48 Hours in Chicago

Let me just start off by mentioning that, if you’re a foodie, Chicago is the place to check out! We were only there for two days, so we only got to try a few places but, oh my geez, they were all good!

We took this trip to celebrate my other half’s 30th because he’s big into music and blues – and what better place to visit? (I mean, we’re from Memphis *ahem*, so I feel like we know good blues 😉 )

We got there around noon on a Friday and checked into our AirBnB (I highly recommend it in a place like Chicago), which was the cutest little basement apartment in Wicker Park: a quaint little neighborhood with some great shops and restaurants within walking distance.

Then we were faced with a hard decision…I mean, very hard….

Where did we want to get our deep-dish Chicago-style pizza? I’d heard great things about quite a few places, but Lou Malneti’s and Giordano’s were continuously mentioned. We went with Giordano’s because of how close it is to Millenium Park, and it certainly did not disappoint! Talk about cheesy melt-y goodness… (Side Note: Don’t be “hangry” when you get to Giordano’s…the good stuff takes about 45 minutes to bake, but it’s SO WORTH IT!)

Giordano's Pizza
Every pizza is a personal pizza, if you believe in yourself. (Thankfully, we did not…we barely made it through half this thing!)

We were on to Millenium Park after that to see the Cloud Gate (“The Bean”) and, honestly, to start walking off our rapidly-approaching food coma after Giordano’s. As you’d expect, there were selfies being taken right and left around The Bean, so go ahead and join in: no judgment here!

Later that night, we headed out for a drink at Buddy Guy’s Legends and then were on to Rosa’s Lounge. If you’re into some good local blues, definitely check out Rosa’s. It was voted local’s favorite last year and the tickets are pretty reasonable. It’s a cozy place near Logan Square, an area a bit outside of the hustle and bustle (it’s definitely a cab or Uber drive). The night we were there, Corey Dennison Band was playing and the house was packed. It.was.amazing…I’d never seen someone playing blues with as much energy and gumption as Corey had.

Rosa's Lounge
This teeny little gem is worth checking out!

On Saturday, our only full day in the city, we checked out Yolk for breakfast. I think this was the food highlight of the trip for both of us. Four words: Cinnamon.Roll.French.Toast… Seriously, GO THERE. It may not be what a foodie deems “local eating” since it’s a small chain, but it was one of my top favorite breakfasts of all time. That French toast was decadent.

Yolk's Cinnamon Roll Stuffed French Toast
Cinnamon Roll Stuffed French Toast with scrambled eggs, bacon and sausage links…need I say more?
Challah French Toast with Cinnamon Apples & Pecans
Yolk’s Challah French Toast with Cinnamon Apples and Pecans. These were pretty tasty, but the Cinnamon Roll Stuffed French Toast takes the cake.
Benedict Caprese & Fresh Fruit
Yolk’s Benedict Caprese with potatoes and fresh fruit

After breakfast, we walked the city, and stumbled upon a Cards Against Humanity exhibit in the Historic Water Tower. Our curiosity got the better of us…a gorgeous historic building with an exhibit about a hilarious, yet profane, card game? To no surprise, the exhibit posters and signs were sarcastic and witty, just like the game. Turns out, the creators are from Chicago, and we learned quite a bit about the success behind what started as a small in-home startup among friends. (My inner nerd kicked in at this point on the trip.)

Cards Against Humanity Exhibit at the Historic Water Tower
Who would’ve thought?
Cards Against Humanity Vending Machine
They really thought of everything…

We continued walking the city (we walked about 9 miles on this day, alone!) and tried to catch the view from the top of Sears Tower, but had no luck due to the wait time.

For dinner, we were the ultimate tourists and got a hot dog from Portillo’s: mainly because of its proximity to a piano lounge we were headed afterward. In my opinion, Portillo’s should be saved for a second or third trip to Chicago: the hot dogs were good, but didn’t live up to the hype everyone had given them.

We spent the rest of Saturday night listening to some great music at the Redhead Piano Bar and then at Chicago Blues: both of which I would highly recommend. Redhead Piano Bar has a certain upscale feel that you don’t quite see very often, excellent piano talent, a great cocktail list and friendly bartenders. What more could you want? Chicago Blues’ ambiance was a bit more casual, with people more anxious to get a good seat to see the blues band than carry on conversation at the bar.


We ended the night with a show at The Second City: a renowned comedy club with a pretty awesome alumni list (Dan Akroyd, Steve Carell, Tina Fey, Bill Murray, Mike Myers, Amy Poehler…to name a few). The sketches were quick-witted, and delivered hilarious Improv mixed with SNL-style scenes. The tickets were lower than expected, especially for the close seats. Needless to say, we had a great time: this was the highlight of our Chicago weekend! And the idea that the cast members we saw that night have a strong likelihood of becoming famous made it even more of a great experience.

Sunday, our last half day in the city, we spent roaming Wicker Park: the neighborhood where our AirBnB was located. We stumbled upon The Bongo Room, off N. Milwaukee Avenue, for an excellent brunch. With it being Sunday, and…ya’ know…everyone and their mother decides to brunch on Sunday, there was a bit of a wait for a table. But, if we had to wait, we were in the right area for it: we killed time in cute little clothing and vintage home accessory boutiques right around the restaurant. Which, by the way, PLEASE try their Brunch menu: it’s small but mighty.

Bongo Room's Deconstructed Lobster Roll Benedict
Bongo Room’s Deconstructed Lobster Roll Benedict served with cheese potatoes
Bongo Room's BLT Benedict
Bongo Room’s BLT Benedict served with cheese potatoes (with an Orange Mango Mimosa at close-hand…yum!)

It was nice to check out more of the “local scene”. Of course, me being the shopper I am (and BONUS POINTS for cute vintage stores!), I was in heaven. But, we were running short on time, and one last spot had yet to be checked off our Chicago To-Do list: The Chicago Music Exchange. My guy is a huge music buff and had made this his “can’t miss” item on our list. Even for the least musically-talented person around (…that would be me….), it was quite impressive.

I’d say ending the weekend at Chicago Music Exchange was perfect for the birthday boy: he was in heaven!

If I had it my way, my weekend trips would revolve mainly around shopping, walking the city, and eating, so it was nice to break it up with some great live music and comedy throughout the weekend. Our 48 hours were jam-packed, but we were able to see and do quite a bit on our list. What are your favorite Chicago spots?



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