Top Chicago Unique Experiences

Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.

Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.

Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.

Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.

Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.

Savor the flavors of the Gold Coast and Old Town neighborhoods on this 3-hour Chicago food walking tour, led by an expert guide. You’ll stop at seven popular shops and eateries, including a specialty tea merchant, confectioner, European bakery and — of course — Chicago-style pizzeria. Explore these culture-rich neighborhoods just north of the downtown and learn about their architecture and history along the way. Numbers are limited to 18 participants for a small-group experience.

Tour Chicago's sights aboard a luxury coach and enjoy some Chicago-style deep-dish pizza on this 5.5-hour guided tour. Visit sites like the Hancock Tower, the Lincoln Park Conservatory and the Loop. Pass through neighborhoods such as Wrigleyville, Lincoln Park and Gold Coast. Top off your tour with a visit to one of Chicago's most popular pizza restaurants to sample the famous Chicago-style deep dish pizza.

Go beyond the selfies and smartphone shots—and walk away from your Chicago vacation with professional-quality photos—when you book this private photo shoot experience. Meet your professional photographer guide at a time and place of your choosing and practice your poses: they’ll capture upwards of 15 high-resolution digital photos of you and your party, with Chicago’s majestic scenery as your backdrop. Your guide will also share insider knowledge and tips about the Windy City’s key attractions and eateries.

Tour Chicago’s Chinatown with local celebrity Jennifer Zhang. Crowned Miss Chicago Chinese 2015, and Miss China International 2017, Jennifer is also a model, actress, singer, social media influencer, and award-winning travel writer. She has written extensively about Chicago’s Chinatown and shares her inside knowledge with you on this tour. Stop to taste local specialities, and to explore significant landmarks on a one and a half hour-tour.

Discover Chicago in a fun new way on this 3-hour scavenger hunt. Jump into the middle of an exciting adventure around the Chicago Loop — to the historic buildings, famous streets and plethora of real-life locations around town. Discover both well-known and overlooked sites, solving clues and completing challenges via smartphone while learning the local history of the Windy City. Teams of 2- to 5-people are welcome.

See Chicago from a new perspective with this art- and pop culture-themed architectural walking tour. Follow an informative guide through the city’s streets, from the Michigan Avenue Bridge to the new Maggie Daley Park, while learning about the city’s history, architecture, and the fascinating connections between art history and Chicago architectural styles. Enrich your understanding of this beautiful American city with this fun and affordable outing.

Satisfy your sweet tooth on a 2.5-hour chocolate tour of Chicago. Follow your cocoa connoisseur guide through the Magnificent Mile neighborhood to four of the city’s top bakeries and chocolate shops. Meet some of the store owners to learn what makes their sugary products so delicious. Enjoy a variety of samples and learn about the city's history and top attractions between bites.

There is a time tested connection between love, romance, and the most delicious dessert in existence—chocolate. That's why true chocolate lovers shouldn't miss this Chicago Valentine's Day seated tasting experience, where you get to enjoy a chocolate tasting at Hannah's Bretzel. As you taste, hear about the history and health benefits of this amazing treat.

Flytographer 60 Minute Vacation Photoshoot Connect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do in Chicago, including where to eat and what to see from your vacation photographer.  Return from your trip with beautiful, high-quality, vacation photos. The best souvenir ever.

Flytographer 90 Minute Vacation Photoshoot Connect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do in Chicago, including where to eat and what to see from your vacation photographer.  Return from your trip with beautiful, high-quality, vacation photos. The best souvenir ever.

Flytographer 120 Minute Vacation Photoshoot Connect with a local professional photographer in Chicago and capture your most memorable moments during this private photoshoot. Get insider tips on the best things to do in Chicago, including where to eat and what to see from your vacation photographer.  Return from your trip with beautiful, high-quality, vacation photos. The best souvenir ever.

Wicker Park is one of Chicago’s coolest and most food-oriented neighborhoods—and on this one-of-a-kind walking tour, you’ll see the sights while seeking out the best donuts that the area has to offer. Meet your guide in the morning in Wicker Park, and set out on foot. You'll visit four popular cafes and bakeries, will sample numerous creative donut flavors, and will learn more about the neighborhood. Additional drinks and treats are also available for purchase, if you wish.