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Cheap flights from San Juan to Chicago from $101

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.
1 adult
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
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$202Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
3:19 pm - 8:04 am
SJU
-
MDW
17h 45m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$213Frontier
Thu, May 14 - Sun, May 17
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$217Frontier
Thu, May 7 - Sun, May 17
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
$223Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:53 am - 2:26 pm
SJU
-
MDW
12h 33m
1 stop
Frontier Logo
7:30 am - 2:53 am
MDW
-
SJU
17h 23m
1 stop
$229Frontier
Thu, Feb 26 - Sun, Mar 1
Frontier Logo
6:00 am - 8:07 pm
SJU
-
MDW
15h 07m
1 stop
Frontier Logo
6:30 am - 1:01 am
MDW
-
SJU
17h 31m
1 stop
$236Frontier
Tue, Apr 7 - Mon, Apr 13
Frontier Logo
6:00 am - 8:07 pm
SJU
-
MDW
15h 07m
1 stop
Frontier Logo
6:30 am - 1:01 am
MDW
-
SJU
17h 31m
1 stop
$237Frontier
Tue, Apr 7 - Mon, Apr 13
Frontier Logo
3:53 am - 2:26 pm
SJU
-
MDW
12h 33m
1 stop
Frontier Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
$244Frontier
Thu, Feb 26 - Sun, Mar 1
Delta Logo
7:30 am - 4:29 pm
SJU
-
MDW
9h 59m
1 stop
Delta Logo
12:52 pm - 11:12 pm
MDW
-
SJU
9h 20m
1 stop
$246Delta
Thu, Apr 16 - Wed, Apr 22
Multiple Airlines Logo
11:52 am - 3:19 pm
SJU
-
MDW
29h 27m
2 stops
Multiple Airlines Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
$249Multiple Airlines
Fri, Feb 27 - Sun, Mar 1

Delta flights from San Juan to Chicago Midway Airport

Our best Delta deals on San Juan to Chicago Midway Airport flight tickets
Delta
Apr 16
SJU7:30 amSan Juan Luis Munoz Marin Intl
9h 59m
1 stop
MDW4:29 pmChicago Midway
Apr 22
MDW12:52 pmChicago Midway
9h 20m
1 stop
SJU11:12 pmSan Juan Luis Munoz Marin Intl
$246
Delta
Feb 24
SJU3:55 pmSan Juan Luis Munoz Marin Intl
8h 38m
1 stop
MDW10:33 pmChicago Midway
Mar 10
MDW12:47 pmChicago Midway
9h 28m
1 stop
SJU11:15 pmSan Juan Luis Munoz Marin Intl
$266
Delta
Feb 28
SJU7:30 amSan Juan Luis Munoz Marin Intl
9h 51m
1 stop
MDW3:21 pmChicago Midway
Mar 4
MDW12:45 pmChicago Midway
9h 13m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
$286

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Feb 27
SJU3:53 amSan Juan Luis Munoz Marin Intl
13h 02m
1 stop
MDW2:55 pmChicago Midway
Mar 2
MDW9:22 pmChicago Midway
10h 32m
1 stop
SJU9:54 amSan Juan Luis Munoz Marin Intl
$202
Frontier
May 14
SJU3:19 pmSan Juan Luis Munoz Marin Intl
17h 45m
1 stop
MDW8:04 amChicago Midway
May 17
MDW9:14 amChicago Midway
15h 47m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$213
Frontier
May 7
SJU3:18 pmSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
MDW10:19 pmChicago Midway
May 17
MDW9:14 amChicago Midway
15h 47m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$217

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 February 17, 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

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/10

6:00 am-2:08 pm

1 stop7h 08m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/14

3:19 pm-8:04 am

1 stop17h 45m

Chicago Midway

Sun 5/17

9:14 am-2:01 am

1 stop15h 47m

$213

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/17

9:14 am-2:01 am

1 stop15h 47m

$217

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Mon 5/4

9:14 am-10:48 pm

1 stop12h 34m

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/26

3:53 am-2:26 pm

1 stop12h 33m

Chicago Midway

Sun 3/1

7:30 am-2:53 am

1 stop17h 23m

$229

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 4/7

6:00 am-8:07 pm

1 stop15h 07m

Chicago Midway

Mon 4/13

6:30 am-1:01 am

1 stop17h 31m

$236

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 4/7

6:00 am-8:07 pm

1 stop15h 07m

Chicago Midway

Mon 4/13

6:30 am-1:01 am

1 stop17h 31m

$237

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/26

3:53 am-2:26 pm

1 stop12h 33m

Chicago Midway

Sun 3/1

6:15 am-2:09 am

1 stop17h 54m

$244

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 4/16

7:30 am-4:29 pm

1 stop9h 59m

Chicago Midway

Wed 4/22

12:52 pm-11:12 pm

1 stop9h 20m

$246

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 2/27

11:52 am-3:19 pm

2 stops29h 27m

Chicago Midway

Sun 3/1

6:15 am-2:09 am

1 stop17h 54m

$249

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 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
8.0
4,294 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
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Portage
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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.

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