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Cheap flights from San Juan to Chicago from $102

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 12/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
4:11 pm - 10:29 pm
SJU
-
MDW
8h 18m1 stop
Frontier Logo
9:51 pm - 9:57 am
MDW
-
SJU
11h 06m1 stop
$180Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
6:00 am - 6:54 pm
SJU
-
MDW
14h 54m1 stop
Frontier Logo
8:19 pm - 12:42 pm
MDW
-
SJU
14h 23m1 stop
$183Frontier
Fri, Jan 16 - Sun, Jan 18
Frontier Logo
5:25 pm - 2:55 pm
SJU
-
MDW
23h 30m1 stop
Frontier Logo
9:32 pm - 2:53 am
MDW
-
SJU
27h 21m1 stop
$184Frontier
Fri, Feb 27 - Mon, Mar 2
Frontier Logo
5:09 pm - 9:58 pm
SJU
-
MDW
29h 49m1 stop
Frontier Logo
6:00 am - 2:01 pm
MDW
-
SJU
7h 01m1 stop
$201Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
5:45 am - 2:06 pm
SJU
-
MDW
10h 21m1 stop
Frontier Logo
11:27 am - 9:25 am
MDW
-
SJU
19h 58m1 stop
$202Frontier
Mon, Jan 12 - Thu, Jan 15
Frontier Logo
5:45 am - 2:06 pm
SJU
-
MDW
10h 21m1 stop
Frontier Logo
4:31 pm - 2:50 am
MDW
-
SJU
8h 19m1 stop
$203Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
4:39 pm - 10:21 pm
SJU
-
MDW
7h 42m1 stop
Frontier Logo
4:31 pm - 2:50 am
MDW
-
SJU
8h 19m1 stop
$204Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
6:00 am - 9:12 pm
SJU
-
MDW
17h 12m2 stops
Frontier Logo
6:15 am - 2:29 am
MDW
-
SJU
18h 14m1 stop
$214Frontier
Thu, Feb 19 - Sun, Feb 22
Frontier Logo
4:25 pm - 2:26 pm
SJU
-
MDW
24h 01m1 stop
Frontier Logo
7:30 am - 12:54 am
MDW
-
SJU
15h 24m1 stop
$215Frontier
Thu, Feb 19 - Sun, Feb 22
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
1:00 pm - 1:08 am
MDW
-
SJU
10h 08m1 stop
$216Frontier
Wed, Feb 4 - Sun, Feb 8

Delta flights from San Juan to Chicago Midway Airport

Our best Delta deals on San Juan to Chicago Midway Airport flight tickets
Delta
Jan 21
SJU2:15 pmSan Juan Luis Munoz Marin Intl
10h 07m
1 stop
MDW10:22 pmChicago Midway
Jan 24
MDW10:46 amChicago Midway
8h 12m
1 stop
SJU8:58 pmSan Juan Luis Munoz Marin Intl
$275
Find similar
Delta
Jan 23
SJU2:15 pmSan Juan Luis Munoz Marin Intl
10h 07m
1 stop
MDW10:22 pmChicago Midway
Feb 3
MDW12:48 pmChicago Midway
6h 10m
1 stop
SJU8:58 pmSan Juan Luis Munoz Marin Intl
$310
Find similar
Delta
Jan 21
SJU2:15 pmSan Juan Luis Munoz Marin Intl
10h 07m
1 stop
MDW10:22 pmChicago Midway
Jan 24
MDW10:46 amChicago Midway
8h 12m
1 stop
SJU8:58 pmSan Juan Luis Munoz Marin Intl
$325
Find similar

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Mar 5
SJU4:11 pmSan Juan Luis Munoz Marin Intl
8h 18m
1 stop
MDW10:29 pmChicago Midway
Mar 9
MDW9:51 pmChicago Midway
11h 06m
1 stop
SJU9:57 amSan Juan Luis Munoz Marin Intl
$180
Find similar
Frontier
Jan 16
SJU6:00 amSan Juan Luis Munoz Marin Intl
14h 54m
1 stop
MDW6:54 pmChicago Midway
Jan 18
MDW8:19 pmChicago Midway
14h 23m
1 stop
SJU12:42 pmSan Juan Luis Munoz Marin Intl
$183
Find similar
Frontier
Feb 27
SJU5:25 pmSan Juan Luis Munoz Marin Intl
23h 30m
1 stop
MDW2:55 pmChicago Midway
Mar 2
MDW9:32 pmChicago Midway
27h 21m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
$184
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 16, 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 3/5

4:11 pm-10:29 pm

1 stop8h 18m

Chicago Midway

Mon 3/9

9:51 pm-9:57 am

1 stop11h 06m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/16

6:00 am-6:54 pm

1 stop14h 54m

Chicago Midway

Sun 1/18

8:19 pm-12:42 pm

1 stop14h 23m

$183

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/27

5:25 pm-2:55 pm

1 stop23h 30m

Chicago Midway

Mon 3/2

9:32 pm-2:53 am

1 stop27h 21m

$184

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/9

5:09 pm-9:58 pm

1 stop29h 49m

Chicago Midway

Mon 4/13

6:00 am-2:01 pm

1 stop7h 01m

$201

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 1/12

5:45 am-2:06 pm

1 stop10h 21m

Chicago Midway

Thu 1/15

11:27 am-9:25 am

1 stop19h 58m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/9

5:45 am-2:06 pm

1 stop10h 21m

Chicago Midway

Mon 1/12

4:31 pm-2:50 am

1 stop8h 19m

$203

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/9

4:39 pm-10:21 pm

1 stop7h 42m

Chicago Midway

Mon 1/12

4:31 pm-2:50 am

1 stop8h 19m

$204

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

6:00 am-9:12 pm

2 stops17h 12m

Chicago Midway

Sun 2/22

6:15 am-2:29 am

1 stop18h 14m

$214

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

4:25 pm-2:26 pm

1 stop24h 01m

Chicago Midway

Sun 2/22

7:30 am-12:54 am

1 stop15h 24m

$215

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/4

4:36 pm-7:52 pm

1 stop29h 16m

Chicago Midway

Sun 2/8

1:00 pm-1:08 am

1 stop10h 08m

$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 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 February is also very affordable. Most momondo users find prices during this month for around $325.

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 time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from San Juan in the evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $580. 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 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
7.9
4,250 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
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Crown Point
Munster
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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