If you're lucky enough to live in Chicago, you know that summer isn't just a season. It's an event. And nowhere does the city come alive quite like the riverfront. From sun-soaked patios and world-class dining to kayaks gliding past skyscrapers, the Chicago Riverwalk is one of the most vibrant stretches of real estate in the entire city. Here's our guide to making the most of it this summer.
Eat & Drink with a View
Beatnik on the River
180 N. Upper Wacker Drive
Step off the sidewalk and into another world. Beatnik on the River is a bohemian escape tucked right along the Chicago River, where the food takes you on a tour from the Eastern Mediterranean through North Africa and all the way to Mexico. Think vibrant small plates, tropical cocktails, and a lush interior filled with over 600 live plants, all with stunning river views. Whether you grab a seat on the outdoor terrace or settle into the colorful, Moroccan-inspired interior, this one is an experience. Reserve ahead, because it fills up fast in summer.
Pizzeria Portofino
317 N. Clark St.
For something sun-drenched and endlessly charming, Pizzeria Portofino is your Italian Riviera moment without the transatlantic flight. This Lettuce Entertain You gem serves hand-stretched pizzas and coastal pastas with an expansive outdoor patio right on the water. Coastal wines, breezy decor, and a relaxed atmosphere make it perfect for a long summer lunch or an easy weeknight dinner. It's one of the few spots on the Riverwalk that stays open year-round, with cozy indoor seating when the weather turns.
Gibsons Italia
233 N. Canal St.
From the team behind the legendary Gibsons Bar & Steakhouse comes this stunning four-level Italian steakhouse right on the Chicago River. Think house-made pastas alongside world-class cuts of Gibsons Prime Angus, Australian grass-fed beef, and Japanese Kobe, all with floor-to-ceiling windows framing the skyline and river below. The second and third floor patios are perfect for summer dining, and the rooftop bar with its retractable roof is one of the best warm-weather perches in the city. Upscale without being stuffy, and the views alone are worth the reservation.
Chicago Cut Steakhouse
Marina City, on the Chicago River
When the occasion calls for something more elevated, Chicago Cut delivers. This old-school steakhouse sits at Marina City with an open patio offering one of the city's most iconic river views. Prime-aged cuts, creamed spinach, bone-in ribeye, and an expansive wine list make it a perennial favorite. There's something deeply satisfying about a perfect steak beside the water on a Chicago summer evening. Note that it's closed on Sundays.
City Winery
11 W Riverwalk South
City Winery is one of the best patios on the entire walk. Locally made wines on tap, a full food menu, live music throughout the summer, and a retractable glass enclosure for those unpredictable Chicago weather days. The burrata and lamb meatballs are reliably excellent, and the riverside tables near Marina Towers are as photogenic as it gets. Dog-friendly and boater-accessible too.
O'Brien's Riverwalk Café
45 E Riverwalk South
A Chicago classic and the only Riverwalk restaurant with full sit-down table service, O'Brien's is the kind of place that never goes out of style. Grab a Cobb salad, a classic corned beef sandwich, or fish and chips while live jazz plays on Thursday evenings. Unpretentious, welcoming, and reliably fun. A true summer staple.
Island Party Hut
355 E Riverwalk South
This is where you go when you want to feel like you're on vacation without leaving the city. Island Party Hut brings the tropical energy with tiki huts, frozen drinks, steel drum music, and an irresistible island vibe. They also operate Island Party Boats with upper decks and water slides out on the lake. Jerk chicken tacos, coconut shrimp, and the house frozen cocktails are the move here.
Tiny Tapp & Café
55 W Riverwalk South
A crowd pleaser from morning to evening, Tiny Tapp serves locally roasted coffee and fresh pastries in the morning and shifts to craft beer, cocktails, ice cream, and American fare as the day goes on. BBQ pulled pork sliders, frozen cocktails, and a reliably fun atmosphere make it one of the most popular stops on the walk. Come for coffee before the crowds, or pull up a riverside chair in the afternoon and stay awhile.
Chicago Brewhouse
31 E Riverwalk South
For craft beer enthusiasts, Chicago Brewhouse is a love letter to the city's brewing scene. Every beer on tap is locally made, including Goose Island, Revolution, Half Acre, Dovetail, Forbidden Root, and more. The food menu takes inspiration from Chicago's global neighborhoods, with standouts like Devon Ave Chicken Tikka Masala and Pilsen Street Tacos. There's even an exhibit on Chicago's beer-making history for the curious.
TacoRio
435 E Riverwalk South
Brought to you by the team behind Urban Kayaks, TacoRio sits at the east end of the Riverwalk near Lake Shore Drive and is one of the best budget-friendly stops on the water. Authentic street-style tacos, margaritas, elote, and live music make it the perfect reward after a kayak rental next door. Relaxed, colorful, and genuinely delicious.
The Northman Beer & Cider Garden
233 E Riverwalk South
Few places capture the spirit of a Chicago summer better than The Northman. With outdoor seating for over 700 people, 16 craft beers and ciders on tap, and 50+ bottled options, this European-style beer garden is a city institution. Free live music plays from the Pergola Stage every day from Memorial Day through Labor Day. Dog-friendly, family-friendly, and the kind of place you can spend an entire afternoon without noticing.
Something Sweet
Sweet Home Gelato
151 W Riverwalk South
Save room for this one. Sweet Home Gelato serves handcrafted, authentic Italian gelato made in small batches, with 12 rotating daily flavors including vegan options. Think amaretto, chai tea, Nutella, panna cotta, and seasonal specials. Adults can upgrade to a boozy float. Located right near the splash pad, it's the perfect family stop and honestly a perfect stop for everyone.
Explore, Relax & Play
The Riverwalk isn't just about eating and drinking. It's a full neighborhood unto itself in the summer months.
Across from Wolf Point, there's a lovely stretch of lawn with Adirondack chairs where you can simply sit, watch the river, and breathe. It's one of the most underrated spots downtown: quiet, green, and a world away from the hustle of the Loop just steps above. Bring a book, grab a coffee from Tiny Café, and settle in.
For families, the Riverwalk playground is a hidden gem and a great stop for kids to burn off energy between bites of gelato and splashes at the nearby splash pad. The fishing pier is another favorite, where you'll find Chicagoans of all ages casting lines into the river on sunny afternoons. The city stocks the Chicago River, and catching something isn't out of the question. It's a surprisingly peaceful slice of outdoor life right in the middle of downtown.
Get Out on the Water
Urban Kayaks
Chicago is arguably one of the best cities in the world to kayak, and you have to do it to understand why. Urban Kayaks operates right from the Riverwalk from May through October and offers solo and tandem kayak rentals starting around $30 per hour. Paddle through the canyon of glass and steel as the city towers above you. They also offer guided historic tours, sunset paddles, and fireworks tours. TacoRio is right next door for a post-paddle reward.
Chicago Architecture Center River Cruise
The Chicago Architecture Center's river cruise aboard Chicago's First Lady has been voted the #1 boat tour in North America by USA Today readers. This 90-minute narrated cruise reveals the stories behind the city's most iconic buildings, and it's one of those activities even lifelong Chicagoans discover they've never done and immediately wish they'd done sooner. Cruises run May through October.
Chicago Water Taxi
For a low-key way to get around and enjoy the river, the Chicago Water Taxi is a summer staple. At just $6 one-way or $10 for an all-day pass, the scenic 30-minute route connects Michigan Avenue to Chinatown with stops along the way. Practical, pleasant, and a genuinely fun way to see the city from a new angle.
Why the Riverfront Matters
For us at the Gillman Group, the Riverwalk isn't just a summer destination. It's a reflection of what makes Chicago real estate so compelling year after year. Homes and condos with river proximity consistently hold their value, and it's easy to see why. This is where the city's energy concentrates every summer, and neighborhoods like the Loop, River North, and West Loop put residents within walking distance of all of it. That walkability is something buyers increasingly seek out and are willing to pay a premium for.
If you're thinking about making a move to be closer to the action, or just curious about what's available near the water, we'd love to show you what's out there.
The Gillman Group is a top-producing Chicago real estate team at Compass with over 50 years of combined experience. We specialize in helping clients find homes they love in every Chicago neighborhood. Reach us at [email protected] or call (312) 925-2700.