Chicago Riverwalk
Food & Drinks

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Our most recommended Chicago Riverwalk Food & Drinks

Chicago: 1.5-Hour Romantic Sunset Cruise

1. Chicago: 1.5-Hour Romantic Sunset Cruise

Relax as you glide over the Chicago River and into Lake Michigan on this cruise. Enjoy the glow of the sunset on Chicago's sparkling skyline. Have the option to purchase delectable drinks and snacks at the onboard bar as you sail. 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: History, Culture and Architecture Walking Tour

3. 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: Food, History and Architecture Tour with Tastings

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

Discover the architecture and food scene of Chicago on a guided day tour. Learn more about the city's history and vibrant food scene as you discover various bustling neighborhoods and historic areas. Start the tour under the dazzling marquee of the Chicago Theater. Explore the bustling city where the 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. This unique feature of Chicago is used by locals and commuters daily to move about the city in a network of underground tunnels. Make your way above ground at City Hall, and admire its classic interior design and architecture. Next, visit a spot for a tasty sweet treat, and a local tradition, Chicago-style popcorn. Take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Sears Tower (now known as the Willis Tower). From there, visit another delicious destination for locally made chocolates from a Chicago staple. Meander through the beautiful lakefront parks along Michigan Avenue, finishing at picturesque Millennium Park, home to the iconic Bean sculpture. Travel by ‘L” train or ride share with your guide from Millennium Park up to the River North neighborhood, the original Chicago foodie destination. Your food tour starts with a very well-known Chicago fare, the Chicago-style hot dog. Every Chicagoan has his or her own preference as to how the dog should be made, and you’ll get a chance to try your guide’s favorite version. Next up is the world-famous Chicago deep-dish pizza. An entire meal unto itself, this staple of the Chicago food scene originated in River North in the 1940s when workers and families needed filling dishes at low prices. Your guide will take you to 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, continue your tasting journey with a classic Chicago sandwich, the Italian beef. Sample this sandwich in a real Chicago institution with no-frills decor. Our tour ends here, and your guide will be happy to direct you back to your accommodation or share tips for what else to see in the city.

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.

Frequently asked questions about Chicago Riverwalk Food & Drinks

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Other Sightseeing Options in Chicago Riverwalk

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What people are saying about Chicago Riverwalk

The Sunset Cruise was excellent! It was lovely cruising out from the city on the river while it was still sunlight and seeing all the sights up close, then sailing out on Lake Michigan and seeing the other boat tourist and boaters in the distance while watching the sunset. Cruising back was gorgeous seeing everything lit up at night with the city reflections on the water. Just breathtaking!

We had a great time, our guide John was very knowledgeable and took the time to provide plenty of details and the background around the places we’ve seen during the tour. He was entertaining as well and very approachable. We’d definitely recommend this tour and John to other people interested in this type of tour.

Such a great tour. The food was awesome and so was Justin. He really did a fabulous job and made it so much fun! This tour is well worth it for anyone that wants a taste of Chicago and it’s rich history! 5 stars!

All of the food was delicious, and our guide was kind and well informed.

Great cruise! Good to go with friends or with your partner!