Choose a Wicker Park Hotel on Your Visit to Chicago

Stay in a genuine Chicago neighborhood on your visit to the Windy City. Three miles northwest of downtown Chicago, Wicker Park blends historical architecture from the 1880s with a modern cultural scene that made it Forbes’ fourth hippest neighborhood in America in 2012. Walk to Zagat-rated restaurants, unique boutiques and late-night entertainment, and use your Wicker Park hotel as a base from which to explore the rest of the city.

Three young people walk past Noir boutique (1726 W. Division St.) in Wicker Park in Chicago.Division Street

In 1967, Studs Terkel metaphorically titled his collection of Chicago stories “Division Street: America.” Today, most locals associate Division Street with the bars, boutiques and restaurants on the blocks between Hermitage and Damen avenues.

Along this stretch you’ll find The Inn at Ruby Room (1743-45 W. Division St.), the only Wicker Park hotel on Division Street. The Inn’s exceptionally luxurious rooms are tucked away on the top floors of the building beside Ruby Room’s salon, spa and retail store.

Spend your afternoon browsing boutiques such as Parisian-owned Noir (1726 W. Division St.) and scouting Division Street dining spots. Choose a Zagat-rated restaurant like Via Carducci La Sorella (1928 W. Division St.), or get a sandwich at neighborhood favorite Jerry’s (1938 W. Division St.).

View of Milwaukee Avenue in Chicago's Wicker Park neighborhood looking toward the Northwest Tower building.Milwaukee Avenue

Originally a Native American trail, Milwaukee Avenue was first paved with wooden planks in 1848. Today it’s home to an eclectic shopping district where nearly half the buildings were built between 1877 and 1895.

Ramble northwest on Milwaukee Avenue. The Italianate architecture of 1360 N. Milwaukee Ave. was popular in the 1880s. Celebrate the 1980s with the arcade games at Emporium Arcade Bar (1366 N. Milwaukee Ave.) and the DeLorean at Wormhole Coffee (1462 N. Milwaukee Ave.).

Shopping begins in earnest on the 1500 block. Find unusual wares at Una Mae’s (1528 N. Milwaukee Ave.) and Myopic Books (1564 N. Milwaukee Ave.). Study the vintage facades at Aldo (1520 N. Milwaukee Ave.) and John Fluevog (1539 N. Milwaukee Ave.).

North, Damen and Milwaukee Intersection

Looking southeast through the intersection of North Avenue, Damen Avenue and Milwaukee Avenue in Chicago's Wicker Park neighborhood.

Nightlife and history mix at this six-corner intersection. The CTA station was built in 1894, while Blue Line Lounge & Grill was built beneath it in 2002. On First Fridays, tour the hundred-year-old Flat Iron building, and then dance till dawn at Ohm, above the Wicker Park Tavern.

IHSP Chicago (1616 N. Damen Ave.) is the only Wicker Park hotel at the epicenter of all this action. Just beyond the white terra-cotta Walgreens, this hostel offers very affordable private rooms as well as dormitory-style accommodations and a second location at 1755 N. Damen Ave.

A block north, in the midst of designer clothing shops, Urban Holiday Lofts (2014 W. Wabansia Ave.) also offers private and dormitory-style lodging. Located above Olivia’s Market, Urban Holiday Lofts features a penthouse clubroom and bicycle rentals.

The swath of Damen Avenue north of North Avenue is filled with luxury shops like BCBG Max Azria and Marc by Marc Jacobs (1714 N. Damen Ave.). South of North Avenue, look for nationally acclaimed speak-easy The Violet Hour (1520 N. Damen Ave.).

Venture west on North Avenue to music venue Subterranean (2011 W. North Ave.) and restaurant Trenchermen (2037-41 W. North Ave.). To the east, browse boutiques and linger over dinner at Piece Brewery and Pizzeria (1927 W. North Ave.) or The Southern (1840 W. North Ave.).

Two buildings on Leavitt Street in Chicago's Bucktown neighborhood.Bucktown

Continue north on Damen Avenue and cross under the elevated Bloomingdale Trail, a former railroad line, to enter the Bucktown neighborhood. If Milwaukee Avenue’s closely packed shops are a bit frenetic for you, you’ll enjoy the calmer pace of Bucktown.

On tree-lined Leavitt Street, three blocks west of Damen Avenue, Ray’s Bucktown Bed and Breakfast (2144 N. Leavitt St.) is the only hotel in Bucktown. According to Ray’s, they’re also the largest bed and breakfast in the city and the only B&B serving a cooked-to-order breakfast.

Reserve your table for farm-to-table, snout-to-tail food at The Bristol (2152 N. Damen Ave.) or the 11-course traditional Japanese “kaiseki” on Sundays at French-American Takashi (1952 N. Damen Ave.). Stop by Bucktown favorite The Map Room (1949 N. Hoyne Ave.) for your morning coffee and your evening beer, wine or liquor.

When you stay at one of these Wicker Park hotels, you’ll be close to dining on Division Street, historical architecture on Milwaukee Avenue, nightlife at the six corners, and the boutiques on Damen Avenue. Make the most of your visit to the Windy City. Experience Wicker Park, a real Chicago neighborhood.