Flights from Chicago to Barrio Pueblo

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Oct 9 - Fri, Oct 10

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$175 Roundtrip, found 3 hours ago

$175

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Thu, Oct 9 from Midway Intl. to Luis Munoz Marin Intl., returning Fri, Oct 10, priced at $175 found 3 hours ago

Mon, Oct 6 - Sat, Oct 11

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$179 Roundtrip, found 3 hours ago

$179

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Mon, Oct 6 from Midway Intl. to Luis Munoz Marin Intl., returning Sat, Oct 11, priced at $179 found 3 hours ago

Thu, Oct 9 - Sun, Oct 12

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$180 Roundtrip, found 3 hours ago

$180

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Thu, Oct 9 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, Oct 12, priced at $180 found 3 hours ago

Sun, Oct 12 - Sun, Oct 12

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$187 Roundtrip, found 3 hours ago

$187

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Sun, Oct 12 from Midway Intl. to Luis Munoz Marin Intl., returning Sun, Oct 12, priced at $187 found 3 hours ago

Sat, Oct 11 - Mon, Oct 13

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$199 Roundtrip, found 3 hours ago

$199

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Sat, Oct 11 from Midway Intl. to Luis Munoz Marin Intl., returning Mon, Oct 13, priced at $199 found 3 hours ago

Tue, Jul 29 - Thu, Aug 7

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$209 Roundtrip, found 2 hours ago

$209

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Aug 7, priced at $209 found 2 hours ago

Sat, Oct 11 - Sat, Oct 11

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$213 Roundtrip, found 3 hours ago

$213

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Sat, Oct 11 from Midway Intl. to Luis Munoz Marin Intl., returning Sat, Oct 11, priced at $213 found 3 hours ago

Thu, Oct 9 - Sun, Oct 12

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$218 Roundtrip, found 3 hours ago

$218

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Thu, Oct 9 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, Oct 12, priced at $218 found 3 hours ago

Fri, Oct 10 - Fri, Oct 10

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$226 Roundtrip, found 3 hours ago

$226

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Fri, Oct 10 from Midway Intl. to Luis Munoz Marin Intl., returning Fri, Oct 10, priced at $226 found 3 hours ago

Tue, Jul 29 - Tue, Aug 5

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$232 Roundtrip, found 2 days ago

$232

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Aug 5, priced at $232 found 2 days ago

Thu, Oct 9 - Thu, Oct 9

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$234 Roundtrip, found 3 hours ago

$234

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Thu, Oct 9 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, Oct 9, priced at $234 found 3 hours ago

Sat, Jul 19 - Sat, Jul 26

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$239 Roundtrip, found 1 day ago

$239

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Jul 26, priced at $239 found 1 day ago

Mon, Jul 28 - Thu, Aug 7

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$239 Roundtrip, found 2 hours ago

$239

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Mon, Jul 28 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Aug 7, priced at $239 found 2 hours ago

Mon, Jul 14 - Tue, Jul 22

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$242 Roundtrip, found 2 days ago

$242

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 22, priced at $242 found 2 days ago

Tue, Jul 8 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$244 Roundtrip, found 1 day ago

$244

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $244 found 1 day ago

Sat, Jul 19 - Sat, Jul 26

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$258 Roundtrip, found 1 day ago

$258

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Jul 26, priced at $258 found 1 day ago

Tue, Oct 7 - Tue, Oct 14

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$343 Roundtrip, found 3 hours ago

$343

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Tue, Oct 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Oct 14, priced at $343 found 3 hours ago

Tue, Oct 7 - Fri, Oct 10

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$347 Roundtrip, found 3 hours ago

$347

Roundtrip

found 3 hours ago

Select Delta flight, departing Tue, Oct 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Oct 10, priced at $347 found 3 hours ago

Thu, Oct 9 - Sun, Oct 12

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$387 Roundtrip, found 3 hours ago

$387

Roundtrip

found 3 hours ago

Select United flight, departing Thu, Oct 9 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, Oct 12, priced at $387 found 3 hours ago

Sat, Jul 19 - Sat, Jul 26

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$432 Roundtrip, found 1 day ago

$432

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Jul 26, priced at $432 found 1 day ago