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Flights from Chicago to San Juan
Selected fares from Chicago to San Juan
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Chicago to San Juan Intro 44
If you are looking to find the best deals on Chicago to San Juan flights, look no further than Orbitz. Orbitz offers guaranteed low prices as well as cutting-edge mobile tools to help you book cheap flights from Chicago to San Juan.
Mobile Apps Make Life Easier
Our mobile apps for Android and iPhone phones as well as tablets and iPads let you find the cheapest flights from Chicago to San Juan—whether you are at home or running errands. Use the apps to also keep track of delays to your Chicago to San Juan flights and baggage claim information.
Get Miles for Your Flights From Chicago to San Juan
It’s easy to earn points or miles for your frequent flyer or airline loyalty program on qualifying Chicago to San Juan flights with Orbitz. You can add your frequent flyer number to your online flight booking, and even store your numbers in your Orbitz account profile so they automatically get added the next time you book a flight.
Stay Informed While You Travel
Orbitz keeps you updated on information that’s relevant to your flights from Chicago to San Juan. We can send you and six of your personal contacts free travel alerts via SMS text, voicemail, or email, so you instantly know about flight delays or changes.
Keep More Money in Your Pocket With Discount Flights
Orbitz looks for the best deals on Chicago to San Juan flights for you. Mix and match airlines for your departing and return flights to fit your travel schedule and budget.
Save more with San Juan Flight + Hotel packages
Sheraton Old San Juan Hotel
4.0 out of 5.0Wed, May 30 - Tue, Jun 5
CHI - SJU
$802
per person
InterContinental San Juan
4.0 out of 5.0Wed, May 30 - Tue, Jun 5
CHI - SJU
$987
per person
San Juan Marriott Resort and Stellaris Casino
4.5 out of 5.0Wed, May 30 - Tue, Jun 5
CHI - SJU
$978
per person
Condado Vanderbilt Hotel
5.0 out of 5.0Wed, May 30 - Tue, Jun 5
CHI - SJU
$1,182
per person
Park Royal Puerto Rico at Club Cala
2.5 out of 5.0Wed, May 30 - Tue, Jun 5
CHI - SJU
$768
per person
San Juan Airport Hotel
3.0 out of 5.0Wed, May 30 - Tue, Jun 5
CHI - SJU
$829
per person
Embassy Suites by Hilton Dorado del Mar Beach Resort
3.5 out of 5.0Sun, Jun 3 - Fri, Jun 8
ORD - SJU
$879
per person
Villa Montana Beach Resort
3.5 out of 5.0Tue, Jun 5 - Mon, Jun 11
CHI - SJU
$1,052
per person
Parguera Plaza Hotel
3.5 out of 5.0Sun, May 27 - Fri, Jun 1
ORD - SJU
$597
per person
Embassy Suites by Hilton San Juan Hotel & Casino
3.5 out of 5.0Sun, May 27 - Fri, Jun 1
ORD - SJU
$810
per person
Courtyard by Marriott San Juan Miramar
3.5 out of 5.0Sun, Jun 17 - Fri, Jun 22
ORD - SJU
$795
per person
More to explore for Chicago to San Juan
Explore San Juan with Orbitz's Travel Guides to find the best flights, cars, vacation packages and more!
Flights from Cities near Chicago
Flights to Cities near San Juan
Other Flights to San Juan
- Chicago to San Juan
- Los Angeles to San Juan
- Raleigh to San Juan
- Washington to San Juan
- Miami to San Juan
- Tampa to San Juan
- New York to San Juan
- Boston to San Juan
- Fort Lauderdale to San Juan
- Charlotte to San Juan
- Hartford to San Juan
- Houston to San Juan
- Dallas to San Juan
- Philadelphia to San Juan
- Baltimore to San Juan
- Orlando to San Juan
- Atlanta to San Juan
* Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from July 1, 2015 to June 30, 2016, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.
