Cultural Experience | Illinois

48 Hours in Chicago

How to make the most of the Windy City: beyond the main attractions

When my sister got a new job and requested help making the move from Boston to Chicago, I jumped at the chance to see the renowned Windy City, despite the rather deplorable 15 hour drive it would require. Originally from Philadelphia, I first had to make the 7 hour bus ride up to Boston. The next day, once the remarkably efficient movers had packed my sister’s life into the back of their gigantic moving truck, we hit the road again, on the first leg of our road trip. 11 hours later, we collapsed in a Hampton Inn in Ohio for the night, only to wake up bright and early and finish up the last 5 hours to Chicago.
As soon as the car rolled up to her apartment in the beautiful neighborhood of Lincoln Park, located in the northeast corner of the city, I was incredibly glad that I had agreed to offer my moving assistance–the payoff was two fun-filled days of adventure and exploration in a city that I can’t wait to return to.

Day 1:

You snooze, you lose! I tend to be a (VERY) late sleeper when I’m at home, but when I’m visiting a new place, I never let myself sleep in too late. If you only have a couple of days in Chicago, get the most out of your stay by heading out in the early a.m. Your first stop: breakfast.

Chicago has no shortage of interesting, unique, and delicious eateries. Most of my meals on this trip were at restaurants local to the Lincoln Park area, but I still had two days of incredibly diverse foods. Breakfast on my first day was at Floriole Cafe and Bakery on Webster Ave.

An adorable place with French-inspired food and decor, Floriole blew me away. They had a great selection of teas and espresso drinks, and a beautiful display of freshly made breads, cakes, and pastries–I settled on a hefty chunk of coffee cake. I sat on the first floor of the cafe’s two-story structure, where I read and people watched. Though slightly pricey, Floriole’s food was worth the extra cash.

To pass the time between breakfast and lunch, I took a long walk to see what the neighborhood was like–it’s always interesting to get a feel for a new city’s day-to-day life. The streets were lined with DePaul University students, bars and restaurants, several gyms, and a few schools. Unfortunately, a sudden downpour caught me off guard, so I had to run home to hide from the rain. This unpleasant bout of gloom luckily lasted only an hour–the sun returned full-force, and I headed back out to explore.


The next stop was lunch at a serene Japanese tea and coffee house called Nada, where I dined on a delicious chicken teriyaki rice bowl and a coffee– one of the best Cafe au Laits I have ever tasted. Light, pretty music and the gracious, attentive staff made Nada an incredible experience.

After lunch, I tried my hand at Chicago’s public transportation system, called the L, using my sister’s Ventra Pass — a convenient card that you can load money onto and use to pay for travel fare. After boardng a red line train northbound from Fullerton Station, I hopped off at Addison Station, located right beside Wrigley Field, the home of the Chicago Cubs.

The view of Wrigley Field from Addison Station on the red line image

The view of Wrigley Field from Addison Station on the red line

A short 10 minute walk brought me to my beloved destination: Bookworks, a used bookstore in the heart of trendy Lake View.

It’s a tradition of mine to visit at least one local, independent bookstore in every city I visit. Bookworks did not disappoint. I must have perused the shelves for at least 45 minutes, dazzled by the vast selection and competitive prices. I left Bookworks grasping a copy of Aldous Huxley’s Crome Yellow in search of a good spot to grab my second coffee of the day (I might be addicted…).

After a few blocks of tree-lined residential streets, which showcased a beautiful sample of Chicago’s unique style of angular but intricate architecture, I stumbled upon Caribou Coffee, a cute and cozy chain in the Chicago area. Feeling fancy, I ordered an iced mint mocha coffee drink, with all the fixings.

I headed back to Addison Station where I took a brown line train to Sedgwick Station. A 15 minute walk brought me to the stunning North Avenue beach, where I lounged lazily along the lake for longer than I care to admit. Although the water was freezing, my towel in the sand was the perfect spot for napping and tanning. With the beautiful Chicago skyline surrounding me and the blue waters of Lake Michigan in front of me, I was in heaven.

Chicago city skyline from North Avenue Beach image

Who could resist that skyline?


Upon returning home from the beach, my sister, her roommate and I walked a few blocks for an incredible Italian dinner at Filippo’s Ristorante on Clybourn Ave. The pinnacle of fine dining, Filippo’s offered a fantastic cheeseplate special that we quickly devoured before our entrees arrived. Between the three of us, we split two pasta dishes, which our waiter assured us were huge. Despite the fact that I am not yet 21, perhaps my favorite part of dinner was the small sip of homemade Limoncello I stole from my sister’s glass. At Filippo’s the chef makes specialty Limoncellos in crazy flavors, ranging from Nutella to orange to licorice.

Day 2:

Determined to try another local breakfast spot, I took a quick walk to CityGrounds Coffee Bar for a scone and a great cappuccino. I can’t recommend this place enough–decently priced food in a two-story building with plenty of seating is the recipe for an ideal place to work or study.

From there, I again jumped on a red line train at Fullerton, this time heading south toward the downtown area. My train went right through “the Loop,” the area of downtown where several train lines travel in a circle. I got off at Roosevelt Station, and took a long walk down bustling Roosevelt Ave in search of some fabric shops (I am as devoted to trying new independent fabric stores as I am to trying independent bookstores!). Roosevelt Ave takes you over the Chicago River (and provides a great view of the city behind the river!) and into the Little Italy neighborhood.

I stopped at New Rainbow Fabrics first, a cute shop across from the second store I popped into, called Vogue Fabrics. New Rainbow was great and had really unique fabrics, but Vogue was way bigger, and offered amazing sales. I ended up with a whopping 6 yards of fabric, all for only $16.00 (which is a great deal, for those of you who aren’t sewing nerds like me!).


After my fabric shopping was declared a success, I boarded a train to Chicago Station, where I took on the Magnificent Mile, a mile-long stretch of upscale shopping along Milwaukee Ave.

After popping into a few stores and taking several tourist-y photos, it was time, once again, for my second coffee of the day! I hunted down the nearest shop that wasn’t Starbucks (if you go to Starbucks during your travels instead of trying local chains or independent shops…shame on you!) and ended up in Lavazza Cafe on E. Ohio Street. I grabbed an iced coffee to beat the sweltering Midwestern heat, and a perfectly flaky almond croissant to hold me over til the late lunch I had scheduled with my sister.

All shopped out, it was time to chill out–and what better spot to do so than back on North Ave Beach? My new favorite spot in the city, North Ave Beach kept me occupied for some time until I needed food!

Once back in Lincoln Park, my sister and I stopped by Pequod’s Pizza for a classic Chicago-style deep dish pizza. When in Chicago, do as the Chicagoans do, and try deep dish! Pequod’s serves big 7-inch personal pizzas, and if you dine-in, you can get one as a lunch special at a discounted price.

This is Chicago's idea of pizza...I'm a little confused, but totally content with it!

This is Chicago’s idea of pizza…I’m a little confused, but totally content with it!


After a nice, long rest back at the apartment, we were ready for some dinner and some fun: queue trivia night! Right in Lincoln Park is Four Shadows, a great spot for drinks if you’re over 21, or just for dinner for those of us not yet of legal age. Tuesday nights are trivia nights at Four Shadows, so me, my sister, and some friends teamed up for a competitive 8 rounds of trivia questions. While I couldn’t indulge in the interesting craft beers they offered, the turkey burger was to die for!

Though I didn’t necessarily spend my time in Chicago hitting up all the classic main attractions, I feel completely satisfied with my trip. I really got a feel for the city–particularly the Lincoln Park neighborhood–by sampling a great many local restaurants and shops. I hate to leave the city I only just met, but maybe I can put my time spent waiting in the airport to use and plan my next visit!

Johanna Gruber

Boston University | 9 stories

I am a Boston University graduate with a passion for writing, traveling, television, and bubble tea. I have a BA in English with a minor in Journalism, and I interned with the College Tourist over the span of a few years as a writer and senior editor. Check out my website for more info and my portfolio:

2 responses to “48 Hours in Chicago”

  1. Emily Snider says:

    So happy I stumbled upon this post – I go to DePaul and call Lincoln Park home, and I’m so glad you enjoyed your time! It’s interesting to see how a tourist views the neighborhood…but in all honesty, you can still find me (two years later) walking around curiously, like I was the first day I moved in!

    • Johanna Gruber says:

      Thanks for the nice comment, Emily! You’re lucky to go to school in such a lovely place. I hope I’ll get back to Chicago soon!

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