One Day in Chicago

Chicago is a fun city and it can make a great vacation spot for anyone looking for a city holiday because it offers so many activities, restaurants, hotels and festivals. But it is also a business city, and many of us just stop in for a day or two at a time. Compared to, say, Los Angeles, Chicago is not a big city and – fortunately for those of us who don’t have weeks to spend there – it is entirely possible to get a good feel for it even if you have only one day to see some of the sights.

Rob and I recently did just this and have a couple of suggestions for things to do if you only have one day in the windy city and want to make the most of it. There are plenty of places to stay, but I have to recommend picking a place downtown (we like the River North area because of its high density of hotels and great restaurants) if you want to maximize your day because it will minimize the amount of travel that you need to do. There are cabs and the “El” train – but nothing beats walking as a great way to see the city.

Start out with a good breakfast. Chicago is full of fun diners and breakfast restaurants. Our hotel was near Rick Bayless’s XOCO, and their hot chocolate and churros are irresistible – and their other Mexican breakfast options are pretty tasty, too.

After a good breakfast to get you started, I’d head down towards Millennium Park. This park is one of the city’s most popular tourist attractions, and not only is it a beautiful and relaxing place to spend some time, but it is filled with public art, including the very popular Cloud Gate. Commonly called “the bean,” the Cloud Gate is a gigantic silver jelly-bean like structure that reflects both the faces of visitors and the entire Chicago skyline when you look into it.

From “the bean,” it is just a short walk to the Art Institute of Chicago, a world renowned art museum that houses a collection of more than 300,000 pieces of American, European and international works. It is easy to spend a couple of hours browsing through the collection, and it is something that neither Rob nor I could resist taking the time to do. They always have new exhibits rotating into the main collection, so there is frequently something new to look at in addition to the most famous pieces from their permanent collection.

Next on the list would be an architectural walking tour of The Loop and the surrounding downtown area. The Chicago Architecture Foundation Tours are consistently the most highly ranked tourist experience in the city (although they’re very interesting for anyone even remotely interested in art or history, not just people passing through on a short trip). The foundation offers walking and boat tours several times each day, pointing out the history of the Chicago skyline, the evolution of the modern skyscraper and the stories behind the unusual – and often impressive – buildings in the city. Downtown Deco and Modern Skyscrapers are two that struck us as being the most interesting (though we certainly haven’t been on all of the tours), and the CAF also offers tours of different neighborhoods further afield from the downtown Loop, like Lincoln Park and Evanston.

You don’t need a tour to take a walk through the historic Marshall Fields building, once home to the flagship Marshall Fields store, a pioneer in the evolution of modern department stores. Now a Macy’s, the store still offers a great food court, beautifully restored fixtures and the impressive 6,000-sq ft mosaic Tiffany Dome for visitors to enjoy. And, of course, you can do some shopping, too and enjoy the fact that this department store still offers great service that you can’t seen to find too many places these days.

After all that touring, this is the point where I vote for heading back to the hotel to clean up for dinner. You definitely have to try a Chicago hot dog at some point on a Chicago visit (or deep dish pizza, although I think that we happen to be bigger fans of the dogs than the deep dish) or find a nice restaurant for dinner. There are tons of restaurant options in Chicago, so it is easy to find one that suits your tastes. If you want a suggestion and are a fan of Mexican food, try Topolobampo or Frontera, as those Rick Bayless spots are definitely places we would eat again – and again and again, if they were closer!

Now, this is just our top itinerary for a one-day trip to Chicago. You’ll get to see a lot of the downtown area of the city this way, but there are plenty of other activities to do. There are shows, improve (Second City), and if the weather is nice you can head to Navy Pier (popular with kids and families, and also has nice fireworks displays twice a week during the summer) or spend the day in Lincoln park visiting the zoo, which is free.