@nicholaskthinks: #alaskaairpartner Here’s my 2-day itinerary if you’re planning a weekend trip from San Diego to Chicago! Feel free to mix and match, or leave me your own suggestions! Day 1: Fly non-stop with @Alaska Airlines from San Diego to Chicago O’Hare International Airport! First stop, get a world famous Chicago hotdog. Architecture Cruise of the city. Dinner (I’d recommend trying one of their Michelin recommended restaurants in Chinatown, but that’s up to you). Find a Speakeasy (Chicago is known for their speakeasies and jazz music, so maybe you can do both at once?). Day 2: Breakfast! Museum (Chicago has more than 50 museums, so choose whichever seems most interesting to you). Chicago 360 (this is a super fun observation deck that gives you views of the entire city!) Deep Dish Pizza (if you know, you know). Walk around “the bean” at night. Of course, Chicago has sooo much more to offer, but I think this itinerary hits a lot of the highlights, and can also be changed around to fit your preferences/travel needs. My favorite part about Alaska Airlines offering non-stop routes from San Diego to Chicago is that I know I can always fly back if there’s anything I missed! Feel free to ask me how you can book your next trip with Alaska Airlines, or any other questions you have! #sandiego #chicago #chicagotravel #chicagotrip @Fly2ohare

Nicholas Kusnir (Travel)

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Monday 24 August 2026 17:14:31 GMT