGA
46h 44m2 stops
$1,957Aeromexico
Useful Info

Good to know

Low seasonMarch
Cheapest flight$153
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 5% 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 4258 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

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.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
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Everything you need to know for your flight to Midway

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