>>>>
Flights from San Juan to Chicago
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Convenient & reliable booking and payment system
Find cheap one-way flights from San Juan to Chicago starting at US$59.
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
- One way
- Round-trip
- SJU21:0713h 48m1 stopORD09:55Wed, May 8|San Juan - Chicago|Spirit AirlinesUS$59US$8228% OFF28% OFFUS$82US$59
- SJU21:0713h 48m1 stopORD09:55Wed, May 15|San Juan - Chicago|Spirit AirlinesUS$59US$8228% OFF28% OFFUS$82US$59
- SJU09:349h 53m1 stopMDW18:27Wed, May 8|San Juan - Chicago|Frontier AirlinesUS$64US$8222% OFF22% OFFUS$82US$64
- SJU09:349h 53m1 stopMDW18:27Wed, May 15|San Juan - Chicago|Frontier AirlinesUS$66US$66
- SJU06:0016h 43m1 stopMDW21:43Wed, May 1|San Juan - Chicago|Frontier AirlinesUS$66US$66
- SJU09:349h 49m1 stopMDW18:23Thu, May 9|San Juan - Chicago|Frontier AirlinesUS$69US$69
- SJU21:0013h 55m1 stopORD09:55Fri, May 10|San Juan - Chicago|Spirit AirlinesUS$69US$69
- SJU15:418h 50m1 stopMDW23:31Sat, May 4|San Juan - Chicago|Frontier AirlinesUS$69US$69
- SJU09:349h 49m1 stopMDW18:23Thu, May 2|San Juan - Chicago|Frontier AirlinesUS$69US$69
- SJU21:0713h 48m1 stopORD09:55Tue, May 14|San Juan - Chicago|Spirit AirlinesUS$69US$69
- SJU13:003h 5mDirectCHI14:00Thu, Apr 25|San Juan - Chicago|Spirit AirlinesFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
When is the cheapest time to book flights from San Juan to Chicago?
We monitor flight fares to help you find the best deals effortlessly
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Cheapest airlines flights from San Juan to Chicago
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Spirit Airlines
From US$59
Frontier Airlines
From US$64
Jetblue Airways
From US$119
American Airlines
From US$128
United Airlines
From US$148
Southwest Airlines
From US$180
Delta Air Lines
From US$224
Silver Airways
From US$521
Cape Air
From US$575
ANA airlines
Find more flights and airlines
Find cheap flights from San Juan to Chicago by different airports
Searching for potential routes that might be cheaper and faster? Check out these alternative flights from San Juan to Chicago.
- CheapestSJU21:0713h 48m1 transferORD09:55Luis Muñoz Marín International Airport - O'Hare International AirportWed, May 8Spirit AirlinesUS$59
- SJU09:349h 53m1 transferMDW18:27Luis Muñoz Marín International Airport - Midway International AirportWed, May 8Frontier AirlinesUS$64
- SJU03:0816h 10m1 transferRFD18:18Luis Muñoz Marín International Airport - Chicago Rockford International AirportFri, Apr 19Frontier AirlinesUS$214
- SJU03:0816h 10m1 transferRFD18:18Luis Muñoz Marín International Airport - Chicago Rockford International AirportFri, Apr 19Frontier AirlinesUS$214Find More Flights
Frequently Asked Questions
How to find a cheap flight from San Juan to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from San Juan to Chicago. Book your flights at the right time and save more.
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
Compare Flight Prices
Compare prices on travel agency and airline websites.
Look Out for Deals
Check airline and travel agency websites for latest flight deals
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
San Juan to Chicago Flight Information
Cheapest nonstop flight price | $59 |
---|---|
Cheapest round-trip ticket price | $156 |
Off-season for travel | December |
Peak season for travel | July |
Flight distance | 3,313.11km |
Average flight time | 5 hours 11 minutes |
Popular airline | Frontier Airlines |
Plan Your Trip Around Chicago
More Travel Options
Popular Flights from San Juan
- Flights from San Juan to Punta Cana
- Flights from San Juan to Santo Domingo
- Flights from San Juan to Saint Thomas
- Flights from San Juan to Bogota
- Flights from San Juan to Barcelona
- Flights from San Juan to Madrid
- Flights from San Juan to Buenos Aires
- Flights from San Juan to Jacksonville
- Flights from San Juan to Pereira
- Flights from San Juan to Saint Barthelemy
- Flights from San Juan to Washington D.C.
- Flights from San Juan to Medellin
- Flights from San Juan to Shanghai Pudong International Airport
- Flights from Luis Muñoz Marín International Airport to Tampa International Airport
- Flights from Luis Muñoz Marín International Airport to Philadelphia International Airport
- Flights from Luis Muñoz Marín International Airport to Trenton Mercer Airport
- Flights from Luis Muñoz Marín International Airport to Punta Cana International Airport
- Flights from Luis Muñoz Marín International Airport to General Edward Lawrence Logan International Airport
- Flights from Luis Muñoz Marín International Airport to Las Américas International Airport
- Flights from Luis Muñoz Marín International Airport to Lahore
- Flights from Luis Muñoz Marín International Airport to Wuzhou
- Flights from Luis Muñoz Marín International Airport to Shenyang
- Flights from Luis Muñoz Marín International Airport to Nagasaki
- Flights from Luis Muñoz Marín International Airport to Miyazaki
- Flights from Luis Muñoz Marín International Airport to Mashhad
- Flights from San Juan to Taizhou Luqiao Airport
- Flights from San Juan to Karamay Airport
- Flights from San Juan to Liuzhou Bailian Airport
- Flights from San Juan to Qiqihar Sanjiazi Airport
- Flights from San Juan to Xingdong International Airport
Recommended Hotels in Chicago
- Hotels near Theater Wit
- Hotels near Adler Planetarium
- Hotels near Formatografia
- Hotels near CSX Intermodal 59th Street Yard
- Hotels near Flashy Trash
- Hotels near Museum of Holography,
- Hotels near Jarvis Bird Sanctuary
- Hotels near Dollar Day Plus
- Hotels near Historic Route 66 Begin Sign
- Hotels near Oliver Peoples
- Hotels near Norwood Park Historical Society
- Hotels near Illini Center
- Hotels near Bubbly Creek
- Hotels near Museum of Broadcast Communications
- Hotels near Dancing Fingers Authentic Chinese Massage
- Hotels near Jewel-Osco
- Hotels near Washington Park Sunken Garden
- Hotels near Bob-O-Link Meadow
- Hotels near Nail Spa
- Hotels near IATA | Clothing Brand
- Hotels near PRIMITIVE
- Hotels near St. Malachy and Precious Blood Church
- Hotels near Faith Tabernacle Baptist Church
- Hotels near La Kaiser Jewelry
- Hotels near Chess Records
- Hotels near T.J. Maxx
- Hotels near North Park Village Nature Center
- Hotels near Old Colony Building
- Hotels near The Spearman
- Hotels near Van Gogh's Bedrooms
Popular Flights to Chicago
- Flights from Hong Kong to Chicago
- Flights from Bangkok to Chicago
- Flights from Taipei to Chicago
- Flights from Seoul to Chicago
- Flights from Shanghai to Chicago
- Flights from New York to Chicago
- Flights from Manila to Chicago
- Flights from Tokyo to Chicago
- Flights from Atlanta to Chicago
- Flights from Singapore to Chicago
- Flights from Istanbul to Chicago
- Flights from Orlando to Chicago
- Flights from Hong Kong International Airport to Chicago
- Flights from Taiwan Taoyuan International Airport to Chicago
- Flights from Narita International Airport to Chicago
- Flights from Shanghai Pudong International Airport to Chicago
- Flights from Ngurah Rai Airport to Chicago
- Flights from Ninoy Aquino International Airport to Chicago
- Flights from Giza Governorate to O'Hare International Airport
- Flights from Honolulu to O'Hare International Airport
- Flights from Honolulu to Chicago Rockford International Airport
- Flights from Honolulu to Midway International Airport
- Flights from Los Angeles to Chicago Rockford International Airport
- Flights from Rajkot International Airport to O'Hare International Airport
- Flights from Hong Kong International Airport to O'Hare International Airport
- Flights from Hong Kong International Airport to Midway International Airport
- Flights from Hong Kong International Airport to Chicago Rockford International Airport
- Flights from Suvarnabhumi Airport to Midway International Airport
- Flights from Los Angeles to Midway International Airport
- Flights from Don Mueang International Airport to Midway International Airport
Recommended Routes
- Flights from San Juan to Orlando
- Flights from San Juan to Miami
- Flights from San Juan to New York
- Flights from San Juan to Tampa
- Flights from San Juan to Philadelphia
- Flights from San Juan to Boston
- Flights from Aguadilla to Orlando
- Flights from San Juan to Atlanta
- Flights from San Juan to Hartford
- Flights from San Juan to Fort Lauderdale
- Flights from San Juan to Raleigh
- Flights from San Juan to Dallas
- Flights from Luis Muñoz Marín International Airport to Orlando International Airport
- Flights from Luis Muñoz Marín International Airport to Miami International Airport
- Flights from Luis Muñoz Marín International Airport to John F. Kennedy International Airport
- Flights from Luis Muñoz Marín International Airport to New York LaGuardia Airport
- Flights from Luis Muñoz Marín International Airport to Stewart Airport
- Flights from Luis Muñoz Marín International Airport to Newark Liberty International Airport
- Flights from Luis Muñoz Marín International Airport to Fort Dodge
- Flights from Luis Muñoz Marín International Airport to Panama City
- Flights from Luis Muñoz Marín International Airport to Juneau
- Flights from Luis Muñoz Marín International Airport to New Bern
- Flights from Luis Muñoz Marín International Airport to Aspen
- Flights from Luis Muñoz Marín International Airport to Madison
- Flights from San Juan to Newark Liberty International Airport
- Flights from San Juan to Meadows Field Airport
- Flights from San Juan to Bob Hope Airport
- Flights from San Juan to Elmira Regional Airport
- Flights from San Juan to Nashville International Airport
- Flights from San Juan to George Bush Intercontinental Airport
Payment Methods
Our Partners
Copyright © 2024 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.
Site Operator: Trip.com Travel Singapore Pte. Ltd.