If you’re just checking in be sure to read my first recap of the Chicago weekend here.
Alright, so when we last left off it was Saturday afternoon, we had just finished 3 deep dish pizza’s and a bunch of Goose Island beer, and had taken an afternoon rest to get ready for the evening ahead.
First on our list for Saturday night was the architecture tour. There are plenty of options for tours and they run most every hour throughout the day. We chose the 6pm tour with Chicago Line Cruises which costs $42 per person (buy online in advanced) and you can add the open bar option for an extra $20. I opted out of the open bar to ensure that I’d be on my best foot for the rest of the evening, but Emily and Lindsay went for it and both agreed that it was definitely worth the money.
I mean look at their happy faces:
This tour mostly focused on getting the boat out on the lake to enjoy the sunset over the city. It was a beautiful night and we had a great time cruising out on the lake. However, I will say that the other tours give much more in depth information on the architecture in the city. I would suggest this tour if you want a sunset booze cruise.
After the cruise we grabbed dinner at Howell’s & Hood. It was a very nice place with plenty of seating and could easily work for a special night out or something more casual. We each had a salad and shared a pitcher of margaritas (not the greatest unless you prefer lots of sour mix).
Then it was time for the Zebra Lounge! Friday night, one of our Uber drivers suggested the Zebra Lounge telling us it was a little-known spot with great live music. Well it was easy to see why people would not know about this place as you could walk by it without a blink! It’s main entrance is off of an apartment entrance so it’s a bit odd to get to. Once inside, we were greeted with a piano player singing and playing the crowd favorites. We immediately grabbed the 3 seats next to the piano and enjoyed the best seats in the house.
Long story short…we ended up meeting a couple and their tag along best friend. They seemed very nice and were giving us tips on where to go and what to do in Chicago. They were headed to an 80’s bar and asked us to tag along so we figured why not, right? The 80’s bar was awesome and we had a great time dancing to classic hits. The people we had met were not awesome and we soon ditched them.
Our night ended with a late night stop at the popular White Palace Grill, a small diner that satisfies the late-night cravings of Chicago. The place was PACKED and with a line nearly out the door we figured ordering to go would be our best option. Of course we later realized that the line moves very quickly so next time it’ll be worth it to wait. I’d rather not admit to the delicious deep-fried everything we ate so let’s just pretend we ordered 3 kale salads because, let’s be real, at 2am everyone is obviously eating kale.
And then it was Sunday. Can you believe we did all that in just a matter of one and a half days??
Sunday was the day to get our authentic Chicago wiener, see the bean, get enough Garrett’s popcorn to give us cavities on the spot, and of course have a classy wine and cheese appetizer on the Chicago riverwalk.
We started at Portillo’s for a classic Chicago hot dog which was AMAZING. Seriously all that fresh produce on a hot dog is just plain smart! No ketchup required or allowed.
Then we headed to the riverwalk to keep things classy with a bottle of Brut Rose and a cheese plate. Lindsay has been dying to try City Winery’s Rose but they have been out every time she goes!
Thankfully the lack of rose and burrata didn't dampen our afternoon.
We headed over to get a classic picture with the big shiny bean and made a pit stop at Garrett's popcorn which came in handy on the plane ride home. Note to self- United doesn't offer free snacks on flights shorter than 3 hours anymore! I'm talking not even a single pretzel!
Chicago once again did not disappoint (this was my 3rd visit). I highly suggest taking a quick weekend trip as it's not that far from most of the US based on its central location. If you go my must do's for you include the following:
1. Deep dish pizza
2. Chicago hot dog (check out the Wiener Circle for dinner and "show")
3. Hancock Tower lounge for drinks
4. Second City Comedy Club
5. Architecture tour
Questions of the day:
What's your favorite Chicago activity?
Do you how Chicago got it's nickname "The Windy City"?
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