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How to Plan the Perfect Weekend in Chicago

Explore lesser-known spots on your next jaunt to the Windy City.

U.S. News & World Report

How to Plan the Perfect Weekend in Chicago

Chicago skyline

Beyond its thriving dining, fashion, arts and music scenes, the Second City's architectural gems and under-the-radar enclaves are sure to charm you.(Getty Images)

The Windy City, with its diverse neighborhoods, architectural splendors, flourishing dining scenes and innovative cultural attractions in its 230 or so square miles, draws visitors far and wide. From world-class museums to thriving theater and music scenes, Chicago's multi-faceted art community is reason enough to visit. Tack on a seemingly endless list of outdoor sights, brand-name shops on the city's iconic Magnificent Mile and one-of-a-kind restaurants, and your Chicago vacation itinerary may seem overwhelming. Well, never fret: After you've crossed Chi-town's can't-miss attractions off your list, make your way to these under-the-radar gems for a weekend getaway to remember.

Embrace the Great Outdoors

Chicago offers much more than top-tier dining and shopping experiences. If you're planning a trip in spring, summer or fall, make sure to take advantage of the outdoors when you're in town – you'll be glad you did. Take a break from taking in the city sights to explore the Chicago River by canoe or kayak. With guided tours available through reputable outfitter Chicago River Canoe and Kayak, you don't have to be a pro to take part in a Chicago River adventure, and chances are, you'll get to see some wildlife too. If you would rather run, bike, swim or enjoy a leisurely coffee along the beach, Jane Addams Memorial Park, a quaint green space, is centrally located next to the Lakefront Trail, Navy Pier and Ohio Street Beach.

Pop into Cutting-Edge Galleries

Home to the famous Art Institute of Chicago, Chi-town is also home to plenty of local galleries – so many, in fact, you'll need much more than one afternoon for a proper Chicago art gallery crawl. While the Chicago Cultural Center might already be on your list of things to see while in Chicago, you may not realize everything the Center has to offer. Previously the central library building, the Chicago Cultural Center is home to two stained-glass domes and plenty of art exhibitions. The Center also hosts film screenings, performances and lectures – all with free options for the community. Meanwhile, the McCormick Gallery, which is known for its post-war abstract expressionist pieces showcases artwork from both contemporary and 20th-century artists. Past exhibitions have included the works of Samuel Feinstein, Vivian Springford and Robert Natkin.

Take a History Lesson

While you can learn quite a bit about Chicago's history with a guided tour, there are a few historic spots across the city you may not immediately think to check out. Political wonks shouldn't miss the opportunity to check out President Obama's campaign headquarters. The 11th floor of the Illinois Center along North Michigan Avenue was home to Obama's 2008 campaign office headquarters, while the entire first floor of One Prudential Plaza on East Randolph Street housed Obama's 2012 campaign headquarters. If you consider yourself a news junkie, head to Tribune Tower on North Michigan Avenue. From the exterior of the Tribune Tower, you'll find elements from a variety of historic sites from around the world. Some noteworthy fragments include pieces from Abraham Lincoln's tomb, the Sydney Opera House the World Trade Center and the Salt Lake City Mormon Temple.

Unleash Your Inner Bookworm

For those looking to browse through the novels lining well-stocked shelves, Chicago overflows with bookstores geared toward lit fans. After-Words' two floors of 70,000-plus new and used books is impressive, as are its entryway book displays. Meanwhile, Open Books is the only independent bookstore in the West Loop, and as a literacy nonprofit that provides reading and writing programs for thousands of students every year. Plus, Open Books' impact goes far beyond the West Loop neighborhood, as their programs serve students all over the city. Even better, all of the store's proceeds are distributed to literacy programs in Chicago.

Discover Under-the-Radar Restaurants

The dining choices are endless in Chicago, but two crowd-pleasing local haunts in particular are worth noting. Greek Islands, which is set in the popular Greektown neighborhood, first opened its doors in 1971, and has continued to cultivate strong roots in the city's food scene since its debut. With ingredients shipped directly from Greece, you can count on an authentic meal. Saganaki is a popular appetizer here, where servers joyfully shout "OPA!" as they bring out this flaming cheese treat to you. Meanwhile, Art Smith's farm-to-table inspired Blue Door Kitchen & Garden opened to the public in July 2016, but as already developed a loyal following. Formerly Oprah's personal chef, Smith named Blue Door Kitchen & Garden after Oprah's farm in Indiana, Blue Door Farm. You can still find Art's famous fried chicken here as well as Oprah's favorite hummingbird cake.

About En Route

Practical advice on the art of traveling smarter with tips, tricks and intel from En Route's panel of experts.

Contributors have experience in areas ranging from family travel, adventure travel, experiential travel and budget travel to hotels, cruises and travel rewards and include Amy Whitley, Claire Volkman, Holly Johnson, Marsha Dubrow, Lyn Mettler, Sery Kim, Kyle McCarthy, Erica Lamberg, Jess Moss, Sheryl Nance-Nash, Sherry Laskin, Katie Jackson, Erin Gifford, Roger Sands, Steve Larese, Gwen Pratesi, Erin Block, Dave Parfitt, Kacey Mya, Kimberly Wilson, Susan Portnoy, Donna Tabbert Long and Kitty Bean Yancey.

Edited by Liz Weiss.

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