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Cheap flights from San Juan to Chicago from $158

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 to Chicago departing on 8/26. 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
1 adult, Economy, 0 bags

Find the cheapest flights from San Juan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
Southwest Logo
8:20 am - 10:45 pm
MDW
-
SJU
13h 25m
1 stop
$256Southwest
Thu, Aug 27 - Sun, Aug 30
Southwest Logo
8:55 pm - 11:25 am
SJU
-
MDW
15h 30m
2 stops
Southwest Logo
3:10 pm - 11:50 pm
MDW
-
SJU
7h 40m
2 stops
$286Southwest
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$296Southwest
Fri, Aug 21 - Fri, Aug 28
Southwest Logo
5:55 am - 1:05 pm
SJU
-
MDW
8h 10m
2 stops
Southwest Logo
11:25 am - 9:30 pm
MDW
-
SJU
9h 05m
2 stops
$306Southwest
Sat, Sep 26 - Sat, Oct 3
Southwest Logo
5:00 am - 12:25 pm
SJU
-
MDW
8h 25m
2 stops
Southwest Logo
2:55 pm - 10:10 pm
MDW
-
SJU
6h 15m
1 stop
$311Southwest
Fri, Aug 28 - Fri, Aug 28
Southwest Logo
2:35 pm - 9:35 pm
SJU
-
MDW
8h 00m
1 stop
Southwest Logo
8:30 am - 6:10 pm
MDW
-
SJU
8h 40m
1 stop
$316Southwest
Thu, Sep 17 - Wed, Sep 23
Southwest Logo
8:55 pm - 8:45 am
SJU
-
MDW
12h 50m
1 stop
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
1 stop
$318Southwest
Thu, Aug 6 - Tue, Aug 18
Southwest Logo
11:50 am - 5:40 pm
SJU
-
MDW
6h 50m
1 stop
Southwest Logo
7:45 am - 6:05 pm
MDW
-
SJU
9h 20m
1 stop
$328Southwest
Tue, Aug 25 - Sat, Aug 29
Southwest Logo
8:55 pm - 11:25 am
SJU
-
MDW
15h 30m
2 stops
Southwest Logo
3:00 pm - 12:30 am
MDW
-
SJU
8h 30m
2 stops
$331Southwest
Thu, Aug 27 - Sun, Aug 30
Southwest Logo
8:55 pm - 8:45 am
SJU
-
MDW
12h 50m
1 stop
Southwest Logo
8:05 pm - 9:10 am
MDW
-
SJU
12h 05m
1 stop
$336Southwest
Thu, Aug 20 - Sun, Aug 23

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Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
Aug 27
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 30m
2 stops
MDW2:30 pmChicago Midway
Aug 30
MDW8:20 amChicago Midway
13h 25m
1 stop
SJU10:45 pmSan Juan Luis Munoz Marin Intl
$256
Southwest
Aug 27
SJU8:55 pmSan Juan Luis Munoz Marin Intl
15h 30m
2 stops
MDW11:25 amChicago Midway
Aug 31
MDW3:10 pmChicago Midway
7h 40m
2 stops
SJU11:50 pmSan Juan Luis Munoz Marin Intl
$286
Southwest
Aug 21
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 30m
2 stops
MDW2:30 pmChicago Midway
Aug 28
MDW3:15 pmChicago Midway
6h 50m
1 stop
SJU11:05 pmSan Juan Luis Munoz Marin Intl
$296

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Oct 21
SJU3:51 pmSan Juan Luis Munoz Marin Intl
7h 07m
1 stop
MDW9:58 pmChicago Midway
Oct 28
MDW7:25 amChicago Midway
7h 00m
1 stop
SJU3:25 pmSan Juan Luis Munoz Marin Intl
$376
Frontier
Aug 12
SJU6:32 amSan Juan Luis Munoz Marin Intl
10h 18m
1 stop
MDW3:50 pmChicago Midway
Aug 19
MDW6:05 amChicago Midway
7h 11m
1 stop
SJU2:16 pmSan Juan Luis Munoz Marin Intl
$385
Frontier
Aug 12
SJU6:32 amSan Juan Luis Munoz Marin Intl
10h 18m
1 stop
MDW3:50 pmChicago Midway
Aug 19
MDW6:05 amChicago Midway
7h 11m
1 stop
SJU2:16 pmSan Juan Luis Munoz Marin Intl
$392

momondo Fare Finder

 
Customize your flight search to find flights from San Juan 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 July 23, 2026.
Use the filters below to find and compare flights from San Juan to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/27

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Sun 8/30

8:20 am-10:45 pm

1 stop13h 25m

$256

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/27

8:55 pm-11:25 am

2 stops15h 30m

Chicago Midway

Mon 8/31

3:10 pm-11:50 pm

2 stops7h 40m

$286

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/21

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Fri 8/28

3:15 pm-11:05 pm

1 stop6h 50m

$296

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 9/26

5:55 am-1:05 pm

2 stops8h 10m

Chicago Midway

Sat 10/3

11:25 am-9:30 pm

2 stops9h 05m

$306
Quickest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 8/28

5:00 am-12:25 pm

2 stops8h 25m

Chicago Midway

Fri 8/28

2:55 pm-10:10 pm

1 stop6h 15m

$311

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/17

2:35 pm-9:35 pm

1 stop8h 00m

Chicago Midway

Wed 9/23

8:30 am-6:10 pm

1 stop8h 40m

$316

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/6

8:55 pm-8:45 am

1 stop12h 50m

Chicago Midway

Tue 8/18

12:45 pm-10:00 pm

1 stop8h 15m

$318

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 8/25

11:50 am-5:40 pm

1 stop6h 50m

Chicago Midway

Sat 8/29

7:45 am-6:05 pm

1 stop9h 20m

$328

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/27

8:55 pm-11:25 am

2 stops15h 30m

Chicago Midway

Sun 8/30

3:00 pm-12:30 am

2 stops8h 30m

$331

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/20

8:55 pm-8:45 am

1 stop12h 50m

Chicago Midway

Sun 8/23

8:05 pm-9:10 am

1 stop12h 05m

$336

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from San Juan 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 typical price of a round-trip flight between San Juan and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $333 to $465.
The lowest price recently found on this route was $256.

What is the cheapest month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from San Juan, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from San Juan during the month August is also very affordable. Most momondo users find prices during this month for around $302.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from San Juan. The lowest ticket price found for a Saturday departure recently was $616. 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, Sunday is the most expensive day to depart from San Juan because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $727.

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

Flying to Chicago Midway Airport from San Juan at noon is the least expensive time of day to depart. momondo users have found prices as low as $616 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $672. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest San Juan to Chicago Midway flight route?

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

What cabin class options are available on San Juan to Chicago Midway Airport flights?

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

Cheap San Juan to Chicago Midway Airport flight deals and tips

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

Fastest flight time

5h 05m

Direct flights

Mon and Sun
The fastest flight from San Juan to Chicago Midway Airport takes 5h 05m
Direct flights go from San Juan to Chicago Midway Airport on Monday and Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from San Juan to Chicago Midway Airport

  • How far is San Juan to Chicago Midway by plane?

    The distance between San Juan and Chicago Midway is about 2052.0 mi. In terms of flight time, this usually takes a little over 5h 05m.

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

    Prices for flights from San Juan to Chicago Midway Airport were last updated today.

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

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

    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 San Juan 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.

Best airlines flying from San Juan to Chicago Midway Airport

Compare and see reviews for airlines that fly from San Juan to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $266Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
Portage
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Schererville
Munster
Chesterton
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Crown Point
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from San Juan to Chicago. momondo saves you time and could save you money on your trip.

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 helps you find the best flight between San Juan and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from San Juan and alert you when they change.

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