I booked a last-minute flight to party with my friends in Chicago

I’ve always wanted to check out Chicago, and when I was invited randomly for a last-minute weekend getaway, I jumped at the opportunity. 

Sometimes, the best plans are unplanned, which was the case with my weekend in The Windy City. I loved the city’s uniqueness, from the bold architecture to the walkability and accessible bike lanes along the Lake Michigan shoreline. Granted, I think I’ll need to return. With so much to do in Chicago, it’s a city that deserves a fair share of attention. 

Normally, I would explore the unique facets and history of a city that’s new to me, but my last-minute trip to Chicago was more of a bar crawl. 

So, here’s the story of how this all happened and how it was unexpectedly some of the most fun I’ve ever had with friends! 

How this Chicago trip came to be

Sometimes, taking a risk and going with the flow is the best thing to do. I truly believe my trip wouldn’t have been as memorable as it was if we planned a Chicago itinerary. 

Now, of course, sometimes planning is necessary. But now and then, leave some room for the unpredictable. I mean, most of adulthood is regiments, schedules, and routines. Why not mix it up a bit? 

I picked up a phone call from my friend, and without a hello, she said, “Want to go to Chicago next week for my brother’s birthday?” I don’t know why I didn’t hesitate, but I immediately said, “Sure.” Great, so it was settled.

A surge of anxiety hit me when I got off the phone. What about the flights, are they expensive? I have so much work to do I ought to think this through. 

Oh well, it’s too late now. Time to figure it out. 

And that’s what I did; I got my affairs in order and went with the flow. Four of us were flying to Chicago from New York, and four were flying to meet us from Florida. This incredible weekend helped create some life-long friendships. I’ll always be grateful, and I have Chicago to thank for it. 

My favorite parts of Chicago 

Chicago is a big city with no shortage of neighborhoods and places to see. While I didn’t see the whole metropolis, I was satisfied with what I managed to accomplish on a short stay. I’ll share a few neighborhoods that stood out as a first-time visitor: 

Of course, you can’t take a trip to Chicago without visiting “the Bean,” the best place to take photos with your friends and admire your reflection on the surface. 

Unfortunately, I didn’t get to visit all of Chicago’s parks, but we did rest at Millenium Park in the heart of downtown. The Crown Fountain is one of the coolest pieces of interactive art I’ve seen in a big city.

If I had to pick a favorite part of the city, I would choose River North. The downtown neighborhood is clean and energetic, with gorgeous views of the Chicago River. It’s unique to have a river in the middle of the action, and I admit, I’m a bit jealous of the locals! 

The neighborhood that surprised me the most? Chicago’s Chinatown. It was expansive, traditional, and inviting. Oh, and the food is incredible. Even in the haze of running around with no plan, I remember the dumplings being the best I’ve ever had (sorry, New York City). If you go to Chicago, please go to Qing Xiang Yuan Dumplings. 

👉 While I didn’t see everything, check out Lea Rose’s list of Chicago’s best neighborhoods. A local perspective is always the best way to go. 

Yes, Chicago really is the “Windy City”

Okay, so I’m used to unpredictable weather. Living in New York City, you can never be too prepared when you leave the house. 

However, dare I say it, Chicago might be worse for weather unpredictability. And I wasn’t even visiting during the infamous winter season. 🥶

Upon returning to New York City, I came down with a ruthless cold. This is wholly my fault; I didn’t bring enough warm clothes. Also, alcohol is not exactly the best for your immune system. So, consider yourself warned to pack well and pack warm.

We took this trip in late May, one of the best times to visit Chicago. However, some days were chilly and windy, and we encountered sporadic thunderstorms. But don’t let the weather discourage you; the sun does shine, and it’s a beautiful city when it does.

Chicago vs. New York City bar scene – Who wins?

We’ve made it to the main plot in this story, the drinking we did throughout the city. Now, I’m not one to encourage reckless behavior in any way, but alas, this was the plan.

My friend, whose birthday we were celebrating, really wanted to check out Chicago’s nightlife, the crux of the trip. I can’t blame him; he barely gets time off work to relax from a demanding job, so this was his chance to let loose! 

We spent one day bar-hopping around River North. Granted, I can’t remember everywhere we went, but I recall having a meal at Beatnik On The River, a fantastic Mediterranean restaurant. We did stop at a waterfront cafe on the Chicago Riverwalk that serves alcohol, and we all had a “birthday shot” (It was all downhill from there). 

However, there were fewer bars directly on the Chicago River, and places tended to close earlier. It was a great place to start, though!

As for nightlife, we got local advice to go out on N Clark Street in the neighborhood of Wrigleyville. I’m glad we did; there was no shortage of bars. The crowd leans younger, and you’ll have a mix of cocktail and dive bars, with a few lounges and clubs. 

The most fun of the night? A gay bar called Sidetrack. We ended up making friends and dancing for hours. My friend lost her shoes, another fell onto a strobe light, and we got home at 6 am. I don’t know if I could do that again, but it was 10/10 at the time. 

As for a winner, it’s tough to say. New York City is bigger and has more bars and restaurants in sheer volume. But Chicago has a lot of culture and I found the staff and locals to be a bit more inviting and down to earth. 

New York City wins for more upscale options and meeting internationals, and Chicago wins for local spots and dive bars. 

Pro Tip: Whether you’re in Chicago, New York City, or anywhere else – drink responsibly…

The Chicago River is New York City’s Central Park 

Every city has a staple that it’s known for. Sometimes more than one, but natural landmarks are a special thing in urban cities. A bit of nature in an otherwise concrete world, if you will. 

I think the Chicago River is to Chicago what Central Park is to New York City. I don’t think Chicago would have that “essence” I felt without its famous river. 

Even if you do nothing else, taking a water taxi to different parts of the city is an experience in its own right. You can book guided tours to learn about the architecture, sightsee, and bond with other passengers. This was the best way to check out different neighborhoods, weather permitting.

I spent most of my time around the River North neighborhood but had a chance to visit the Navy Pier before heading to the airport. We got lucky with the weather, and it was a beautiful place to walk around, take in views of the Chicago skyline, and enjoy Lake Michigan’s gorgeous shoreline. Sadly, I didn’t ride the Centennial Wheel; there’s always next time! 

Would I have done anything differently? 

On the one hand, spontaneity was the selling point of this trip and cultivated the “thrill of the unknown.” I went to Chicago blind and ended up loving the city. 

But, as with anything, you reflect on how things could have had a few minor tweaks here and there, and my Chicago trip was no different. 

To start, I would have spent less time in the Loop area downtown after seeing the main attractions. I’ve learned through experience that the underrated parts of a city are often the less touristy ones. Whenever I make a trip back, I’ll explore some of the lesser-known spots and find the hidden gems. 

Another rookie mistake? The Airbnb was a bit further away from the city than I would have liked. The location was close to the Chicago O’Hare International Airport, and we weren’t within walking distance of much. With better preparation, I would have stayed in a different area of Chicago.

All in all, it was still an amazing trip, and these small things didn’t put a damper on the fun! 

So, should you book a last-minute trip to Chicago?

A resounding yes! Chicago is one of the best cities in the United States, and there’s a reason it’s world-renowned. I have it on my bucket list to go for St. Patrick’s Day at some point and watch the Chicago River turn emerald green. 

The city was a remarkable place and a nice middle ground for meeting with friends from afar. There was so much to do that our biggest complaint was that we didn’t have enough time to see everything. 

Another great selling point is that you don’t need a car to get around the city. It’s quite rare to have so much all in one place that you don’t need to drive. Especially if you plan on drinking like we did! 

We still laugh about our trip today. We have fond memories of gallivanting around the city and laughing as we were up against the wind, napping in Millenium Park in the middle of rush hour, and taking loads of funny photos. 

If you’re ever thinking about booking a quick getaway at the last minute, Chicago will not disappoint. 

P.S. – Before I forget, Chicago deep-dish pizza is worth ALL the hype. We went to a place called Lou Malnati’s Pizzeria, which has a few locations throughout the city. I love going to Brooklyn for pizza when I’m In New York City, but Chicago wins in a landslide victory for their deep dish.