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Cheap flights from San Juan to Chicago from $124

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 10/22. 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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Find the cheapest flights from San Juan to Chicago

Cheap round-trip flights

Frontier Logo
6:22 am - 10:47 pmSJU-MDW
17h 25m2 stops
Frontier Logo
9:32 am - 9:24 pmMDW-SJU
10h 52m1 stop
$203Frontier
Find Deal
Sat, Oct 25 - Fri, Oct 31
Frontier Logo
4:22 pm - 10:47 pmSJU-MDW
7h 25m1 stop
Frontier Logo
6:20 am - 2:19 pmMDW-SJU
6h 59m1 stop
$204Frontier
Find Deal
Sat, Oct 25 - Fri, Oct 31
Southwest Logo
5:50 am - 2:20 pmSJU-MDW
9h 30m1 stop
Southwest Logo
9:45 am - 9:55 pmMDW-SJU
11h 10m1 stop
$227Southwest
Find Deal
Thu, Oct 23 - Mon, Oct 27
Frontier Logo
6:22 am - 11:20 pmSJU-MDW
17h 58m2 stops
Frontier Logo
12:17 pm - 7:56 pmMDW-SJU
6h 39m1 stop
$244Frontier
Find Deal
Tue, Oct 21 - Mon, Oct 27
Frontier Logo
9:26 pm - 1:38 pmSJU-MDW
17h 12m2 stops
Frontier Logo
10:33 am - 7:56 pmMDW-SJU
8h 23m1 stop
$249Frontier
Find Deal
Mon, Oct 6 - Fri, Oct 17
Frontier Logo
3:00 pm - 11:25 pmSJU-MDW
10h 25m1 stop
Frontier Logo
2:15 pm - 2:50 amMDW-SJU
10h 35m1 stop
$251Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Multiple Airlines Logo
6:00 am - 9:35 pmSJU-MDW
17h 35m2 stops
Multiple Airlines Logo
6:26 pm - 3:33 amMDW-SJU
31h 07m1 stop
$253Multiple Airlines
Find Deal
Sat, Nov 15 - Tue, Nov 18
Frontier Logo
1:59 am - 8:21 pmSJU-MDW
19h 22m2 stops
Frontier Logo
9:26 pm - 3:24 pmMDW-SJU
16h 58m2 stops
$255Frontier
Find Deal
Wed, Oct 22 - Sun, Oct 26
Frontier Logo
1:59 am - 8:21 pmSJU-MDW
19h 22m2 stops
Frontier Logo
9:26 pm - 3:24 pmMDW-SJU
16h 58m2 stops
$256Frontier
Find Deal
Wed, Oct 22 - Sun, Oct 26
Southwest Logo
9:40 am - 7:25 pmSJU-MDW
11h 45m1 stop
Southwest Logo
1:25 pm - 12:35 amMDW-SJU
9h 10m2 stops
$311Southwest
Find Deal
Tue, Nov 4 - Sun, Nov 9

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Oct 25
SJU6:22 amSan Juan Luis Munoz Marin Intl
17h 25m
2 stops
MDW10:47 pmChicago Midway
Oct 31
MDW9:32 amChicago Midway
10h 52m
1 stop
SJU9:24 pmSan Juan Luis Munoz Marin Intl
$203
Find similar
Frontier
Oct 25
SJU4:22 pmSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW10:47 pmChicago Midway
Oct 31
MDW6:20 amChicago Midway
6h 59m
1 stop
SJU2:19 pmSan Juan Luis Munoz Marin Intl
$204
Find similar
Frontier
Oct 21
SJU6:22 amSan Juan Luis Munoz Marin Intl
17h 58m
2 stops
MDW11:20 pmChicago Midway
Oct 27
MDW12:17 pmChicago Midway
6h 39m
1 stop
SJU7:56 pmSan Juan Luis Munoz Marin Intl
$244
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
Oct 23
SJU5:50 amSan Juan Luis Munoz Marin Intl
9h 30m
1 stop
MDW2:20 pmChicago Midway
Oct 27
MDW9:45 amChicago Midway
11h 10m
1 stop
SJU9:55 pmSan Juan Luis Munoz Marin Intl
$227
Find similar
Southwest
Nov 4
SJU9:40 amSan Juan Luis Munoz Marin Intl
11h 45m
1 stop
MDW7:25 pmChicago Midway
Nov 9
MDW1:25 pmChicago Midway
9h 10m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
$311
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 September 17, 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

Sat 10/25

6:22 am-10:47 pm

2 stops17h 25m

Chicago Midway

Fri 10/31

9:32 am-9:24 pm

1 stop10h 52m

$203

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/25

4:22 pm-10:47 pm

1 stop7h 25m

Chicago Midway

Fri 10/31

6:20 am-2:19 pm

1 stop6h 59m

$204

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/23

5:50 am-2:20 pm

1 stop9h 30m

Chicago Midway

Mon 10/27

9:45 am-9:55 pm

1 stop11h 10m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 10/21

6:22 am-11:20 pm

2 stops17h 58m

Chicago Midway

Mon 10/27

12:17 pm-7:56 pm

1 stop6h 39m

$244

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 10/6

9:26 pm-1:38 pm

2 stops17h 12m

Chicago Midway

Fri 10/17

10:33 am-7:56 pm

1 stop8h 23m

$249

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/4

3:00 pm-11:25 pm

1 stop10h 25m

Chicago Midway

Mon 12/8

2:15 pm-2:50 am

1 stop10h 35m

$251

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 11/15

6:00 am-9:35 pm

2 stops17h 35m

Chicago Midway

Tue 11/18

6:26 pm-3:33 am

1 stop31h 07m

$253

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/22

1:59 am-8:21 pm

2 stops19h 22m

Chicago Midway

Sun 10/26

9:26 pm-3:24 pm

2 stops16h 58m

$255

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/22

1:59 am-8:21 pm

2 stops19h 22m

Chicago Midway

Sun 10/26

9:26 pm-3:24 pm

2 stops16h 58m

$256

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 11/4

9:40 am-7:25 pm

1 stop11h 45m

Chicago Midway

Sun 11/9

1:25 pm-12:35 am

2 stops9h 10m

$311

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 $294. If you are unable to visit Chicago Midway Airport during the month of December, then departing from San Juan during the month October is also very affordable. Most momondo users find prices during this month for around $316.

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 $610. 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

5h 15m

Direct flights

Mon and Sun
The fastest flight from San Juan to Chicago Midway Airport takes 5h 15m
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 6h 39m.

  • 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
FrontierPriceFrom $148Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
SouthwestPriceFrom $320Free CancellationRating
8.0
4,242 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
Lansing
Portage
Schererville
Valparaiso
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.

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