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How to Spend a Weekend in Chicago

  • Writer: Brian Klein
    Brian Klein
  • Jul 13, 2017
  • 5 min read

With over 78,000 steps taken over the course of a two and a half day visit, you can say that we definitely were able to see Chicago. After living in the city for 10 years, it was great to get to go back and explore a city that we know and love. For this particular visit, my wife and I were celebrating our anniversary. The great thing about Chicago is how it changes with the seasons…and there is now better time to visit than the summer when sidewalks transform into cafes and people are actually a bit more friendly and not hunkered down below 6 layers of clothes.

TO STAY

For this particular visit, the newly transformed Hotel Alise was our home base. Sitting at the corner of State and Washington, this hotel is at the center of it all. You are minutes from Millennium Park, across the street from Marshall Fields, excuse me – Macys, provides easy access to the Willis Tower, Michigan Avenue, the museums and the L (Chicago’s subway). This hotel has a 100 year + history and melds a grand history within its walls with contemporary design and amenities today’s travelers demand. What we loved most were the brass room keys, the mahogany doors, spectacular ironwork scattered along the stairs, the guestroom floors and elevators and a sense of design that I wish my house adorned.

The service was attentive and on point, and due to the recent change in ownership – the new group had quite a few amenities that definitely helped bring smiles to its guest including afternoon coffee + cupcakes, pineapple infused water, crazy dog treats and yellow bicycles.

Atwood Café is the hotels only restaurant, but the few times I have been there it has always been delicious. Their salads are large and refreshing, their burgers are to die for, but don’t order their Tater tot Chili while sitting on the patio during the summer. It was delicious, but just not the right time to enjoy. It would have been much better to have after a night of drinking. But all in all, this was a great hotel and very reasonably priced.

TO DO

As mentioned above, we walked over 78,000 steps over the course of our 2.5 day visit. Getting out and exploring is truly the best thing about Chicago. Despite what you hear, this is a fairly safe city…as long as you stay in the right part of town. Nonetheless, our ventures took us up and down Michigan Avenue several times where we were able to get our shopping fix in. After we had enough we made it up through the Gold Coast where we encountered a number of farmers markets and street festivals…which are two things we always loved about being in the city. As we continued our walk North, we also stoped by the Lincoln Park Zoo and Lincoln Park Conservatory for a

quick visit. Both of these world class attractions are free to visit. The Conservatory features four display houses showcasing their collection of Palms, Orchids, Ferns and exotic plants. The zoo situated in the heart of Lincoln Park covers over 35 acres and was founded in 1868 making it one of the oldest zoos in North America. They feature over 1,100 animals including a magnificent collection of gorillas and apes. Another couple of miles up Clark we finally got to Wrigley Field. Even though we lived less than a 1,000 yards from Wrigley when we lived here and have been to countless Cubs games, this is still a great place to visit. And over the past 2 years they have done some extensive renovations adding some new signage (which unfortunately kills the rooftop views) building out corporate offices, adding great outdoor space and repairing some of the building that has deteriorated over the years. Nonetheless, this place was hopping and full of energy as the crowd shuffled in. And Wrigley is still one of the best game day experiences in the world. And if we hadn’t already jam packed enough into this trip, we also paid a quick visit to Navy Pier (Chicago’s #1 attraction) to check out the new Ferris Wheel and take a quick walk around the place to see if anything exciting was going on. The place was packed and had been completely revitalized with a whole slue of new restaurants and bars which had replaced the gimmicky tourist traps of the past. This is actually a great place to hang out and have a beer in one of their beer gardens which showcases live music during the summer.

Our last day in town, we made our way down to the Field Museum (one of the few buildings left over from the Columbian Exposition of 1893) and did a quick lap through the museum. While individual tickets are expensive ($37 yikes) if you have a science museum pass from another city, they provide reciprocity here. Our favorites here were always visiting the Egypt exhibit which includes extensive mummies and antiquities from ancient Egypt, seeing Sue – the most complete T-Rex skeleton in the world, and trying to always walk away from a visit learning something new. For this particular trip we learned two things 1) about the Lions of Tsavo who were two lions that killed over 35 men who were constructing a railroad in Africa back in the late 1800s. And 2) that one of the first items featured in the museum (and located in the great hall) were the two elephants that were caught in Africa and brought back to Chicago by Carl Akeley so he could perform taxidermy (the first time ever) and share this magnificent with the people who visited the museum.

TO EAT AND DRINK

While you typically come to Chicago to participate in the gastro experience and partake in a $250 tasting

menu….we were a bit more low key with this visit looking for a more exciting patio scenes and beer lists. And I have to say, that besides one reservation we had made months ago at Rick Bayless’s Frontera Grill, almost all of our experiences were first time discoveries.

Oak Street Beach – a hidden gem located on the iconic Oak Street Beach, this is a great beachside bar that serves up great food, great drinks in a lakefront, beachfront setting. This is a great place to hang with friends and enjoy the beach.

Roscoes – When we lived in Boystown years ago, Roscoes was always one of our favorite hang-outs due to its great patio and people watching. Fast forward 15 years and the drinks are still delicious, the patio is still great and the people watching is still more fun than ever.

Vapaino Pizza – an interesting self service pizza, pasta, salad concept that we stumbled upon at 11 at night when we were looking for a place to eat after the theatre.

Frontera Grill - The most famous Mexican restaurant in Chicago – owned by celebrity chef Rick Bayless), this place definitely didn’t disappoint. The foot was high end Mexican, yet simple at the same time. All ingredients are sourced locally with the exception of the corn used in the tortillas which still is imported regularly from Oaxaca

Cindy’s – Cindy’s is one of the hottest rooftop bars in the city right now (as it should be) with gorgeous views of Millenium Park and the lake. While they had a food menu, people come here for the views and their extensive spirit menu and cleverly concocted cocktails.

What got me mostly excited about the food scene in Chicago was the beer revolution. When we last lived here, Goose Island was about all we really had. We only drank one beer two times and definitely got to try a lot…and they were all incredible.

  • Revolution Brewery Anti-Hero IPA

  • Half Acre Daisy Cutter Pale Ale

  • Solemn Oath Farmhouse Ale

  • Revolution Brewery Rev Pils

  • Two Brothers – Domaine DuPage French Style Country Ale

 
 
 

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