At the beginning of the year, around the time people are making New Year’s resolutions, my husband and I decided 2019 was the year of travel. We got so excited we picked two random cities notorious for good eating, lined up a sitter for the kids, booked our flights and headed out in under 30 days. Our destinations: Chicago and New Orleans.
How to Do Chicago in Two Days
Some may think it was completely crazy and it probably was. We traveled from Tampa to Chicago (in the winter) for two days before heading on to NOLA for another 2.5 days and back home.
Where to Stay
Location was key for us. While Ubering is easy, we wanted to stay in a prime location and avoid the additional expense. The Kimpton Hotel Palomar is a gorgeous boutique hotel located in the River North area. The hotel’s location granted us prime access to the best eats, easy access to tourist attractions like Millennium Park where the Bean is situated, Willis Tower, preciously known as the Sears Tower and stands tall at 1,450 ft in the air, the Art Institute and so much more. Read our full review of the hotel.
Where to Eat
Sable Kitchen & Bar
505 N, State St., Chicago, IL
We dined at Sable Kitchen & Bar, Kimpton’s Contemporary American restaurant, for dinner one evening. The restaurant was clearly the preferred choice for evening cocktails, smalls plates and date nights for couples and I found out why.
The staff is friendly, meals come out quick and the drinks were flowing. While Sable is known for their small plates, we opted for a little more and ordered the Salmon and Niman Ranch 14 oz NY Strip. Both extremely tender, full of bold flavors and absolutely melted in your mouth.
Just when we didn’t think we could eat anymore, Sable’s executive Chef Amber Lancaster surprised us by sending out the most decadent of desserts, the Caramel Budino. Holy smokes this dessert! The layers of chocolate crumbs and thick caramel sauce had my husband practically licking the cup afterwards. It’s safe to say we enjoyed every bit of Sable.
155 W. Van Buren St., Chicago, IL.
Taureaux Tavern is a French inspired bar and restaurant located in Chicago’s Loop. The crowd was mostly business people on a Thursday afternoon for lunch, but I can easily see this location as being a good happy hour spot for drinks or date night. We started with the Lobster Thermidor Bites. Hands down, best appetizer ever. Tender baby lobster and spinach in a light sherry wine sauce and served with crackers. For our entrees, we ordered the Le Patty Melt Royale and Mussels & Frites. Both had really great flavor. My husband enjoyed his 8 oz burger melt and I sucked up every last drop of juice at the bottom of my bowl of mussels.
We sampled a few of their desserts (shown below) and the flourless chocolate cake was my favorite! If nothing else, head to Taureaux Tavern if you have a sweet tooth.
130 E. Randolph St., Chicago, IL.
Considering we booked this trip based on food, Chicago Deep Dish was an absolute must. We were told to head to Giordano’s for the best deep dish pizza and they brought their A game. We ordered a small pizza and mozzarella triangles for an appetizer.
I polled my Instagram Story viewers asking if getting an appetizer with deep dish pizza was a rookie mistake or genius. I’m here to say it was 100% a rookie mistake LOL. I underestimated the amount of cheese and carb loading that came with this Chicago classic. We headed straight for a food coma afterwards, but it was totally worth it.
Portillo’s Hot Dogs
100 W. Ontario St., Chicago, IL.
We had the deep dish pizza and of course needed to try the city’s 2nd famous food, the Chicago hot dog. If you’re not familiar, the Chicago-style Hot Dog has an all-beef dog on a poppy seed bun with onion, sweet relish, mustard, tomato slices, pickled sport peppers and a pickle. I love a good hot dog, but considering I’m a basic mustard girl I was concerned about all the toppings. There was no need to worry. This is one great hot dog. (It was recommend after we left to try the Italian Beef.)
What to Do
If you need a break from all of the food Chicago has to offer, there is plenty to do in the city from shopping to exploring and taking in the breathtaking views 1,450 feet in the air.
The Art Institute of Chicago
111 S. Michigan Ave., Chicago, IL.
201 E. Randolph St., Chicago, IL.
We ordered tickets for both the Skydeck Chicago and 360 Chicago on Groupon. (You can save on ticket prices and get cash back using Ebates.) If you have a fear of heights, these may not be for you. I will say that 360 Chicago went better for me and my husband. I did Tilt! which tilts you out over 1,000 feet above The Magnificent Mile. You get a great view of the city!
Skydeck Chicago is located on the 103rd floor of the old Sears Tower. It’s essentially a 4.3 ft glass box at 1,353 ft above the city. This was hard for me and I’m not afraid of heights. (My husband went nowhere near the box.) There’s a great view, and while super safe and sturdy, my legs were shaking as I attempted to inch my way to the far side of the glass. But then there are people jumping in the air and laying down getting great shots. Anything for the ‘gram, I suppose.
233 S. Wacker Dr., Chicago, IL.
875 N. Michigan Ave., 94th Fl., Chicago, IL.
Special thanks to Sable Kitchen & Bar and Taureaux Tavern for graciously hosting us. All thoughts and opinions are our own.