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Cheap flights from San Juan to Chicago from $122

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 5/7. 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
3:21 am - 10:28 am
SJU
-
MDW
8h 07m
1 stop
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
$176Frontier
Thu, Apr 30 - Sat, May 2
Frontier Logo
3:21 am - 10:28 am
SJU
-
MDW
8h 07m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$186Frontier
Thu, Apr 30 - Sun, May 3
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
8:41 am - 2:01 am
MDW
-
SJU
16h 20m
1 stop
$187Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:03 am - 3:57 pm
SJU
-
MDW
13h 54m
1 stop
Frontier Logo
4:52 pm - 2:08 am
MDW
-
SJU
8h 16m
1 stop
$196Frontier
Thu, May 7 - Mon, May 11
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$197Frontier
Thu, Apr 23 - Sun, Apr 26
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:07 pm
MDW
-
SJU
7h 07m
1 stop
$211Frontier
Fri, May 1 - Tue, May 5
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
Frontier Logo
9:14 am - 9:54 am
MDW
-
SJU
23h 40m
1 stop
$216Frontier
Thu, Apr 23 - Mon, Apr 27
Frontier Logo
3:21 am - 8:04 am
SJU
-
MDW
29h 43m
1 stop
Frontier Logo
9:14 am - 9:54 am
MDW
-
SJU
23h 40m
1 stop
$220Frontier
Sat, Apr 18 - Mon, Apr 27
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
Frontier Logo
6:00 am - 2:13 pm
MDW
-
SJU
7h 13m
1 stop
$221Frontier
Thu, Apr 30 - Mon, May 4
Frontier Logo
3:08 am - 7:26 am
SJU
-
MDW
29h 18m
1 stop
Frontier Logo
6:49 pm - 3:37 pm
MDW
-
SJU
19h 48m
1 stop
$226Frontier
Tue, Apr 21 - Fri, Apr 24

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Apr 30
SJU3:21 amSan Juan Luis Munoz Marin Intl
8h 07m
1 stop
MDW10:28 amChicago Midway
May 2
MDW9:14 amChicago Midway
12h 34m
1 stop
SJU10:48 pmSan Juan Luis Munoz Marin Intl
$176
Frontier
Apr 30
SJU3:21 amSan Juan Luis Munoz Marin Intl
8h 07m
1 stop
MDW10:28 amChicago Midway
May 3
MDW6:00 amChicago Midway
7h 08m
1 stop
SJU2:08 pmSan Juan Luis Munoz Marin Intl
$186
Frontier
May 1
SJU3:23 pmSan Juan Luis Munoz Marin Intl
8h 03m
1 stop
MDW10:26 pmChicago Midway
May 4
MDW8:41 amChicago Midway
16h 20m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$187

Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
May 6
SJU5:05 amSan Juan Luis Munoz Marin Intl
11h 45m
2 stops
MDW3:50 pmChicago Midway
May 13
MDW1:25 pmChicago Midway
6h 40m
1 stop
SJU9:05 pmSan Juan Luis Munoz Marin Intl
$316
Southwest
May 6
SJU5:05 amSan Juan Luis Munoz Marin Intl
11h 45m
2 stops
MDW3:50 pmChicago Midway
May 12
MDW12:50 pmChicago Midway
8h 50m
2 stops
SJU10:40 pmSan Juan Luis Munoz Marin Intl
$326
Southwest
Apr 21
SJU5:35 amSan Juan Luis Munoz Marin Intl
7h 35m
1 stop
MDW12:10 pmChicago Midway
Apr 26
MDW9:05 amChicago Midway
7h 00m
1 stop
SJU5:05 pmSan Juan Luis Munoz Marin Intl
$336

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 April 9, 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

Cheapest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/30

3:21 am-10:28 am

1 stop8h 07m

Chicago Midway

Sat 5/2

9:14 am-10:48 pm

1 stop12h 34m

$176

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/30

3:21 am-10:28 am

1 stop8h 07m

Chicago Midway

Sun 5/3

6:00 am-2:08 pm

1 stop7h 08m

$186

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 5/4

8:41 am-2:01 am

1 stop16h 20m

$187

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:03 am-3:57 pm

1 stop13h 54m

Chicago Midway

Mon 5/11

4:52 pm-2:08 am

1 stop8h 16m

$196

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/23

3:03 pm-10:19 pm

1 stop8h 16m

Chicago Midway

Sun 4/26

6:00 am-2:08 pm

1 stop7h 08m

$197
Quickest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Tue 5/5

6:00 am-2:07 pm

1 stop7h 07m

$211

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/23

3:03 pm-10:19 pm

1 stop8h 16m

Chicago Midway

Mon 4/27

9:14 am-9:54 am

1 stop23h 40m

$216

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 4/18

3:21 am-8:04 am

1 stop29h 43m

Chicago Midway

Mon 4/27

9:14 am-9:54 am

1 stop23h 40m

$220

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/30

3:03 pm-10:19 pm

1 stop8h 16m

Chicago Midway

Mon 5/4

6:00 am-2:13 pm

1 stop7h 13m

$221

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 4/21

3:08 am-7:26 am

1 stop29h 18m

Chicago Midway

Fri 4/24

6:49 pm-3:37 pm

1 stop19h 48m

$226

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 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

Frequently asked questions about flying from San Juan to Chicago Midway Airport

  • 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 $394Free CancellationRating
8.0
4,338 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
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.

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