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Cheap flights from San Juan to Chicago from $117

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 4/14. 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

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Find the cheapest flights from San Juan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
8:41 am - 10:48 pm
MDW
-
SJU
13h 07m
1 stop
$196Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
4:33 pm - 9:21 pm
SJU
-
MDW
29h 48m
1 stop
Frontier Logo
6:00 am - 7:56 am
MDW
-
SJU
24h 56m
1 stop
$216Frontier
Wed, Apr 8 - Sat, Apr 11
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$221Frontier
Fri, Apr 24 - Sun, Apr 26
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$222Frontier
Fri, Apr 17 - Mon, Apr 27
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
8:41 am - 2:01 am
MDW
-
SJU
16h 20m
1 stop
$242Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$243Frontier
Fri, Apr 17 - Mon, Apr 27
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
8:41 am - 2:01 am
MDW
-
SJU
16h 20m
1 stop
$245Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:08 am - 8:04 am
SJU
-
MDW
29h 56m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$246Frontier
Tue, Apr 14 - Sat, Apr 18
Frontier Logo
3:21 am - 7:59 am
SJU
-
MDW
29h 38m
1 stop
Frontier Logo
8:26 am - 2:01 am
MDW
-
SJU
16h 35m
1 stop
$248Frontier
Wed, Apr 15 - Thu, Apr 23
Frontier Logo
3:21 am - 7:59 am
SJU
-
MDW
29h 38m
1 stop
Frontier Logo
9:04 am - 2:01 am
MDW
-
SJU
15h 57m
1 stop
$249Frontier
Wed, Apr 15 - Sun, Apr 19

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
May 1
SJU3:23 pmSan Juan Luis Munoz Marin Intl
8h 03m
1 stop
MDW10:26 pmChicago Midway
May 4
MDW8:41 amChicago Midway
13h 07m
1 stop
SJU10:48 pmSan Juan Luis Munoz Marin Intl
$196
Frontier
Apr 8
SJU4:33 pmSan Juan Luis Munoz Marin Intl
29h 48m
1 stop
MDW9:21 pmChicago Midway
Apr 11
MDW6:00 amChicago Midway
24h 56m
1 stop
SJU7:56 amSan Juan Luis Munoz Marin Intl
$216
Frontier
Apr 24
SJU3:23 pmSan Juan Luis Munoz Marin Intl
8h 03m
1 stop
MDW10:26 pmChicago Midway
Apr 26
MDW6:00 amChicago Midway
7h 08m
1 stop
SJU2:08 pmSan Juan Luis Munoz Marin Intl
$221

Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
May 7
SJU6:50 amSan Juan Luis Munoz Marin Intl
14h 45m
2 stops
MDW8:35 pmChicago Midway
May 10
MDW7:35 amChicago Midway
6h 05m
1 stop
SJU2:40 pmSan Juan Luis Munoz Marin Intl
$316
Southwest
Apr 9
SJU3:45 pmSan Juan Luis Munoz Marin Intl
9h 20m
1 stop
MDW12:05 amChicago Midway
Apr 13
MDW1:10 pmChicago Midway
9h 45m
2 stops
SJU11:55 pmSan Juan Luis Munoz Marin Intl
$336
Southwest
Apr 2
SJU7:00 amSan Juan Luis Munoz Marin Intl
9h 20m
2 stops
MDW3:20 pmChicago Midway
Apr 6
MDW5:00 pmChicago Midway
6h 25m
1 stop
SJU12:25 amSan Juan Luis Munoz Marin Intl
$546

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 March 21, 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

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 5/4

8:41 am-10:48 pm

1 stop13h 07m

$196

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/8

4:33 pm-9:21 pm

1 stop29h 48m

Chicago Midway

Sat 4/11

6:00 am-7:56 am

1 stop24h 56m

$216
Quickest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 4/24

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Sun 4/26

6:00 am-2:08 pm

1 stop7h 08m

$221

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 4/27

6:00 am-2:08 pm

1 stop7h 08m

$222

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 5/4

8:41 am-2:01 am

1 stop16h 20m

$242

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 4/27

6:00 am-2:08 pm

1 stop7h 08m

$243

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 5/4

8:41 am-2:01 am

1 stop16h 20m

$245

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 4/14

3:08 am-8:04 am

1 stop29h 56m

Chicago Midway

Sat 4/18

9:14 am-2:01 am

1 stop15h 47m

$246

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/15

3:21 am-7:59 am

1 stop29h 38m

Chicago Midway

Thu 4/23

8:26 am-2:01 am

1 stop16h 35m

$248

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/15

3:21 am-7:59 am

1 stop29h 38m

Chicago Midway

Sun 4/19

9:04 am-2:01 am

1 stop15h 57m

$249

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 December is, on average, the cheapest month to fly to Chicago Midway Airport from San Juan, with most prices found around $302. If you are unable to visit Chicago Midway Airport during the month of December, then departing from San Juan during the month November is also very affordable. Most momondo users find prices during this month for around $336.

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 flights?

There is only 1 cabin class available to choose from on San Juan to Chicago Midway 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

  • 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 $419Free CancellationRating
8.0
4,325 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
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Portage
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Valparaiso
Schererville
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 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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