From floating tiki bars to fine dining, and architecture tours to kayaking, here are 10 things Chicagoans love — and visitors love to discover — about the Chicago Riverwalk. 

1. Party Island Style

Island Bar Hut RiverwalkPhoto: Ross Buchanan Moore

Island Party Hut Tiki Bar & Grill (355 E Riverwalk South) is a vacation within a vacation —and in many ways the best of both party worlds. Set along a serene stretch of the Riverwalk, tiny lights are strung upon tall, shady trees, sheltering the bar hut, a stage (where live music lives), and a ton of outdoor games — corn hole, bocce ball and the Bimini island ring game among them. In the meantime, look beyond the boat-laden waters and you’ll see the skyscrapers and architectural gems for which Chicago is famous. 

The Island Party Hut bar menu features all your island favs, including margaritas on the rocks and Mai Tais, complemented with belt-busting bites such as burgers, brats and slow-smoked pulled pork.

If you don’t fancy being land-locked, then buy your ticket for the Island Party Boat, aka Floating Tiki Bar. Departing from Monroe Harbor and the Riverwalk, this Floating Bar takes you on a cruise along the Chicago River, with Island tunes playing and Island cocktails beckoning at the cash bar. Cruises last 75 minutes, with tickets costing $30. On Wednesdays at 9pm, your cruise includes evening fireworks at Navy Pier. Both afternoon and evening cruises are scheduled.

See all the great places to dine on the Riverwalk.

2. Kayak down the Chicago River

Chicago Riverwalk ©Ranvestel PhotographicPhoto: Ranvestel Photography

Chicago is often thought of as “the resort in the city.” And one glimpse at kayakers paddling along the Chicago River in the shadow of towering skyscrapers definitely proves the point. Urban Kayaks, which sits right next door to Island Party Hut Tiki Bar, offers a range of kayak tours and rentals from both this, its Riverwalk location, and its nearby Monroe Harbor location. Tours include the Ultimate Fireworks Outing (90 mins; $70pp), the Historic Chicago Tour (90 mins; $65pp), the Sunset Tour (90 mins; $65pp), the Riverwalk Intro Paddle ($45pp) and the Fireworks Paddle ($50pp). Reservations aren’t required for kayak rentals; rates are $30pp per hour. 

Find more fun things to do on the water.

3. Take One of the best architecture boat tours in the country

Chicago's First Lady

Sign up for a Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady Cruises to hear about the storied pasts of some of the city’s most iconic buildings. Ranked the #1 tour in the city based on TripAdvisor user reviews, this is the only cruise to be partnered with the Chicago Architecture Center (CAC). That means highly trained and passionate volunteer docents who provide a detailed narrative of Chicago's various architectural styles and the stories of the people who designed and built the city.

The 90-minute daily tour, which features indoor and outdoor seating and a full-service bar, departs from the Chicago Riverwalk at Michigan Avenue and Wacker Drive (southeast corner of the DuSable/Michigan Avenue Bridge). Check out ticket options.

See all the Riverwalk's cruise and boat rental options.

4. Dine on a glass-encased vessel

Odyssey Chicago River ExperiencePhoto: Odyssey Chicago River Experience

Launching in September, Odyssey Chicago River Experience offers up a rather elegant and supremely unique experience on the Chicago River in the form of a state-of-the-art, European-styled, glass-enclosed vessel — think 360-degree city views! The new ship was designed specifically in response to growing demand for more out-of-the-ordinary experiences on the river. The idea is to showcase Chicago’s incredible architecture and jaw-dropping vistas, and to create a refined environment in which to enjoy an upscale menu, with plated service. Curated live music will add to the refinement.

See all the Riverwalk's cruise and boat rental options.

5. Savor Chicago wines on a riverfront patio 

Marina Plaza, City Winery, SpeedboatsPhoto: Ranvestel Photography

City Winery Chicago at the Riverwalk is a fabulous place, with six house-made wines on tap and an outdoor wine patio with views across the river. This is the very best place to people watch, whether its strollers or sailors about to board one of the bobbing docked boats.

City Winery RiverwalkPhoto: Ross Buchanan Moore

This is, in fact, City Winery’s outpost location. Its original site is located in the West Loop, where you’ll find Chicago's premier fully operational urban winery.

The menu at Riverwalk features top-selling items from the winery’s West Loop restaurant, while wine is served through a unique tap system to showcase the company's commitment to sustainability.

See all the great places to dine on the Riverwalk.

6. View art en plein air

Riverwalk ArtSam Kirk’s Vejigante, Mask On. Photo: Ross Buchanan Moore

Public art transforms the Riverwalk into an open-air gallery. Works include: Riverwalk Gateway by Ellen Lanyon, located beneath the Lake Shore Drive Bridge; 10-foot cast aluminum Allium by Carolyn Otters, which is located between Columbus Drive and Lake Shore Drive; Sam Kirk’s Vejigante, Mask On, a single panel graffiti work located along the Riverwalk between Franklin Street and Lake Street, right alongside Ballerinas, a four-panel work completed by Tyrue “Slang” Jones.

Vietnam War Memorial RiverwalkPhoto: Ross Buchanan Moore

The Vietnam Veteran's Memorial Plaza is also worth a visit. Designed by Ross Barney and Jankowski Architects, it's located at 25 E Riverwalk South, near the State Street entrance to the Riverwalk. It’s one of the largest memorials in the nation outside of Washington, D.C. The design echoes that of Maya Lin’s D.C Memorial wall, commemorating the 58,000 men and women across America who lost their lives in the Vietnam War. 

On the top of the wall is a plaque that states, “Chicago Remembers.” Below is a timeline of events that took place during the confrontation. 

The plaza offers a poignant and contemplative area where visitors can pay tribute to the 2900 Illinois veterans who are no longer with us. The space also features a fountain with 14 water jets, a waterfall sculpture of the Vietnam Service medal and seating areas.

Next up is the highly anticipated Art on the Mart, a permanent large-scale lighting installation that will run across nearly three acres of TheMART’s south-facing façade. TheMART will provide ‘the largest canvas in the world’ for video art, with a curated, ongoing series of ever-changing images becoming a permanent nighttime riverfront feature. Expect to see it at the close of the summer season.

Read more about art on the Riverwalk.

8. Climb to the top of the Bridgehouse Museum

McCormick Bridgehouse & Chicago River Museum ©Ranvestel PhotographicPhoto: Ranvestel Photography

The 5-story McCormick Bridgehouse Museum is such a gem. Celebrating Chicago’s world-famous moveable bridges, the museum is also your chance to explore an historic landmark bridgehouse in all its steampunk glory. 

At river level, visitors can view the massive gears that move Chicago’s famous bridges up and down. As they ascend, they learn all about the Chicago River. Once at the very top, visitors are treated to magnificent 360-degree views of the city. (Note: Only the first floor is handicap accessible.) 

Find out more about Chicago history on the Riverwalk.

8. Get eye level with the world’s tallest buildings at the CAC

Chicago Architecture CenterChicago Architecture Center, courtesy of Chicago Architecture Foundation

The Chicago Architecture Center (CAC), opening its doors on August 31 as the new home of the Chicago Architectural Center, is the Riverwalk’s jewel in the crown. Housed at One Illinois Center (111 E Wacker Dr), the building was designed by Modernist genius Ludwig Mies van der Rohe and is located above the dock for the Chicago Architecture Foundation River Cruise Aboard Chicago’s First Lady Cruises.

One of the CAC’s premier exhibits is located in the Skyscraper Gallery on the second floor, in a dramatic space with 40-foot windows overlooking the Chicago River and the Michigan Avenue Bridge. The exhibit, Building Tall, will be filled with supersized scale models of famous skyscrapers from Chicago and around the world, including a nearly 40-foot model of Saudi Arabia’s Jeddah Tower, which will be the world’s tallest building when construction is completed in 2020.

Find out more about Chicago history on the Riverwalk.

9. Fish along a skyscraper canyon

Floating gardens and piers at the JettyPhoto: Caroline Staublin

The Jetty is one of six coves that populate the 1.25-mile stretch of the Chicago Riverwalk. Extending from Wells to Franklin (aka the west end of the Riverwalk), the Jetty features a fishing pier that offers the rather unique experience of casting your line in the midst of a canyon of skyscrapers. Breathtaking is an understatement. Fishing on the Riverwalk is free, but make sure you have an Illinois fishing license before you go. 

10. Bird watch on The Jetty

The Jetty at the Chicago RiverwalkPhoto: Caroline Staublin

Mallards, ring-billed and herring gulls, rock pigeons, American robins, European starlings, Peregrine Falcons that swoop between towering skyscrapers are among the species of bird you’ll glimpse at the Riverwalk. Audubon Great Lakes offers a monthly walk along the river to gaze upon fascinating feathered creatures every first Friday at 8 am, July through October. (Meet on the Riverwalk just east of the bridge at State Street and Wacker Drive, and bring your binoculars!) And as the regional office of the highly respected National Audubon Society, you know they know their stuff.

Read more about the Chicago Riverwalk at Choose Chicago.

EVENT ALERT: Chicago Friday Night Flights at the Chicago Riverwalk

September 14, 6-9pm
Water Plaza & Jetty coves (Clark St – Franklin St)

Friday Night Flights

Season two of Chicago Friday Night Flights wraps up on the Chicago Riverwalk this year, with over 15 award-winning breweries from across the city offering samples of their craft beer artistry.

 A tasting pass will allow you to sample 10 3oz pours for $15 pre-purchase or $20 at the door (cash and credit cards accepted). Great food (for purchase) and live music round out the event. Buy your tickets today! And check out more Chicago Friday Night Flight events.

Chicago Friday Night Flights is produced by the Illinois Craft Brewers Guild in partnership with Choose Chicago.

See the Chicago Riverwalk's upcoming events here.