$120 Cheap flight deals from Ponce (SJU) to Chicago (CHI)

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This Weekend's Flight Deals from Ponce 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, Jun 20 - Wed, Jun 25
BQN
Rafael Hernandez
ORD
O'Hare Intl.
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jun 20 from Rafael Hernandez to O'Hare Intl., returning Wed, Jun 25, priced at $294 found 1 day ago
Fri, Jun 20 - Thu, Jun 26
SJU
Luis Munoz Marin Intl.
ORD
O'Hare Intl.
$312 Roundtrip, just found
$312
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jun 20 from Luis Munoz Marin Intl. to O'Hare Intl., returning Thu, Jun 26, priced at $312 just found
Sat, Jun 21 - Sun, Jul 20
SJU
Luis Munoz Marin Intl.
MDW
Midway Intl.
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 21 from Luis Munoz Marin Intl. to Midway Intl., returning Sun, Jul 20, priced at $314 found 1 day ago
Sun, Jun 22 - Thu, Jun 26
PSE
Mercedita
MDW
Midway Intl.
$448 Roundtrip, found 4 days ago
$448
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Jun 22 from Mercedita to Midway Intl., returning Thu, Jun 26, priced at $448 found 4 days ago

Airfares from $120 One Way, $221 Round Trip from Ponce to Chicago

Prices starting at $221 for return flights and $120 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.

Fri, Jun 27 - Tue, Jul 8
SJU
San Juan
ORD
Chicago
$221 Roundtrip, found 5 days ago
$221
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Fri, Jun 27 from San Juan to Chicago, returning Tue, Jul 8, priced at $221 found 5 days ago
Thu, Sep 25 - Mon, Sep 29
SJU
San Juan
MDW
Chicago
$240 Roundtrip, found 3 days ago
$240
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Sep 25 from San Juan to Chicago, returning Mon, Sep 29, priced at $240 found 3 days ago
Fri, Aug 15 - Mon, Aug 18
BQN
Aguadilla
ORD
Chicago
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Aug 15 from Aguadilla to Chicago, returning Mon, Aug 18, priced at $268 found 1 day ago
Wed, Jul 9 - Wed, Jul 16
SJU
San Juan
ORD
Chicago
$277 Roundtrip, found 3 days ago
$277
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Jul 9 from San Juan to Chicago, returning Wed, Jul 16, priced at $277 found 3 days ago
Fri, Jun 27 - Sun, Jun 29
SJU
San Juan
ORD
Chicago
$298 Roundtrip, just found
$298
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jun 27 from San Juan to Chicago, returning Sun, Jun 29, priced at $298 just found

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
3.5-star property

Congress Plaza Hotel

8/10 Very Good! (8,858 reviews)

Jul 19 - Jul 26

7 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to San Juan (SJU)

Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
It’s was easy- we were in our rooms within a Few minutes of arriving

Reviewed on Jun 1, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,008 reviews)

Aug 1 - Aug 4

3 night stay

San Juan (SJU) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to San Juan (SJU)

Spirit Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 18 hours ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Embassy Suites by Hilton Chicago Downtown River North
4.0-star property

Embassy Suites by Hilton Chicago Downtown River North

8.4/10 Very Good! (4,196 reviews)

Jul 19 - Jul 26

7 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to San Juan (SJU)

Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Excellent stay. Room was clean and well-designed for our family. Fantastic complimentary breakfast every morning.

Reviewed on Jun 13, 2025

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Chicago first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,008 reviews)

Jul 25 - Jul 28

3 night stay

San Juan (SJU) to Chicago (ORD)

United • Roundtrip • FirstClass
per person
found 22 hours ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,609 reviews)

Jul 25 - Jul 28

3 night stay

San Juan (SJU) to Chicago (ORD)

United • Roundtrip • FirstClass
per person
found 22 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Nobu Hotel Chicago
5.0-star property

Nobu Hotel Chicago

9.4/10 Exceptional! (678 reviews)

Jul 25 - Jul 28

3 night stay

San Juan (SJU) to Chicago (ORD)

United • Roundtrip • FirstClass
per person
found 22 hours ago
Best hotel I ever been in

Reviewed on Jul 16, 2024

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More About Flying To Chicago from Ponce

Route Information for Flights from Ponce 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
3:06PM UTC
Latest Flight Arrival
12:15AM UTC

Ponce to Chicago

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Frequently asked questions

Are there non-stop flights from Ponce to Chicago?
United Airlines and American Airlines offer nonstop flights from SJU to Chicago, IL (ORD-O’Hare Intl.), which means you won’t need to stress about switching planes or being bored during a layover.
What is the shortest flight from Ponce to Chicago?
The fastest flight from SJU to ORD is 5 hours and 29 minutes. Pack a few things in your carry-on to keep you amused, like a gripping book or your travel journal.
What airlines fly from Ponce to Chicago most frequently?
The carriers that fly frequently between Luis Munoz Marin Intl. Airport (SJU) and O’Hare Intl. Airport (ORD) include United Airlines (UA). This popular option offers 30 flights on the route every month. American Airlines (AA) also services the route from Ponce to Chicago. It’s another reliable choice and offers 26 flights every 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.