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The Best of Chicago in a Day for Bleisure Travelers

Discover Chicago in a day. Spend one day in Chicago. Explore what to see in Chicago in one day if you are a bleisure traveler.
Planning a business trip to Chicago? Perhaps you are hoping to add on a day to do something fun (or squeeze in a few fun activities during the business trip itself). 

You may be wondering what to do in Chicago for a day. I recently visited Chicago to speak at a conference for my "day job". During my trip, I discovered some fun places to see and things to do in the Windy City. 

Read on for ideas about how to spend a day in Chicago for business travelers with plenty of options to add to your Chicago itinerary.
Chicago in a day: reflections in Cloud Gate (aka The Bean)

Chicago Coffee and Breakfast Options

Downtown Chicago

I always try to get up a little earlier when I travel for business to make time for some morning sightseeing before heading to work. Of course, the first stop by necessity is for coffee. 

Chicago has some great coffee places to try around Downtown. Consider Intelligentsia where you'll get a tiny well-crafted cappuccino that still packs a punch! 

Fairgrounds is another strong choice for a morning coffee. Nestled in a cozy corner of the Chicago Athletic Association, the baristas here know what they are doing.
Chicago in a day: morning coffee options
Chicago Coffee: (left) Fairgrounds (middle) Sawada Coffee (right) Intelligentsia

Now here are some words to live by!
"Eat Now, Caffeinate"
If you have time for a slightly more leisurely breakfast (to eat in rather than take away), head to Goddess and the Baker. Indulge in a pepper and egg sandwich plus a coffee cake muffin warm from the oven. Wash it all down with a cappuccino of course. 

Goddess and the Baker also seems to be known for rainbow cake. I visited a little too early to justify a dense wedge of cake but others didn't have the same requirements. 

Goddess and the Baker's rainbow cake is served up with whipped cream that looks like clouds at the end of the rainbow. I wonder if its as good as it looks!
What to do in Chicago in a day: breakfast at Goddess and the Baker

Fulton Market

Fulton Market on the Near West Side of Chicago, is an up and coming neighborhood to explore. Also known as West Loop, Fulton Market used to be a meatpacking warehouse area with an industrial edge. 

My company has an office in Fulton Market (in a former refrigerated warehouse!) Now Fulton Market is home to great restaurants and bars including a number of Chicago Black owned restaurants

If you find yourself in Chicago's Fulton Market district in the morning, head to Sawada Coffee for a perfectly prepared cappuccino in a cool venue. 

Sawada Coffee shares space with a BBQ joint. Admire the edgy street art both inside and out while queuing for your morning coffee.

SIDEWALK SAFARI SPOTLIGHT: Looking for more ideas of things to do in the U.S. Midwest? Why not check out Cleveland for a day or discover fun things to do in Pittsburgh like going for a photowalk in the Mexican War Streets neighborhood.

Morning Walks Chicago Lakefront

If you take your coffee to go and assuming the weather cooperates, get some fresh air with a walk along Chicago's lakefront. There are over 5 miles of parks and green spaces along Lake Michigan. 

Seek out Cloud Gate (also known as The Bean) in Millennium Park. Keep an eye out for interactive art installations as you walk south in the park. Even further south, Grant Park is home to Agora, an installation of rusty headless statues by Polish artist Magdalena Abakanowicz. 

We actually saw a very similar art installation during a weekend in Poznan Poland earlier in the year. Interestingly, the figures in Chicago are about twice the size of those in Poland. I suppose they were sculpted to be proportional to their surroundings and there are certainly more skyscrapers in Chicago than there are in Poznan.

Make sure to take a detour to catch a glimpse of Lake Michigan itself. The Great Lakes are so big that it feels like you're looking out to sea rather than at a fresh water lake. 

Do not miss the morning Golden hour by Buckingham Fountain in Chicago. Buckingham Fountain is located almost on the shores of Lake Michigan. 

Position yourself on the Lake Michigan side to see an extraordinary view of the fountain with a backdrop of some awesome Chicago architecture.

If you have more time, the Art Institute of Chicago and Field Museum are also located in Chicago's waterfront parks.
Things to do in Chicago in a day
(left) Buckingham Fountain (middle) Agora (right) Art installation in Grant Park

Chicago Pre-Dinner Exploration 

Visiting a place on a work trip typically means that business hours are spoken for. That doesn't mean that your one day in Chicago ends after breakfast though. Seize the day! 

When the conference ended, I looked outside and realized that it was a gorgeous day to take myself on a self-guided walking tour. Since I visited Chicago in the summer that meant I still had plenty of daylight left. While tourists may flock to the Magnificent Mile, I was looking for something further afield.

Little Italy

Google Maps told me I was near Little Italy. I chanced upon Mario's Italian Lemonade. Mario's is located in the heart of Chicago's Little Italy and only open in the summer (they close on September 15th). 

The staff recommended the watermelon flavor which is made by mashing real fruit into the slushy lemonade. Just beware of the inevitable "brain freeze"!
What to do in Chicago for a day: Mario's Italian Lemonade
Mario's Italian Lemonade

UIC Campus and Greektown

The University of Illinois Chicago campus is located between Little Italy and Greektown. Oh, and the campus has awesome Willis Tower (formerly Sears Tower) views! 

Walk through the UIC campus. While many of the buildings on campus are a bit brutalist, the campus does feature some amazing Chicago skyline views. A subsequent stroll through Chicago's Greektown is worth it for the views and atmosphere alone.
Things to do in Chicago in a day: Explore UIC Campus and Greektown
left, middle: Greektown
right: Views of Willis Tower from the UIC Campus

Fulton Market to West Town

Alternatively, consider taking a walk from Fulton Market to West Town. The neighborhood is a little edgy but I felt reasonably safe during daylight hours. 

The best part about this walk on your day out in Chicago is the Hubbard St. murals. The collection spans a few blocks and features some local themes. 
Chicago in a Day: Check out Hubbard Street Murals

Dinner and Evening Entertainment in Chicago

While your daytime hours may be occupied on a business trip, the evening is all yours. What evening entertainment should you add to your Chicago in a day itinerary? The first step is to pick a neighborhood for the evening.

SIDEWALK SAFARI SPOTLIGHT: Did you know that Chicago, Illinois and Buffalo, New York have a lot in common including amazing architecture, great food, and a rich waterfront history?

Downtown Chicago

If you are staying in Downtown Chicago, go for a nightcap with views at Cindy's in Chicago. Cindy's is the rooftop bar at the Chicago Athletic Association. 

I tried the Farmer's Gin and Tonic which was described as having a wedge of iceberg lettuce. I was expecting a leafy garnish. Instead, the lettuce essence was in the drink. 

My Gin and Tonic was a bit weird for me but worth trying. Seeing the shiny Bean from above made it all worthwhile.
Things to do in Chicago in a day: drinks at Cindy's on the roof of the Chicago Athletic Club
Cocktails and views at Cindy's on the Chicago Athletic Club rooftop.

Fulton Market

Chicago's Fulton Market District is another great place to spend the evening. Start with drinks at Ballast Point Brewery. I loved the Sour Cherry Sour Wench and Golden Apricot Sour Ale. 

They also serve snacks including sweet treats like chocolate chip ice cream sandwiches. Have dinner at Bar Siena. The waitstaff described several dishes as "Legendary". 

That may be a little exaggerated but the food was fab. My favorites included Spicy Cocktail No. 13, wagyu beef meatballs, focaccia, and corn ravioli.
Things to do in Chicago in a day: places to eat in Fulton Market District
left: Spicy Cocktail No. 13 at Bar Siena
middle: Ballast Point taps
right: Jeni's Splendid ice cream

There was a line out the door at Jeni's Splendid Ice Creams so we had to stop even though our stomachs were practically bursting from the filling dinner we'd had at Bar Siena. 

It was hard to choose because there are so many flavors but I opted for the Orange Blossom Chiffon instead of the Salted Peanut Butter with Chocolate Flecks. The gent making the amazing smelling waffle cones gave advice on what flavors to pick based on his experience.

West Town

Another option to finish off a visit to Chicago for a day is West Town. I walked to West Town because I wanted to try a jibarito, a Puerto Rican sandwich with green plantains instead of bread that Chicago is known for. 

The roasted pork jibarito with spicy garlic sauce at Cafe Central was amazing. I also tried a pionono: sweet plantains with ground beef fried up.
What to eat in Chicago in a day: Puerto Rican jibarito

Map of What to See in Chicago in a Day

Click on the image of the map below to open up an interactive map in Google Maps highlighting the things to do in Chicago in a day covered in this post.
Map of things to do in Chicago in a day

Where to Stay in Chicago

This post assumes that you have time to explore Chicago for a day but that this is embedded in a bigger business trip. Because of this, you'll need advice on places to stay in Chicago

I stayed at The Blackstone, a Marriott Autograph Collection property on South Michigan Avenue. Some rooms enjoy views of Lake Michigan and Chicago's lakefront parks. 

The Blackstone is located in a historic skyscraper complete with period details and an art gallery on the conference level. The Blackstone is centrally located and a great home base for a trip to Chicago.

SIDEWALK SAFARI SPOTLIGHT: Did you know that workcations are the new hotness? Travel somewhere interesting and work while you explore.  We recently spent a one week workcation in Poughkeepsie, NY.

Did you enjoy this post about exploring Chicago in a day when you're in town for business? I hope you'll agree that Chicago is one of the most fun places to visit in the United States if not all of North America.

One Day in Chicago IllinoisOne Day in Chicago Illinois


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Sidewalk Safari | Part-time Travel Blog: The Best of Chicago in a Day for Bleisure Travelers
The Best of Chicago in a Day for Bleisure Travelers
Discover Chicago in a day. Spend one day in Chicago. Explore what to see in Chicago in one day if you are a bleisure traveler.
Sidewalk Safari | Part-time Travel Blog