Walk the Riverwalk on a Thursday evening this month and start at LaSalle Street. There's a valet stand now, a hostess with a tablet, and a line of people checking their phones for a text that their table is ready. Keep walking one block toward Wells and the scene resets entirely: open patio seats at a beer garden, a gelato counter with no wait, a taco window where you order and eat standing up. Same stretch of pavement, same river view, two completely different evenings.
That split is new, and it didn't happen gradually. It happened in one afternoon, on June 1, when Naia opened its doors at 300 N. LaSalle Street.
The Block That Now Runs on Reservations
Naia is not a normal Riverwalk addition. The Greek-Levantine restaurant from DineAmic Hospitality, the group behind Siena Tavern, Prime & Provisions and Lyra, occupies 12,000 square feet stretching nearly the entire river-level block between LaSalle and Wells, tucked below Chicago Cut Steakhouse in a tower that its owner, Irvine Company, folded into a larger renovation of the building. Chef Athinagoras Kostakos, who won Top Chef Greece and built his reputation on concepts like Scorpios in Mykonos, runs the kitchen, pulling from Greek, Southern French, Spanish, Italian and Levantine traditions across a menu built for shared plates.
The part that actually changes how you plan an evening is the reservation system. Naia takes bookings exclusively through OpenTable, and those slots don't open on a rolling basis. They release exactly 14 days out, at midnight. Miss that window and your options narrow to three moves: set an OpenTable alert and grab a cancellation, walk in and ask the host stand directly for a future date within the 14-day range, or skip the dining room and head for the bar, which takes walk-ins only. There's also a fourth option unique to this stretch of the river: Naia partnered with Downtown Docks so guests can arrive by boat and step off directly into the restaurant, a dock-and-dine setup that's become something of a signature move for the space.
Naia is currently listed open daily, with hours running into the late evening on weeknights and stretching past midnight Friday and Saturday. That's a longer daily runway than most of its Riverwalk neighbors, and it's part of why the block has taken on a different character. This isn't a place you wander into because you happen to be walking by. It's a place you plan for.
Every Other Block Still Runs on Walk-Up Rules
Move past Wells Street and the Riverwalk reverts to the version most residents already know. Sweet Home Gelato, a few doors down on West Riverwalk South, still serves gelato in a fresh waffle cone with no line to speak of, and it's also one of the better vantage points for the nightly art projection down the block, which we'll get to. Northman Beer & Cider Garden keeps its European beer-garden setup going with 16 taps and its own Rose and Pub ciders, no booking required. City Winery's Riverwalk location pours locally made wine alongside a full bar, and TacoRio, run by the same team behind Urban Kayaks, serves tacos from a window at the east end near Lake Shore Drive with the same order-and-eat pace it's always had.
Further east, Haire's Gulf Shrimp, which started as a train caboose operation on the South Side back in 1992, still does Louisiana-style seafood beneath the Michigan Avenue Bridge. O'Brien's Riverwalk Café runs live jazz on Thursday evenings and contemporary music on Tuesdays, with happy hour Monday through Thursday from 3 to 6 p.m., all walk-up, all first-come seating. Brews & Bites, over near the Wells-Franklin stretch, keeps serving craft beer, cocktails and crepes to whoever shows up.
None of that changed when Naia opened. What changed is that the Riverwalk now has a genuine split personality: one reservation-driven block bookended by two very different informal drinking-and-eating cultures on either side of it.
| Where | What's there | How you get a table |
|---|---|---|
| LaSalle to Wells | Naia | OpenTable, 14 days out at midnight, or bar walk-in, or arrive by boat |
| East toward Michigan Ave | Haire's Gulf Shrimp, O'Brien's Riverwalk Café | Walk up, no reservation |
| West toward Franklin | Sweet Home Gelato, Northman Beer & Cider Garden, City Winery, Brews & Bites, TacoRio | Walk up, no reservation |
The Free Show That Ties the Two Halves Together
Here's the detail that makes the new layout actually useful instead of just a curiosity: the best viewing spot for Art on the Mart sits almost directly next door to Naia's front door.
Art on the Mart projects across the 2.5-acre river-facing facade of the Merchandise Mart using 34 digital projectors, and it's billed as the largest permanent digital art installation in the world. The optimal viewing point is the Riverwalk jetty between Wells and Franklin Streets, which means it's a one-block walk west from Naia's dining room. This summer's headline run, Trazos, from Chicago artists Alan Medina and Wills Glasspiegel, wrapped August 2 after building its imagery around the public art history of Pilsen, projecting the murals and street life of that neighborhood onto a building on the opposite side of downtown.
Trazos may be finished, but the nightly show itself isn't. Through Labor Day weekend, projections run Thursday through Sunday at 9 to 9:30 p.m., before the schedule shifts to an earlier 7:30 to 8 p.m. slot starting September 10 as the nights get shorter. That leaves a real window this week and next for the current summer timing before it moves.
What this means in practice: you don't have to choose between the two Riverwalks anymore. Get a table at Naia, or skip the wait entirely and grab a drink at Northman or City Winery, and either way you're a five-minute walk from a free, no-reservation, genuinely large-scale art show that starts right around the time most dinners are wrapping up. One diner reviewing Naia online called it the hottest Mediterranean restaurant in Chicago right now, and reservations disappearing within hours of that 14-day window opening backs that up. The projection down the block doesn't need a booking at all.
What This Means If You're Down There Most Weeks
If the Riverwalk is part of your regular routine, the practical shift is small but real. You can no longer treat the LaSalle-to-Wells stretch the way you treat the rest of it. That block now requires either advance planning or a willingness to take the bar seat and skip the dining room. Everywhere else on the Riverwalk, the old rules hold: show up, find a spot, order at the counter.
That contrast is worth knowing whether you're grabbing a weeknight drink after work or figuring out where to take out-of-town guests before Labor Day closes out the summer schedule. The Riverwalk isn't one thing anymore. It's two, sitting one block apart, and the free show in between is the best reason to experience both in the same evening.
Chicago's neighborhoods keep changing in ways like this, block by block, one opening at a time, and that's exactly the kind of granular, on-the-ground detail our team at Spacematch Inc. tracks across Chicago and the surrounding suburbs. When the day comes that you're ready to talk about buying, selling or investing anywhere in the city, we'd love to be the ones who help. We Spacematch you to the right home.
