An inexpensive weekend getaway to Chicago to walk along Lake Michigan, take in the skyscrapers on the Chicago River, see the polar bear playing and drink the coffee treats. Plus Chicago offers so many parks!
Chicago, Illinois Highlights for Sunday, October 8:
- Millennium Park and the Bean
- Walk along Lakeshore path
- Navy Pier
- Lincoln Park Zoo – the polar bear
- Dropshot Coffee & Snack Bar
Let’s start off by stating two important facts: 1) We slept in a Wal-mart parking lot and 2) we managed to get 61,204 steps by the day’s end. We arrived the morning of the Chicago marathon, so not surprisingly, many streets were blocked off and my initial parking plan was not going to work. We were SUPER lucky and stumbled upon free parking on Lincoln Avenue not too far from Lincoln Park.
We walked a few miles before arriving at Grant Park, which was closed for the marathon, so we started down Michigan Avenue and I bought a unique pour over coffee at Fairgrounds Coffee. As a bonus, this place had a nice bathroom. We wandered across the street to Millennium Park and the Bean. Walking around and through the Bean, posing for selfies was fun as you can get some awesome reflection pictures with the skyscrapers in the backdrop. We made our way from here to Maggie Daley Park where we saw the rock climbing walls and then to Lake Michigan along the Lakeshore path.
Renting bikes probably would have been a great idea, but we chose to walk the path up to and around Navy Pier before continuing to the Lincoln Park Zoo.
The zoo is incredible and it’s free! The zoo was beautifully decorated for the fall season and the animals were lively in the warm weather. The polar bear playing in the water with its toys was an absolute highlight. Check out my video on Instagram. The macaque monkeys were also very playful to watch and there were babies! Baby animals of any kind are always top notch in my book!
Another notable animal included the pygmy hippo, which you can see a video of its snack time on my Instagram as well. There were other large animals like double-humped camels, rhinos and big cats. I was bummed not to see the red panda, which is my favorite animal, but this just means I will have to return to this zoo in the future. We exited on the west side of the zoo, regrouped for a bit and then made our walk up Michigan Avenue.
I was craving a second coffee treat of the day, and read good reviews about Dropshot Coffee & Snack Bar. The decorations were incredible – it’s a sports themed coffee shop! There’s everything from bleachers to a scoreboard on the wall and the prices were reasonable. Don’t leave without checking out the lower level which looks like a pool and has lots of games, plus clean bathrooms.
Michigan Avenue was fun to walk along, full of people, especially marathon runners sporting their completion medals. It was pretty exciting to learn that an American won the men’s marathon earlier in the day. One thing to note about Michigan Avenue is the stores close around 7 pm on Sunday nights.
Chicago, Illinois Highlights for Monday, October 9:
- Buckingham Fountain in Grant Park
- View from the BP Bridge between Maggie Daley and Millennium Parks
- French Market
- View of the city from Adler Planetarium
- Wicker Park (The Wormhole Coffee)
We got lucky again and found an amazing, free parking spot near the location of the Maxwell Street Market (which I don’t recommend). We walked a little under a mile to Grant Park and found the most magnificent fountain, Buckingham Fountain. The park was pretty desolate with remnants of the marathon from the day before. We walked through the park and smelled some beautiful roses before coming to the BP Bridge between Maggie Daley and Millennium Park. The BP Bridge is about 925 feet long and is a great viewing point for the city’s skyscrapers.
We took a few more Bean (aka Cloud Gate) pictures and then started our walk along the Chicago River from the Michigan Avenue entrance.
The skyscraper reflections, public art and river pathway make this a great stroll. We loved stumbling across the oversized deer statue.
After the river, we headed to the French Market which is inside the train station. It’s about 30 booths with delicacies like macaroons. Whether you plan to eat or not, it’s a neat place to check out. From here we took a rather lengthy walk along Michigan Avenue, past Millennium and Grant Parks to the museum area by Shedd Aquarium (highly recommend) and the Adler Planetarium. I cannot recommend this view of the city skyline enough! You can see Navy Pier in the distance and get a full view of the city skyline to include the Willis Tower. Lots of people were picnicking in this area.
We walked back to our car and drove about four miles to Wicker Park. The first time we had to pay for parking, but fortunately it was only $2 per hour and we were there less than two hours.

We went into The Wormhole Coffee, which is a nostalgic coffee bar filled with Gremlins, Bowser in his castle, Ninja Turtles and E.T. stuff among lots of other things. It’s pretty expensive, but unique. I loved the “Cool But Rude” latte that I got made with fresh ginger and curry sauce. We wandered through the park and on our way back to Milwaukee Ave., I spotted Andre Royo, the man who played Bubbles in the television show The Wire and Thirsty in the show Empire.

He was extremely down to Earth, chatted with us for a few minutes, and took an awesome selfie! Keep your eyes peeled for the street art around Wicker Park that shouldn’t be missed!
Since we still had about two hours of vacation before returning our rental car, we drove to the Magic Hedge Bird Sanctuary. There’s nothing too noteworthy here, except for another nice place to view the city skyline and it connects in with the Lakeshore path. Then right outside the airport, we parked at Robinson Woods South. It’s a park where we spotted over 9 deer grazing close to dusk. It’s also a good place to view planes that have just taken off from the Chicago O’Hare airport. Our car rental return and ride home on Spirit Airlines were uneventful, which is the way we like it.
Chicago is a world class city and we will definitely be back. What did we miss and should plan to do next time?