Explore Chicago Through the Eyes of a Texan

Travel Pick

The thing about Chicago is that there are a lot of things people will tell you all about Chicago: The public transportation is great, but keep your wits about you on the L’s Red Line. Check all the tourist boxes (Magnificent Mile! Italian beef! That shiny, shiny bean!) and wander outside the Downtown Loop. You can’t toss deep-dish pizza dough without hitting a world-class restaurant, but dirty martinis until closing time at 4 a.m. is called a Set-Up-To-Fail any day of the week. The winters are brutal, but the summers make up for it.

I can vouch for all of these things. Due to an impending move, I spent my summer holiday exploring my new city and found these things to be true.

But there are also many things for which I cannot vouch. A born-and-raised-and-then-some Texan, more than one Chicagoan has gently, but correctly, guessed my state of origin. (What gave me away? That the martini was Tito’s, or that in drinking it, I immediately assumed my mom’s accent?) I don’t claim to know all there is to know about the Windy City, perhaps best articulated by the fact that I just used that tired epithet. But I have listened to the things people have told me about Chicago and checked them out for myself; now I’m humbly here to share them with you.

Let’s start with the obvious: Visit before snow hits the ground. August through October is a sweet spot, with festival season still in swing and temperatures easing up into fall. Lollapalooza will take over the city the first weekend of August (2-5) in Grant Park, trailed by local favorites like the Randolph Street Market (25 & 26) in the West Loop and the Chicago Jazz Festival (August 30 – September 2) at Millennium Park.

If you visit on a weekend without festivities, you can enjoy the Lakefront Trail with a little less foot traffic. The paved path runs past 13 neighborhoods and along 18 miles of Lake Michigan shoreline. (A thing people will tell you about the lake is that it’s huge and you won’t understand how huge it is until you see it. This is true.) While walking or biking (Divvy bikes can be rented throughout the city for $3-a-ride for up to 30 minutes) along the trail, good stops include the Field Museum and the Art Institute of Chicago toward the southern end, past Navy Pier near Streeterville, and up to the free Lincoln Park Zoo. Bonus: The trail just north of Oak Street Beach offers a picture-perfect view of sand-meets-land.

From high up, the best view of the Third Coast is at the top of Hotel Lincoln. Its rooftop bar, The J. Parker, is ideal for a pre- or post-dinner cocktail with a sea-blue backdrop. For city views, the Up rooftop lounge at The Robey hotel boasts a 180-degree of the historic skyline from the west Chicago neighborhood Wicker Park. The art deco boutique hotel, which was originally designed in the ’20s as an office building, opened last year at the corner of Damen, Milwaukee, and North avenues. It’s definitely my pick for a stay a little outside of the well-traveled path, but head to the West Loop’s Ace Hotel if you want somewhere more central.

Next up, the less obvious: where to eat. This is a topic people will tell you the most things about. The good news is that there’s an ever-growing number of restaurants in the city, from multiple Michelin-star spots to the new 6,000-square-foot McDonald’s inside the brand’s new West Loop global headquarters. Here are some picks in between for where to dine and drink.

Piccolo Sogno follows through on its translation. Italian for “little dream,” the West Loop restaurant can be spotted by its tiny yellow “tent-rance” and navy façade. The menu is refined, rustic Italian and is complemented by a lovely wine list. I still think about its pappardelle con cinghiale (pasta with spiced wild-boar ragu). I’m unsure if Portillo’s, which has 35 locations around Chicagoland, is sit-down or fast food, but everyone has an opinion on it. For that reason alone, eat a hot dog there and don’t put ketchup on it. If you really want to make the effort, venture into the wild and eat a dog at a joint whose sign proudly displays the blue-and-red Vienna Beef logo. Continue to nix the ketchup. Depending on the time of day, get breakfast or dessert at Dinkel’s Bakery, a fourth-generation German spot in Roscoe Village.

The same rule for food follows for where to grab drinks. River North’s Green Door Tavern, built the year after the Great Chicago Fire, is one of the few remaining wood-frame structures downtown. Beneath the pub is an actual speakeasy from Prohibition days, now called The Drifter. Great cocktails and quirky burlesque shows are worth the wait, so put your name on the list and grab a beer upstairs until your table is ready. Another hidden gem is Three Dots and a Dash, a tiki dreamscape whose entrance is marked by torches in a River North alleyway. I don’t really care what you do as long as you end up at Second City for its main-stage revue, “Dream Freaks Fall From Space.”

I’ve made peace with the fact that one Chicagoan’s tourist trap may be a Texan’s treasure. I’ve snapped pictures from an Architecture Foundation River Cruise and been a band-wagoner at Wrigley Field. You should too.

Photographs courtesy of Adrian Gaut, Anthony Farinas, Choose Chicago, Galdones Photography, and Spencer Lowell.