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Cheap Flights from San Juan to Chicago from $269

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Cheap SJU to ORD Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Mar 4 - Wed, Mar 11
SJU
San Juan
to
ORD
Chicago
$269

roundtrip

found 15 hours ago

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Tue, Aug 13 - Tue, Aug 20
SJU
San Juan
to
ORD
Chicago
$272

roundtrip

found 5 hours ago

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Tue, Aug 27 - Sat, Sep 14
SJU
San Juan
to
ORD
Chicago
$279

roundtrip

found 1 hour ago

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Sat, Aug 17 - Wed, Aug 28
SJU
San Juan
to
ORD
Chicago
$284

roundtrip

just found

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Sat, Aug 17 - Wed, Aug 28
SJU
San Juan
to
ORD
Chicago
$285

roundtrip

just found

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Thu, Sep 5 - Sat, Sep 14
SJU
San Juan
to
ORD
Chicago
$286

roundtrip

found 13 hours ago

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Tue, Aug 13 - Tue, Aug 27
SJU
San Juan
to
ORD
Chicago
$289

roundtrip

found 21 hours ago

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Fri, Aug 16 - Sat, Aug 17
SJU
San Juan
to
ORD
Chicago
$291

roundtrip

found 21 hours ago

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Tue, Aug 27 - Wed, Aug 28
SJU
San Juan
to
ORD
Chicago
$292

roundtrip

found 1 day ago

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Tue, Nov 5 - Tue, Nov 12
SJU
San Juan
to
ORD
Chicago
$293

roundtrip

found 5 hours ago

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Tue, Aug 27 - Sun, Sep 1
SJU
San Juan
to
ORD
Chicago
$294

roundtrip

found 16 hours ago

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Mon, Aug 26 - Wed, Sep 4
SJU
San Juan
to
ORD
Chicago
$295

roundtrip

found 16 hours ago

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Tue, Aug 13 - Sat, Aug 17
SJU
San Juan
to
ORD
Chicago
$296

roundtrip

found 21 hours ago

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Thu, Sep 12 - Sun, Sep 15
SJU
San Juan
to
ORD
Chicago
$297

roundtrip

just found

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Sat, Aug 24 - Sat, Sep 7
SJU
San Juan
to
ORD
Chicago
$298

roundtrip

found 3 hours ago

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Tue, Oct 1 - Tue, Oct 8
SJU
San Juan
to
ORD
Chicago
$306

roundtrip

found 21 hours ago

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Wed, Mar 4 - Tue, Mar 17
SJU
San Juan
to
ORD
Chicago
$308

roundtrip

found 15 hours ago

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Wed, Sep 18 - Fri, Oct 4
SJU
San Juan
to
ORD
Chicago
$334

roundtrip

found 2 days ago

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Thu, Sep 5 - Fri, Sep 6
SJU
San Juan
to
ORD
Chicago
$353

roundtrip

found 6 days ago

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Fri, Nov 15 - Sat, Nov 16
SJU
San Juan
to
ORD
Chicago
$364

roundtrip

found 3 days ago

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San Juan to Chicago route information

Origin Airport Luis Munoz Marin Intl.
Destination Airport O'Hare Intl.
Airlines Serving American Airlines, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, United
Flight Price $269
Distance 2,073 mi

Ponce

PSE-Mercedita

$390.28

Vieques

VQS-Antonio Rivera Rodriguez

$716.12

Chicago

MDW-Midway Intl.

$364.40

Top Routes from San Juan

Top Routes to Chicago

Cheap SJU to ORD Flights

  • Question : How long is the flight from SJU to ORD?
    Answer : United Airlines can get you there in four hours and 55 minutes. So, if you were to leave San Juan at 3:10 PM AST, you would get to Chicago at 6:05 PM CDT. Giving you enough time if you want to catch up on your television shows before you land. Don't forget the two-hour time change. So, synchronize your watches.
  • Question : What is the cheapest day to fly to Chicago?
    Answer : As of Jul 15th, the best day for deals to Chicago (ORD) is Aug 6th. A ticket will run you $328, which is 36% below this route's average price.
  • Question : What is the cheapest airline flying from San Juan to Chicago?
    Answer : Spirit Airlines is the leader in keeping costs low for their passengers over the next three months. Fares are being booked at just $292 and, when compared to the pricier bookings of $2,236, it's quite a deal.
  • Question : Can I change the date of my flight?
    Answer : Yes, you can switch your departure date. If you would like to save a little cash in doing so, the cheapest day to fly in July is Wednesday. If you like to go with the flow, you may just find that you can pocket some additional cash.
  • Question : Which airline has the least delays from San Juan to Chicago?
    Answer : Booking with American Airlines means you will arrive to Chicago around the time you were supposed to. In fact, this timely airline has an 85% on-time average. It never hurts to be prepared. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.
  • Question : From San Juan to Chicago, which day is going to have the most flight times?
    Answer : When you’re flying from SJU to ORD, the day with the most flight times is Saturday, with seven different options. However, with two flight times, Thursday doesn't offer quite as many options when finding that perfect departure time.
  • Question : How much is a plane ticket to Chicago (ORD) from San Juan (SJU)?
    Answer : Cost can range from $292 to $2,236, prices for SJU to ORD do change more than most routes from Puerto Rico. Prices tend to be lower the further out you book.

San Juan to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from San Juan to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with SJU to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind San Juan for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Jul 9, 2019

Thanks to our wonderful flight attendant Silvia for making our flight so enjoyable

A verified traveler
San Juan to Chicago · American Airlines
Jun 14, 2019

Great trip

A verified traveler
San Juan to Chicago · American Airlines
Jun 10, 2019

Great experience with United...

A verified traveler
San Juan to Chicago · United
Apr 22, 2019

Seats too small, not enough rest rooms!

A verified traveler
San Juan to Chicago · American Airlines
Mar 21, 2019

We came in early!

A verified traveler
San Juan to Chicago · United
Mar 13, 2019

I will definitely fly again with United.

A verified traveler
San Juan to Chicago · United
Feb 22, 2019

Good

A verified traveler
San Juan to Chicago · American Airlines
Dec 18, 2018

ENJOYED FLIGHT

A verified traveler
San Juan to Chicago · United
Oct 20, 2018

Offer any other type of snacks

A verified traveler
San Juan to Chicago · United
Oct 1, 2018

Disembarkment was horrible, we waited on tarmac for 25 minutes.

A verified traveler
San Juan to Chicago · American Airlines