welcome to the neighborhoods

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3-5 Days | 75 Miles | in 4-5 Days, Arts & Culture & History

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experience Chicago's hottest neighborhoods

The best way to get to know a city is to do as the locals do. Stop by the indie shops and authentic restaurants. Participate in a baseball tradition dating back to 1914 at the corner of Clark and Addison. Explore the treasured landmarks only those with a 606 zip code seem to know. Chicago has over 75 community areas, each one full of hidden gems for you to find.

Day 1

Heritage Bicycles

Wrigley Field

Polar Bear at Lincoln Park Zoo

bike the lakefront

There’s no better way to get acquainted with Chicago’s lakefront than biking. Heading north of downtown, many neighborhoods are accessible from the Lakefront Trail and make great spots to explore along the way. In Lincoln Park, stroll through 35 acres of the Lincoln Park Zoo. Grab a coffee in Lakeview and inspect the two-wheeled classics on display at Heritage Bicycles, one of our Illinois Made Makers. Just further north is Wrigleyville, featuring the iconic home of the Chicago Cubs — Wrigley Field. Take a pic outside the iconic marquee and explore all the shops and restaurants in the neighborhood. As you continue on to Andersonville, immerse yourself in the area’s nordic roots at the Swedish American Museum.

Day 2

Bucktown

wander west

Head West to Wicker Park, Bucktown and Logan Square. Browse an eclectic range of literature at Myopic Books in Wicker Park. Or, if you’re more musically inclined, check out Reckless Records for your musical fix. If you’d prefer a more structured start to your day, a Bizarre Bucktown Walking Tour will clue you up on all the hauntings, scandals and more from the now quiet residential area’s past. In Logan Square, a visit to Galerie F or Comfort Station will satisfy your appetite for art, while Katherine Anne Confections has your sweet tooth covered.

Day 3

The Berghoff

American Writer's Museum

Giordano's Deep Dish

Shoreline Sightseeing Architecture River Tour

head downtown

Time to explore downtown Chicago! Start your day with a stroll through Millennium Park and be sure to snap a pic with the iconic Cloud Gate sculpture - a.k.a The Bean. An architecture river tour is the perfect way to take in the skyscrapers while learning about some of the city’s most iconic structures. Chicago-style deep dish is a must — try Giordano’s or Lou Malnati’s. In the afternoon, stop into the American Writers Museum, do some shopping at Illinois Made Maker Optimo Hats, and then continue on to The Berghoff or Russian Tea Time for dinner, both unique culinary landmarks.

Days 4 & 5

The best burger in America? | Au Cheval

The Obama Home

explore cultural hubs

South of the Loop you can find lively neighborhoods like Pilsen, Chinatown, Bronzeville and Hyde Park. From the colorful murals in Pilsen to the incredibly detailed Nine Dragon Wall in Chinatown, there’s so much to discover. The Bronzeville neighborhood is rich in African-American culture — take the young ones for an enriching exploration of the Bronzeville Children’s Museum. The Museum of Science and Industry is located in Hyde Park. Plus you can stroll the tree-lined streets of the adjacent Kenwood neighborhood, perhaps taking a peek at the Obama private residence.

North of downtown is Ravenswood/Lincoln Square, home to KOVAL, the first distillery in Chicago since Prohibition. Avondale is filled with historic buildings like the opulent St. Hyacinth Basilica, plus a wide array of Eastern European restaurants, delis and grocers. Greektown and West Rogers Park (try Nepal House) are also great cultural hubs to explore while you’re in the city. The Fulton Market area (west of downtown) is a great option for dining, including the "best burger in America" at Au Cheval (get in line early!).

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experience Chicago's hottest neighborhoods