My 72 hours in Chicago were…. sweaty. I happened to visit on a weekend of “record-breaking temperatures” in the mid to high 90s. Not exactly ideal for exploring a city, right? (We talked about this in my post about why I hate summer travel). But I made the best of it and even though we skipped a few things due to pure heat exhaustion, still saw plenty of awesome stuff in the Windy City. I also spent a lot of time in air conditioned bars. Don’t judge.

Things to Do in Chicago

On Friday, we were all about snapping the city’s impressive skyscrapers from every point of view. We began by walking along the river on our way to Millennium Park to see The Bean. You can’t visit Chicago without taking a photo by this iconic sculpture, formally called Cloud Gate.  By the time we got there, however, we were literally dripping in sweat. Not exactly photo-ready!

We spent the rest of the morning and early afternoon wandering around the city, in awe of the ridiculously tall buildings. Chicago is so shiny and fancy looking. New York City’s skyline might still win in a fight thanks to how long it goes on for, but the Chicago buildings are definitely more interesting to look at (and a lot more photogenic).

Speaking of the buildings, the best way to learn about them is the Chicago Architecture Foundation River Cruise. While I’m not that interested in architecture (confession: architecture tours in Italy made me yawn), literally every single person who I told I was going to Chicago recommended this one. And since it was on a boat that had a bar, it couldn’t be too bad, right?

Well, despite the oppressive heat, it was actually awesome and informative. There was a story for every building we went by, and the tales were really interesting. For example, one building used to be a cold storage facility, and when it was converted into offices, the developers had to take time out to let it defrost. And the Merchandise Mart, which has a whopping 4.2 million square feet of space, was the largest building in the world when it opened in 1930. It was so big that it even had its own zip code until 2008!

While the view from the river was awesome, I still wanted to see the city from above. One of the best places to do just that is The Signature Lounge on the 96th floor of the John Hancock Tower. No reservations are necessary – you can simply show up and wait for a table to have a drink in the sky. We were lucky enough to snag the place’s best seats, right next to the window overlooking the skyline and Lake Michigan.

I probably took about 100 photos because… that view! But what really entertained us were the spiders. Yes, somehow spiders made it up to the 96th floor of a building. Normally these creatures freak me out, but since they were on the other side of the window, I was fine. We probably spent an hour trying to take weird spider photos and make it look like they were attacking the city and/or climbing the towers. I’m 26 years old, I swear.

Aside from a stroll down The Magnificent Mile, the famous shopping district along Michigan Avenue, we didn’t really hit up any additional tourist attractions after the first day in Chicago. It was simply way too hot, and all we wanted to do was sit and sip on cold beverages.

Places to Eat in Chicago

After landing on Friday morning I was absolutely STARVING and immediately started Yelping breakfast spots within walking distance of our hotel, the Courtyard Marriott in River North. We found a great spot called Yolk, which basically served every brunch dish you could ever imagine. Five different versions of eggs benedict? I’m sold.

Another delicious breakfast spot in Chicago was actually located inside our hotel. Typically hotel restaurants give me a case of the eye rolls, but the Italian-inspired brunch dishes at Davanti Enoteca were amazing to literally roll out of bed and eat.

If you’re into Greek food, you’ll definitely want to check out Greektown, a historically Greek neighborhood that’s still home to numerous authentic restaurants. After walking around, we decided to eat at Athena Restaurant, which clearly won for best patio. I mean, in addition to views of the Chicago skyline, it had a waterfall! The food was pretty good too.

My favorite neighborhood that I visited during my 72 hours in Chicago was Wicker Park, a quieter, greener neighborhood west of downtown on the Blue Line. It’s a little bit hipster. I mean, we waited out a rain storm in an arcade bar and when you get off the “L,” you’re met with a mural of a can of PBR.

Wicker Park has a ton of fun restaurants and bars. If you like to shop for souvenirs when you travel, definitely check out Transit Tees, a boutique selling locally-produced Chicago apparel and home wares.

I am absolutely addicted to tacos, so while in Wicker Park I couldn’t miss eating at Big Star, the city’s most famous taco joint. While the atmosphere inside was lively and fun, and I couldn’t complain about the drinks, I sadly did not love the tacos. It was disappointing after all the hype.

Fortunately I happened upon a better taco experience nearby by chance…

One of the coolest gems we found in the Wicker Park/Ukrainian Village area was a liquor store that was also a bar called Rite Liquors. I don’t know why I found this to be awesome, but it was. Why hasn’t anyone in Boston thought of this? I’m sure we have some weird Puritan law banning it. But anyway, apparently Chicago has quite a few bar-liquor-store combos, according to Time Out. Sadly we weren’t able to get the alcoholic root beer we wanted at the bar (again, yes, 26 years old), only the check out, so we had to take ours to go.

We couldn’t actually drink our adult root beers on-the-go since that’s, like, illegal. So we stumbled upon a place called The Tamale Spaceship that was BYOB. We weren’t that hungry, but went inside and ordered some tacos so we could sit down and enjoy our beverages.

Best. Tacos. Ever. OK, that’s probably an exaggeration, but the cochinita pibil tacos rivaled those that I had when I was actually in the Yucatan, Mexico.

So I’ve talked a lot about food, but you really can’t go to Chicago without eating hot dogs and deep dish pizza. That would be like going to NYC and not getting a bagel. Blasphemous!

I’m not going to debate whether the hot dogs and pizza I had are the best because in my experience, people get very stirred up about these types of things. All I can say is that both were delicious, and I recommend consuming them.

Hot Dogs: Portillo’s. Yummy and open late at night for post-bar snacking.

Deep Dish Pizza: Gino’s East. I thought it was cool that the restaurant was also a brewery serving their own beers. The pizza, my last meal in Chicago, definitely held me over for the flight back to Boston.

So lesson learned: don’t visit Chicago in the smack dab middle of summer if you’re planning to try and see the entire city in a weekend. You will need a lot of water breaks, air-conditioned-bar breaks and cold-hotel-room breaks. Oh, and don’t forget to pack sunscreen. Trust me on that one!

• *I spent 72 Hours in Chicago in July 2015.
• *I was able to redeem American Airlines miles (earned through the Barclaycard credit card sign up bonus) for the flight there on Friday, and flew back on Southwest for $189.
• *We stayed at the Marriott Courtyard in River North, a neighborhood very conveniently located for tourists. The rate, via Hotels.com, was $250 per night and we split that between four people. It was $125 total each for the weekend.
• *I worked remotely on the plane in the morning on Friday and took the rest of the day off.

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