Booking a hotel in an urban neighborhood provides a visitor with the tools to feel like a local — and for Chicago-bound tourists seeking out a hipster vibe, the Wicker Park/Bucktown area is the place to be. Here, you'll find the addition of the 606, Chicago’s version of the High Line, where you can rent a Divvy bike or jog along the paved 2.7-mile path carved from abandoned elevated rail line. Below, you’ll witness streets filled with locally owned boutiques, bistros, and bars (with a few chain stores and juice shops thrown in).
Perfect for all budgets are the neighborhood’s music shops and bookstores. Head to Myopic for poetry readings, live music, and used books or grab a beverage at Volumes Book Cafe. Fans of vintage records will find their heads — and their turntables — spinning. The vinyl frontier includes Dusty Groove, Reckless Records, and Shuga. And there's plenty of places to eat, drink, and sleep. From budget to splurge, here's our guide.
Where to Eat: There are plenty of cheap eats in this area. Try Irazu for a Costa Rican take on Latin American cuisine. You can grab three empanadas for $9 or casado, a typical Costa Rican meat and rice dish for $15. It’s open for breakfast, lunch, and dinner. Need a snack? Try the horchata or a uniquely flavored shake. Just bring cash — they don’t take credit cards. Continuing the international cheap eats theme, En Hakkore dishes out bibimbap bowls ($9) and Korean-inspired tacos (two for $8).
What to Do: By day, hang out at Wicker Park. The park for which the neighborhood is named is a playground for kids and adults. In addition to its sports fields, the park often hosts free movie nights and farmers markets. By night, sneak into the Hideout, a Prohibition-style bar with live music. From January to April, there’s free soup and bread, made by local foodies and artists; your donations go to local food banks.
Where to Stay: Urban Holiday Lofts offers up shared rooms with shared baths, along with private rooms with shared or private baths. Don’t be surprised to be sleeping in a bunk bed, though. The rooms are barebones (no TVs, no lotion), and the lobby is a bit dingy, but the place is certainly well-located, and it has convenient amenities like free breakfast, a common room with a pool table and television, and a guest kitchen. (Dormitory style room with shared bath go for $39 per night; private room sleeping up to four with private bath: $137.)
Where to Eat: Enoteca Roma is one of those family-run Italian joints with scratch-made food and a rustic feel reminiscent of the Old Country. On a nice day, mosey to the back patio for an al fresco dinner (a pizza for $20 and plenty of wines for less than $10 a glass). Despite its name, Dove’s Luncheonette provides counter service for three squares a day. Menu items (between $12 and $17) are inspired by south of the border and Southern fare.
What to Do: Head to Trap Door Theatre for avant-garde performances of challenging and obscure works. The Den Theatre has five unique venues, which present productions developed by its multiple resident companies. After a show, head to the Den’s bar for live music. (Ticket prices average about $25 each.)
Where to Stay: The Robey ($250 per night) has the same high design and unique amenities sported by many of the downtown hotels, but at a cheaper price tag. Located in an Art Deco building at the triangular intersection of Damen, Milwaukee, and North Avenues, the hotel offers easy access to the city. If you have a choice, go for the extra-roomy industrial-style rooms in the Annex Loft. The El’s Blue Line, which runs downtown and to O’Hare Airport, is right next door (and can be heard from some rooms — so if you are a light sleeper, be sure to ask for a room on the quiet side).
Where to Eat: Mirai Sushi is a stylish sushi and sake bar. The menu includes the standard items you’d expect, plus more creative fare. For sushi, it’s not that expensive, but is still one of the pricier restaurants in the neighborhood with shared plates that run $7-$17. Another nice date night option is Cafe Robey, serving upscale American fare.
What to Do: It’s not a huge splurge, as entertainment options in the neighborhood aren’t excessively pricey, but WhirlyBall offers bowling, laser tag, and Whirlyball courts that can keep anyone entertained for hours. What’s Whirlyball? It’s a made-up sport that marries lacrosse and hockey and involves riding around in souped-up bumper cars. Fuel up before, during, or after your session at the on-site bistro. ($15 per per for a half-hour; bowling starts at $60 per hour for 8 people.)
Where to Stay: The Hotel at Midtown is on the northernmost end of Bucktown, and while it feels a bit isolated from the rest of the neighborhood, it's an easy 10-minute walk to the main drag. Even though it’s the highest-priced hotel in the neighborhood, consider that the cost of your room (plus the $25 a day resort fee) gains you free entry into the fancy-schmancy Midtown Athletic Club. In addition to having access to the latest gym equipment, you can choose from dozens of daily classes, ranging from barre to yoga, without paying extra for the privilege. (Rates go for $250-$300 per night plus the resort fee.)