Two Days, Two Chicago Waterfronts

Published: Wednesday, January 1, 2020

The waterfront is a center of life in Chicago. It’s where discoveries are made and adventures begin. Dedicate one day each to exploring the Chicago River and Lake Michigan. We’ve rounded up the best places to eat, play and, of course, splash.

Day 1: Chicago River

Stroll the Chicago Riverwalk, an attractions-filled path that stretches from Lake Shore Drive to Lake Street. The hottest restaurant seats in town can be found along the riverbank. Sip a house-made vintage at City Winery, eat juicy steak sandwiches at O’Brien’s Riverwalk Café, dig into a Chicago hot dog at Tiny Tapp Riverwalk, or go gastropub at The Northman Beer & Cider Garden and Chicago Brewhouse. The vibes and drinks are tropical at Island Party Hut, where you can up the exotic ante aboard a chartered Island Party Boat. Be transported to Italy at Portofino Pizzeria, located in a sunny spot on the riverfront. Their hand-stretch pizzas, coastal wines, expansive patio, and breezy décor will make you wonder if you’re in Chicago or the Italian Riviera.

Sit back and relax in the glass-enclosed Odyssey Chicago River, featuring lunch, brunch, and dinner cruises all year round. If an open-air sightseeing cruise is more your style, book a guided jaunt on the award-winning Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady, Wendella, or Mercury Chicago’s Skyline Cruiseline. Chicago Water Taxi and Shoreline Water Taxi excursions, while not guided, are great ways to get to various points along the river. You can travel all the way to Chinatown from the Chicago Riverwalk.

The experience is interactive aboard Chicago Cycleboats, which are small boats powered by your own pedaling from a bike seat perch. Another fun (and environmentally friendly) option is captaining a private boat from Chicago Electric Boat Company, or skimming the water on a rental from Urban Kayaks.

McCormick Bridgehouse & Chicago River Museum showcases the river’s history, particularly its storied moveable bridges. A stroll along the pedestrian walkway affords a great view of the bridges, as well as vibrant public art that ranges from cast iron sculptures to graffiti. You can’t miss the bold Vietnam Veterans Memorial Plaza, a tiered plaza and waterfall that honors our soldiers. Catch Art on theMART, featuring digital art projected onto the Chicago River-facing side of theMART, from March through December.

Day 2: Lake Michigan

Thrill-seekers can get their fix with watersports on Lake Michigan, from stand-up paddleboarding with ChicagoSUP at North Avenue Beach to flyboarding at 31st Street Harbor with Chicago Water Sport Rentals. Or rent some wheels from Bike and Roll Chicago and leisurely pedal along the Chicago Lakefront Trail that hugs the curves of the shoreline. Head further south to 12th Street Beach situated on the eastern edge of Northerly Island, a man-made peninsula that stretches along the lakefront. The beach is located on the Lake Michigan side of the island, just south of the Adler Planetarium. Bring your camera, as the spot is a perfect photo op.

Spend the day at Navy Pier, a former naval ship dock transformed into a lakefront playground. Enter via Polk Bros Park, featuring a fountain with magnificent water jets and the new Peoples Energy Welcome Pavilion, which greets guests in various languages. Enjoy live music and theatre at Fifth Third Bank Family Pavilion, immerse yourself in a flick at the AMC Navy Pier IMAX Theatre, climb through a schooner at the Chicago Children’s Museum and head to Pier Park for a spin on the nearly 200-foot-tall Centennial Wheel. The entertainment continues with works by The Bard at The Yard at Chicago Shakespeare and live music coupled with great water views at the Miller Lite Beer Garden. End the day with a drink at Offshore Rooftop and Bar. Offshore is the nation’s largest rooftop venue and sits at the very edge of Navy Pier, providing unmatched panoramic views of Lake Michigan and the city’s skyline.

Hungry? Stop at the food court or sit-down restaurants like Harry Caray’s Tavern, Giordano’s (for deep-dish pizza), and Riva Crabhouse. You can also hit the water for a multi-course meal and cruise aboard Odyssey Lake Michigan, Mystic Blue, or the Spirit of Chicago. Or simply enjoy a feast for the eyes aboard a sightseeing cruise on a classic Shoreline Sightseeing vessel, Seadog Chicago speedboat, or historic Tall Ship Windy sailboat.

Make a splash at one of the city’s sunny beaches. Close to Navy Pier is Ohio Street Beach, where you can lunch at Caffe Oliva. Sun, snack and sip at Oak Street Beach, home to Oak Street Beach Food + Drink. Go for Del Campo’s Tacos when hunger strikes at 12th Street Beach. And catch rays in style at North Avenue Beach, home to Castaways (known for frozen drinks) and the chic Shore Club Chicago (serving healthful Mediterranean cuisine).