Chicago Riverwalk
Culinary & Nightlife

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Our most recommended Chicago Riverwalk Culinary & Nightlife

Chicago: 1.5-Hour Romantic Sunset Cruise

1. Chicago: 1.5-Hour Romantic Sunset Cruise

Start your sunset cruise on the Chicago River at Michigan Avenue. Make your way along the main branch of the river towards Lake Michigan before entering the Chicago Locks, a modern engineering marvel, that will transfer the vessel onto the great Lake Michigan. The vessel will cruise along Lake Michigan as the sun sets behind the wonderful skyline offering several amazing views. Your local tour guide will give a very brief commentary along the Chicago River and entrance to Lake Michigan, but most of the 1.5-hour cruise is spent without narration, leaving you to watch the sun put on a beautiful display with the City skyline. Admire the many angles of the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Capture magical views of Chicago's twin super-skyscrapers, the famous Willis (formerly Sears) Tower and the John Hancock Building. You'll also get to admire the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. During your cruise, treat yourself at the full-service cash bar featuring authentic Chicago products. Try local beer and spirits and Garrett’s Popcorn. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

2. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

Chicago: Food, History and Architecture Tour with Tastings

3. Chicago: Food, History and Architecture Tour with Tastings

Discover the best of Chicago on a comprehensive guided tour. Learn more about the city's history and vibrant food scene as you discover various bustling neighborhoods and historic areas. Start your tour under the dazzling marquee of the Chicago Theater, recognizable from movie-musical Chicago before heading off into the bustling city. First, stop at the Chicago Pedway, used by locals and commuters daily to move about the city in a network of underground tunnels. From here, head towards the official seat of the government for the city at City Hall. Check out its classic interior design and architecture.  Next, enjoy your first food tasting of the day, traditional Chicago-style popcorn. Weather permitting, your guide will take you for a stroll along the Chicago Riverwalk, pointing out familiar buildings such as the Marina Towers, the Britannica Building, and the Willis Tower. From here, make your way to another delicious destination where you can sample locally made chocolate from a local shop.  Then, you will either hop on the ‘L’ train or a water taxi on the Chicago River, depending on the weather and time of year. Either option offers a uniquely local Chicago experience. Feel like a local as you zip past buildings and catch even more awesome views. Next, take a stroll through the beautiful lakefront parks along Michigan Avenue. Arrive at the picturesque Millennium Park, home to the iconic Bean sculpture. By then, you’ll hopefully have built up an appetite because it’s time to begin your ultimate food experience. Travel with your guide up to the River North neighborhood, the original Chicago foodie destination. Your first food sampling is a local favorite, a Chicago-style hot dog. Next up is the world-famous Chicago deep-dish pizza, the staple of the Chicago food scene. Visit a pizza place that’s an icon to Chicago natives to try the real deal for yourself. After you’ve filled up on pizza and hot dogs, take a stroll through two more establishments, each one essential to Chicago’s food culture. Then continue your tasting journey with a classic Chicago sandwich: Italian beef. Sample this sandwich in a true Chicago institution. Your tour ends here, but don’t forget to get some recommendations from your guide of where else you visit or eat during tour time in the city.

Chicago: History, Culture and Architecture Walking Tour

4. Chicago: History, Culture and Architecture Walking Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, make your way to another delicious destination. Along the way, enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building, the heart of Chicago’s thriving and historic journalism industry. Your second tasty confection is locally made chocolate from a Chicago staple. Finally, take a stroll through the beautiful lakefront parks along Michigan Avenue. Round up your tour in the picturesque Millennium Park, home to the iconic Bean sculpture. Here, your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or drink recommendations.

Chicago: Downtown Family Food Tour by Bike with Sightseeing

5. Chicago: Downtown Family Food Tour by Bike with Sightseeing

Hop on a bike and enjoy this easy ride around Downtown Chicago to explore the cities best sights and food. Cruise through Millenium Park, Museum Campus and along the lakefront with regular stops to sample delicious treats as you go. Your guide will take you to some of the best spots to try deep-dish pizza, a true Chicago hot dog, Italian beef, and a dessert for good measure. Try them all (or their veggie alternatives) and learn about the foods that made Chicago famous. In between snacking, visit some of Chicago’s most popular downtown districts as you cruise through Grant Park (Buckingham Fountain), the Chicago Riverwalk, and more. Along the way, your guide will point out highlights like Navy Pier, the Magnificent Mile and the Chicago River. The stops are well-timed so, even though you’ll be working up an appetite, all ages and fitness levels can get involved and enjoy this ride. If you want the full experience, upgrade to the VIP Craft Beer Tour to enjoy beer pairings with many of the food stops.

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What people are saying about Chicago Riverwalk

Me and my friends had a really nice time. The views were breathtaking. I just wish that there were less people on the boat so that everyone had a seat on the upper deck. We had a spot on the lower beck and couldn’t hear the guide talk or enjoy 360 views

Had a great time on our food tour! It’s a great way to learn about foods that were improved upon by this city, some of the history and see a few blocks of downtown.

Enjoyed the ambiance and historical overview. Seeing the skyline at sunset was so worth it.

Fun, informative, very tasty tour. Dylan, the guide, was knowledgeable and super fun.

Justin was phenomenal! So enthusiastic about the city. Made it so fun! Also, the food