Last updated on January 11th, 2019 at 10:31 pm

GUYS! I have travel plans!

I was pretty sure that I wouldn’t be traveling for a while after my trip to Belize, but then Luke and I decided we wanted to take a week to visit Seattle.

After booking my flight to Seattle, I was preparing this post when a friend asked if I wanted to go to Chicago for a weekend. You can guess I said yes!

Of course, it is the off-season for both cities. The best time to visit Seattle is between September and October. Temperatures usually range between 40 and 50 degrees in November and Chicago is about the same. So I will be packing lots of sweaters, hats, and scarves and preparing myself for some very cold weekends.

Both cities seem to have a lot to offer so I plan to make the most of the time I have. I will have a measly two days in Chicago the first weekend of November.  Then, just two weeks later, Luke and I have a two and a half days to see everything we need to see in Seattle.

Check out my plans below!

Chicago:

1. Getting up early to take a picture of the Cloud Gate (or the Bean, as I prefer) in Millennium Park. I’ve heard this is the only way to get a picture without a ton of tourists.
2. Feel my knees shake at the Sky Deck of Willis Tower, of course.
3. Visit 360 Chicago, which provides a different view (I must decide for myself which one is better), or the Signature Room. Both are in the John Hancock Tower.
4. Stuff my face with some deep dish pizza, Chicago dogs, and donuts!
5. Walk along the Navy Pier.
6. A speakeasy, possibly The Drifter, which was an actual speakeasy during Prohibition!
7. Check out the street art in Logan Square.
8. Spend some time at the Art Institute of Chicago, The Shedd Aquarium, or the Lincoln Park Zoo.
9. Stroll along the Magnificent Mile.

There is probably not time for all of these activities, but I am going to squeeze in as many as I can!

Planning a trip to Chicago? Check out my itinerary here.

Seattle:

1. Get a picture of the gorgeous view at Kerry Park. 
2. Check out the Chihuly Garden and Glass. I’ve seen the Chihuly exhibit in the Bellagio in Las Vegas and it was beautiful!
3. The Fremont Troll… because that seems necessary. Also Fremont in general sounds awesome.
4.  Breweries! Being from Colorado means I love my breweries and I’ve got to see if Seattle is just as good!
5. Coffee. Not sure where yet, but I will probably drink as much as possible.
6. Hiking (hopefully). It will be cold and possibly snowy, but it seems like there are some trails that are winter friendly in the Cougar Mountain and Squak Mountain area.
7. Piroshky Prioshky – this is a bakery that offers Piroshkies (an Eastern European pie type thing) of the savory and sweet variety. Sounds great to me!
8. Pike Place Market, of course. I’m especially excited to see the Fish Market. 
9. A speakeasy – I’m thinking Needle & Thread or Smith Tower Temperance Café and Bar.
10. Beecher’s Handmade Cheese. Anything with cheese in the title and I’m there.
11. If possible, whale watching. I would love to see some Orca’s, having been mildly obsessed with Free Willy as a child. However, I hear that November is not peak time for Orca viewing.

So that is the list of stuff I really want to do in Seattle, but knowing me, my plans will completely change!

What did you do in Chicago or Seattle? What do I need to add to my lists?

Check out my guide to a weekend in Seattle fit for any foodie!

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