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Cheap flights from San Juan to Chicago from $96

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 2/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
4:11 pm - 10:37 pm
SJU
-
MDW
8h 26m1 stop
Frontier Logo
8:00 am - 2:53 am
MDW
-
SJU
16h 53m1 stop
$176Frontier
Thu, Feb 19 - Sat, Feb 28
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m1 stop
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m1 stop
$180Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m1 stop
Frontier Logo
6:15 am - 10:45 pm
MDW
-
SJU
15h 30m1 stop
$196Frontier
Wed, Feb 25 - Mon, Mar 9
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m1 stop
Frontier Logo
9:22 pm - 5:58 pm
MDW
-
SJU
42h 36m2 stops
$198Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
9:04 pm - 9:09 am
SJU
-
MDW
14h 05m1 stop
Frontier Logo
6:10 am - 3:27 pm
MDW
-
SJU
7h 17m1 stop
$199Frontier
Thu, Jan 15 - Mon, Jan 19
Frontier Logo
6:00 am - 2:26 pm
SJU
-
MDW
10h 26m1 stop
Frontier Logo
4:46 pm - 10:45 pm
MDW
-
SJU
27h 59m1 stop
$200Frontier
Thu, Feb 19 - Sat, Mar 7
Frontier Logo
4:11 pm - 10:37 pm
SJU
-
MDW
8h 26m1 stop
Frontier Logo
6:00 am - 3:40 pm
MDW
-
SJU
7h 40m1 stop
$214Frontier
Thu, Feb 19 - Sun, Mar 1
Frontier Logo
4:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
Frontier Logo
1:00 pm - 1:08 am
MDW
-
SJU
10h 08m1 stop
$215Frontier
Thu, Jan 29 - Sun, Feb 1
Frontier Logo
4:35 pm - 10:19 pm
SJU
-
MDW
7h 44m1 stop
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
$216Frontier
Tue, Jan 13 - Fri, Jan 23
Frontier Logo
4:11 pm - 10:29 pm
SJU
-
MDW
8h 18m1 stop
Frontier Logo
6:15 am - 2:09 pm
MDW
-
SJU
6h 54m1 stop
$217Frontier
Thu, Mar 5 - Mon, Mar 9

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Feb 19
SJU4:11 pmSan Juan Luis Munoz Marin Intl
8h 26m
1 stop
MDW10:37 pmChicago Midway
Feb 28
MDW8:00 amChicago Midway
16h 53m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
$176
Find similar
Frontier
Feb 27
SJU3:53 amSan Juan Luis Munoz Marin Intl
13h 02m
1 stop
MDW2:55 pmChicago Midway
Mar 2
MDW9:22 pmChicago Midway
10h 32m
1 stop
SJU9:54 amSan Juan Luis Munoz Marin Intl
$180
Find similar
Frontier
Feb 25
SJU5:25 pmSan Juan Luis Munoz Marin Intl
23h 01m
1 stop
MDW2:26 pmChicago Midway
Mar 9
MDW6:15 amChicago Midway
15h 30m
1 stop
SJU10:45 pmSan Juan Luis Munoz Marin Intl
$196
Find similar

Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
Jan 14
SJU5:40 amSan Juan Luis Munoz Marin Intl
7h 35m
1 stop
MDW11:15 amChicago Midway
Jan 22
MDW3:15 pmChicago Midway
7h 20m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
$275
Find similar
Southwest
Jan 13
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
Jan 23
MDW1:55 pmChicago Midway
8h 40m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
$360
Find similar
Southwest
Jan 9
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
Jan 13
MDW2:20 pmChicago Midway
8h 15m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
$505
Find similar

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 December 31, 2025.
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

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

4:11 pm-10:37 pm

1 stop8h 26m

Chicago Midway

Sat 2/28

8:00 am-2:53 am

1 stop16h 53m

$176

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/27

3:53 am-2:55 pm

1 stop13h 02m

Chicago Midway

Mon 3/2

9:22 pm-9:54 am

1 stop10h 32m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/25

5:25 pm-2:26 pm

1 stop23h 01m

Chicago Midway

Mon 3/9

6:15 am-10:45 pm

1 stop15h 30m

$196

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/26

6:00 am-1:56 pm

1 stop9h 56m

Chicago Midway

Mon 3/2

9:22 pm-5:58 pm

2 stops42h 36m

$198

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/15

9:04 pm-9:09 am

1 stop14h 05m

Chicago Midway

Mon 1/19

6:10 am-3:27 pm

1 stop7h 17m

$199

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

6:00 am-2:26 pm

1 stop10h 26m

Chicago Midway

Sat 3/7

4:46 pm-10:45 pm

1 stop27h 59m

$200

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

4:11 pm-10:37 pm

1 stop8h 26m

Chicago Midway

Sun 3/1

6:00 am-3:40 pm

1 stop7h 40m

$214

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/29

4:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

Sun 2/1

1:00 pm-1:08 am

1 stop10h 08m

$215

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 1/13

4:35 pm-10:19 pm

1 stop7h 44m

Chicago Midway

Fri 1/23

1:00 pm-11:59 pm

1 stop8h 59m

$216

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-10:29 pm

1 stop8h 18m

Chicago Midway

Mon 3/9

6:15 am-2:09 pm

1 stop6h 54m

$217

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 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 $297. 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 day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from San Juan. The lowest ticket price found for a Friday departure recently was $154. 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, Saturday 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 $580.

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
4,251 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
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.

An easier way to manage your Chicago Midway Airport trip

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