$106 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, Jul 19 - Sun, Jul 27
SJU
Luis Munoz Marin Intl.
ORD
O'Hare Intl.
$282 Roundtrip, found 1 hour ago
$282
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jul 19 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $282 found 1 hour ago
Fri, Jul 18 - Sat, Jul 19
SJU
Luis Munoz Marin Intl.
MDW
Midway Intl.
$294 Roundtrip, found 3 days ago
$294
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jul 18 from Luis Munoz Marin Intl. to Midway Intl., returning Sat, Jul 19, priced at $294 found 3 days ago

Airfares from $106 One Way, $193 Round Trip from San Juan to Chicago

Prices starting at $193 for return flights and $106 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, Aug 21 - Tue, Aug 26
SJU
San Juan
ORD
Chicago
$193 Roundtrip, found 5 days ago
$193
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, Aug 21 from San Juan to Chicago, returning Tue, Aug 26, priced at $193 found 5 days ago
Thu, Jul 31 - Tue, Aug 5
SJU
San Juan
ORD
Chicago
$203 Roundtrip, found 18 hours ago
$203
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Thu, Jul 31 from San Juan to Chicago, returning Tue, Aug 5, priced at $203 found 18 hours ago
Thu, Jul 31 - Sat, Aug 9
SJU
San Juan
ORD
Chicago
$216 Roundtrip, found 4 days ago
$216
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Jul 31 from San Juan to Chicago, returning Sat, Aug 9, priced at $216 found 4 days ago
Fri, Nov 7 - Tue, Nov 11
SJU
San Juan
ORD
Chicago
$233 Roundtrip, found 5 hours ago
$233
Roundtrip
found 5 hours ago
Select Delta flight, departing Fri, Nov 7 from San Juan to Chicago, returning Tue, Nov 11, priced at $233 found 5 hours ago
Sat, Aug 16 - Sun, Sep 7
SJU
San Juan
MDW
Chicago
$264 Roundtrip, found 19 hours ago
$264
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Aug 16 from San Juan to Chicago, returning Sun, Sep 7, priced at $264 found 19 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Wade
4.5-star property

The Wade

8.2/10 Very Good! (1,066 reviews)

Aug 27 - Sep 3

7 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
We had a beautiful view of lake Michigan and the room had modern updates that gave it a cool ambience.

Reviewed on Jul 13, 2025

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,000 reviews)

Aug 20 - Aug 25

5 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 hour ago
Front desk staff was very attentive! We celebrated my sisters 30th birthday and they upgraded our room!

Reviewed on Feb 13, 2023

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

8.8/10 Excellent! (2,374 reviews)

Aug 28 - Sep 1

4 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Clean and attentive staff

Reviewed on Jun 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

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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.