$66 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.

Fri, Feb 6 - Mon, Feb 9
SJU
Luis Munoz Marin Intl.
ORD
O'Hare Intl.
$174 Roundtrip, found 7 hours ago
$174
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Fri, Feb 6 from Luis Munoz Marin Intl. to O'Hare Intl., returning Mon, Feb 9, priced at $174 found 7 hours ago
Fri, Feb 6 - Mon, Feb 9
SJU
Luis Munoz Marin Intl.
MDW
Midway Intl.
$293 Roundtrip, found 2 days ago
$293
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Feb 6 from Luis Munoz Marin Intl. to Midway Intl., returning Mon, Feb 9, priced at $293 found 2 days ago

Airfares from $66 One Way, $127 Round Trip from San Juan to Chicago

Prices starting at $127 for return flights and $66 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, Feb 26 - Tue, Mar 3
SJU
San Juan
ORD
Chicago
$127 Roundtrip, found 18 hours ago
$127
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Thu, Feb 26 from San Juan to Chicago, returning Tue, Mar 3, priced at $127 found 18 hours ago
Thu, Feb 26 - Tue, Mar 3
SJU
San Juan
ORD
Chicago
$128 Roundtrip, found 18 hours ago
$128
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Thu, Feb 26 from San Juan to Chicago, returning Tue, Mar 3, priced at $128 found 18 hours ago
Thu, Feb 26 - Tue, Mar 3
SJU
San Juan
ORD
Chicago
$135 Roundtrip, found 18 hours ago
$135
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Thu, Feb 26 from San Juan to Chicago, returning Tue, Mar 3, priced at $135 found 18 hours ago
Tue, Mar 10 - Tue, Mar 17
SJU
San Juan
ORD
Chicago
$151 Roundtrip, found 6 days ago
$151
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Mar 10 from San Juan to Chicago, returning Tue, Mar 17, priced at $151 found 6 days ago
Wed, Feb 25 - Tue, Mar 3
SJU
San Juan
ORD
Chicago
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Feb 25 from San Juan to Chicago, returning Tue, Mar 3, priced at $184 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
2.0-star property

Illinois Beach Hotel

8/10 Very Good! (478 reviews)

Mar 10 - Mar 15

5 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $529, price is now $377 per person
$377
per person
found 1 day ago
Private beach on Lake Michigan. Very beautiful.Nature trails right out side the door. Great staff . Good restaurant.

Reviewed on Oct 20, 2024

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Mar 13 - Mar 16

3 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,121, price is now $777 per person
$777
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,229 reviews)

Mar 10 - Mar 15

5 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $960, price is now $701 per person
$701
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

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Chicago packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Arlington Heights - Schaumburg
3.0-star property

Comfort Inn & Suites Arlington Heights - Schaumburg

8.4/10 Very Good! (782 reviews)

Mar 6 - Mar 9

3 night stay

San Juan (SJU) to Chicago (ORD)

United • PremiumEconomy

Chicago (ORD) to San Juan (SJU)

JetBlue Airways • PremiumEconomy
Price was $895, price is now $849 per person
$849
per person
found 9 hours ago
Smells a little weird in the room. But over pretty clean. The bathroom needs updating. The tub has lots of stains and the toilet has one of those buttons that use different amounts of water between the two buttons. The larger one didn’t work so that was annoying. Close to a lot of things if you have a car or take the bus. Can walk to a big gas station across the street

Reviewed on Dec 13, 2025

Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.2/10 Very Good! (2,158 reviews)

Mar 6 - Mar 9

3 night stay

San Juan (SJU) to Chicago (ORD)

United • PremiumEconomy

Chicago (ORD) to San Juan (SJU)

JetBlue Airways • PremiumEconomy
Price was $1,169, price is now $1,037 per person
$1,037
per person
found 9 hours ago
Awesome hotel, an island of peace and calm and first class treatment in a sea of chaos at O'Hare airport. Staff, restaurant, services--worth every penny. Early departure? Stay here the night before. We did. Calmly woke up and walked to the terminal thru the underground walkways. Truly pleasant and memorable stay.

Reviewed on Nov 11, 2025

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
4.0-star property

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

8.6/10 Excellent! (1,001 reviews)

Mar 6 - Mar 9

3 night stay

San Juan (SJU) to Chicago (ORD)

United • PremiumEconomy

Chicago (ORD) to San Juan (SJU)

JetBlue Airways • PremiumEconomy
Price was $1,034, price is now $986 per person
$986
per person
found 9 hours ago
Great place to stay!

Reviewed on Jun 4, 2024

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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

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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.

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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.