What to do in downtown chicago

What to do in downtown chicago

I was inspired to write this itinerary after watching the Taste Buds take over Chicago. To watch them is to love them.

You’ll hear talk that nothing happens in downtown Chicago after 5 p.m. and that’s partially true. Businesses in the Loop cater to office workers who pour in by the hundreds for quick lunches and generous happy hours – which are, by the way, now legal. If you live outside of this radius, and most do, there’s little chance you’ll be returning after work to compete for road space with tourists and taxis or to spend a fortune on meter fees (the most expensive in North America at $6.50 per hour).

So, who even needs a day itinerary for the Loop? First, the casual tourist. They’re most likely to mistake this area as being in the center of it all when really anything you want, except Lake Michigan, is further northwest. Second, the business traveler who requires convenient office access. Lastly, the staycation-er who’s looking to play the tourist in their own city, if only for a day.

There’s nothing these three groups are in search of more than freedom to do what they want, when they want. With that in mind, here’s a flexible guide to Chicago’s Loop neighborhood, just in time for the three day weekend. The focus here is on art and shopping and business listed are those I can personally recommend. If you have additional suggestions, please feel free to list them in the comments below.

24 Hours in the Loop

Accommodations: The Palmer House Hilton (17 E. Monroe Street, 60603 – map)

Picking a hotel in the downtown area of any major city can be tricky. Resting solely on their location, some hotels are huge disappointments once inside. The Palmer is pleasantly what you would expect from a traditional hotel in a historic building. It is clean, classy, and conveniently near everything. Also, they’ve got a pretty nice spa and fitness center.

What to do in downtown chicago
– Goddess & The Baker –

9:30 a.m. Breakfast: Goddess & The Baker (33 S. Wabash Avenue – walk 1 minute)

This is no time to count calories but even if you are there’s sure to be something you’ll love at Goddess & the Baker. From steel-cut oats and a salmon spread to baguettes and croissants, eating here will hold you over for the next few hours.

10:30 a.m. Sightseeing: The Art Institute of Chicago (111 S. Michigan Avenue – walk 4 minutes)

Listen. Chicago’s full of great art museums and galleries but The Art Institute reigns queen of the court. This is not debatable. Recently ranked #1 museum in the world, it holds some of my top favorite pieces (such as, anything by Ivan Albright). Section off a few hours and linger here.

1:30 p.m. Lunch: Hot Woks Cool Sushi (30 S. Michigan Avenue – walk 5 minutes)

Delicious sushi and affordable prices.

The Art Institute of Chicago
– The Art Institute of Chicago –

2:00 p.m. Shopping: State Street between Monroe and Randolph (walk 3 minutes west) and Michigan Avenue between Illinois and Walton Street (walk 15 minutes north from lunch). For a list of stores on State Street, check out an article by Choose Chicago here. For details on Michigan Avenue’s “Magnificent Mile” click here.

5 p.m. Rooftop Happy Hour: Cerise (inside of Virgin Hotels Chicago, 203 N. Wabash Avenue – walk 4 minutes)

The newly opened Cerise is competing for best party under the stars with a few nearby rooftops. Currently, it’s in the lead. This is either by the coattails of its opening night, which boasted music spun by Quest Love, or because everything Richard Branson touches turns to cool.

6 p.m. Dinner: Sullivan’s Steakhouse (415 N. Dearborn Street – walk 10 minutes)

I usually don’t recommend chain restaurants but Sullivan’s offers a dependably well prepared steak. I recently tried their new surf and turf summer menu and was blown away. From the fruit infused vodka to the peanut butter black bottom pie which is so good it should be illegal. Seriously, it’s hard to forget how great the food is here. On top of that, they must have missed the snooty staff for every steakhouse memo because waiters and managers are down to earth and friendly among each other and patrons alike.

Try the filet mignon and lobster (surf and turf), and the peanut butter black bottom pie because: vacation. Remember, no calorie counting!

What to do in downtown chicago
– Sullivan’s Peanut Butter Black Bottom Pie –

8 p.m. Cocktails: Three Dots and a Dash (435 N. Clark Street – walk 2 minutes)

Here’s a bit of Polynesia for you. Everyone’s favorite Tiki bar is worth the walk and possible wait for a seat.

9 p.m. Sightseeing: Millennium Park, “The Bean”, and the Jay Pritzker Pavilion (201 E. Randolph Street – walk 20 minutes)

Grab a blanket and relax under the stars in Chicago’s most famous park.

Midnight and Later

  • Three Dots and a Dash closes at 2 a.m. or later
  • Cerise closes at 2 a.m. or later but their outdoor section closes at midnight
  • Not including Sundays, Roof at the Wit closes at 2 a.m. or later

Things to do nearby

Pampering and Gym

Watch the Taste Buds take over Chicago

Taste Buds is a new YouTube video series featuring two best friends who travel the country in their Ford Edge reviewing restaurants and punching people in the face – with awesomeness. Okay, no punching. Just awesomeness. Taste bud(die)s. Get it? Cute, right?

Their latest episode is, of course, my favorite because it’s all about Chi City. Watch as they try out Furious Spoon with amazing photographer and all around Chicago cool kid Paul Octavious. Plus, they visit a couple spots that are probably on your “one day I will” list.

Bonus: I received the following email from Krissy (she’s wearing glasses in the video):

“Chicago was my favorite city on our whole trip. It’s clean and beautiful and the people are nice AND it has everything you want in a city: comedy, music, great food and art. We had an incredible time there and are so happy to be collaborating with you on this episode.”

Sorry, Krissy but that was too good not to share. You girls are so much fun! Come back soon! ♥

Images: The Goddess and the Baker via the company’s Facebook page. All photos taken by Kari Herrera of Chicagoings unless otherwise noted.

Compensation was provided by Ford via Collectively. Ford is the sponsor of Taste Buds – a fun, new travel series on YouTube. The opinions expressed herein are those of the author and are not indicative of the opinions or positions of Ford.