Beyond deep-dish pizza and Navy Pier: here’s how to see and experience the real Chicago.
As a mecca for architecture and the leading cultural capital of the Midwest, if Chicago is not on your radar than it definitely should be. Lake Michigan’s ribbon of blue rims the far eastern edge of this city (the country’s third largest, after New York City and Los Angeles), including in the Loop, and neighborhoods—from Chicago Cubs fever in Wrigleyville to River North’s trendy eateries—are destinations all on their own.
Don’t miss more helpful Fodor’s Chicago Travel Tips online, or with the indispensable Fodor’s Chicago guidebook, or with Fodor’s Ultimate Things to Do in Chicago Guide. Need a place to stay while you’re in town? Here are some Chicago hotels great for proximity to historic landmarks or featuring design-centric architecture.
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Don’t Fly in and out of O’Hare
O’Hare International Airport is barely even in Chicago. It’s a 45-minute car ride from downtown in far northwestern Chicago. While you can hop “the “L” (the elevated train) Blue Line between the airport and downtown for a hands-off one-hour trip, this still cuts into vacation time. Midway International Airport on the South Side is serviced by Southwest Airlines and Delta Airlines. The Orange Line’s trip into downtown Chicago is only 40 minutes. Midway welcomed a new food hall earlier this year in Concourse A that includes Billy Goat Tavern & Grill, an Irish pub and Woodgrain (Neapolitan-style pizza).
Don’t Book a Chain Hotel
Twenty years ago, Chicago’s hotel roster—particularly in the Loop—featured all the big brands, but thankfully there are now a slew of cool boutique hotels to book a night or two at. This year’s newcomers include St. Jane Hotel (inside a gorgeous Art Deco building on North Michigan Avenue) and in recent years Kimpton Gray debuted in the Loop with a Mad Men vibe while Hotel EMC2 is a quirky ode in River North to, of all people, Albert Einstein. You might even want to eat dinner and order a drink at these hotels because they are that awesome.
Don’t Visit Only the Art Institute of Chicago
This revered art museum on South Michigan Avenue, flanked by two stone lions out front, gets all the credit for Chicago’s rise as an arts destination—but few shows feature local artists. To witness homegrown talent that’s more edgy and experimental, spread your wings a bit and check out Museum of Contemporary Art Chicago in the Streeterville neighborhood just north of downtown Chicago or Chicago Cultural Center, just four blocks north of the Art Institute along North Michigan Avenue.
Don’t Visit When It’s Cold
Like most Northern cities—from Amsterdam to Boston—shoulder seasons of fall and spring are the best time to visit. You aren’t slipping and sliding on icy pavement and the wind chill is a non-issue. Traveling to Chicago during a warmer month means you can dip your toes in the sand at one of the 26 beaches dotting the Lake Michigan shoreline. Oak Street Beach at 1000 N. Lake Shore Drive is easy to get to from downtown and the Near North Side, while Shore Club at North Avenue Beach is worth the trip for its chic SoCal environment.
Don’t Waste Money on Broadway Shows
We’re not saying you shouldn’t go to the theater. Just think outside of the box here. All the Broadway musicals and household-name shows (like Hamilton and Book of Mormon perform in downtown Chicago and ticket prices are steep. Support homegrown thespian talent at the Neo-Futurist Theater (think two- to three-minute plays in rapid succession, $10-$20) on the North Side or a comedy act at Second City (if you roar with laughter at Saturday Night Live, this is your place, $23-$80). You just might meet the next SNL cast member (many started out here).
Don’t Drink Solely Goose Island Beer
Every city has “its beer” and for Chicago, that sudsy anchor is Goose Island Beer Company. But the problem is that you can find this beer outside of Chicago quite easily. Shift your palate to the local craft-beer scene instead. Something like 20 craft breweries have opened in Chicago within the last five years. Each taproom has a unique personality, from the historic-turned-haute Motor Row Brewery (check out “Blues and Brews” Monday nights) or Band of Bohemia’s Ravenswood perch—and the very first Michelin-starred brewpub, where menu items are cooked on a wood-burning grill by Alinea alum.
Don’t Only Shop on Michigan Avenue
Once you’ve got your Burberry trench coat or Top Shop outfit at one of the big retailers along North Michigan Avenue (affectionately dubbed “The Mag Mile”), leave the area immediately. Eclectic boutique shopping lies in Old Town, including a quirky general-store type concept from actress Joan Cusack called Judy Maxwell Home. Armitage and Halsted Avenues in Lincoln Park are where you can pick up Warby Parker specs or antique furniture at Revival.
Don’t Cheer for Only the Cubs
While the Chicago Cubs winning the World Series in 2016 definitely went down in the history books (it was the team’s first World Series win since 1908), don’t forget there are other sports teams. The Chicago Bulls are the city’s NBA team and play home games at the United Center (as does NHL team Chicago Blackhawks, who have won six Stanley Cups since 1926); and the Chicago Bears’ NFL home games at Soldier Field are convenient to downtown Chicago. Home field for Chicago’s other MLB team, Chicago White Sox, is at Guaranteed Rate Field.
Don't Wait in Line for the Willis Tower Skydeck
It’s imperative that you get schooled on Chicago’s amazing architecture. However, waiting in line and plunking down $24 to view it from the top—via Willis Tower’s Skydeck, which features a cantilevered glass-floor ledge on the 103rd floor—is not the only way. Nor is it the best way. Chicago Architecture Foundation offers 1.5-hour-long guided riverboat cruises on the Chicago River that sprinkle in facts and stats about the buildings seen along the way. Or take a walking tour, also hosted by the foundation’s docents.
Don't Confine Yourself to the City Limits
Seasoned travelers know to stray beyond the city center. But do you know which Chicago ’burbs to check out for dining, entertainment, attractions, and outdoor adventure? If you’re an architecture buff, head to Oak Park, the birthplace of Frank Lloyd Wright and where he raised his own family (learn more in an hour-long guided tour of the Frank Lloyd Wright Home & Studio). Highland Park’s Ravinia is the country’s first outdoor-music pavilion and the summer home for the Chicago Symphony Orchestra. In Evanston, you can easily find culture and art—including at Northwestern University’s Block Museum of Art—plus cool shared-plate restaurants like Found.