Published September 24, 2025 by

Nonstop Flights: Chicago to/from San Diego, St. Louis, or Portland Oregon $77-$187 r/t [October-March] – Alaska Airlines / United

[09/23/2025 @ 04:46 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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Alaska Airlines and United have round-trip flights from Chicago (ORD) to San Diego, St. Louis, or Portland Oregon (SAN, STL, PDX) for $77-$187, NONSTOP. Flights October to March. Origin/Destination reversible.

Alaska Airlines allows one carry-on bag and one personal item for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

United’s “Basic Economy” fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.

The personal item size on United is smaller (9 x 10 x 17 inches) than Frontier or Spirit (8 x 13 x 18 inches).

If you use the United℠ Explorer Card, your first standard checked-bag for you and your companion is free, you get priority boarding, two United Club passes per year, and you get a 25% discount on inflight purchases on United-operated flights as a statement credit.

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: [2025-10-01 07:13:00] 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.

St. Louis fares: [2025-10-26 09:58:00] 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.

Portland, Oregon fares: [2025-10-01 08:51:00] 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 to Portland, Oregon - Extended Weekend Dates: (Skyscanner) Jan 17 - Jan 20 / Other dates: There are more dates available than the ones we list here, experiment on your own.

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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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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