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Cheap flights from San Juan to Chicago from $125

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 9/27. 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

Frontier Logo
3:16 pm - 11:17 pmSJU-MDW
9h 01m1 stop
Frontier Logo
10:51 am - 11:59 pmMDW-SJU
12h 08m1 stop
$262Frontier
Find Deal
Sat, Sep 27 - Sat, Oct 4
Delta Logo
7:15 am - 4:09 pmSJU-MDW
9h 54m1 stop
Delta Logo
12:48 pm - 9:59 pmMDW-SJU
8h 11m1 stop
$263Delta
Find Deal
Fri, Oct 24 - Sun, Oct 26
Frontier Logo
3:39 am - 9:51 amSJU-MDW
7h 12m1 stop
Frontier Logo
6:15 am - 2:11 pmMDW-SJU
6h 56m1 stop
$266Frontier
Find Deal
Fri, Sep 26 - Sat, Oct 4
Frontier Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
Frontier Logo
6:15 am - 2:11 pmMDW-SJU
6h 56m1 stop
$267Frontier
Find Deal
Thu, Sep 18 - Sat, Sep 27
Frontier Logo
3:16 pm - 11:20 pmSJU-MDW
9h 04m1 stop
Frontier Logo
6:20 am - 2:11 pmMDW-SJU
6h 51m1 stop
$268Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
Frontier Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
Frontier Logo
6:20 am - 2:11 pmMDW-SJU
6h 51m1 stop
$271Frontier
Find Deal
Wed, Oct 1 - Mon, Oct 6
Frontier Logo
12:28 am - 7:11 amSJU-MDW
7h 43m1 stop
Frontier Logo
8:15 am - 11:23 pmMDW-SJU
14h 08m1 stop
$274Frontier
Find Deal
Wed, Sep 10 - Thu, Sep 18
Logo
7:05 am - 6:43 pmSJU-MDW
12h 38m1 stop
Logo
8:19 am - 2:34 amMDW-SJU
17h 15m1 stop
$335
Find Deal
Sun, Sep 21 - Mon, Sep 22
Southwest Logo
1:20 pm - 10:30 pmSJU-MDW
10h 10m1 stop
Southwest Logo
1:00 pm - 10:45 pmMDW-SJU
8h 45m2 stops
$351Southwest
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Thu, Sep 11 - Tue, Sep 16
Southwest Logo
5:00 am - 12:50 pmSJU-MDW
8h 50m2 stops
Southwest Logo
1:00 pm - 10:45 pmMDW-SJU
8h 45m2 stops
$357Southwest
Find Deal
Thu, Sep 11 - Tue, Sep 16

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Sep 27
SJU3:16 pmSan Juan Luis Munoz Marin Intl
9h 01m
1 stop
MDW11:17 pmChicago Midway
Oct 4
MDW10:51 amChicago Midway
12h 08m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
$262
Find similar
Frontier
Sep 26
SJU3:39 amSan Juan Luis Munoz Marin Intl
7h 12m
1 stop
MDW9:51 amChicago Midway
Oct 4
MDW6:15 amChicago Midway
6h 56m
1 stop
SJU2:11 pmSan Juan Luis Munoz Marin Intl
$266
Find similar
Frontier
Sep 18
SJU12:28 amSan Juan Luis Munoz Marin Intl
7h 43m
1 stop
MDW7:11 amChicago Midway
Sep 27
MDW6:15 amChicago Midway
6h 56m
1 stop
SJU2:11 pmSan Juan Luis Munoz Marin Intl
$267
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
Sep 11
SJU1:20 pmSan Juan Luis Munoz Marin Intl
10h 10m
1 stop
MDW10:30 pmChicago Midway
Sep 16
MDW1:00 pmChicago Midway
8h 45m
2 stops
SJU10:45 pmSan Juan Luis Munoz Marin Intl
$351
Find similar
Southwest
Sep 11
SJU5:00 amSan Juan Luis Munoz Marin Intl
8h 50m
2 stops
MDW12:50 pmChicago Midway
Sep 16
MDW1:00 pmChicago Midway
8h 45m
2 stops
SJU10:45 pmSan Juan Luis Munoz Marin Intl
$357
Find similar
Southwest
Aug 28
SJU7:40 pmSan Juan Luis Munoz Marin Intl
13h 25m
1 stop
MDW8:05 amChicago Midway
Sep 2
MDW6:15 amChicago Midway
10h 10m
1 stop
SJU5:25 pmSan Juan Luis Munoz Marin Intl
$438
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 August 14, 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 9/27

3:16 pm-11:17 pm

1 stop9h 01m

Chicago Midway

Sat 10/4

10:51 am-11:59 pm

1 stop12h 08m

$262

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/24

7:15 am-4:09 pm

1 stop9h 54m

Chicago Midway

Sun 10/26

12:48 pm-9:59 pm

1 stop8h 11m

$263

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/26

3:39 am-9:51 am

1 stop7h 12m

Chicago Midway

Sat 10/4

6:15 am-2:11 pm

1 stop6h 56m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/18

12:28 am-7:11 am

1 stop7h 43m

Chicago Midway

Sat 9/27

6:15 am-2:11 pm

1 stop6h 56m

$267

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

3:16 pm-11:20 pm

1 stop9h 04m

Chicago Midway

Mon 9/15

6:20 am-2:11 pm

1 stop6h 51m

$268

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/1

12:28 am-7:11 am

1 stop7h 43m

Chicago Midway

Mon 10/6

6:20 am-2:11 pm

1 stop6h 51m

$271

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/10

12:28 am-7:11 am

1 stop7h 43m

Chicago Midway

Thu 9/18

8:15 am-11:23 pm

1 stop14h 08m

$274

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sun 9/21

7:05 am-6:43 pm

1 stop12h 38m

Chicago Midway

Mon 9/22

8:19 am-2:34 am

1 stop17h 15m

$335

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

1:20 pm-10:30 pm

1 stop10h 10m

Chicago Midway

Tue 9/16

1:00 pm-10:45 pm

2 stops8h 45m

$351

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/11

5:00 am-12:50 pm

2 stops8h 50m

Chicago Midway

Tue 9/16

1:00 pm-10:45 pm

2 stops8h 45m

$357

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 $234. 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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from San Juan when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $421 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from San Juan for as low as $254 on momondo.

What cabin class options are available on San Juan to Chicago Midway flights?

There are 1 cabin classes 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

Best Price Found

$125

Fastest flight time

6h 41m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from San Juan in the past 72 hours is $125. The best round-trip flight deal from San Juan to Chicago Midway Airport found on momondo in the last 72 hours is $262.
The fastest flight from San Juan to Chicago Midway Airport takes 6h 41m
Direct flights go from San Juan to Chicago Midway Airport on Sunday. The only airline offering direct flights is Southwest.
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 7h 12m.

  • 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 $130Free CancellationRating
5.8
3,219 reviews
Search Frontier flights
SouthwestPriceFrom $312Free CancellationRating
8.0
4,244 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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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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