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Cheap flights from San Juan to Chicago from $102

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 5/24. 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

Enter your travel dates to find the best prices.
Southwest Logo
5:00 am - 11:45 am
SJU
-
MDW
7h 45m
1 stop
Southwest Logo
8:05 am - 5:05 pm
MDW
-
SJU
8h 00m
1 stop
$226Southwest
Thu, Aug 13 - Sun, Aug 16
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
$246Southwest
Wed, Aug 12 - Wed, Aug 19
Frontier Logo
6:09 pm - 3:57 pm
SJU
-
MDW
22h 48m
1 stop
Frontier Logo
4:52 pm - 1:15 pm
MDW
-
SJU
19h 23m
1 stop
$251Frontier
Thu, May 14 - Mon, May 18
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
6:05 am - 6:15 pm
MDW
-
SJU
11h 10m
1 stop
$256Southwest
Thu, Aug 27 - Sat, Aug 29
Frontier Logo
3:51 pm - 9:58 pm
SJU
-
MDW
7h 07m
1 stop
Frontier Logo
7:25 am - 3:25 pm
MDW
-
SJU
7h 00m
1 stop
$276Frontier
Wed, Oct 21 - Wed, Oct 28
Frontier Logo
6:25 am - 2:12 pm
SJU
-
MDW
8h 47m
1 stop
Frontier Logo
3:07 pm - 4:49 am
MDW
-
SJU
12h 42m
1 stop
$281Frontier
Sat, May 23 - Tue, May 26
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
$296Southwest
Thu, Aug 27 - Sat, Aug 29
Frontier Logo
3:03 am - 10:02 pm
SJU
-
MDW
19h 59m
2 stops
Frontier Logo
4:52 pm - 2:08 am
MDW
-
SJU
8h 16m
1 stop
$297Frontier
Tue, May 12 - Fri, May 15
Frontier Logo
6:09 pm - 3:57 pm
SJU
-
MDW
22h 48m
1 stop
Frontier Logo
6:00 am - 2:07 pm
MDW
-
SJU
7h 07m
1 stop
$311Frontier
Thu, May 14 - Sat, May 16
Frontier Logo
6:41 pm - 10:02 pm
SJU
-
MDW
28h 21m
2 stops
Frontier Logo
12:04 pm - 4:01 am
MDW
-
SJU
14h 57m
2 stops
$314Frontier
Mon, Jun 1 - Wed, Jun 3

Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
May 14
SJU6:09 pmSan Juan Luis Munoz Marin Intl
22h 48m
1 stop
MDW3:57 pmChicago Midway
May 18
MDW4:52 pmChicago Midway
19h 23m
1 stop
SJU1:15 pmSan Juan Luis Munoz Marin Intl
$251
Frontier
May 23
SJU6:25 amSan Juan Luis Munoz Marin Intl
8h 47m
1 stop
MDW2:12 pmChicago Midway
May 26
MDW3:07 pmChicago Midway
12h 42m
1 stop
SJU4:49 amSan Juan Luis Munoz Marin Intl
$281
Frontier
May 12
SJU3:03 amSan Juan Luis Munoz Marin Intl
19h 59m
2 stops
MDW10:02 pmChicago Midway
May 15
MDW4:52 pmChicago Midway
8h 16m
1 stop
SJU2:08 amSan Juan Luis Munoz Marin Intl
$297

Delta flights from San Juan to Chicago Midway Airport

Our best Delta deals on San Juan to Chicago Midway Airport flight tickets
Delta
May 6
SJU12:55 pmSan Juan Luis Munoz Marin Intl
10h 33m
1 stop
MDW10:28 pmChicago Midway
May 10
MDW10:59 amChicago Midway
10h 18m
1 stop
SJU10:17 pmSan Juan Luis Munoz Marin Intl
$296
Delta
May 6
SJU6:15 amSan Juan Luis Munoz Marin Intl
11h 11m
1 stop
MDW4:26 pmChicago Midway
May 10
MDW12:53 pmChicago Midway
8h 24m
1 stop
SJU10:17 pmSan Juan Luis Munoz Marin Intl
$316
Delta
May 6
SJU12:55 pmSan Juan Luis Munoz Marin Intl
10h 33m
1 stop
MDW10:28 pmChicago Midway
May 9
MDW6:23 amChicago Midway
9h 10m
1 stop
SJU4:33 pmSan Juan Luis Munoz Marin Intl
$342

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 May 2, 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 8/13

5:00 am-11:45 am

1 stop7h 45m

Chicago Midway

Sun 8/16

8:05 am-5:05 pm

1 stop8h 00m

$226

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 8/12

5:15 am-12:05 pm

2 stops7h 50m

Chicago Midway

Wed 8/19

12:45 pm-10:00 pm

2 stops8h 15m

$246

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/14

6:09 pm-3:57 pm

1 stop22h 48m

Chicago Midway

Mon 5/18

4:52 pm-1:15 pm

1 stop19h 23m

$251

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/27

6:30 am-1:45 pm

2 stops8h 15m

Chicago Midway

Sat 8/29

6:05 am-6:15 pm

1 stop11h 10m

$256
Quickest round-trip

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 10/21

3:51 pm-9:58 pm

1 stop7h 07m

Chicago Midway

Wed 10/28

7:25 am-3:25 pm

1 stop7h 00m

$276

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 5/23

6:25 am-2:12 pm

1 stop8h 47m

Chicago Midway

Tue 5/26

3:07 pm-4:49 am

1 stop12h 42m

$281

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 8/27

6:30 am-1:45 pm

2 stops8h 15m

Chicago Midway

Sat 8/29

7:50 am-6:05 pm

2 stops9h 15m

$296

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 5/12

3:03 am-10:02 pm

2 stops19h 59m

Chicago Midway

Fri 5/15

4:52 pm-2:08 am

1 stop8h 16m

$297

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/14

6:09 pm-3:57 pm

1 stop22h 48m

Chicago Midway

Sat 5/16

6:00 am-2:07 pm

1 stop7h 07m

$311

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 6/1

6:41 pm-10:02 pm

2 stops28h 21m

Chicago Midway

Wed 6/3

12:04 pm-4:01 am

2 stops14h 57m

$314

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 March is, on average, the cheapest month to fly to Chicago Midway Airport from San Juan, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from San Juan during the month December is also very affordable. Most momondo users find prices during this month for around $104.

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

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 $346Free CancellationRating
8.0
4,314 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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Hammond
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Benton Harbor
Portage
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Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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