The Chicago Riverwalk is hands-down one of my favorite places in the city to eat, drink, and soak up the skyline. Whether I’m meeting friends for lunch, sipping wine on a sunny afternoon, or grabbing a bite with out-of-town guests, the Riverwalk never disappoints. There’s something magical about dining right by the water—with boats drifting by, live music in the air, and the city buzzing all around you.
If you’re hungry and strolling the Riverwalk, you’re in luck—there’s no shortage of amazing places to stop for a drink or a meal. And yes, I’ve actually eaten at each one of these spots (some more than once—okay, way more than once!). Here are my favorite Chicago Riverwalk restaurants, what I recommend ordering, and why I keep going back.
Seasonal Note: Most Riverwalk restaurants operate from early May through October, when their outdoor patios are open and the riverfront is buzzing. Some, like Pizzeria Portofino, stay open year-round thanks to their indoor dining areas. Be sure to check hours before visiting in cooler months.
Pizzeria Portofino — Waterfront Pizza with a Side of Glam
📍317 N. Clark St., Chicago, IL 60654
Pizzeria Portofino is my go-to spot for family birthdays, special occasions, or anytime friends come to town. No matter the season, the views of the river are always stunning. The breezy, coastal vibe makes you feel like you’re dining somewhere along the Italian Riviera—and the food? Always a hit. Bonus: it’s open year-round with cozy indoor seating in winter and that unbeatable patio in warmer months. Don’t overlook the pizza, it’s some of the best pizza in Chicago , especially if you’re a fan of thin crust.
What to Order:
- Black Truffle & Three Cheese Pizza — Rich, indulgent, and packed with flavor. If you love truffle, don’t skip this one.
- Charred Pepperoni Pizza — Crispy Ezzo pepperoni, Mama Lil’s peppers, and hot honey. It’s got that spicy-sweet combo I crave.
City Winery — Wine on Tap + Riverfront Chill
📍 11 W Riverwalk South, Chicago, IL 60601
This is one of my go-to hangouts when I want to kick back with a glass of rosé and people-watch. City Winery offers great food, local wines, and live music all summer long. Their riverside patio is one of the best on the walk. They typically open in early May and close in late October, weather depending. This spot is a must for any tour of the Chicago Riverwalk, whether you are just visiting or a city-dweller.
What to Order:
- Lamb Meatballs — Juicy and flavorful, served with tzatziki and warm pita.
- Burrata — Creamy burrata with roasted tomatoes and basil, perfect for sharing.
O’Brien’s Riverwalk Café — Classic Chicago Vibes
📍 45 E Riverwalk South, Chicago, IL 60601
O’Brien’s is a Chicago staple—relaxed, friendly, and perfect for grabbing a casual lunch or a drink by the Chicago riverwalk. They often have live music, and the vibe is always upbeat and welcoming. Open seasonally, usually May through early fall, with outdoor seating only. Don’t miss this spot during the annual dyeing of the Chicago River on St. Patrick’s Day– this is one great party!
What to Order:
- Corned Beef Sandwich — Piled high and packed with flavor.
- Cobb Salad — Fresh, filling, and perfect on a warm day.
Island Party Hut — Tiki Bar Energy on the River
📍 E Riverwalk South, Chicago, IL 60601
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—think tiki huts, frozen drinks, and steel drum music. It’s strictly seasonal, open from spring through early fall, and all seating is outdoors.
What to Order:
- Jerk Chicken Tacos — Spicy, flavorful, and packed with island flavor.
- Coconut Shrimp — Crispy and sweet, perfect with a fruity drink.
There’s truly something for everyone on the Chicago Riverwalk, whether you’re in the mood for a glass of wine, a crispy pizza, or a tropical taco moment. These are my favorite spots not just because the food is great—but because they each bring something special to the Riverwalk experience.
Tiny Tapp & Café — Crowd Pleaser with a View
📍55 W Riverwalk South, Chicago, IL 60601
Tiny Tapp is one of the most popular stops on the Riverwalk for good reason. The food is solid, the drink list is long, and the river views are top-notch. It’s casual, fun, and great for groups. This spot opens for patio season and typically closes in late fall.
What to Order:
- BBQ Pulled Pork Sliders — Tender, messy, and delicious.
- Caprese Panini — Fresh mozzarella, tomatoes, and basil on crispy bread.
Why These Riverwalk Restaurants Are Always Worth the Stop
If you’ve tried one (or all!) of these, I’d love to hear your favorites. And if you haven’t yet—this summer is the perfect time to explore them. Bon appétit, Chicago-style!