Spending Three Days In Chicago For First Timers

I got off the flight in Chicago like I already knew the place. Have you ever been somewhere brand new and have it feel as familiar to you as a second home? Like the way you know your way around your best friends parents house? That’s how Chicago felt to me. I walked in, opened the fridge, grabbed a drink and sunk myself comfortably into its worn in sofa.

I only had a few days to spend in this new city and was amazed by the end of it how much I was actually able to squeeze in. A little planning ahead of time and a lot of room for flexibility made for a pretty perfect first weekend in Chicago.

The Hotel

Arriving at the The Warwick Allerton only to learn that a large quantity of hotels in Chicago were on strike made for an interesting first night. It turned out the hotel had no rooms ready when I got there. But I made the best of it by dropping off my stuff and heading out to explore the city.

By the time I had finished dinner, I was able to check in. Everything about the hotel was completely perfect except the way they handled the inconvenience of the strike. I was told I would receive a call when the room was ready, but ended up having to call myself for an update.

I did however, forget about the inconvenience as soon as I crashed into the large comfortable bed. Although it was a rough start, I would give the hotel another chance for the rest of the experience I had there. If you’re looking for a nice hotel at a reasonable cost and a very central location, you could do a lot worse than the Warwick Allerton.

I made the mistake of buying a 3 day CTA pass (for $20) and only used it a few times. If you stay at the Warwick Allerton, you can almost certainly get by on just walking or a quick Lyft ride.

A City to Remember

The thing that struck me most about Chicago was that everything I did was completely unforgettable. Sometimes when I’m traveling things and places slip through my memory faster than I can take out a pen to write it down. But everything I did in Chicago was vividly memorable.

Everyone I spoke to before my trip about what to do in Chicago unanimously claimed a river architecture tour was the highlight of their trip. So of course it was at the top of my to do list. I opted for Chicago’s First Lady Cruises tour organized by the Architecture Foundation Center for the simple reason that it’s a nonprofit organization. The entire tour was amazing from the adorable little tour guide with her thick Chicago accent to the beautiful weather we had. I cannot recommend this tour more.

If I had to give Chicago some serious points over New York, I would give it a lot for the stunning river they have flowing through downtown and reflecting all the gorgeous architecture. It makes Chicago truly one of the most picturesque cities I’ve been to and the river cruise is the best way to enjoy it.

A Walk In The Park

I find myself normally a pretty early riser compared to most of my friends (although I wish I could force myself out of bed even earlier). Because of this, I am pretty diligent about getting to massive touristy areas early to beat the crowd. Getting to Cloud Gate (The Bean) at 8am was one of the best things I can recommend. You’ll get the better photos and it’s totally worth the extra hour or two of sleep you’ll lose.

I found that walking around Millennium Park and stumbling through the Chicago Art Institute was some of the best experiences I’ve ever had traveling. When I knew I only had a few days in Chicago I wasn’t sure initially if I’d have the time to make it through a museum, and mostly resolved to not pushing to cram it in.

But after a little walking tour from the Bean, I found myself with a museum map in hand and making my way through the highlights of the Chicago Art Institute. One of the best things I did on accident was go in through the back entrance and was able to see a lot of the back side galleries before I collided with the crowds entering from the front.

I saw my first Andy Warhol pieces in person and some of the most stunning stained glass I’ve seen outside of Europe. I’m not a huge museum freak so how much I enjoyed this particular art museum was a little surprising.

Fear of Falling

Even something as terrifying as the Willis Tower Sky Deck was a fond memory. Terrifying because I am absurdly afraid of heights and walking out onto a clear window ledge at any height is nearly impossible for me. I can still feel myself sinking into the fear that took over just stepping out onto the glass, even though it was extremely cloudy that day and clear visibility came and went quickly. I still refused to look down.

Have you ever felt like you were walking on air and just waiting for gravity to do its thing and take you down? Or when you know your feet aren’t planted firmly on the ground and your legs feel like the lightest thing in the world? It didn’t matter how scared I was, I forced myself to sit, and scoot, and make my way onto the 103-story window without looking down.

It was amusing and terrifying and thrilling and entertaining for everyone who witnessed my full blown fear of heights take on a life of its own. But I laughed through the tears and even now as I write this, my heart is beating just a little bit faster.

Home Run

The real star of the show was seeing Wrigley Field. I don’t follow baseball and don’t consider myself a fan. But I do remember watching videos of the Cubs fans reacting to them finally winning the World Series a few years ago and I got emotional. I knew I couldn’t leave Chicago without spending some time in this iconic venue.

It was amazing to see a baseball team play in such a historic stadium with the energy of their fans who never gave up on them. I’ll probably always find myself rooting for the Cubs after that game, and I’m holding onto my Cubs hat for the occasion.

(Side note: don’t have several beers and a shot of Malort before going into the Cubs official shop. You may insist you need a hat and a foam cub claw for no reason at all.)

With a million and one things to do on a weekend in Chicago, a first timers itinerary still seems like a no brainer. I was able to cram all of the major sites in without ever feeling rushed and still having time for pit stops. The highlights of the city really stand out and if I had it to do over again I wouldn’t change a thing.

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