Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from San Juan Luis Munoz Marin Intl Airport to Chicago from $95

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago departing on 1/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from San Juan Luis Munoz Marin Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
4:06 pm - 11:42 pm
SJU
-
MDW
8h 36m1 stop
Frontier Logo
3:10 pm - 1:50 am
MDW
-
SJU
9h 40m1 stop
$180Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
7:00 pm - 12:43 am
MDW
-
SJU
27h 43m1 stop
$181Frontier
Sat, Feb 7 - Mon, Feb 9
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
$182Frontier
Thu, Jan 29 - Mon, Feb 2
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m1 stop
Frontier Logo
9:22 pm - 12:43 am
MDW
-
SJU
25h 21m1 stop
$202Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
1:00 pm - 1:08 am
MDW
-
SJU
10h 08m1 stop
$216Frontier
Thu, Jan 29 - Sun, Feb 1
Frontier Logo
4:11 pm - 10:29 pm
SJU
-
MDW
8h 18m1 stop
Frontier Logo
6:15 am - 2:09 pm
MDW
-
SJU
6h 54m1 stop
$217Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
4:11 pm - 10:29 pm
SJU
-
MDW
8h 18m1 stop
Frontier Logo
6:15 am - 2:09 pm
MDW
-
SJU
6h 54m1 stop
$218Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
8:00 am - 7:58 pm
SJU
-
MDW
13h 58m1 stop
Frontier Logo
1:00 pm - 3:26 pm
MDW
-
SJU
24h 26m1 stop
$231Frontier
Mon, Jan 26 - Mon, Feb 2
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m1 stop
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m1 stop
$232Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
4:35 pm - 10:19 pm
SJU
-
MDW
7h 44m1 stop
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
$236Frontier
Tue, Jan 13 - Fri, Jan 23

Frontier flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Our best Frontier deals on San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flight tickets
Frontier
Apr 9
SJU4:06 pmSan Juan Luis Munoz Marin Intl
8h 36m
1 stop
MDW11:42 pmChicago Midway
Apr 13
MDW3:10 pmChicago Midway
9h 40m
1 stop
SJU1:50 amSan Juan Luis Munoz Marin Intl
$180
Find similar
Frontier
Feb 7
SJU4:36 pmSan Juan Luis Munoz Marin Intl
29h 16m
1 stop
MDW7:52 pmChicago Midway
Feb 9
MDW7:00 pmChicago Midway
27h 43m
1 stop
SJU12:43 amSan Juan Luis Munoz Marin Intl
$181
Find similar
Frontier
Jan 29
SJU4:36 pmSan Juan Luis Munoz Marin Intl
29h 16m
1 stop
MDW7:52 pmChicago Midway
Feb 2
MDW1:00 pmChicago Midway
8h 59m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
$182
Find similar

Southwest flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Our best Southwest deals on San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flight tickets
Southwest
Jan 14
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
Jan 21
MDW8:30 amChicago Midway
6h 35m
1 stop
SJU5:05 pmSan Juan Luis Munoz Marin Intl
$245
Find similar
Southwest
Jan 14
SJU6:10 amSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW11:35 amChicago Midway
Jan 22
MDW1:15 pmChicago Midway
7h 55m
1 stop
SJU11:10 pmSan Juan Luis Munoz Marin Intl
$265
Find similar
Southwest
Jan 15
SJU8:00 amSan Juan Luis Munoz Marin Intl
8h 20m
1 stop
MDW2:20 pmChicago Midway
Jan 19
MDW2:05 pmChicago Midway
6h 10m
1 stop
SJU10:15 pmSan Juan Luis Munoz Marin Intl
$266
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport 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 January 2, 2026.
Use the filters below to find and compare flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/9

4:06 pm-11:42 pm

1 stop8h 36m

Chicago Midway

Mon 4/13

3:10 pm-1:50 am

1 stop9h 40m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 2/7

4:36 pm-7:52 pm

1 stop29h 16m

Chicago Midway

Mon 2/9

7:00 pm-12:43 am

1 stop27h 43m

$181

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/29

4:36 pm-7:52 pm

1 stop29h 16m

Chicago Midway

Mon 2/2

1:00 pm-11:59 pm

1 stop8h 59m

$182

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/27

3:53 am-2:55 pm

1 stop13h 02m

Chicago Midway

Mon 3/2

9:22 pm-12:43 am

1 stop25h 21m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/29

4:36 pm-7:52 pm

1 stop29h 16m

Chicago Midway

Sun 2/1

1:00 pm-1:08 am

1 stop10h 08m

$216

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-10:29 pm

1 stop8h 18m

Chicago Midway

Mon 3/9

6:15 am-2:09 pm

1 stop6h 54m

$217

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-10:29 pm

1 stop8h 18m

Chicago Midway

Mon 3/9

6:15 am-2:09 pm

1 stop6h 54m

$218

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 1/26

8:00 am-7:58 pm

1 stop13h 58m

Chicago Midway

Mon 2/2

1:00 pm-3:26 pm

1 stop24h 26m

$231

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/27

3:53 am-2:55 pm

1 stop13h 02m

Chicago Midway

Mon 3/2

9:22 pm-9:54 am

1 stop10h 32m

$232

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 1/13

4:35 pm-10:19 pm

1 stop7h 44m

Chicago Midway

Fri 1/23

1:00 pm-11:59 pm

1 stop8h 59m

$236

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

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 Chicago Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from San Juan Luis Munoz Marin Intl Airport, with most prices found around $297. If you are unable to visit Chicago Midway Airport during the month of December, then departing from San Juan Luis Munoz Marin Intl Airport during the month November is also very affordable. Most momondo users find prices during this month for around $336.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from San Juan Luis Munoz Marin Intl Airport. The lowest ticket price found for a Friday departure recently was $154. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from San Juan Luis Munoz Marin Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $580.

What is the cheapest San Juan Luis Munoz Marin Intl to Chicago Midway flight route?

Fly from San Juan Luis Munoz Marin Intl to Chicago Midway for the best San Juan Luis Munoz Marin Intl - Chicago Midway flight prices

What cabin class options are available on San Juan Luis Munoz Marin Intl to Chicago Midway flights?

There is only 1 cabin class available to choose from on San Juan Luis Munoz Marin Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flights?

You could potentially save up to 11% on your flight if you consider stops on a San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flight.

How have San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flight prices changed over time?

As of January 2026, prices for San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport flights are approximately 39% more expensive when compared to flights at the same time last year.

When to book flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport (SJU to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Fastest flight time

4h 50m

Direct flights

Mon and Sun
The fastest flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport takes 4h 50m
Direct flights go from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • How far is San Juan Luis Munoz Marin Intl to Chicago Midway by plane?

    Chicago Midway is 2057.4 mi away from San Juan Luis Munoz Marin Intl. 4h 50m is a normal flight duration for this route.

  • When did momondo last update prices for flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

    Prices for flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

  • What is the most popular airline from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

Best airlines flying from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $419Free CancellationRating
8.0
4,254 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from San Juan to Chicago?

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

Can I find flights from San Juan to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from San Juan which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from San Juan to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Juan to Chicago.

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

Of course. momondo tracks the price of San Juan to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 2/1
Sun 2/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago