Chicago Travelers Recommend - page 2

Home to everything from bars and craft breweries to comedy clubs and critically-acclaimed restaurants, the Windy City has a lot to offer after the sun sets. Here are a few of the best ways to spend an evening in Chicago. 

Prohibition-Themed Excursions

Chicago’s insalubrious past has since become part of the Windy City’s allure; 1920s and ’30s-themed tours typically introduce you to former residents such as Al Capone and visit some historic speakeasies. Book an evening excursion to discover local history and enjoy classic cocktails in flapper fashion.

Craft Beer Crawls

The existence of dozens of breweries show that Chicago takes its beer seriously. Explore some of the city’s pioneering breweries and destination-worthy bars on a bar crawl or freewheeling beer tour, and leave the logistics (and driving) to your guide.

See a Show

The Windy City is packed with theaters and performance venues, all of which offer after-dark entertainment. If you’re visiting with kids, take in a blockbuster musical at the Loop’s historical theaters. Or, if you’re into late-night laughs, Chicago has a surfeit of comedy clubs, including the renowned Second City.

Dinner Cruises

Combine sightseeing with dinner on an evening cruise of the Windy City’s waterways. Whether you sail on the Chicago River or head to the waters of Lake Michigan for glittering skyline views, you’ll enjoy gourmet eats, delectable wine pairings, and incomparable scenery. 

Many well-known Chicago landmarks are celebrated the world over, from the Willis Tower and Millennium Park to the Art Institute. But there’s more to the Windy City than meets the eye. Step off the beaten path, and see a side of the city that many visitors miss at these unconventional Chicago attractions.

Prairie District

A quick trip from the architectural behemoths and cultural heavyweights of the Loop, you find the Prairie District: a petite neighborhood in the Near South Side with its own history and landmarks. Occupied by elite Chicagoans at the turn of the 20th century, the area—also known as the Prairie Avenue District—now boasts the Clarke House Museum (the city's oldest surviving house), John J. Glessner House, and more. Take a walking tour to explore up close.

American Writers Museum

Established in 2017, the American Writers Museum is one of Chicago’s newer institutions. It provides a much less crowded experience than at better-known spots such as the Field Museum of Natural History or the Art Institute of Chicago. The museum celebrates literary cultures and offers interactive exhibitions designed to fire up your creativity, whether you’re an avid reader or aspiring novelist. Prebook tickets in advance for seamless sightseeing.

The 606

Beyond the bustle of Millennium Park or Grant Park, Chicago has other less trafficked green spaces that provide urban escapes. One such option is the 606, often described as the Windy City’s answer to New York’s High Line as it's a public park located on a disused, elevated train track. Opened in 2015, the park is outfitted with art installations, greenery, and walking and biking trails. Explore it on a walking tour to see its highlights.

Pilsen

Chicago is known for its characterful neighborhoods, each of which has its own, unique personality. Venture beyond the Loop, and see how real Chicagoans live on a walking and cultural tour of the eclectic and dynamic Pilsen. Home to beautiful murals and street art, the National Museum of Mexican Art, and a range of destination-worthy restaurants and cafes, the neighborhood offers a slice of local life.

Driehaus Museum

One of Chicago’s most distinctive museums, the Driehaus is a treasure trove of decorative arts pieces. The small museum, housed in the restored Nickerson Mansion, offers a glimpse into the Windy City’s Gilded Age splendors and excesses. Book your tickets before you travel, and explore at your own pace.

Naperville

A Chicago suburb—and a thriving mini city in its own right—Naperville serves up plenty of charm, plus historical landmarks and family-run restaurants to boot. Stroll the pretty Naperville Riverwalk on a scavenger hunt, admire the soaring Moser Tower, and visit the city’s many eateries, from brewpubs to traditional pizzerias.

Chicago is a food-lover's dream, as there’s no shortage of great dining experiences to satisfy any palate. From Chicago-style hot dogs and deep-dish pizza to diverse cuisine from around the world, here are a few ways to make the most of your visit.

Pizza Tours

It should come as no surprise that you’ll have plenty of options to choose from when it comes to pizza in Chicago. Walking and bus tours highlight the city’s unique take on deep-dish, coal-fired, and other styles, and you can even take a cooking class to learn how to make Chicago’s most popular dish yourself. 

Dining at the Skydeck

Enjoy VIP after-hours access to the Skydeck at the Willis Tower, one of the tallest buildings in the Western Hemisphere. Dine on a three-course meal featuring Chicago-style deep-dish pizza with your choice of toppings while taking in incredible views of the city from the 103rd floor. Breakfast and lunch options are also available, with each experience lasting about two hours.

Dinner Cruises

Cruise Lake Michigan on a luxury yacht while enjoying a gourmet three-course meal and amazing views of the Chicago skyline. Departing from Navy Pier, cruises last about three hours. On summer Wednesdays and Saturdays, upgrades are available to include the fireworks show over Navy Pier.

Neighborhood Food Walking Tours

There’s no better way to get to know the unique ethnic flavors of Chicago’s neighborhoods than a food walking tour. Sample Vietnamese cuisine in Argyle, Scandinavian in Andersonville, or Polish in West Town. Learn about Chicago history over pizza in the Gold Coast, German fare downtown, or a Chicago-style hot dog in Wrigleyville.

The Windy City offers plenty of cultural, recreational, and culinary attractions, but destinations beyond the city limits let you explore the best of the region too. From national parks and destination-worthy wine regions to nearby cities, here are some of the most enticing day trips from Chicago.

Naperville – about 28 miles (45 kilometers) away

Head just outside Chicago city limits and venture to charming Naperville. The Chicago suburb, home to roughly 150,000 people, is a city in its own right. Trains link the two destinations, and full-day tours make getting there simple. Upon arrival, browse the shops and restaurants in Naperville’s downtown and stroll along the Riverwalk. For an unconventional way to explore the area, try a smartphone scavenger hunt game featuring Naperville’s key attractions.

Indiana Dunes National Park – about 49 miles (79 kilometers) away

Though Indiana Dunes National Park is only a quick drive around Lake Michigan’s southernmost shore from Chicago, the park feels a world away with its beachy ambiance and Saharan sand dunes. Enjoy a day at the beach; explore the titular dunes, marshes, and forests; and even discover (and taste) the highlights of the Duneland Wine Country on a full-day tour.

Milwaukee – about 83 miles (134 kilometers) away

Book a day trip to Milwaukee, Wisconsin, and head across state lines to discover another thriving city. As the historic home of the Miller Brewing Company, Pabst Brewing Company, and a slew of modern craft breweries, Milwaukee is renowned for its long-running beer scene. The cosmopolitan city also boasts the impressive Milwaukee Art Museum, soaring Milwaukee City Hall, and other attractions. A one-day tour is enough time to discover the highlights.

Southwest Michigan – about 90 miles (145 kilometers) away

Discover the thriving Great Lakes wine region, and sip in style on a full-day excursion from Chicago to scenic southwest Michigan. The Lake Michigan Wine Trail features dozens of banner wineries. Rieslings, pinot gris, and Rhone varietals are some of what’s planted on Michigan’s slopes, and you can find a selection of fruit wines and brandies, too. Head out on a full-day tour—and leave the driving to your guide.

Indianapolis – about 185 miles (298 kilometers) away

Indiana’s thriving state capital, Indianapolis offers one more incentive to travel across state lines. The accessible city is a popular choice for visitors of all ages as it's home to the famous Speedway, which hosts the Indianapolis 500, as well as museums and other cultural stops. Take part in a scavenger hunt game for a fun-filled sightseeing option, go on a guided walk of the Indy Beer Mile, or follow a local guide to the tasty eateries of Massachusetts Avenue.

Chicago has long been a cultural melting pot, one where different culinary influences all bring something of their own to the table. With such a strong food scene, it can be hard to know where in the Windy City to start. From deep-dish pizza to Chicago dogs, here are our picks for can’t-miss food experiences.

Must-Try Dishes

It’s easy to detect the strong Italian influence on Chicago’s culinary scene; after all, some of the city’s most iconic dishes reflect this tradition. Don’t miss deep-dish pizza, known for its buttery crust, bright tomato sauce, and generous sprinkling of mozzarella. Sandwich lovers should sample an Italian beef : a roll topped with thinly sliced roast beef and sweet or hot peppers, then dipped in its own cooking liquids. And Chicago’s sizable Mexican community has made tacos a must-eat as well.

With two pro baseball teams in town, the prevalence of Vienna hot dogs should come as no surprise, but unlike in New York City, Chicagoans load up their hot dogs with mustard, peppers, pickles, relish, tomatoes, and celery salt—but no ketchup. If you head to a stadium, sample Chicago mix popcorn, made with a combination of caramel- and cheese-coated kernels.

Must-Do Experiences

• Eat your way through the Chicago food scene—pizza, Chicago-style hot dogs, local chocolate, and craft beer—on a guided walking tour of some of the city’s best restaurants.

• Treat yourself to an unforgettable meal on the Willis Tower Skydeck, which rises 1,353 feet (412 meters) above Chicago.

• Enjoy a sunset dinner cruise aboard a luxury yacht on Lake Michigan—the city’s iconic skyline makes for a wonderful backdrop.

• Cycle your way through neighborhoods like Wrigleyville, Old Town, Lakeview, and Lincoln Park while stopping to fuel up at local culinary haunts.