Flights from San Juan to Chicago

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Sample Roundtrip* fares starting at:  $293.60

* All fares below were last found on:Oct 12, 2015 and 9:52:07 AM

* Fares are round trip, Fares incl. all fuel surcharges, our service fees and taxes. Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions

FromToTravel DatesSample Fares*

San JuanChicagoNov 06 - Nov 08$293.60
San JuanChicagoNov 02 - Nov 17$301.60

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Chicago Reviews

Visiting a Friend  4

What a smooth trip! I was very pleased with how my flight from Minneapolis to Chicago was. I am sad that Sun Country has discontinued their rountrip flights to Chicago and Minneapolis. I went to them over Spirit. But now that will have to chance.

Cordelia - Oct 08, 2015
Write a review for Chicago »

San Juan Reviews

Great Experience  5

Canada is simply beautiful and the people are very welcoming and kind. OneTravel provided me with a route that was very reasonable and would surely go for every time that I travel.

Kyle - Aug 03, 2015
Write a review for San Juan »

San Juan to Chicago Flight Route Facts

In the Last 12 Months:
  • 100% of visitors spent less than 3 days in the city.

Sky High Flight Facts for Your Trip:
San Juan to Chicago

Book your flights from San Juan to Chicago and save big on airfares. Have passion for excellent music, spectacular architecture and amazing art, then Chicago is definitely the destination for you. Most populous city in Illinois, US, a vacation in Chicago would certainly refresh your soul. Plan a picnic at Millennium Park which is decorated with beautiful art and architecture and is also popular for its ice rink and theatre performances. Watch some of the best dramas at the Chicago Shakespeare Theater and don’t forget to enjoy 360 degree views of the city from the top of Willis Tower which also boasts of spectacular architecture.

To reach Chicago from San Juan, you may choose amongst the premier airlines such as US Airways, American Airlines, Air Tran Airways and United Airlines. Take advantage of exclusive deals on flights to Chicago and save more to splurge on a vacation. Your flight to Chicago from San Juan takes about five hours and fifty minutes to cover a distance of about 2,061 miles excluding layover time, so make sure you have a good book or an interesting company to keep yourself engaged for the travel.

  • When does the earliest flight depart Chicago?
  • 12:54PM  United Airlines  Flight #2004
  • When does the latest flight depart Chicago?
  • 4:05PM  United Airlines   Flight #712
  • What is the busiest month to travel from San Juan to Chicago?
  • May
  • What is the least busy month to travel from San Juan to Chicago?
  • October

Low Fare Promise

In the unlikely event that you find a lower rate on OneTravel or on another U.S.-based website within 4 hours of booking with, we will credit or refund you the difference. Should you contact us after 4 hours but no later than 24 hours, we will give you a US$50.00 coupon good on a future booking at The Low Fare Promise is subject to the terms and conditions listed below. This offer is good for website bookings only, and not on phone bookings.

* Terms and Conditions

Fares are roundtrip and include all fuel surcharges, our service fees and taxes. Tickets are nonrefundable, nontransferable, non-assignable. Name changes are not permitted. Fares are subject to change without notice. Fares subject to availability. There is a higher probability of seats being available at this fare on Tuesday, Wednesday and Thursday, and may require a Saturday night stay at your destination. Lowest fares may require an advance purchase of up to 21 days. Certain blackout dates may apply. Holidays and weekend travel may have a surcharge. Other restrictions may apply. Additional terms and conditions of purchase.

§ Instant Discount

This $10 off sale applies to our transaction service fees only. All fares displayed above are after the 10 USD instant discount applied. Maximum discount amount is the amount of the transaction service fees for that transaction or 10 USD, whichever is less. Some discounted and other special sale fare offers may not be eligible for this instant discount promotion. This offer may be revised or discontinued without notice.

Promo Code Offer

Applies to all international travel. Book by October 31, 2015. Enter Promo Code at time of check out. The advertised Promo Code provides discounts against our service fees on stated routes. A maximum of $5 per person can be saved by using this promo code; 4 passengers are needed to redeem the full value. Promo Code and Instant Savings offers can be combined up to the amount of our service fees. Excess savings will not be applied. Promo Code expires on date indicated and can be withdrawn at anytime without notice. Our standard service fees are $0 to $35 per person one-way/roundtrip for economy class tickets.