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Cheap flights from Chicago Midway Airport to Central America from $104

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Central America departing on 10/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Central America

Cheap round-trip flights

Frontier Logo
6:15 am - 1:09 pmMDW-SAL
6h 54m1 stop
Frontier Logo
2:24 pm - 10:11 pmSAL-MDW
7h 47m1 stop
$256Frontier
Find Deal
Sat, Nov 8 - Mon, Nov 17
Multiple Airlines Logo
8:05 am - 11:22 amMDW-GUA
28h 17m2 stops
Multiple Airlines Logo
11:25 am - 9:47 amGUA-MDW
21h 22m1 stop
$264Multiple Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Multiple Airlines Logo
1:37 pm - 12:04 pmMDW-GUA
23h 27m1 stop
Multiple Airlines Logo
1:22 pm - 10:08 pmGUA-MDW
32h 46m2 stops
$274Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Delta Logo
6:00 am - 12:00 pmMDW-LIR
7h 00m1 stop
Delta Logo
1:05 pm - 10:14 pmLIR-MDW
8h 09m1 stop
$309Delta
Find Deal
Sun, Oct 26 - Thu, Oct 30
Delta Logo
6:00 am - 12:00 pmMDW-LIR
7h 00m1 stop
Delta Logo
1:05 pm - 8:40 amLIR-MDW
18h 35m2 stops
$313Delta
Find Deal
Sun, Oct 26 - Thu, Oct 30
Southwest Logo
8:45 pm - 11:20 amMDW-SJO
15h 35m2 stops
Southwest Logo
12:35 pm - 10:35 pmSJO-MDW
9h 00m1 stop
$345Southwest
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Fri, Oct 3 - Wed, Oct 8
Southwest Logo
5:50 am - 1:15 pmMDW-SJO
7h 25m1 stop
Southwest Logo
9:00 am - 10:35 pmSJO-MDW
13h 35m2 stops
$349Southwest
Find Deal
Thu, Nov 6 - Tue, Nov 11
WestJet Logo
9:20 am - 1:29 pmMDW-LIR
29h 09m3 stops
WestJet Logo
3:20 pm - 5:43 pmLIR-MDW
26h 23m2 stops
$857WestJet
Find Deal
Thu, Oct 30 - Thu, Nov 6
Aeromexico Logo
10:47 am - 1:27 pmMDW-SAL
26h 40m2 stops
Aeromexico Logo
2:43 pm - 11:32 pmSAL-MDW
32h 49m2 stops
$1,102Aeromexico
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Sun, Nov 9 - Fri, Nov 21
Aeromexico Logo
6:00 am - 11:30 amMDW-MGA
30h 30m2 stops
Aeromexico Logo
12:30 pm - 10:14 pmMGA-MDW
32h 44m2 stops
$1,494Aeromexico
Find Deal
Thu, Oct 2 - Sun, Oct 5

Southwest flights from Chicago Midway Airport to Central America

Our best Southwest deals on Chicago Midway Airport to Central America flight tickets
Southwest
Sep 30
MDW6:25 amChicago Midway
13h 30m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Oct 3
SJO1:30 pmSan José Juan Santamaria Intl
10h 15m
1 stop
MDW12:45 amChicago Midway
$340
Find similar
Southwest
Oct 3
MDW8:45 pmChicago Midway
15h 35m
2 stops
SJO11:20 amSan José Juan Santamaria Intl
Oct 8
SJO12:35 pmSan José Juan Santamaria Intl
9h 00m
1 stop
MDW10:35 pmChicago Midway
$345
Find similar
Southwest
Nov 6
MDW5:50 amChicago Midway
7h 25m
1 stop
SJO1:15 pmSan José Juan Santamaria Intl
Nov 11
SJO9:00 amSan José Juan Santamaria Intl
13h 35m
2 stops
MDW10:35 pmChicago Midway
$349
Find similar

Delta flights from Chicago Midway Airport to Central America

Our best Delta deals on Chicago Midway Airport to Central America flight tickets
Delta
Sep 30
MDW6:00 amChicago Midway
7h 00m
1 stop
LIR12:00 pmLiberia
Oct 3
LIR1:25 pmLiberia
7h 11m
1 stop
MDW9:36 pmChicago Midway
$309
Find similar
Delta
Oct 26
MDW6:00 amChicago Midway
7h 00m
1 stop
LIR12:00 pmLiberia
Oct 30
LIR1:05 pmLiberia
18h 35m
2 stops
MDW8:40 amChicago Midway
$313
Find similar
Delta
Oct 21
MDW6:00 amChicago Midway
6h 58m
1 stop
SJO11:58 amSan José Juan Santamaria Intl
Oct 24
SJO1:23 pmSan José Juan Santamaria Intl
7h 51m
1 stop
MDW10:14 pmChicago Midway
$340
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Central America that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Central America that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Salvador

MDW - SAL

MDWSAL

Chicago Midway

Sat 11/8

6:15 am-1:09 pm

1 stop6h 54m

San Salvador El Salvador Intl

Mon 11/17

2:24 pm-10:11 pm

1 stop7h 47m

$256

ChicagoGuatemala City

MDW - GUA

MDWGUA

Chicago Midway

Wed 10/15

8:05 am-11:22 am

2 stops28h 17m

Guatemala City La Aurora

Wed 10/22

11:25 am-9:47 am

1 stop21h 22m

$264

ChicagoGuatemala City

MDW - GUA

MDWGUA

Chicago Midway

Thu 10/30

1:37 pm-12:04 pm

1 stop23h 27m

Guatemala City La Aurora

Thu 11/6

1:22 pm-10:08 pm

2 stops32h 46m

$274

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sun 10/26

6:00 am-12:00 pm

1 stop7h 00m

Liberia

Thu 10/30

1:05 pm-10:14 pm

1 stop8h 09m

$309

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Sun 10/26

6:00 am-12:00 pm

1 stop7h 00m

Liberia

Thu 10/30

1:05 pm-8:40 am

2 stops18h 35m

$313

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 10/3

8:45 pm-11:20 am

2 stops15h 35m

San José Juan Santamaria Intl

Wed 10/8

12:35 pm-10:35 pm

1 stop9h 00m

$345

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 11/6

5:50 am-1:15 pm

1 stop7h 25m

San José Juan Santamaria Intl

Tue 11/11

9:00 am-10:35 pm

2 stops13h 35m

$349

ChicagoLiberia

MDW - LIR

MDWLIR

Chicago Midway

Thu 10/30

9:20 am-1:29 pm

3 stops29h 09m

Liberia

Thu 11/6

3:20 pm-5:43 pm

2 stops26h 23m

$857

ChicagoSan Salvador

MDW - SAL

MDWSAL

Chicago Midway

Sun 11/9

10:47 am-1:27 pm

2 stops26h 40m

San Salvador El Salvador Intl

Fri 11/21

2:43 pm-11:32 pm

2 stops32h 49m

$1,102

ChicagoManagua

MDW - MGA

MDWMGA

Chicago Midway

Thu 10/2

6:00 am-11:30 am

2 stops30h 30m

Managua Augusto C Sandino

Sun 10/5

12:30 pm-10:14 pm

2 stops32h 44m

$1,494

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to Central America

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Central America?

In general, August is the cheapest month to fly from Chicago Midway Airport to Central America. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $477. If you don’t want to visit Central America in August, then you should wait until September to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $477.

What is the cheapest day to depart on your flight to Central America?

The cheapest day to depart from Chicago Midway Airport to Central America is on a Thursday. Travelers who choose to depart for Central America on a Thursday will often find tickets for as low as $633. On the other hand, Sunday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,128.

Can stopping save me money on Chicago Midway Airport to Central America flights?

You could potentially save up to 41% on your flight if you consider stops on a Chicago Midway Airport to Central America flight.

Cheap Chicago Midway Airport to Central America flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Central America

Direct flights

None
There are no direct flights from Chicago Midway Airport to Central America. There are no popular flight routes from Chicago Midway Airport to Central America.
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Central America?

    Prices for flights from Chicago Midway Airport to Central America refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Central America?

  • How old do you have to be to fly from Chicago Midway Airport to Central America?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Central America.

  • What documentation or ID do you need to fly to Central America?

    The travel and health documents you'll need for your trip to Central America may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Central America. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago Midway Airport to Central America

Compare and see reviews for airlines that fly from Chicago Midway Airport to Central America with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $175Free CancellationRating
7.9
7,957 reviews
Search Delta flights
SouthwestPriceFrom $394Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Central America?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Central America. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Central America with flexible booking policies on momondo?

All flight searches from Chicago to Central America on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Central America?

Once all potential Chicago to Central America flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Central America right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Central America now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Central America and let you know when they change.

An easier way to manage your Central America trip

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Find better results for your trip to Central America

Popular cities in Central America

Popular flights according to clicks in the last 7 days on momondo
Flights to San José, San José Provincefrom $135
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Flights to Liberiafrom $243
Flights to San Pedro Sulafrom $107
Flights to Belize Cityfrom $263
Flights to Coxen Holefrom $335
Flights to Floresfrom $370
Flights to Bocas del Torofrom $516
Flights to Davidfrom $296