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Cheap flights from San Juan to Chicago from $124

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from San Juan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
2:35 pm - 9:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 55m1 stop Orlando
Southwest Logo
9:40 am - 9:00 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 20m1 stop Orlando
$226Southwest
Thu, Sep 10 - Tue, Sep 15
Southwest Logo
6:00 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 30m2 stops Tampa Louisville Intl
Southwest Logo
6:15 am - 4:25 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
9h 10m1 stop Orlando
$226Southwest
Thu, Sep 10 - Tue, Sep 15
Southwest Logo
2:35 pm - 10:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 10m1 stop Orlando
Southwest Logo
7:30 am - 7:05 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 35m1 stop Tampa
$226Southwest
Thu, Sep 24 - Tue, Sep 29
Southwest Logo
6:00 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 30m2 stops Tampa Louisville Intl
Southwest Logo
12:45 pm - 10:05 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 20m2 stops Cincinnati Cinci./N. Kentucky Baltimore/Washington
$226Southwest
Thu, Sep 24 - Tue, Sep 29
Southwest Logo
2:35 pm - 9:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 55m1 stop Orlando
Southwest Logo
9:40 am - 9:00 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 20m1 stop Orlando
$226Southwest
Thu, Sep 10 - Wed, Sep 16
Southwest Logo
8:20 am - 2:45 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 25m1 stop Orlando
Southwest Logo
2:15 pm - 12:20 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
9h 05m1 stop Orlando
$226Southwest
Wed, Sep 30 - Mon, Oct 5
Southwest Logo
6:30 am - 3:35 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
10h 05m1 stop Orlando
Southwest Logo
7:30 am - 7:05 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 35m1 stop Tampa
$226Southwest
Fri, Sep 18 - Tue, Sep 22
Southwest Logo
6:00 am - 2:30 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 30m2 stops Tampa Louisville Intl
Southwest Logo
9:40 am - 9:00 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 20m1 stop Orlando
$226Southwest
Thu, Sep 10 - Wed, Sep 16
JetBlue Logo
6:00 am - 7:05 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
14h 05m1 stop Baltimore/Washington
JetBlue Logo
8:40 pm - 9:20 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
11h 40m1 stop Orlando
$247JetBlue
Tue, Sep 29 - Thu, Oct 1
JetBlue Logo
6:25 am - 5:15 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
11h 50m1 stop Orlando
JetBlue Logo
8:40 pm - 9:20 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
11h 40m1 stop Orlando
$247JetBlue
Sat, Aug 29 - Thu, Oct 1

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Frontier flights from San Juan to Chicago Midway Airport

Our best Frontier deals on San Juan to Chicago Midway Airport flight tickets
Frontier
Sep 9
SJU6:30 amSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
MDW5:51 pmChicago Midway
Sep 12
MDW1:06 pmChicago Midway
12h 07m
2 stops
SJU2:13 amSan Juan Luis Munoz Marin Intl
$293
Frontier
Sep 12
SJU9:30 amSan Juan Luis Munoz Marin Intl
9h 21m
2 stops
MDW5:51 pmChicago Midway
Sep 16
MDW6:25 amChicago Midway
7h 54m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
$299
Frontier
Sep 9
SJU6:30 amSan Juan Luis Munoz Marin Intl
12h 21m
1 stop
MDW5:51 pmChicago Midway
Sep 16
MDW6:25 amChicago Midway
7h 54m
1 stop
SJU3:19 pmSan Juan Luis Munoz Marin Intl
$306

Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
Sep 10
SJU2:35 pmSan Juan Luis Munoz Marin Intl
7h 55m
1 stop
MDW9:30 pmChicago Midway
Sep 15
MDW9:40 amChicago Midway
10h 20m
1 stop
SJU9:00 pmSan Juan Luis Munoz Marin Intl
$226
Southwest
Sep 17
SJU2:35 pmSan Juan Luis Munoz Marin Intl
9h 10m
1 stop
MDW10:45 pmChicago Midway
Sep 21
MDW3:15 pmChicago Midway
6h 55m
1 stop
SJU11:10 pmSan Juan Luis Munoz Marin Intl
$246
Southwest
Aug 26
SJU11:50 amSan Juan Luis Munoz Marin Intl
8h 25m
1 stop
MDW7:15 pmChicago Midway
Sep 1
MDW12:45 pmChicago Midway
8h 15m
2 stops
SJU10:00 pmSan Juan Luis Munoz Marin Intl
$261

momondo Fare Finder

 
Use the filters below to find and compare flights from San Juan to Chicago Midway Airport that are best for you.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/10

2:35 pm-9:30 pm

1 stop7h 55m

Chicago Midway

Tue 9/15

9:40 am-9:00 pm

1 stop10h 20m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/10

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Tue 9/15

6:15 am-4:25 pm

1 stop9h 10m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/24

2:35 pm-10:45 pm

1 stop9h 10m

Chicago Midway

Tue 9/29

7:30 am-7:05 pm

1 stop10h 35m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/24

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Tue 9/29

12:45 pm-10:05 pm

2 stops8h 20m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/10

2:35 pm-9:30 pm

1 stop7h 55m

Chicago Midway

Wed 9/16

9:40 am-9:00 pm

1 stop10h 20m

$226
Quickest round-trip

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 9/30

8:20 am-2:45 pm

1 stop7h 25m

Chicago Midway

Mon 10/5

2:15 pm-12:20 am

1 stop9h 05m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 9/18

6:30 am-3:35 pm

1 stop10h 05m

Chicago Midway

Tue 9/22

7:30 am-7:05 pm

1 stop10h 35m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 9/10

6:00 am-2:30 pm

2 stops9h 30m

Chicago Midway

Wed 9/16

9:40 am-9:00 pm

1 stop10h 20m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 9/29

6:00 am-7:05 pm

1 stop14h 05m

Chicago Midway

Thu 10/1

8:40 pm-9:20 am

1 stop11h 40m

$247

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 8/29

6:25 am-5:15 pm

1 stop11h 50m

Chicago Midway

Thu 10/1

8:40 pm-9:20 am

1 stop11h 40m

$247

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?

Prices are currently low for flights on this route.

Typical prices usually range from $266 to $386.
The lowest price recently found on this route was $226.

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 September is also very affordable. Most momondo users find prices during this month for around $291.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from San Juan. The lowest ticket price found for a Saturday departure recently was $552. 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, Sunday 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 $726.

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 morning is the least expensive time of day to depart. momondo users have found prices as low as $552 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $726. 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 Airport flights?

There is only 1 cabin class available to choose from on San Juan to Chicago Midway Airport 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

$124

Fastest flight time

5h 05m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from San Juan in the past 72 hours is $124. The best round-trip flight deal from San Juan to Chicago Midway Airport found on momondo in the last 72 hours is $226.
The fastest flight from San Juan to Chicago Midway Airport takes 5h 05m
Direct flights go from San Juan to Chicago Midway Airport on 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 5h 05m.

  • 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 $266Free CancellationRating
8.0
4,219 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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