Chicago In A Weekend

Looking for the perfect destination for a quick weekend getaway? If the city life is your speed, you cannot go wrong with Chicago, Illinois. From the landmarks to the nightlife to the food, of course, Chicago is a perfect weekend destination. I’ve been to Chicago many times but decided to revisit and take a weekend trip last October. Here is everything you need to know about my solo trip!

Where to Stay?

You might have gathered by now that as a solo traveler I am all about hostel stay. If not, check out my blog post on why hostels are fantastic after reading this one! Anyway, locating a hostel was the first thing I did for my weekend trip. The HI Hostel Chicago did not disappoint. It is located right in the city, and within walking distance to several unique Chicago must-sees. One thing I love about hostels are the events they offer, and during my stay, they had several options such as historical walking tours of the city.

What to Do?

With headphones on, I ventured out with a few places in mind, but no real plan. My first stop; the infamous bean, actually called Cloud Gate, a world-known sculpture in Millennium Park. Walk underneath the sculpture’s large mirrored bean-shaped arch for a unique selfie. While you are at Millennium park enjoy live music by local street artists, or grab a frozen treat at one of the many vendors.

I am a lover of contemporary art, and fashion. Not only does Chicago have an incredible Museum of Contemporary Arts, but even better, I was lucky enough to catch the Virgil Abloh “Figures of Speech” exhibition.

Navy Pier was my next stop, and ended up being a highlight! I had my reservations at first seeing that it is a particularly touristy area complete with boat tours and carnival games, however, the view of the city from the pier was incredible! I was also surprised to stumble across Crystal Garden, which is an indoor botanical garden located right in the center of the pier.

Perhaps my favorite area of Chicago was Wicker Park. This area was artsy, full of vintage shops, boutiques, cool eateries, and bars serving trendy upscale cocktails to dark mysterious dive spots with cheap beer. This area is perfect for a day of fun or a night of dancing!

Where to eat?

Where should you go for an authentic Chicago City lunch? This one is easy; locals continuously guided me towards the serving place of the Chicago style hotdog, Portillo’s. This 1950’s decorated establishment featured checkered table clothes, vintage neon signs, and classic cars! I opted for the original Chicago dog, complete with a pickle spear, peppers, tomato, and mustard on a sesame bun. Delicious!

They’ve got world-famous hotdogs, and great hamburgers to? I know what you are thinking, Chicago for hamburgers? Having grown up in Texas there are a few foods that I rarely ever find done right north of my state; Mexican food, BBQ, and hamburgers. I was completely proven wrong when I tried the burger at Au Cheval. I mean it when I say this might have been the best damn burger I’ve ever eaten!

Looking for something a little more upscale to unwind with a glass of wine? Etta, located in Wicker Park, was incredible! Some of my favorite dishes were the fire-baked focaccia, bucatini cacio e pepe, and the chilled walo crudo. Grab a couple of friends, order a bottle of wine a share several dishes. This is the perfect restaurant to take your time and socialize.

For lunch or dinner, Ramen-san Whiskey Bar in Fulton Market has a super cool vibe, not to mention Fulton Market area is super walkable, with tons of unique bars and social clubs. If you want a night out, start here for some sake and classic Japanese ramen before venturing out.

Last but not least, when in Chicago you must stop at Garrett’s Popcorn Shop and Stan’s Donuts for some classic Chicagoan sweet treats.

Chicago is a lively city full of fun surprises! I highly recommend that you book a ticket and check it out for a weekend, whether you are with friends, or traveling solo. Venture out and explore the city’s culture and excitement. I promise you won’t be disappointed! xxx

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