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Cheap flights from San Juan to Chicago from $141

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 10/6. 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
8:55 pm - 11:25 am
SJU
-
MDW
15h 30m
2 stops
Southwest Logo
8:30 am - 4:25 pm
MDW
-
SJU
6h 55m
1 stop
$246Southwest
Thu, Aug 27 - Tue, Sep 1
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:11 am - 4:38 pm
MDW
-
SJU
9h 27m
1 stop
$251Delta
Thu, Aug 27 - Sat, Aug 29
Southwest Logo
8:20 am - 2:45 pm
SJU
-
MDW
7h 25m
1 stop
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
$256Southwest
Wed, Aug 26 - Tue, Sep 1
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
$286Southwest
Wed, Aug 26 - Tue, Sep 1
Southwest Logo
2:35 pm - 10:40 pm
SJU
-
MDW
9h 05m
1 stop
Southwest Logo
8:05 pm - 9:10 am
MDW
-
SJU
12h 05m
1 stop
$291Southwest
Thu, Aug 20 - Sun, Aug 23
Southwest Logo
5:00 am - 12:25 pm
SJU
-
MDW
8h 25m
2 stops
Southwest Logo
7:10 am - 5:05 pm
MDW
-
SJU
8h 55m
2 stops
$296Southwest
Thu, Sep 17 - Sun, Sep 20
Southwest Logo
5:30 am - 2:55 pm
SJU
-
MDW
10h 25m
2 stops
Southwest Logo
1:30 pm - 11:25 pm
MDW
-
SJU
8h 55m
2 stops
$301Southwest
Thu, Aug 27 - Sun, Aug 30
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
12:46 pm - 10:29 pm
MDW
-
SJU
8h 43m
1 stop
$306Delta
Wed, Aug 19 - Thu, Aug 27
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:11 am - 4:38 pm
MDW
-
SJU
9h 27m
1 stop
$311Delta
Wed, Aug 26 - Sat, Aug 29
JetBlue Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
JetBlue Logo
12:46 pm - 10:29 pm
MDW
-
SJU
8h 43m
1 stop
$316JetBlue
Thu, Aug 6 - Tue, Aug 11

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JetBlue flights from San Juan to Chicago Midway Airport

Our best JetBlue deals on San Juan to Chicago Midway Airport flight tickets
JetBlue
Aug 6
SJU2:59 pmSan Juan Luis Munoz Marin Intl
8h 37m
1 stop
MDW10:36 pmChicago Midway
Aug 11
MDW12:46 pmChicago Midway
8h 43m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
$316
JetBlue
Jul 20
SJU7:30 amSan Juan Luis Munoz Marin Intl
9h 45m
1 stop
MDW4:15 pmChicago Midway
Jul 25
MDW10:55 amChicago Midway
8h 50m
1 stop
SJU8:45 pmSan Juan Luis Munoz Marin Intl
$356
JetBlue
Jul 20
SJU9:50 amSan Juan Luis Munoz Marin Intl
9h 10m
1 stop
MDW6:00 pmChicago Midway
Jul 25
MDW7:55 amChicago Midway
4h 50m
SJU1:45 pmSan Juan Luis Munoz Marin Intl
$367

Delta flights from San Juan to Chicago Midway Airport

Our best Delta deals on San Juan to Chicago Midway Airport flight tickets
Delta
Aug 27
SJU2:59 pmSan Juan Luis Munoz Marin Intl
8h 37m
1 stop
MDW10:36 pmChicago Midway
Aug 29
MDW6:11 amChicago Midway
9h 27m
1 stop
SJU4:38 pmSan Juan Luis Munoz Marin Intl
$251
Delta
Aug 19
SJU2:59 pmSan Juan Luis Munoz Marin Intl
8h 37m
1 stop
MDW10:36 pmChicago Midway
Aug 27
MDW12:46 pmChicago Midway
8h 43m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
$306
Delta
Aug 26
SJU12:56 pmSan Juan Luis Munoz Marin Intl
10h 40m
1 stop
MDW10:36 pmChicago Midway
Aug 29
MDW6:11 amChicago Midway
9h 27m
1 stop
SJU4:38 pmSan Juan Luis Munoz Marin Intl
$311

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 10, 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

8:55 pm-11:25 am

2 stops15h 30m

Chicago Midway

Tue 9/1

8:30 am-4:25 pm

1 stop6h 55m

$246

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/27

2:59 pm-10:36 pm

1 stop8h 37m

Chicago Midway

Sat 8/29

6:11 am-4:38 pm

1 stop9h 27m

$251
Quickest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/26

8:20 am-2:45 pm

1 stop7h 25m

Chicago Midway

Tue 9/1

12:45 pm-10:00 pm

2 stops8h 15m

$256

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/26

5:15 am-12:05 pm

2 stops7h 50m

Chicago Midway

Tue 9/1

12:45 pm-10:00 pm

2 stops8h 15m

$286

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/20

2:35 pm-10:40 pm

1 stop9h 05m

Chicago Midway

Sun 8/23

8:05 pm-9:10 am

1 stop12h 05m

$291

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/17

5:00 am-12:25 pm

2 stops8h 25m

Chicago Midway

Sun 9/20

7:10 am-5:05 pm

2 stops8h 55m

$296

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/27

5:30 am-2:55 pm

2 stops10h 25m

Chicago Midway

Sun 8/30

1:30 pm-11:25 pm

2 stops8h 55m

$301

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/19

2:59 pm-10:36 pm

1 stop8h 37m

Chicago Midway

Thu 8/27

12:46 pm-10:29 pm

1 stop8h 43m

$306

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/26

12:56 pm-10:36 pm

1 stop10h 40m

Chicago Midway

Sat 8/29

6:11 am-4:38 pm

1 stop9h 27m

$311

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/6

2:59 pm-10:36 pm

1 stop8h 37m

Chicago Midway

Tue 8/11

12:46 pm-10:29 pm

1 stop8h 43m

$316

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?

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 December is also very affordable. Most momondo users find prices during this month for around $104.

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 50m

Direct flights

Mon and Sun
The fastest flight from San Juan to Chicago Midway Airport takes 4h 50m
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 4h 50m.

  • 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
7.9
4,248 reviews
Search Southwest flights

Traveling to a place near Chicago?

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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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