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Cheap flights from San Juan to Chicago from $128

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 8/27. 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
1:20 pm - 7:10 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
6h 50m1 stop Tampa
Southwest Logo
7:30 am - 7:05 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 35m1 stop Tampa
$256Southwest
Wed, Sep 16 - Tue, Sep 22
Southwest Logo
6:30 am - 1:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
8h 15m2 stops Orlando Sarasota Bradenton Intl
Southwest Logo
8:05 pm - 9:10 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
12h 05m1 stop Orlando
$256Southwest
Thu, Sep 10 - Sun, Sep 13
Southwest Logo
6:00 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 30m2 stops Tampa Louisville Intl
Southwest Logo
8:05 pm - 9:10 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
12h 05m1 stop Orlando
$256Southwest
Fri, Sep 11 - Sun, Sep 13
Southwest Logo
2:35 pm - 10:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 10m1 stop Orlando
Southwest Logo
8:05 pm - 9:10 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
12h 05m1 stop Orlando
$256Southwest
Fri, Sep 11 - Sun, Sep 13
Southwest Logo
2:25 pm - 8:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 20m1 stop Baltimore/Washington
Southwest Logo
12:45 pm - 10:05 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 20m1 stop Baltimore/Washington
$266Southwest
Tue, Sep 1 - Wed, Sep 9
Southwest Logo
2:35 pm - 9:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 55m1 stop Orlando
Southwest Logo
8:05 pm - 9:10 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
12h 05m1 stop Orlando
$266Southwest
Thu, Sep 10 - Sun, Sep 13
Southwest Logo
2:25 pm - 8:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 20m1 stop Baltimore/Washington
Southwest Logo
12:20 pm - 9:10 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
7h 50m1 stop Orlando
$266Southwest
Tue, Sep 1 - Tue, Sep 8
Southwest Logo
5:15 am - 12:05 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 50m2 stops Orlando Atlanta Hartsfield-Jackson
Southwest Logo
7:30 am - 7:05 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 35m1 stop Tampa
$266Southwest
Wed, Sep 16 - Tue, Sep 22
Delta Logo
2:59 pm - 10:44 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
8h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 1:45 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
6h 40m1 stop Atlanta Hartsfield-Jackson
$276Delta
Wed, Sep 16 - Wed, Sep 23
Delta Logo
2:59 pm - 10:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
8h 46m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 1:45 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
6h 40m1 stop Atlanta Hartsfield-Jackson
$348Delta
Thu, Sep 17 - Wed, Sep 23

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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
$356
Frontier
Sep 9
SJU6:30 amSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
MDW5:51 pmChicago Midway
Sep 16
MDW6:25 amChicago Midway
7h 54m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
$370
Frontier
Sep 16
SJU6:30 amSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
MDW5:51 pmChicago Midway
Sep 20
MDW6:25 amChicago Midway
8h 41m
1 stop
SJU4:06 pmSan Juan Luis Munoz Marin Intl
$382

Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
Sep 11
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 30m
2 stops
MDW2:30 pmChicago Midway
Sep 13
MDW8:05 pmChicago Midway
12h 05m
1 stop
SJU9:10 amSan Juan Luis Munoz Marin Intl
$256
Southwest
Sep 5
SJU10:25 amSan Juan Luis Munoz Marin Intl
10h 20m
1 stop
MDW7:45 pmChicago Midway
Sep 15
MDW9:40 amChicago Midway
7h 30m
1 stop
SJU6:10 pmSan Juan Luis Munoz Marin Intl
$266
Southwest
Nov 3
SJU5:40 amSan Juan Luis Munoz Marin Intl
7h 40m
1 stop
MDW11:20 amChicago Midway
Nov 3
MDW1:20 pmChicago Midway
7h 00m
1 stop
SJU10:20 pmSan Juan Luis Munoz Marin Intl
$271

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 August 6, 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 San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/16

1:20 pm-7:10 pm

1 stop6h 50m

Chicago Midway

Tue 9/22

7:30 am-7:05 pm

1 stop10h 35m

$256

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/10

6:30 am-1:45 pm

2 stops8h 15m

Chicago Midway

Sun 9/13

8:05 pm-9:10 am

1 stop12h 05m

$256

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/11

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Sun 9/13

8:05 pm-9:10 am

1 stop12h 05m

$256

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/11

2:35 pm-10:45 pm

1 stop9h 10m

Chicago Midway

Sun 9/13

8:05 pm-9:10 am

1 stop12h 05m

$256

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 9/1

2:25 pm-8:45 pm

1 stop7h 20m

Chicago Midway

Wed 9/9

12:45 pm-10:05 pm

1 stop8h 20m

$266

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/10

2:35 pm-9:30 pm

1 stop7h 55m

Chicago Midway

Sun 9/13

8:05 pm-9:10 am

1 stop12h 05m

$266
Quickest round-trip

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 9/1

2:25 pm-8:45 pm

1 stop7h 20m

Chicago Midway

Tue 9/8

12:20 pm-9:10 pm

1 stop7h 50m

$266

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/16

5:15 am-12:05 pm

2 stops7h 50m

Chicago Midway

Tue 9/22

7:30 am-7:05 pm

1 stop10h 35m

$266

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/16

2:59 pm-10:44 pm

1 stop8h 45m

Chicago Midway

Wed 9/23

6:05 am-1:45 pm

1 stop6h 40m

$276

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/17

2:59 pm-10:45 pm

1 stop8h 46m

Chicago Midway

Wed 9/23

6:05 am-1:45 pm

1 stop6h 40m

$348

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 typical for flights on this route.

Typical prices usually range from $256 to $346.
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 $301.

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 $552. 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 $726.

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

Flying to Chicago Midway Airport from San Juan in the morning is the least expensive time of day to depart. momondo users have found prices as low as $552 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $726. 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

4h 55m

Direct flights

Sun
The fastest flight from San Juan to Chicago Midway Airport takes 4h 55m
Direct flights go from San Juan to Chicago Midway Airport on 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 4h 55m.

  • 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
4,218 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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Hammond
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Benton Harbor
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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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