Top 5 Things to Do for a Short Trip to Chicago (If You’ve Never Been)

Let’s say you’re just here on business or you’ve only got a weekend in the city and you’ve never been here before.  What are things can you do to really get a great sense of the city quickly?  Here are my top 5 suggestions (in no particular order) for seeing Chicago in a time crunch.

1. Giordano’s or Lou Malnati’s Deep Dish Pizza
People argue which is better.  I’ve had both and like them both and if you’ve never been here chances are you won’t know the difference.  So ask your concierge which is closer to your hotel and eat!

Signature Lounge

2. Drinks at Signature Lounge (John Hancock Building), 96th floor
You don’t have time for a bunch of tours and it’s a great way to conserve your time.  You get the same views as you would from the Sky Deck and the best part is you can switch the admission fee for a cocktail for about the same price.  While it’s a bit touristy, the views are breathtaking and certainly a great way to see the city after a long day.

3. Architecture Tour

I said you won’t have time for a bunch  of tours, but I say make time for this one (if it’s not the winter, this tour is seasonal).  It’s just around an hour and it’s an enjoyable boat ride down the river giving you a rich combination of Chicago history while viewing some of Chicago’s most famous buildings.  It really gives a full view of how the city started and is still working!

4. Millennium Park & Grant Park

“The Bean” in Millennium Park

Just to be clear, Millennium Park is newer and chances are you’ve seen “The Bean” that is there.  Starting on Randolph & Michigan, Millennium Park was built for the new millennium and hosts concert events, ice skating and Park Grill.  While considered separate, the 2 parks blend into each other the farther south you walk along Michigan Avenue.  Grant Park includes the incredible Buckingham Fountain, is where Taste of Chicago is held yearly and is near the Art Institute.

5. Pick a Museum
Not everyone is artsy, but you don’t have to be!  We have amazing museums in this city: Art Institute, Field Museum, Shedd Aquarium, History Museum… the list goes on.  I suggest the Art Institute because of some of the incredibly famous art that lives there including Georges Seurat’s A Sunday on La Grande Jatte, Monet’s famous Haystacks, works by Rembrandt, Picasso, Renoir, Georgia O’Keefe, Edward Hopper’s Nighthawks (famously recreated into ‘Boulevard of Broken Dreams’ with and is one of my favorites) and of course, Grant Wood’s American Gothic.

The Recreation of Hopper’s “Nighthawks” featuring Old Hollywood Celebrities

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