You’re not going to see everything when you visit Chicago, so let’s just get that out of the way from the start. If you don’t believe me give it a try and let me know if you had any fun running around like a maniac. There’s so much going on in Chicago, and the city is so vast that it’s impossible to see everything in one trip.
So the real question is how do you plan a trip to one of the world’s great cities, so you feel like you got to see some of the things you wanted to, had time to explore, and found things you didn’t even know existed.
It helps to think of Chicago as a city of neighborhoods, each with its own history and its own set of stories. At the center of those stories is The Loop, the connective tissue that holds the city together and the place where most people start when they visit Chicago for the first time.
As Chicago’s downtown, the Loop is a mix of skyscrapers, museums, parks, shops, and public art that overlook the green grassy fields of Grant Park and the cloudy gray waters of Lake Michigan. The Loop gets its name from the elevated train or L that loops through downtown. It’s also where the city shows off its industrious nature and worldly ambitions.
Plan Ahead, But Not Too Much
The best way to see Chicago is to have a general idea of what you want to do when you get there; things like I want to see amazing art, eat at a famous restaurant, dance naked in Buckingham Fountain.
There are some places and things you need to schedule before you get there or you’re not getting in. You’re not going to get a reservation at Frontera Grill on Saturday at 7 pm if you call Friday morning. The same goes for lots of other restaurants and shows. So pick a couple of things you really want to do and book them ahead of time.
The reason it’s a good idea to have a few things scheduled is so you can spend the rest of your time exploring, without feeling guilty about all the things you’re not doing. A good resource for seeing what’s happening in Chicago is Choose Chicago.
Morning on Michigan Avenue
There’s this great energy when you’re walking down Michigan Avenue in the morning. It feels like there’s a parade around the corner with the sound of the drummers tap tap tapping on their homemade drums outside the Chicago Art Institute, scores of students streaming their way to class, and well-dressed professionals making a beeline to whatever uber important meeting they have that morning.
One of my first stops, whenever I’m staying downtown, is the Chicago Cultural Center. Located across the street from Millennium Park in the former downtown library the Center is a tribute to Chicago’s gilded age ambition. In addition to having one of the city’s visitor information centers, staffed with people who are actually happy to help you find fun things to do, the Center also has interesting exhibits on the Chicago’s history, art, and culture.
Across the street is Hot Tix, which offers discounted tickets for plays, musicals, and comedy shows happening around town. Part of what makes it fun to get tickets there is you never really know what you’re going to end up seeing, sometimes you see amazing shows like Red about Mark Rothko and other times you end up watching a very strange version of what you thought was the Tempest tucked into the back corner of an old L station.
Because Chicago is so big and there is so much ground to cover, a great way to start your trip is to take a tour or two. There are so many tours and tour guides in Chicago that at times it feels like the city’s three most common professions are tour guide, hot dog vendor, and guy in suit with two other guys in suits talking about the Cubs.
There are two questions you need to answer when you’re picking a tour in Chicago. The first is what are you interested in because as long as it falls under history, food, architecture, art, sports, or gangsters, there’s a tour. The second is how do you want to get around, as long as you’re ok sitting on a bus, sailing on a boat, walking on your feet, zipping on a Segway, or paddling a kayak there’s a tour. The only tour we haven’t found yet is the kayak gangster tour, which would rock.
The best place we’ve found for getting started is a walking tour from the Chicago Architecture Foundation. Whether you want to sit, walk, or ride the Foundation offers a cornucopia of tours that cover the city’s history and culture. The tours are led by docents who love showing off their city and know what they’re talking about. Their Historic Treasurers of Culture and Commerce tour provides a good introduction to where everything is downtown and to Chicago’s ongoing love affair with architecture.
When You’re in Chicago Eat
When you’re in Chicago eat, whether you like to eat at world renowned restaurants run by Iron Chefs or Top Chef Masters, or prefer little mom and pop shops that offer amazing cuisine from every corner of the world there are dozens of choices. A part of what makes the Chicago culinary scene so interesting is how the City celebrates such a wide variety of styles and cuisines.
Food in Chicago is such a rich mix of traditional cuisine, blending of cultures, and new ideas that a good way to figure out where to spend your vacation calories is to take a food tour towards the beginning of your trip. Food tours are a great combination of site seeing and eating that lets you taste lots of different things while helping you learn about a part of the city.
Eating out is one those things where it can help to plan ahead for a couple of meals, especially if you’re staying in The Loop or going to be in town over a weekend. To get a table at a lot of the most popular restaurants, you’ll need to make a reservation, sometimes several weeks in advance. Also, in a lot of ways, The Loop isn’t going to be your best bet for food. Like a lot of cities, most of the great restaurants aren’t located downtown; they live in the neighborhoods where there are more regulars and more affordable rents.
Helpful hints when eating in Chicago
- If you recognize the name of the chain, go somewhere else – so no Potbelly, Chipotle, or Starbucks.
- Have at least one Chicago Style Hot Dog, fully dragged through the garden – best served from a guy on the street, preferably with a cart.
- Have a slice or two of Chicago Style Deep Dish Pizza, it’s amazing if you like cheesy, bready, deliciousness.
- Try mixing up your meals between innovative chef-driven restaurants and mom and pop places – both are rightly celebrated in Chicago and are a great way to experience the city’s culinary traditions.
When you’re looking for a drink downtown, try something different and hit one of the hotel bars. The bars in the big old hotels have character and style. When you’re sitting at the bar in the lobby of the Palmer House with it’s painted frescos over head, it feels like you’re at the center of everything happening in Chicago.
Then there are the bars in the new boutique hotels opening up in historic buildings all over The Loop. Places like Cerise, which is an almost whimsical interpretation of an after hours Japanese bar at the Virgin Hotel and the Game Room located in the old Chicago Athletic Association’s former billiards room that has been beautifully restored with dark wood, good drinks, and an indoor bocce ball court. You can even get a drink at the bar in the Hampton Inn, located in the Art Deco home of the old Chicago Motor Club.
Time Better Spent
Not all cultural attractions in Chicago are equal. When you look at a map of Chicago, you’ll see at least one of every cultural attraction under the sun. If you’re interested in going to one or two around The Loop, the Art Institute of Chicago is one of the best art museums in the world, particularly if you like Impressionist paintings. When you walk through the museum, you realize pretty quickly what an amazing collection they have as you pass by original paintings that you’ve seen pictures of your whole life and stumble on Monet’s hanging in little side galleries.
Like many natural history museums, the Field Museum has everything from old dioramas to multi-media extravaganzas. The museum also has the resources and know-how to go in depth on a range of cultural and natural history subjects that make it worth a stop.
The Shed Aquarium and Museum of Science and Industry are both fine, but unless there’s a special exhibit you’re interested in visiting, there’s probably a better way to spend your time. Both are full of exhibits that look like they came from and have stayed in one of those old newsreels expounding the wonders of tomorrow.
In a lot of ways, they’re like Navy Pier, another Chicago tourist trap that everyone goes to because they’re supposed to, but aren’t sure why they went when they leave. It’s the type of place worth saving, but since no one knows what to do with it, it ends up as the type of place where Jimmy Buffet and Ronald McDonald open up restaurants across the food court from each other. The one thing Navy Pier does have is nice views of downtown along its boardwalk, although there are much better views from the walking path by the Shed Aquarium.
If you’re not sure what to do or need a break head to Millennium Park, grab a seat by the Cloud Gate or Crown Fountain and watch people play with the art. It’s fun seeing people smile back at the faces of Chicago as they splash around in the fountain and see how everyone, including the French biker gang I saw on my last visit, is drawn towards the undulating images reflected in the Bean’s shimmering surfaces.
Grabbing a seat and people watching is a great way to pass some time while resting your tired legs, because the best way to see Chicago and The Loop is to put on a good pair of walking shoes and explore.
Trip Planning Resources
Mark is Umami's publisher