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Cheap flights from San Juan to Chicago from $97

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 1/29. 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
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
1:00 pm - 12:57 pm
MDW
-
SJU
21h 57m1 stop
$170Frontier
Wed, Feb 4 - Mon, Feb 9
Frontier Logo
6:00 am - 2:26 pm
SJU
-
MDW
10h 26m1 stop
Frontier Logo
6:15 am - 12:39 pm
MDW
-
SJU
28h 24m1 stop
$171Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
3:22 pm - 10:19 pm
SJU
-
MDW
7h 57m1 stop
Frontier Logo
4:33 pm - 11:58 pm
MDW
-
SJU
6h 25m1 stop
$176Frontier
Tue, Mar 24 - Tue, Mar 31
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
1:00 pm - 11:59 pm
MDW
-
SJU
8h 59m1 stop
$179Frontier
Wed, Feb 4 - Mon, Feb 9
Frontier Logo
8:00 am - 7:52 pm
SJU
-
MDW
13h 52m1 stop
Frontier Logo
6:15 am - 2:35 am
MDW
-
SJU
18h 20m1 stop
$182Frontier
Thu, Feb 5 - Thu, Feb 12
Multiple Airlines Logo
11:52 am - 2:26 pm
SJU
-
MDW
28h 34m1 stop
Multiple Airlines Logo
6:15 am - 2:29 am
MDW
-
SJU
18h 14m1 stop
$188Multiple Airlines
Wed, Feb 18 - 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
$203Frontier
Wed, Feb 4 - Sun, Feb 8
Frontier Logo
3:55 am - 9:58 pm
SJU
-
MDW
19h 03m1 stop
Frontier Logo
3:10 pm - 12:34 pm
MDW
-
SJU
20h 24m1 stop
$204Frontier
Wed, Apr 8 - Sun, Apr 12
Frontier Logo
4:36 pm - 7:52 pm
SJU
-
MDW
29h 16m1 stop
Frontier Logo
7:00 pm - 12:57 pm
MDW
-
SJU
15h 57m1 stop
$210Frontier
Wed, Feb 4 - Mon, Feb 9
Frontier Logo
11:07 am - 6:13 pm
SJU
-
MDW
8h 06m1 stop
Frontier Logo
6:00 am - 1:21 am
MDW
-
SJU
18h 21m1 stop
$211Frontier
Tue, Mar 17 - Thu, Mar 26

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Feb 4
SJU4:36 pmSan Juan Luis Munoz Marin Intl
29h 16m
1 stop
MDW7:52 pmChicago Midway
Feb 9
MDW1:00 pmChicago Midway
21h 57m
1 stop
SJU12:57 pmSan Juan Luis Munoz Marin Intl
$170
Frontier
Feb 19
SJU6:00 amSan Juan Luis Munoz Marin Intl
10h 26m
1 stop
MDW2:26 pmChicago Midway
Feb 26
MDW6:15 amChicago Midway
28h 24m
1 stop
SJU12:39 pmSan Juan Luis Munoz Marin Intl
$171
Frontier
Mar 24
SJU3:22 pmSan Juan Luis Munoz Marin Intl
7h 57m
1 stop
MDW10:19 pmChicago Midway
Mar 31
MDW4:33 pmChicago Midway
6h 25m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
$176

Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
Jan 16
SJU7:00 amSan Juan Luis Munoz Marin Intl
7h 55m
1 stop
MDW12:55 pmChicago Midway
Jan 18
MDW1:50 pmChicago Midway
8h 45m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
$396
Southwest
Jan 16
SJU11:10 amSan Juan Luis Munoz Marin Intl
10h 35m
2 stops
MDW7:45 pmChicago Midway
Jan 18
MDW6:50 amChicago Midway
10h 15m
2 stops
SJU7:05 pmSan Juan Luis Munoz Marin Intl
$426
Southwest
Jan 10
SJU9:10 amSan Juan Luis Munoz Marin Intl
8h 20m
1 stop
MDW3:30 pmChicago Midway
Jan 17
MDW6:40 amChicago Midway
6h 40m
1 stop
SJU3:20 pmSan Juan Luis Munoz Marin Intl
$671

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 January 8, 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

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

Mon 2/9

1:00 pm-12:57 pm

1 stop21h 57m

$170

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

Thu 2/26

6:15 am-12:39 pm

1 stop28h 24m

$171

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 3/24

3:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

Tue 3/31

4:33 pm-11:58 pm

1 stop6h 25m

$176

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

Mon 2/9

1:00 pm-11:59 pm

1 stop8h 59m

$179

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/5

8:00 am-7:52 pm

1 stop13h 52m

Chicago Midway

Thu 2/12

6:15 am-2:35 am

1 stop18h 20m

$182

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 2/18

11:52 am-2:26 pm

1 stop28h 34m

Chicago Midway

Sun 2/22

6:15 am-2:29 am

1 stop18h 14m

$188

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

$203

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 4/8

3:55 am-9:58 pm

1 stop19h 03m

Chicago Midway

Sun 4/12

3:10 pm-12:34 pm

1 stop20h 24m

$204

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

Mon 2/9

7:00 pm-12:57 pm

1 stop15h 57m

$210

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 3/17

11:07 am-6:13 pm

1 stop8h 06m

Chicago Midway

Thu 3/26

6:00 am-1:21 am

1 stop18h 21m

$211

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 $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 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

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
4,250 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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