I love a great walking tour, and Chicago is a perfect city for one because there’s so much to see within The Loop. Downtown Chicago is referred to as the Loop, as it’s commonly thought to have been named after the elevated (“L”) rail track that circles downtown. I took advantage of a cheap flight from Boston to enjoy a quick, one day visit to the Chicago Loop. It might seem like a lot of effort for a day, but weekends are made for exploring! I’ve never flown anywhere for just one night, but since my full-time (non-travel) job offers limited time off, I thought a quick trip might be a good opportunity to squeeze in travel without needing to take time off from work.
One of the benefits of exploring a city is the ability to remain active throughout the day by walking. While it might not be an activity that leaves you out of breath or sweating a lot (it might, depending on the weather), the simple act of walking has tremendous health benefits for all age groups. We often associate a good sweat session at the gym with a good workout, but don’t forget that you most likely only spent 30-90 minutes of your day at the gym. The amount of time you move the rest of the day is just as important as the gym session. Moving regularly helps control weight, increase muscle strength and balance and helps prevent heart disease and high blood pressure. In addition to the physical benefits, walking will improve your mood and foster creative thinking. Now that you’re geared up for your walk around Chicago, let’s dive into where you should go to experience Chicago’s culture, history and unique architecture!
Table of Contents
The Art Institute of Chicago
This museum is most definitely wo
rth a few hours of your time. The building’s architecture alone is worth seeing. Beyond that, there is an enormous collection of priceless artwork ranging from Monet and Renoir to artifacts from 300 B.C. On your way there, don’t miss a small but fun piece of Americana at the corner of Michigan and Monroe (across the street from the museum). The sign marking the beginning of historic Route 66 sits unassumingly on a light pole. Yes, I was that tourist taking a picture of it. Most people walked right past, not noticing or perhaps not caring, but I think it’s fun to take note of the small things. It’s those small things most people skip over that create a unique vacation experience if you take the time to notice and enjoy them.
Millennium Park
Conveniently located next to the Art Institute is a beautiful park in the heart of the city. This is definitely a tourist attraction but features several cool public art installations worthy of a visit. Don’t let the large crowds scare you away! Cloud Gate, better known as The Bean, is the featured attraction in the park. It’s a huge sculpture in the shape of a kidney bean and its mirrored exterior makes it selfie-heaven. A clear day allows for a beautiful reflection of the surrounding buildings and blue sky, making this a very Instagrammable spot!
Nearby you’ll find the Crown Fountain, a “live” art installation that showcases a rotating stream of faces belonging to Chicagoans. I’m not gonna lie, I was a little freaked out by the larger than life faces adorning the two bookends that comprise this fountain. You can find truly living art by walking to the opposite side of the park to see the beautiful Lurie Garden. This four season garden highlights Chicago’s culture and history through native plants and the use of colors. Note how the boardwalk separates the light and dark color plates.
Architecture
Chicago is renowned for its architecture and is the birthplace of the modern skyscraper. Typically, I would rather be looking at trees than skyscrapers but it’s hard not to appreciate the beautifully designed buildings as you walk around the Loop and the Chicago Riverwalk. Since Chicago is a very walkable city all you need is a good pair of walking shoes and you’re set to see the sites. A few architectural highlights to look for:
- Marina City, aka the corncob towers (300 N. State St.)
- Chicago Theatre (175 N. State St.)
- Aqua (225 N. Columbus Dr.)
- Chicago Board of Trade (141 W. Jackson Blvd.)
- Art Institute of Chicago (111 S. Michigan Ave.)
- Tribune Tower (435 N. Michigan Ave.)
- Wrigley Building (400 N. Michigan Ave.)
- Willis Tower, formerly the Sears Tower (233 S. Wacker Dr.)
I chose a self-guided tour but there are many options available for guided tours. Choose Chicago is a great resource for all the options for architecture tours throughout the city. I suggest trying Chicago Greeter for a free tour from a local guide. One of the most popular architecture tours is the Chicago Architecture Center’s River Cruise. It’s the most popular tour in the city so be sure to buy your tickets early if there is a particular time slot you need. And tickets are non-refundable so don’t miss the boat! There is a great opportunity to squeeze in a little extra exercise as you make your way to the boat. The stairs leading down to the Chicago Riverwalk are steep, so three times jogging up and down will get your heart pumping and legs burning! How manny times can you make it up and down? Just be careful. We don’t want anyone collapsing on the steps from jello legs.
Where To Stay
After a long day exploring you’ll want to rest and freshen up before heading to dinner. I stayed in the Loop at the Palmer House Hilton. I arrived in Chicago in the morning so had already been to the hotel to check my bag at the bell desk. Most hotels will store your luggage if you arrive before your room is available, so always head to your hotel upon arrival to drop off your luggage. I knew the Palmer House was a historic hotel, but I wasn’t prepared for the grandeur I encountered when I walked through the doors. Even if you don’t stay at the hotel I recommend walking through the Monroe St. entrance to view the famed Peacock Doors. Make your way to the lobby on the second level to see the soaring, hand-painted ceiling and enjoy a glass of wine at the lobby bar. The Palmer House, along with many other hotels, is located in the Loop. For convenience, I recommend staying in this area, especially if you’re just in Chicago for a quick visit like I was. If you’re on a budget, as with most cities, you can find perfectly good accommodations in the surrounding neighborhoods or with Airbnb.
Exercise and Fitness
If walking around the Loop and running the Riverwalk stairs aren’t enough and you want more workout time while in Chicago, here are a few options.
Cycleboat
Chicago Cycleboats offers a unique way to combine biking and boating. Use pedal power (and a motor if you get tired) to cruise the Chicago River, taking in the incredible views and architecture along the way. And since you’re on vacation don’t forget to take advantage of the BYOB policy. Bring along a couple cans of Revolution Brewing beers to enjoy. After all, beer is 90% water so you’ll be hydrating! Ok, you got me. Beer won’t keep you hydrated but if you conveniently ignore the science it’s a good excuse to drink beer.
Kayak and SUP
I love kayaking and paddle boarding and Chicago’s waterways provide great opportunities for both. If you want to explore The Loop via the Chicago River check out Urban Kayaks and Wateriders for tours and rentals. Kayak Chicago has locations on the Chicago River and Lake Michigan and offers tours, rentals and classes. Did you know Lake Michigan is the only one of the Great Lakes to be located entirely in the United States?
Hotel Gym
The Palmer House has a pretty decent gym with all the basics you need for a good workout. Hop on the treadmill for a quick run to energize yourself after a long or early morning flight. Be sure to incorporate sprinting if you’re short on time. You’ll kick your metabolism into gear and get more bang for your workout buck. If you prefer a larger gym you can check this list of Chicago gyms offering day passes.
Bonus Tips
- I can’t resist a good dessert! It’s even better when it comes with a unique history. Bertha Palmer tasked the Palmer House chef with creating a unique dessert for the World’s Fair in Chicago in 1898. The glorious result was the brownie! You can buy the original recipe brownie at the Palmer House Hilton’s restaurant or bar, or you can make it on your own to share with family and friends.
- A popular activity is a paid trip up Willis Tower to view Chicago from the Skydeck but a very similar view can be had for free by visiting the Signature Lounge and Restaurant at the top of the John Hancock building. I hear the view from the women’s bathroom is amazing! The restaurant is pricey so consider going for lunch or visiting the lounge for a pre-dinner drink or appetizer.
