Summer Road Trip: 36 Hours in Chicago

Selfie central at the Bean, in Chicago.
Selfie central at the Bean, in Chicago. Photo by Dave Emerson Flickr CC

Sweet home, Chicago. Composed of 77 neighborhoods, the Windy City is a national treasure trove of delicious food, exciting nightlife, unique experiences and plenty of tourist attractions. For those who have yet to have the pleasure, Chicago is so much more than the spot for Ferris Bueller's Day Off.

As a lifelong Chicagoan, I'm here to give you a guide to the city from the perspective of someone who actually knows the hidden gems, not just someone who watched The Blues Brothers a lot and knows how to work Google.

First things first, find yourself some free parking on one of the side streets in Wrigleyville. Chicago famously has some of the best public transit in the country, with the Chicago Transit Authority (CTA) train and bus systems the absolute best way to get around the city.

My suggestion is to find a CVS Pharmacy or Walgreens and get yourself a Ventra Pass. You can even request a day pass and spend $10 for unlimited rides on the train and bus. This way, you can travel all the way around the city without having to worry about finding parking or paying the insane parking fines imposed when you accidentally and inevitably park somewhere you shouldn't.

Wrigleyville is the most accessible neighborhood for Clevelanders, because it is arguably the most "proudly Chicago" area in the whole damn city. The bars can be a little bro-ish, but if you've ever hung out on East Fourth Street, you'll feel right at home.

Regardless of your feelings about the outcome of the 2016 World Series, you absolutely have to swing by Wrigley Field. As the second oldest ballpark in the country, there's something magical about visiting the brick and ivy up close.

Grab a Chicago-style hot dog from Byron's Hot Dogs if you haven't gotten your fix from inside the ballpark, and don't ask for ketchup unless you want everyone within earshot to make fun of you. The Graystone Tavern is just down the road, so be sure to stop by afterward and grab a can of Old Style, the Chicago staple and PBR's angry uncle.

Once you've gotten your fix, walk over to the Addison Red Line train stop and head toward the Fullerton stop. It's only a few miles, but you'll thank me for suggesting you take the "L" train.

After you've arrived at Fullerton, it's time to go on a mile walk. You'll pass by the St. Josaphat Catholic Church, a historic and stunning chapel that has to be seen to be believed. You're currently in the Lincoln Park neighborhood, one of the safest and friendliest areas of the city, with some of the most unique shops Chicago has to offer.

Upon completing your mile walk, you should have worked off all of your Chicago dogs and have a belly ready for Chicago-style pizza. Look, I'm sure you've had friends visit the city who will suggest Gino's East, Lou Malnati's or Giordano's, but your friends are wrong and have no idea what perfect Chicago pizza actually tastes like.

Enter the holy grail of Chicago pizzerias, Pequod's. Your mouth never has and never will experience anything like the deliciousness that is a slice of Pequod's. The joint is open until 2 a.m. and tasting the caramelized crust is like what I imagine it would feel like to hold hands with an angel.

Once you've awaken from your food coma, haul ass back to the Red Line station and head to the Belmont stop — we're going to Boystown.

The nightlife in Boystown is unlike anything else. While the neighborhood is traditionally "gay," it's one of the safest places to grab a drink and dance your face off. Town Hall Pub is great for casual fare (and for those afraid of getting hit on by gay dudes); but Roscoe's is the spot to be. If you're looking for something familiar, Replay is like going to 16-Bit Bar + Arcade, and is just as crowded. Sign yourself up for an Airbnb in this neighborhood to experience for one night what it feels like to live in a $3,500 a month apartment.

Saturday morning, grab brunch at the world famous Chicago Diner, one of the oldest and most established meat-free restaurants in the country. Trust me. You'll flip over the vegan food. There are amazing stores like Beatnix and the Hollywood Mirror that are like traveling into a chaotic vintage costume nightmare, but you'll snag some threads you can't find anywhere else.

Once you've settled up, head back to the same train stop, but this time, hop on the Brown Line and take the train to the Washington/Wells stop in the Loop. (Don't worry about your car parked in Wrigleyville. It's safe. Promise.)

Once you're in the Loop, you're in the heart of downtown. From here, your options are endless. You can walk a little over half a mile to visit Cloud Gate in Millennium Park (aka "The Bean") for the ultimate selfie; head over to the Lyric Opera House for a show; visit the multitude of museums; try to win a lottery ticket to Hamilton; flip off Trump Tower; sit on "the ledge" of Willis Tower (the tower formerly known as Sears); donate some spare change to the street musicians echoing bucket drums off of the Magnificent Mile; or admire the Chicago River on the Riverwalk.

Personally, I'd get the hell out of that tourist nightmare, but I also accept that out-of-towners are going to want to visit these landmarks. One of my favorite hidden spots is the Buckingham Fountain in Grant Park. As one of the largest fountains in the world, you may remember it as the opening shot from Married ... with Children. Grant Park is also just a gorgeous walking spot, filled with interesting sculptures, that is normally less bombarded with people than Millennium Park.

For lunch, you can go with classic Chicago fare like Miller's Pub or, my personal favorite, FlatTop Grill. If you like Mongolian BBQ in Coventry, you'll lose your mind over FlatTop. There are other Chicago staples in the area like Al's Beef for the tastiest Italian beef you'll ever eat in your life, or Max's Takeout if you couldn't get enough of the dogs from yesterday.

If you want to check on that car of yours, hit the Red Line back to Wrigleyville; but once you're done, hop on the Blue Line from the Addison station and head in the direction of Logan Square.

Logan Square is like if Lakewood and Cleveland Heights had a fist fight and then made a baby together. It's artsy but tough and filled with wild nightlife that will impress even the most hipster-y of hipsters. After all of your sightseeing, you should probably be ready to grab a drink.

My suggestion will always be the Rocking Horse Chicago Bar and Tavern. I've had many a night at the Rocking Horse, some I can remember, some I cannot, and Malort is 100 percent to blame.

Regardless, get anything on the menu: It's all delicious. The Cold War burger is unreal, and you'll be shocked that food this good comes from what is largely considered a dive bar. Unique shops surrounding the square, such as Toy de Jour, will ease your sadness over the closing of Big Fun. I'd also suggest Bric-A-Brac record store to grab some hard-to-find-favorites and a visit to their giant mural of Robocop busting through a wall.

Hop back on the Blue Line and head to the Western stop. We're going to Wicker Park/Bucktown. These neighborhoods are similar to Logan Square but have the odd sensibilities of what you'd expect in Gordon Square.

Grab a late-night play at the Trapdoor Theater in Bucktown or enjoy some local live music at the Empty Bottle. Whatever you do, make sure you wind up at the Blue Line Lounge and Grill for martinis so strong and delicious, you'll forget why you live in a city where drinks are less than $10 a pop.

Before the trains shut down for the night, hop back on the Blue Line to Wrigleyville. You should check on your car and crash for the night somewhere fancy, like the Hotel Zachary at Gallagher Way.

In the morning, hit up Pick Me Up Cafe; it's another vegan brunch spot, but I'd argue that vegan food is best in the mornings. If you're sick of vegan fare, Uncommon Ground has an organic rooftop farm guaranteeing their grub is some of the freshest you'll ever consume.

On your way out of the city, be sure to make a detour to visit Navy Pier. If the giant Ferris wheel can't put a little joy in your life, I don't think anything will.

Are there more traditional landmarks, like the Shedd Aquarium and the Adler Planetarium, Daley Plaza, the Second City, Lincoln Park Zoo, the Observatory on the John Hancock building, Water Tower, Soldier Field, and everything else your parents have probably taken you to on family vacations? Of course. But to experience Chicago like a Chicagoan, you need to think a little outside the box of John Hughes movie landmarks.

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