$93 Cheap flight deals from San Juan (SJU) to Chicago (CHI)

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This Weekend's Flight Deals from San Juan to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 3 - Sat, May 10
SJU
Luis Munoz Marin Intl.
ORD
O'Hare Intl.
$241 Roundtrip, found 11 hours ago
$241
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, May 3 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sat, May 10, priced at $241 found 11 hours ago
Fri, May 2 - Mon, May 5
SJU
Luis Munoz Marin Intl.
MDW
Midway Intl.
$308 Roundtrip, found 4 hours ago
$308
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, May 2 from Luis Munoz Marin Intl. to Midway Intl., returning Mon, May 5, priced at $308 found 4 hours ago

Airfares from $93 One Way, $179 Round Trip from San Juan to Chicago

Prices starting at $179 for return flights and $93 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, May 1 - Sat, May 10
SJU
San Juan
ORD
Chicago
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, May 1 from San Juan to Chicago, returning Sat, May 10, priced at $179 found 3 days ago
Fri, May 9 - Sun, May 11
SJU
San Juan
ORD
Chicago
$212 Roundtrip, found 1 hour ago
$212
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, May 9 from San Juan to Chicago, returning Sun, May 11, priced at $212 found 1 hour ago
Fri, May 9 - Sun, May 11
SJU
San Juan
ORD
Chicago
$215 Roundtrip, found 1 hour ago
$215
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, May 9 from San Juan to Chicago, returning Sun, May 11, priced at $215 found 1 hour ago
Fri, Sep 12 - Mon, Sep 15
SJU
San Juan
ORD
Chicago
$298 Roundtrip, found 1 day ago
$298
Roundtrip
found 1 day ago
Select United flight, departing Fri, Sep 12 from San Juan to Chicago, returning Mon, Sep 15, priced at $298 found 1 day ago
Fri, Sep 12 - Mon, Sep 15
SJU
San Juan
ORD
Chicago
$307 Roundtrip, found 1 day ago
$307
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Sep 12 from San Juan to Chicago, returning Mon, Sep 15, priced at $307 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG
3.0-star property

Staybridge Suites, Lincolnshire by IHG

8.8/10 Excellent! (1,002 reviews)

May 29 - Jun 1

3 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
Too many young patrons running down the halls and stairs.

Reviewed on Mar 16, 2025

Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,665 reviews)

Jun 5 - Jun 8

3 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Nice hotel. Great location. Nice room. Pictures made hotel seem like it was so much more. It was just one small hallway. Nothing more. Very disappointed with the lobby. I thought by the pictures I was getting so much more! Payed a $150 resort fee for two night. There was absolutely no resort and no resort benefits. That was purely a money grab. Didn’t even get my room cleaned each day. Nice room. Nice hotel. Just less that I thought!

Reviewed on Oct 13, 2024

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0-star property

Hotel Chicago Downtown, Autograph Collection by Marriott

9/10 Wonderful! (1,001 reviews)

Jun 19 - Jun 22

3 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
It’s a very nice hotel

Reviewed on Mar 21, 2025

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More About Flying To Chicago from San Juan

Route Information for Flights from San Juan to Chicago

Origin Airport IATA Code
SJU
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

San Juan to Chicago

When you’re searching for San Juan to Chicago flights for your family vacation, check out the guaranteed low prices at Orbitz. If you are looking for the best prices on hotels too, you’ll be sure to find great deals to suit your budget. You’ll also benefit from the following features:

Suitable Schedules

Orbitz simplifies the process of finding and booking budget flights from San Juan to Chicago. Since we monitor hundreds of flight fares, you can compare several flights from a range of different airlines to find the best fares and most suitable departure and arrival times. Mix and match your departure and return flight for even more discounts and travel flexibility.

Mobile Apps

Taking a lunch break or waiting to pick up the kids? Orbitz’s cutting-edge mobile tools will help you search for cheap San Juan to Chicago flights anywhere you are. Get exclusive mobile deals on flights, hotels, vacation packages, and cruises too.

Flight Alerts

Orbitz won’t leave you wondering whether your flight will take off on time. We can send you free alerts about your flights from San Juan to Chicago to your mobile phone and email. Whether your flights from San Juan to Chicago are running just a few minutes to a few hours late, we will let you know.

Miles and Points

If you travel regularly, you can still earn miles and points when you book qualifying San Juan to Chicago flights. Enter your frequent flyer number with your reservation to see the miles rack up.

Frequently asked questions

Are there non-stop flights from San Juan to Chicago?
There are, which is excellent news if you’re not a big fan of swapping planes en route. United Airlines and American Airlines fly straight from Luis Munoz Marin Intl. Airport (SJU) to O’Hare Intl. Airport (ORD).
What is the shortest flight from San Juan to Chicago?
The fastest flight time from San Juan to Chicago is 5 hours and 29 minutes, which gives you lots of time to enjoy a beverage or lose yourself in a good book.
What airlines fly from San Juan to Chicago most frequently?
Have a look at United Airlines (UA). This airline offers some of the most frequent flights from San Juan (SJU-Luis Munoz Marin Intl.) to ORD. It operates 30 services on this route every month and is a favorite with travelers. American Airlines (AA) also operates services from San Juan to Chicago. It’s another great option and has 26 flights each month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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.