Image Credits: Larry Johnson, Creative Commons 2.0
Published October 20, 2025 by

Cheap Flights: New York to San Diego, San Jose CA, Colorado Springs, Salt Lake City, New Orleans, Houston, Denver, or Chicago $98-$198 r/t [December-February] (No Christmas) – Southwest

[10/19/2025 @ 09:55 PM CT] Deal time-stamp.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

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Or book with these sites: Priceline, Skyscanner, Expedia, Travelocity, Tripadvisor, Orbitz, CheapTickets, Kayak.

Southwest has round-trip flights from New York (LGA) to San Diego, San Jose CA, Colorado Springs, Salt Lake City, New Orleans, Houston, Denver, or Chicago for $98-$198 with a connection. Flights December to February. No Christmas dates available.

  • Chicago, Denver, Houston, and New Orleans fares are NONSTOP, other destinations have a connection.

Use a card like the Southwest Rapid Rewards® Plus Credit Card to earn points towards a Companion Pass®. Companion Pass is the benefit that allows you to choose one person to fly with you, free of airline charges* every time you purchase or redeem points for a flight. *Companion Pass doesn’t cover taxes and fees.

It is common to find Southwest gift-cards for sale at a discount of about -$70 to -$20 off the redeemable value at Costco and Sam’s Club. Before you finalize your booking you should check to see if you can save more money by using a gift card.

You can usually save more money by booking your flight+hotel together as a package instead of separately.

We post new flight deals often! You can check out our other deals by returning to the Front Page of our website: escape.flights (linked).

Here are some other offers that we think are worth mentioning. List updated 04/21/2026.

We now track coupon codes, discount codes, gift card discounts, and credit card offers that have a better value than their historical averages.

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Use the example date links on our website to pull up the fare.

San Diego fares: [2025-10-24 10:46:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

San Jose, California fares: [2025-10-22 09:25:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Colorado Springs fares: [2025-10-24 12:04:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Salt Lake City fares: [2025-10-24 06:33:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

New Orleans fares: [2025-10-25 10:16:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Houston fares: [2025-11-21 11:54:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Denver fares: [2025-10-24 07:33:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Chicago fares: [2025-11-21 07:27:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

When you are ready to book your flight or hotel, please use the links on our site to begin your booking process so we receive credit for the referral.

  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on Expedia, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.


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  • [Budget Travel] – list all the posts that deal with Budget Travel (filter out all the flight deal posts)

Ren P. Artemio

Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

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