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Cheap flights from San Juan to Chicago from $119

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 4/23. 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
8:00 am - 4:13 pm
SJU
-
MDW
9h 13m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$176Frontier
Sat, Apr 25 - Sat, May 2
Frontier Logo
8:00 am - 4:13 pm
SJU
-
MDW
9h 13m
1 stop
Frontier Logo
6:00 am - 2:37 pm
MDW
-
SJU
7h 37m
1 stop
$183Frontier
Sat, Apr 25 - Sat, May 2
Frontier Logo
6:07 pm - 2:01 pm
SJU
-
MDW
20h 54m
1 stop
Frontier Logo
5:30 am - 8:00 pm
MDW
-
SJU
13h 30m
1 stop
$186Frontier
Thu, Apr 9 - Mon, Apr 13
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
$187Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
6:07 pm - 2:01 pm
SJU
-
MDW
20h 54m
1 stop
Frontier Logo
5:05 am - 11:18 am
MDW
-
SJU
29h 13m
1 stop
$196Frontier
Thu, Apr 9 - Sun, Apr 12
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
$197Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
10:54 am - 7:59 am
SJU
-
MDW
22h 05m
1 stop
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
$206Frontier
Sat, Apr 18 - Mon, Apr 20
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
$211Frontier
Fri, Apr 24 - Mon, Apr 27
Frontier Logo
6:07 pm - 2:01 pm
SJU
-
MDW
20h 54m
1 stop
Frontier Logo
5:30 am - 1:26 pm
MDW
-
SJU
6h 56m
1 stop
$213Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
6:00 am - 2:01 pm
SJU
-
MDW
9h 01m
1 stop
Frontier Logo
6:30 am - 11:53 pm
MDW
-
SJU
16h 23m
1 stop
$216Frontier
Fri, Apr 10 - Mon, Apr 13

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Apr 25
SJU8:00 amSan Juan Luis Munoz Marin Intl
9h 13m
1 stop
MDW4:13 pmChicago Midway
May 2
MDW9:14 amChicago Midway
15h 47m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$176
Frontier
Apr 25
SJU8:00 amSan Juan Luis Munoz Marin Intl
9h 13m
1 stop
MDW4:13 pmChicago Midway
May 2
MDW6:00 amChicago Midway
7h 37m
1 stop
SJU2:37 pmSan Juan Luis Munoz Marin Intl
$183
Frontier
Apr 9
SJU6:07 pmSan Juan Luis Munoz Marin Intl
20h 54m
1 stop
MDW2:01 pmChicago Midway
Apr 13
MDW5:30 amChicago Midway
13h 30m
1 stop
SJU8:00 pmSan Juan Luis Munoz Marin Intl
$186

Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
Apr 9
SJU1:00 pmSan Juan Luis Munoz Marin Intl
8h 50m
1 stop
MDW8:50 pmChicago Midway
Apr 12
MDW10:50 amChicago Midway
9h 05m
2 stops
SJU8:55 pmSan Juan Luis Munoz Marin Intl
$366
Southwest
Apr 9
SJU8:40 pmSan Juan Luis Munoz Marin Intl
13h 35m
1 stop
MDW9:15 amChicago Midway
Apr 13
MDW12:00 pmChicago Midway
10h 25m
2 stops
SJU11:25 pmSan Juan Luis Munoz Marin Intl
$369
Southwest
Apr 9
SJU10:00 amSan Juan Luis Munoz Marin Intl
8h 45m
2 stops
MDW5:45 pmChicago Midway
Apr 12
MDW3:15 pmChicago Midway
7h 30m
2 stops
SJU11:45 pmSan Juan Luis Munoz Marin Intl
$430

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 28, 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

Sat 4/25

8:00 am-4:13 pm

1 stop9h 13m

Chicago Midway

Sat 5/2

9:14 am-2:01 am

1 stop15h 47m

$176

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 4/25

8:00 am-4:13 pm

1 stop9h 13m

Chicago Midway

Sat 5/2

6:00 am-2:37 pm

1 stop7h 37m

$183

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/9

6:07 pm-2:01 pm

1 stop20h 54m

Chicago Midway

Mon 4/13

5:30 am-8:00 pm

1 stop13h 30m

$186

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

$187

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/9

6:07 pm-2:01 pm

1 stop20h 54m

Chicago Midway

Sun 4/12

5:05 am-11:18 am

1 stop29h 13m

$196

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

$197

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 4/18

10:54 am-7:59 am

1 stop22h 05m

Chicago Midway

Mon 4/20

9:14 am-10:48 pm

1 stop12h 34m

$206
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

Mon 4/27

6:00 am-2:08 pm

1 stop7h 08m

$211

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/9

6:07 pm-2:01 pm

1 stop20h 54m

Chicago Midway

Mon 4/13

5:30 am-1:26 pm

1 stop6h 56m

$213

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 4/10

6:00 am-2:01 pm

1 stop9h 01m

Chicago Midway

Mon 4/13

6:30 am-11:53 pm

1 stop16h 23m

$216

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

5h 20m

Direct flights

Mon and Sun
The fastest flight from San Juan to Chicago Midway Airport takes 5h 20m
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 5h 20m.

  • 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
4,333 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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Benton Harbor
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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