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 my 3 days in Chicago began. I walked in, opened the fridge, grabbed a drink and sunk myself comfortably into its worn in sofa.
I only had a 3 days to spend in this new city. By the end I 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.
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Where to Stay
I arrived at the The Warwick Allerton only to learn that a large quantity of hotels in Chicago were on strike. This made for an interesting first night because there were no rooms ready when I got there. I made the best of it though 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.
A City to Remember
The thing that struck me most about Chicago was that everything I did was 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.
Do Not Miss the River Architecture Tour
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. I chose it 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. It flows right through downtown and reflects all the gorgeous architecture. It makes Chicago truly one of the most picturesque cities I’ve been to. A river cruise is seriously the best way to enjoy it.
Get up early for a walk in the park.
I find myself normally a pretty early riser compared to most of my friends. Even though I wish I could force myself out of bed even earlier sometimes. But 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 did. You’ll get the best photos and it’s totally worth the extra hour or two of sleep you’ll lose. Then you’ll have ample time to walk through Millennium Park.
I found that wandering the park and stumbling through the Chicago Art Institute was one 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.
Make sure you go to the Art Institute of Chicago.
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. I accidentally went in the back entrance which I would recommend. I was able to see a lot of the back side galleries before I collided with the crowds entering from the front.
The most memorable exhibit was the Andy Warhol gallery. I also saw 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 at the Willis Tower Sky Deck
Even something as terrifying as the Willis Tower Sky Deck was a fond memory. Terrifying because I am absurdly afraid of heights. 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, it was still scary. I refused to look down.
Have you ever felt like you were walking on air and just waiting for gravity to do its thing? 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 of the Willis Tower without looking down.
It was amusing and terrifying and thrilling and entertaining for everyone there. They 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.
See the Cubs game at Wrigley Field
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.)
There’s a million and one things to do in 3 days in Chicago. But 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 having time for pit stops. The highlights of the city really stand out. If I had it to do over again I wouldn’t change a thing.