The common theme I hear from people who first visit Chicago is, “Wow, everything is within walking distance.” When you decide to visit Chicago you have made the choice to visit perhaps the best walking city in the United States.
I should preface that with a friendly reminder that you do have to be a fan of walking and a couple of miles of moving along on your feet has to be what you consider fun. If this describes you, it is easy to have a fun and inexpensive time in this very impressive town.
Before we start, you will need to find a hotel in the Downtown area, sure public transportation can get you around, but if you aim to use your feet you will have to seek out good lodging deals in the Downtown area. They do exist and depending on the season they can easily beat out comparable hotels in big cities across the country.
Next, utilize public transportation, even though most of the attractions that you want to see may be close by there are a few spots that are best seen via train or bus. Grab a 1, 3 or 5-day rail pass and you’ll save money on getting around. The train is faster but the bus allows you to see more of the city. (Note: the bus tends to crawl around during high traffic times, so be aware of scheduling conflicts and allow for extra time if you utilize the bus).
Navigating the city is very simple, just remember that Michigan Avenue is where you’ll do most of your sightseeing as your trip starts. (it runs north to south) You will branch out, but getting the lay of the land is simple once you understand that a river crosses Michigan Ave. (Chicago River) and heads east toward Lake Michigan. Grant Park is between Michigan and the Lake. Simple, right? Keep heading north and you’ll get to Oak Street Beach. If you head south you’ll get to Hyde Park and the University of Chicago as well as the neighborhood that President Barack Obama calls home.
Things You Should See in Chicago
- Oak Street Beach – Yes, I am telling you to go and see a beach in a city that is so dynamic and interesting. The views from this side of town are spectacular and you’ll realize it the minute you frame a shot with Lake Michigan on the left and the city on the right. (Hint: It seems like city views are spectacular from so many points of interest in Chicago)
- Lincoln Park Zoo (Free) : One of the oldest zoos in the US. Typically crowded on the weekends, but a really peaceful and immersive treat during the weekdays. My favorite thing to do is go to the McCormick Bird House during the birds’ feeding and watch the tentative interaction between the zookeeper and the pair of Blyth’s Hornbills (the zookeeper uses a clicker to distract the hornbills and throws a few grapes in its beaks before quickly plopping down the bowl of food). Also, when they flap their wings, it sounds like thunder—very loud and disarming.
- Lincoln Park Conservatory (Free) (Next to the Lincoln Park Zoo): A stunning sea glass-colored structure that houses a verdant fern room. Make a game out of finding the semi-hidden dinosaur figurines.
- Free Concerts in Orchestra Hall at Symphony Center (Free): Concerts are not given by the CSO, but by the Civic Orchestra. There are typically 6 concerts per season. There’s a pre-concert lecture as well for folks who want to learn more about the evening’s performance.
- Graceland Cemetery (Free): Self-guided walking tour is available at the visitor’s center. Beautiful Victorian-era cemetery/park that’s well-maintained. All the architectural greats and business magnates are buried here: Mies Van Der Rohe, Louis Sullivan, Daniel Burnham, Marshall Fields, George Pullman, etc. Personally, I would recommend going on a walking tour guided by a Chicago Architecture Foundation docent to maximize your time. You have to leave before 4pm, though, or risk getting locked in for the night!
- Chicago Architecture Foundation Walking Tours (starts at $15): So many great walking tours that last about 2 hours. I would recommend any of the walking tours that take place in the Loop (e.g., “Downtown Deco” or the “Daniel Burnham: Architect, Planner, Leader” tours) which provides the most shot-to-the heart stunning view of Chicago’s strong architectural heritage.
- Maxwell Street Market (free): One of the oldest street/flea markets in Chicago. Known for their vibrant Mexican food vendors. One of Rick Bayless’s favorite places to grab a meal.
Free Museum Days: Pretty self-explanatory. The line for the Shedd Aquarium is always the longest and free is always good.