Day 1: Navy Pier
Morning
Start your day close to Navy Pier at the Streeterville location of Kanela Breakfast Club, where your group can fill up on hearty and healthy Greek-infused American dishes such loukoumades (Greek doughnuts with lemon honey syrup and toasted walnuts), spicy feta omelets, and potato pancakes.
Then, stroll through the 13-acre Polk Bros Park at the entryway of Navy Pier, where expansive green spaces and a 12,500-square-foot water fountain with dancing streams of water welcome visitors.
Make the most of warm summer weather by renting bicycles from Bike and Roll Chicago to cruise along the 18.5-mile paved Lakefront Trail. Or, take Bike and Roll‘s Lincoln Park Bike Adventure (departs at 10 a.m.) for a tour of nearby beaches, Lincoln Park Zoo and the Conservatory.
Afternoon
Back at Navy Pier, your group will have plenty of fast, convenient options for lunch at Navy Pier’s food court. Or take them for an iconic experience at the new location of Giordano’s, where visitors can indulge in famous stuffed-crust pizza on the outdoor patio. After lunch, take your group for a ride on the Centennial Wheel, featuring closed, climate-controlled gondolas, each holding eight adults and two children.
Evening
Combine dining and entertainment with a dinner boat cruise by Spirit of Chicago, Odyssey, or Mystic Blue.
Or indulge in steaks and seafood in the upscale Riva Crab House, and then make your way to the lakefront Navy Pier Beer Garden, offering live music Wednesdays through Sundays from Memorial Day through Labor Day.
Or, experience the magic of Shakespeare with a performance at Chicago Shakespeare Theater.
And all the months between Memorial Day and Labor Day, catch an Aon Summer Fireworks show at Navy Pier: Wednesdays at 9:30 p.m. and Saturdays at 10:15 p.m.
Day 2: Chicago Riverwalk
Morning
Start the day with a group adventure on the water at the Chicago Riverwalk. Book the 1-hour Intro Paddle (departs at 10:30 a.m.) with Urban Kayaks for an easy beginner excursion along the Chicago River, or bring your group on the 90-minute Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady Cruises to learn about Chicago’s incredible history and architecture.
Afternoon
For lunch, dine on farm-to-table fare and fresh seafood at The Kitchen on the riverfront, or take in dramatic river views while enjoying gastro-pub fare at River Roast.
For a behind-the-scenes look at Chicago’s most famous moveable bridges, tour the McCormick Bridgehouse & Chicago River Museum. Then stroll along the established areas of the Chicago Riverwalk to see Heald Square Monument, the Vietnam Veterans Memorial, and the Bataan-Corregidor Memorial Bridge. As you follow along the walkway, you’ll discover the newly developed Riverwalk areas, offering beautiful landscaping, convenient concession areas and welcoming places to sit and enjoy the river views.
Nearby, take groups to The Magnificent Mile for a bit of shopping. This eight-block stretch between the Michigan Avenue Bridge and Oak Street offers everything from expansive mega-malls to designer boutiques.
Evening
Once the sun goes down, explore all the excitement of the River North neighborhood. At Untitled Supper Club, flavorful seafood and meat dishes pair with specialty cocktails and live music for an all around dazzling night out. For another dining and live music experience, Andy’s Jazz Club & Restaurant boasts Southern-style dishes and sophisticated jazz music.
Keep the night going with a trip to one of Chicago’s many piano bars or blues clubs, such as The Redhead Piano Bar or Blue Chicago.
Day 3: The 606
Morning
Hit The 606 first thing and start the trail at Walsh Playground Park, and continue on to Churchill Field Park. Nearby, you’ll find Damen Arts Plaza, the location of “Brick House,” a three-ton curvilinear sculpture made of recycled rubber tires and stainless steel.
Afternoon
Just a few blocks off The 606, explore some of the shops along Damen Avenue. You’ll find unusual upscale brands. Then stop for seasonal, local fare with lunch at Feast or HotChocolate. Once you’ve continued walking along the trail, be sure to stop for a picture at Humboldt Overlook, as you take in views of century-old homes in this national historic district.
For groups that don’t want to walk the entire way, rent a Divvy bike from the rental station near Julia de Burgos Park and pedal your way to Kimball Park to admire local artwork on the “graffiti garden.” The trail ends at the Western Trailhead Garden.
Evening
Plan a casual evening with dinner at Revolution Brewing, where your guests can enjoy a pint of locally made craft beer paired with salads, pizzas, sandwiches, and more. Meanwhile, late-night fun abounds at Rosa’s Lounge, a mainstay in the Chicago blues scene.
