There are plenty of reasons to visit the wonderful city of Chicago, but deciding what to do can sometimes be a bit overwhelming. There are so many interesting museums, delicious restaurants and fun activities, so let me help narrow down your Chicago weekend to-do list.
Since I have family that lives in the city, I have had several opportunities to figure out what I absolutely must do every time I am in town. Keep in mind when I visit I stay in the River West area so many of the places I choose to go to are on the west side of town, but I will also list other options to choose from. So this is what my ideal weekend visit to Chicago would consist of:
When I arrive to the city I head straight to Goose Island Brewery for some amazing beers and fish tacos. My favorite beers are their nut brown ale’s, but 312 is always a classic choice. Remember to ask for an MBA book, so you can keep track of all the beers you try. I keep mine in my wallet, so whenever I make a visit to the brewery I can add to it. Hopefully one of these days I’ll fill it up and get my name on the wall and some free goodies!
My favorite breakfast spot is The Bongo Room located in Bucktown, which is my favorite neighborhood. The Bongo Room offers several over the top styled pancakes and french toast, as well as gourmet omelets. It’s a great spot to go with a friend, so you can share something sweet and something savory. There is always a long wait, so I will immediately add my name to the list and then walk a few doors down to The Wormhole Coffee shop. I’ll order a coffee and spend my time waiting playing video games on the old Nintendo gaming systems.
Since I’m usually pretty darn stuffed after the Bongo Room, the architectural boat tour is a great activity to do. Enjoy the fresh air while cruising down the river and learning about the history or the city. I think Chicago has some of the most beautiful buildings and they all have fascinating stories.
After the boat tour, I’m usually ready to work off the massive meal I recently consumed, so I’ll make my way south toward Millennium Park to stand under the Cloud Gate (better known as The Bean), and watch the LED faces spit water at Crown Fountain. But in case I do work up an appetite, for lunch I’ll grab a bag of popcorn at Garrett Popcorn Shop on my way to the park. Garrett’s popcorn is the best afternoon treat!
Before dinner I will go to The Violet Hour for a drink or two. Trust me, you won’t need more than a couple. You cannot make reservations, so I suggest arriving at 6pm when they open and the line isn’t too long because later in the evening it can sometimes take a couple of hours to get inside. I absolutely love this bar, because it serves artisanal cocktails based on pre-prohibition style libations. There is no sign, but you’ll know if you’re in the right spot if there is a short line leading to a facade with a lantern hanging above a non-distinct door.
For dinner travel south to the West Loop to Grange Hall Burger Bar, which feels like you’re dining inside a rustic farmhouse and everything is made with local fresh ingredients. Make sure to save room for the homemade pie and ice cream of the month. If you want to go really wild, try a spiked milkshake!
Although the main dishes at Ann Sather’s are simple fare, the swedish diner’s cinnamon rolls alone are enough to bring me back again and again. And not only will you get the chance to get a single roll with your main dish, but you can get two. With every meal you get to choose two side dishes.
After breakfast my last stop before leaving town is the Museum of Science and Industry. This museum is incredibly interactive and delivers a hands-on experience. Check out the Science Storms exhibit and U-505 Submarine, the only German U-boat in the United States.
There is just so much to do and see in Chicago, so here are some more ideas in case you want to swap out some of the restaurants and activities I chose for the suggested itinerary above.
If you are interested in spending your time shopping then head to the Magnificent Mile for high-end name brand fashion. The Gold Coast is where all the high-end boutiques are located, but if you are looking for more affordable unique boutiques make your way to Bucktown.