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Cheap flights from Puerto Rico to Chicago from $113

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Puerto Rico to Chicago

Recent round-trip flight deals from Puerto Rico to Chicago

Enter your travel dates to find the best prices.
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:21 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 45m1 stop Atlanta Hartsfield-Jackson
$225Frontier
Fri, Oct 16 - Wed, Oct 21
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:21 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 45m1 stop Atlanta Hartsfield-Jackson
$225Frontier
Fri, Oct 16 - Wed, Oct 21
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:24 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 42m1 stop Atlanta Hartsfield-Jackson
$226Frontier
Tue, Oct 13 - Sun, Oct 18
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Atlanta Hartsfield-Jackson
$226Frontier
Fri, Oct 16 - Mon, Oct 19
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Atlanta Hartsfield-Jackson
$226Frontier
Fri, Oct 16 - Mon, Oct 19
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:21 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 45m1 stop Atlanta Hartsfield-Jackson
$226Frontier
Sat, Oct 10 - Tue, Oct 13
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:24 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 42m1 stop Atlanta Hartsfield-Jackson
$226Frontier
Thu, Oct 15 - Sun, Oct 18
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:24 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 42m1 stop Atlanta Hartsfield-Jackson
$226Frontier
Fri, Oct 16 - Sun, Oct 18
Southwest Logo
10:50 pm - 8:45 amSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
10h 55m1 stop Orlando
Southwest Logo
2:40 pm - 10:15 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
6h 35m1 stop Baltimore/Washington
$246Southwest
Thu, Oct 22 - Sat, Oct 24
Southwest Logo
5:50 pm - 11:15 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 25m1 stop Baltimore/Washington
Southwest Logo
4:25 pm - 12:50 amMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
6h 25m1 stop Orlando
$246Southwest
Fri, Nov 13 - Tue, Nov 17

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Frontier flights from Puerto Rico to Chicago Midway Airport

Our best Frontier deals on Puerto Rico to Chicago Midway Airport flight tickets
Frontier
Oct 16
SJU5:11 pmSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
MDW11:43 pmChicago Midway
Oct 21
MDW6:21 amChicago Midway
8h 45m
1 stop
SJU4:06 pmSan Juan Luis Munoz Marin Intl
$225
Frontier
Oct 8
SJU5:11 pmSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
MDW11:43 pmChicago Midway
Oct 13
MDW6:21 amChicago Midway
8h 45m
1 stop
SJU4:06 pmSan Juan Luis Munoz Marin Intl
$226
Frontier
Oct 8
SJU5:11 pmSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
MDW11:43 pmChicago Midway
Oct 13
MDW6:21 amChicago Midway
8h 45m
1 stop
SJU4:06 pmSan Juan Luis Munoz Marin Intl
$228

Southwest flights from Puerto Rico to Chicago Midway Airport

Our best Southwest deals on Puerto Rico to Chicago Midway Airport flight tickets
Southwest
Nov 12
SJU5:50 pmSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW11:15 pmChicago Midway
Nov 15
MDW12:50 pmChicago Midway
8h 45m
1 stop
SJU11:35 pmSan Juan Luis Munoz Marin Intl
$246
Southwest
Oct 13
SJU5:05 amSan Juan Luis Munoz Marin Intl
10h 35m
2 stops
MDW2:40 pmChicago Midway
Oct 27
MDW1:40 pmChicago Midway
8h 30m
2 stops
SJU11:10 pmSan Juan Luis Munoz Marin Intl
$266
Southwest
Nov 24
SJU10:30 pmSan Juan Luis Munoz Marin Intl
15h 30m
2 stops
MDW12:00 pmChicago Midway
Dec 8
MDW4:25 pmChicago Midway
6h 20m
1 stop
SJU12:45 amSan Juan Luis Munoz Marin Intl
$286

momondo Fare Finder

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

Fly from

Fly to

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

Fri 10/16

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Wed 10/21

6:21 am-4:06 pm

1 stop8h 45m

$225

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/16

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Wed 10/21

6:21 am-4:06 pm

1 stop8h 45m

$225

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 10/13

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Sun 10/18

6:24 am-4:06 pm

1 stop8h 42m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/16

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Mon 10/19

6:15 am-4:06 pm

1 stop8h 51m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/16

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Mon 10/19

6:15 am-4:06 pm

1 stop8h 51m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 10/10

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Tue 10/13

6:21 am-4:06 pm

1 stop8h 45m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/15

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Sun 10/18

6:24 am-4:06 pm

1 stop8h 42m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 10/16

5:11 pm-11:43 pm

1 stop7h 32m

Chicago Midway

Sun 10/18

6:24 am-4:06 pm

1 stop8h 42m

$226

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 10/22

10:50 pm-8:45 am

1 stop10h 55m

Chicago Midway

Sat 10/24

2:40 pm-10:15 pm

1 stop6h 35m

$246
Quickest round-trip

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - MDW Chicago Midway

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 11/13

5:50 pm-11:15 pm

1 stop7h 25m

Chicago Midway

Tue 11/17

4:25 pm-12:50 am

1 stop6h 25m

$246

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 Puerto Rico 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 March is, on average, the cheapest month to fly to Chicago Midway Airport from Puerto Rico, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Puerto Rico during the month September is also very affordable. Most momondo users find prices during this month for around $276.

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 Puerto Rico. 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 Puerto Rico 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 Puerto Rico 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 Puerto Rico to Chicago Midway flight route?

Fly from San Juan Luis Munoz Marin Intl to Chicago Midway for the best Puerto Rico - Chicago Midway flight prices

What cabin class options are available on Puerto Rico to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Puerto Rico 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 Puerto Rico to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Puerto Rico to Chicago Midway Airport

Best Price Found

$113

Fastest flight time

5h 10m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from Puerto Rico in the past 72 hours is $113. The best round-trip flight deal from Puerto Rico to Chicago Midway Airport found on momondo in the last 72 hours is $225.
The fastest flight from Puerto Rico to Chicago Midway Airport takes 5h 10m
Direct flights go from Puerto Rico to Chicago Midway Airport on Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Puerto Rico to Chicago Midway Airport

  • When did momondo last update prices for flights from Puerto Rico to Chicago Midway Airport?

    Prices for flights from Puerto Rico to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Puerto Rico to Chicago Midway Airport?

  • How old do you have to be to fly from Puerto Rico to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Puerto Rico to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Puerto Rico to Chicago Midway Airport?

Best airlines flying from Puerto Rico to Chicago Midway Airport

Compare and see reviews for airlines that fly from Puerto Rico to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $266Free CancellationRating
8.0
4,202 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
Saint Joseph
Lansing
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 Puerto Rico to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Puerto Rico.

Can I find flights from Puerto Rico to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Puerto Rico on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Puerto Rico to Chicago?

momondo helps you find the best flight between Puerto Rico 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 Puerto Rico to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Puerto Rico to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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