$69 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, Jun 8 - Tue, Jun 11
SJU
Luis Munoz Marin Intl.
MDW
Midway Intl.
$238 Roundtrip, found 3 days ago
$238
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jun 8 from Luis Munoz Marin Intl. to Midway Intl., returning Tue, Jun 11, priced at $238 found 3 days ago
Sun, Jun 9 - Sun, Jun 16
SJU
Luis Munoz Marin Intl.
ORD
O'Hare Intl.
$309 Roundtrip, found 11 hours ago
$309
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Sun, Jun 9 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Jun 16, priced at $309 found 11 hours ago

Airfares from $69 One Way, $127 Round Trip from San Juan to Chicago

Prices starting at $127 for return flights and $69 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, Aug 28 - Tue, Sep 10
SJU
San Juan
ORD
Chicago
$127 Roundtrip, found 16 hours ago
$127
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Aug 28 from San Juan to Chicago, returning Tue, Sep 10, priced at $127 found 16 hours ago
Wed, Aug 28 - Tue, Sep 10
SJU
San Juan
ORD
Chicago
$137 Roundtrip, found 16 hours ago
$137
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Aug 28 from San Juan to Chicago, returning Tue, Sep 10, priced at $137 found 16 hours ago
Tue, Sep 10 - Sat, Sep 14
SJU
San Juan
ORD
Chicago
$144 Roundtrip, found 11 hours ago
$144
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Tue, Sep 10 from San Juan to Chicago, returning Sat, Sep 14, priced at $144 found 11 hours ago
Wed, Sep 4 - Tue, Sep 10
SJU
San Juan
ORD
Chicago
$147 Roundtrip, found 12 hours ago
$147
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Wed, Sep 4 from San Juan to Chicago, returning Tue, Sep 10, priced at $147 found 12 hours ago
Wed, Aug 28 - Tue, Sep 10
SJU
San Juan
ORD
Chicago
$149 Roundtrip, found 16 hours ago
$149
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Aug 28 from San Juan to Chicago, returning Tue, Sep 10, priced at $149 found 16 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
4.5-star property

JW Marriott Chicago

9.2/10 Wonderful! (1,007 reviews)

Jul 26 - Jul 29

3 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
We had a nice stay. Clean, quiet room.

Reviewed on May 21, 2024

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

8.8/10 Excellent! (208 reviews)

Jul 25 - Jul 31

6 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates

Reviewed on Feb 16, 2024

W Chicago - Lakeshore
4.5-star property

W Chicago - Lakeshore

8.2/10 Very Good! (1,008 reviews)

Jul 7 - Jul 13

6 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
They had a great view , great customer service, very clean and walking distance to navy pier and downtown. Then only negative part was there parking fee.

Reviewed on May 28, 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
2:09PM UTC
Latest Flight Arrival
12:20AM 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.