$63 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 11 - Sun, May 19
SJU
Luis Munoz Marin Intl.
ORD
O'Hare Intl.
$184 Roundtrip, just found
$184
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, May 11 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, May 19, priced at $184 just found
Sat, May 11 - Sun, May 19
SJU
Luis Munoz Marin Intl.
MDW
Midway Intl.
$228 Roundtrip, just found
$228
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 11 from Luis Munoz Marin Intl. to Midway Intl., returning Sun, May 19, priced at $228 just found

Airfares from $63 One Way, $117 Round Trip from San Juan to Chicago

Prices starting at $117 for return flights and $63 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.

Wed, May 15 - Tue, May 21
SJU
San Juan
ORD
Chicago
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, May 15 from San Juan to Chicago, returning Tue, May 21, priced at $117 found 1 day ago
Wed, Jun 5 - Tue, Jun 18
SJU
San Juan
ORD
Chicago
$130 Roundtrip, found 5 hours ago
$130
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Wed, Jun 5 from San Juan to Chicago, returning Tue, Jun 18, priced at $130 found 5 hours ago
Wed, Jun 5 - Tue, Jun 18
SJU
San Juan
ORD
Chicago
$131 Roundtrip, found 5 hours ago
$131
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Wed, Jun 5 from San Juan to Chicago, returning Tue, Jun 18, priced at $131 found 5 hours ago
Thu, May 9 - Wed, May 15
SJU
San Juan
ORD
Chicago
$163 Roundtrip, found 13 hours ago
$163
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Thu, May 9 from San Juan to Chicago, returning Wed, May 15, priced at $163 found 13 hours ago
Thu, Sep 12 - Fri, Sep 13
SJU
San Juan
ORD
Chicago
$223 Roundtrip, found 1 day ago
$223
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Sep 12 from San Juan to Chicago, returning Fri, Sep 13, priced at $223 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile
4.0-star property

Chicago Marriott Downtown Magnificent Mile

8.4/10 Very Good! (1,007 reviews)

Jun 10 - Jun 14

4 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
This property was very nice and there were eating options and a great bar/lounge.

Reviewed on Apr 22, 2024

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.2/10 Wonderful! (1,152 reviews)

Jun 10 - Jun 14

4 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
Everything was outstanding

Reviewed on Apr 2, 2024

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

8.8/10 Excellent! (206 reviews)

Jun 7 - Jun 13

6 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates

Reviewed on Feb 16, 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
2073 mi
Direct Flight Airlines
American Airlines, Alaska Airlines, Air Canada, Air New Zealand, United Airlines, Spirit Airlines
Earliest Flight Arrival
2:20PM UTC
Latest Flight Arrival
12:01AM UTC

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.

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.