Chicago

Chicago Travel Guide

Chicago’s diverse blend of design, art, culture, music, and architecture means you’ll never run out of things to do in Chicago. For a relaxing, loosely structured day, visit Millennium Park to take in views of the Chicago waterfront and admire Cloud Gate, Chicago’s famous reflective bean sculpture. Stimulate your artistic side with a visit to Museum Campus, which houses three museums in one, and showcases the world’s most complete Tyrannosaurus skeleton, among other amazing treasures. One of the most popular things to do in Chicago is to visit the Chicago Blues Festival. Taking place over three days and across five stages, this festival, celebrating Chicago’s foundational role in the blues movement, draws more than half a million fans from around the world to celebrate the scene’s past, present and future. Created in 1984 to honor Muddy Waters, one of the progenitors of the Chicago blues style, the festival has hosted famous performers like BB King, Ray Charles, Bonnie Raitt, and Chuck Berry. (Jazz lovers can take in the Chicago Jazz Festival, too).

More cerebral Chicago activities come courtesy of the Chicago Architecture Foundation, which operates nearly 90 different tours, which you can take by boat, by bus, or on foot, and which cover everything from the city’s ultramodern skyscrapers to the historic downtown district and tours of various neighbourhoods. The foundation also organizes an Appetite for Design series, which merges culinary and architectural appreciation at some of Chicago’s top restaurants.

River North’s neighborhood blues bar, Blue Chicago is notorious for its songstresses. Grana Louise, Big Time Sarah, Laretha Weathersby, Dimetria Taylor, and Shirley Johnson are just some of the blues women who shake up the stage. Catch remarkable acts, nightly.

Shopping on Halsted is plentiful, but MOI Boutique stands out. Occupying a cozy space on the trendy street, the shop features feminine clothes at moderate prices. Pick up a flutter-sleeved dress and white blazer.

In a neighborhood dotted with music venues, this instrument shop fits right in. Even if you’re not in the market for a vintage Fender, the sheer number of guitars in this place is remarkable, making it seem more a museum than a store.

This delightful nonprofit boutique sells fair-trade and eco-friendly clothing, jewelry, housewares, and foodstuffs from artisans in more than 60 countries. Pick up a recycled messenger rice bag made by artisans in Cambodia or a Tornillo wood platter made by Peruvian carvers.

Those on the hunt for soul classics—as well as classic and contemporary jazz, funk, and reggae beats—can easily kill a day digging in this renowned record shop’s bins overflowing with CDs, LPs, 45s, and other music of the nondigital and downloadable variety.

Vintage furniture, local art, grilled sandwiches, and locally roasted Metropolis coffee beans are the stars of this hipster hangout, which dominates the corner of Logan and Milwaukee.

On a clear, warm day, admire Chicago’s architecture from a unique vantage point: the Chicago River. Wateriders offers guided kayak tours through downtown Chicago for a truly one-of-a-kind sightseeing experience that includes Willis Tower, Wrigley Building, and Merchandise Mart.

The airy, bright atmosphere of Greektown’s Atropolis is a welcome respite from the concrete of the city.

A distinguished independent research institution with over 1.5 million books, the stately Newberry Library holds free exhibitions and lectures, all open to the public. Whether or not you’re in the mood to crack some spines, the magnificence of the building itself is worth the visit.

Founded by two Polish brothers, Gene’s boasts 40 varieties of artisan smoked meats and naturally cased sausages, prepared in-house, as well as an equally impressive assortment of imported beers and wines, and European candies, condiments, and foodstuffs for picnicking.

Specializing in artisanal cheese, bread, and wine, Pastoral is a neighborhood favorite. Its sandwiches, made with crusty bread from beloved Bennison’s Bakery and stacked with top-quality meats and cheeses, are some of the best in the city.

Experience downtown at your own pace with Chicago’s Hop On Hop Off Tours. Tours leave from 14 downtown locations every 20-30 minutes. Visitors can buy tickets at various locations, including the Park Shop below the Bean in Millennium Park or online.