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Cheap flights from San Juan to Chicago from $122

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.
Frontier Logo
7:17 am - 7:47 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
14h 30m1 stop Orlando
Frontier Logo
1:16 pm - 1:36 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 20m1 stop Atlanta Hartsfield-Jackson
$233Frontier
Sun, Nov 22 - Thu, Nov 26
Frontier Logo
5:01 am - 11:33 amSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
8h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:28 pm - 1:07 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
10h 39m1 stop Atlanta Hartsfield-Jackson
$234Frontier
Tue, Dec 8 - Sat, Dec 12
Frontier Logo
5:01 am - 4:07 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
13h 06m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:37 pm - 11:29 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
24h 52m1 stop Orlando
$239Frontier
Thu, Dec 3 - Thu, Dec 10
Frontier Logo
5:01 am - 4:07 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
13h 06m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:37 pm - 11:29 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
24h 52m1 stop Orlando
$240Frontier
Fri, Dec 4 - Sun, Dec 6
Frontier Logo
5:01 am - 4:07 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
13h 06m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:37 pm - 11:29 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
24h 52m1 stop Orlando
$240Frontier
Thu, Dec 3 - Sun, Dec 6
Frontier Logo
5:01 am - 4:07 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
13h 06m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:37 pm - 11:29 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
24h 52m1 stop Orlando
$241Frontier
Thu, Dec 3 - Sun, Dec 6
Frontier Logo
5:19 am - 12:21 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 02m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:37 pm - 2:13 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
27h 36m1 stop Orlando
$242Frontier
Thu, Nov 26 - Sun, Dec 6
Frontier Logo
5:01 am - 11:33 amSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
8h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:37 pm - 2:13 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
27h 36m1 stop Orlando
$245Frontier
Wed, Dec 2 - Sun, Dec 6
Southwest Logo
6:35 am - 4:00 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
11h 25m1 stop Baltimore/Washington
Southwest Logo
3:00 pm - 12:50 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
7h 50m1 stop Orlando
$266Southwest
Fri, Dec 11 - Tue, Dec 15
Southwest Logo
8:10 am - 4:00 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
9h 50m2 stops Orlando Nashville Intl
Southwest Logo
3:40 pm - 1:00 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
7h 20m1 stop Baltimore/Washington
$286Southwest
Fri, Jan 29 - Sun, Jan 31

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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
Nov 22
SJU7:17 amSan Juan Luis Munoz Marin Intl
14h 30m
1 stop
MDW7:47 pmChicago Midway
Nov 26
MDW1:16 pmChicago Midway
10h 20m
1 stop
SJU1:36 amSan Juan Luis Munoz Marin Intl
$233
Frontier
Dec 8
SJU5:01 amSan Juan Luis Munoz Marin Intl
8h 32m
1 stop
MDW11:33 amChicago Midway
Dec 12
MDW12:28 pmChicago Midway
10h 39m
1 stop
SJU1:07 amSan Juan Luis Munoz Marin Intl
$234
Frontier
Dec 3
SJU5:01 amSan Juan Luis Munoz Marin Intl
13h 06m
1 stop
MDW4:07 pmChicago Midway
Dec 10
MDW8:37 pmChicago Midway
24h 52m
1 stop
SJU11:29 pmSan Juan Luis Munoz Marin Intl
$239

Southwest flights from San Juan to Chicago Midway Airport

Our best Southwest deals on San Juan to Chicago Midway Airport flight tickets
Southwest
Dec 3
SJU10:45 amSan Juan Luis Munoz Marin Intl
9h 40m
2 stops
MDW6:25 pmChicago Midway
Dec 7
MDW3:00 pmChicago Midway
7h 50m
1 stop
SJU12:50 amSan Juan Luis Munoz Marin Intl
$286
Southwest
Nov 13
SJU5:50 pmSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW11:15 pmChicago Midway
Nov 17
MDW3:00 pmChicago Midway
7h 50m
1 stop
SJU12:50 amSan Juan Luis Munoz Marin Intl
$306
Southwest
Nov 13
SJU11:20 amSan Juan Luis Munoz Marin Intl
9h 00m
2 stops
MDW6:20 pmChicago Midway
Nov 15
MDW8:40 pmChicago Midway
11h 15m
1 stop
SJU9:55 amSan Juan Luis Munoz Marin Intl
$340

momondo Fare Finder

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

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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

Sun 11/22

7:17 am-7:47 pm

1 stop14h 30m

Chicago Midway

Thu 11/26

1:16 pm-1:36 am

1 stop10h 20m

$233

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 12/8

5:01 am-11:33 am

1 stop8h 32m

Chicago Midway

Sat 12/12

12:28 pm-1:07 am

1 stop10h 39m

$234

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/3

5:01 am-4:07 pm

1 stop13h 06m

Chicago Midway

Thu 12/10

8:37 pm-11:29 pm

1 stop24h 52m

$239

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/4

5:01 am-4:07 pm

1 stop13h 06m

Chicago Midway

Sun 12/6

8:37 pm-11:29 pm

1 stop24h 52m

$240

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/3

5:01 am-4:07 pm

1 stop13h 06m

Chicago Midway

Sun 12/6

8:37 pm-11:29 pm

1 stop24h 52m

$240

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/3

5:01 am-4:07 pm

1 stop13h 06m

Chicago Midway

Sun 12/6

8:37 pm-11:29 pm

1 stop24h 52m

$241

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 11/26

5:19 am-12:21 pm

1 stop9h 02m

Chicago Midway

Sun 12/6

8:37 pm-2:13 am

1 stop27h 36m

$242

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 12/2

5:01 am-11:33 am

1 stop8h 32m

Chicago Midway

Sun 12/6

8:37 pm-2:13 am

1 stop27h 36m

$245

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/11

6:35 am-4:00 pm

1 stop11h 25m

Chicago Midway

Tue 12/15

3:00 pm-12:50 am

1 stop7h 50m

$266
Quickest round-trip

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/29

8:10 am-4:00 pm

2 stops9h 50m

Chicago Midway

Sun 1/31

3:40 pm-1:00 am

1 stop7h 20m

$286

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 $354 to $468.
The lowest price recently found on this route was $233.

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from San Juan, with most prices found around $276. If you are unable to visit Chicago Midway Airport during the month of September, then departing from San Juan during the month August is also very affordable. Most momondo users find prices during this month for around $301.

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

$122

Fastest flight time

5h 10m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from San Juan in the past 72 hours is $122. The best round-trip flight deal from San Juan to Chicago Midway Airport found on momondo in the last 72 hours is $233.
The fastest flight from San Juan to Chicago Midway Airport takes 5h 10m
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 10m.

  • 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
4,215 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
Lansing
Saint Joseph
Benton Harbor
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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