Houses, Jewelers and Appointments
Oak Street's luxury block is short: it runs from Michigan Avenue west toward Rush and State in the Gold Coast, and at its east end the street meets Michigan and becomes East Lake Shore Drive. Because there is so little room, the luxury houses have spilled around the corner onto Rush Street and Walton Street. This guide is less a walk than a plan: which house is at which address, who wants an appointment, and when each door opens.
The short version: go Monday to Saturday, book the jewelers before you arrive, and start after 11am if you want every door open. Most of the block closes at 6pm, so a shopping day here is shorter than on Michigan Avenue.
Book Ahead: The Jewelers
Van Cleef & Arpels (63 E Oak St) is seeing clients by appointment only, so reserve through its site before you go. The boutique carries jewelry, high jewelry, engagement rings and watches, with engraving, sizing and polishing.
Cartier (15 E Oak St) does take walk-ins, but the store says they can face longer waits, so book if you are buying. Its two floors cover jewelry, bridal, leather goods, fragrance and eyewear, plus repair, customization and leather embossing.
Harry Winston (55 E Oak St) keeps its Chicago salon mid-block. It opens at 11am, later than most of its neighbors, and is open Sunday afternoons. At the Michigan Avenue end, Lugano Diamonds (100 E Oak St) stacks a ground-floor boutique, a second-level Maison and a members-only Privé on top. It keeps Monday to Saturday, 11am to 6pm, with no Sunday hours listed.
Watches: Razny and the Rest
For watches, Razny Jewelers (109 E Oak St) is the main stop: a three-story store from a family jeweler, an official Rolex dealer and Chicago's only authorized Patek Philippe retailer, also carrying Cartier and Tudor. It is also where to bring a watch you already own. Razny's watchmakers work in-house and were trained by Swiss brands, and the store does custom design, jewelry repair, insurance and estate appraisals, hand and computer engraving, and gold buying. Razny posts no hours, so call the showroom at 312-663-8500 or email chicago@razny.com before you make the trip. Van Cleef & Arpels also sells watches, and on Rush, Dior's boutique includes timepieces.
The Fashion Houses on Oak
Hermès (25 E Oak St) sells apparel, handbags, silk scarves, shoes and home goods. Appointments can be booked online but are not required, and the store is closed on Sundays. Tom Ford (66 E Oak St) is the brand's only Chicago store, for men's and women's clothing, eyewear and fragrance, and stays open until 6pm on Sundays. At 68 E Oak St, Dolce&Gabbana carries men's suits, women's accessories, corsetry and jewelry, and offers one-to-one styling by appointment. It posts no hours, so book ahead for a fitting.
Moncler (59 E Oak St) carries women's and men's collections and opens at 11am. Akris (101 E Oak St) sits at the east end of the block, open seven days, and takes inquiries by phone and at chicago@akris.com. Prada (30 E Oak St) and Loro Piana (39 E Oak St) round out the block; Prada stays open until 7pm Thursday to Saturday, and Loro Piana is the cashmere house's only Chicago store.
Between the houses, Bravco Beauty Boutique (43 E Oak St) has been family-owned for more than fifty years and is the one affordable stop on the block, with skincare, haircare and a travel-size shelf of Oribe and Kérastase.
Around the Corner on Rush
South of Oak, Dior (931 N Rush St) is a full boutique: ready-to-wear, bags, exotic leather goods, shoes, jewelry, timepieces, Dior Maison home pieces and La Collection Privée. Brunello Cucinelli (937 N Rush St) carries the women's and men's collections, and Oliver Peoples (941 N Rush St) does optical frames and sunglasses with in-store fittings and adjustments. David Yurman has signed a lease for 933 N Rush St, the current Versace space, but no opening date had been announced as of January 2026.
Save SKIMS (1000 N Rush St) for last. The Chicago flagship stays open until 8pm Monday to Saturday and 7pm on Sunday, after the Oak Street boutiques have closed.
Appointments, Services and Hours
Shopping here works differently from Michigan Avenue, and a few calls before the day saves a lot of standing around.
Appointments
Van Cleef & Arpels is by appointment only. Cartier takes walk-ins but recommends booking. Hermès lets you book online without requiring it. Dolce&Gabbana books one-to-one styling sessions. Lugano's top floor is a members-only Privé.
After-Sale Services
Several stores are as useful for things you already own. Cartier repairs and customizes pieces and embosses leather goods. Van Cleef & Arpels engraves, sizes and polishes. Razny's in-house watchmakers service watches and its jewelers do engraving and appraisals. Oliver Peoples fits and adjusts frames.
Hours at a Glance
Cartier, Hermès, Loro Piana, Van Cleef & Arpels, Akris, Tom Ford, Dior, Brunello Cucinelli and Oliver Peoples open at 10am. Prada, Harry Winston, Moncler and Lugano open at 11am. Almost everything closes at 6pm. On Sunday most of Oak and Rush opens only from noon to 5pm, Hermès is closed and Lugano lists no hours; Cartier and Tom Ford stay until 6pm.
Parade Day
The Magnificent Mile Lights Festival parade steps off from Oak Street and Michigan Avenue at 5:30pm on Saturday, Nov 21, 2026, and street closures start as early as 3pm. Shop Oak Street in the morning, then walk south to watch: the parade lights more than a million lights on 200-plus trees along the avenue, and fireworks go up over the river at Michigan Avenue at 7:30pm.
Restaurant Row, Upstairs
The Gold Coast's restaurant row is back, but upstairs. None of its reopened anchors returned at street level, so look up.
Carmine's (1037 N Rush St) reopened on Jan 20, 2026 after a $4 million rebuild that took nearly three years. The Rosebud Restaurant Group's red-sauce Italian now fills about 10,000 square feet on the second floor, up a curved staircase, with a four-season terrace overlooking Mariano Park. Order the square noodles, eight-finger cavatelli, meatball salad or a parmesan. Tavern on Rush now sits inside the Thompson Chicago hotel at 1015 N Rush St, after 25 years at 1031 N Rush, in a two-level, 16,000-square-foot space with a patio.
ARLA opened on June 18, 2026 on the sixth floor of the former Barneys New York building at 15 E Oak St, the same address as Cartier and the space that once held Fred's. It is the Adalina team's Mediterranean-Japanese restaurant, with two open-air terraces over Michigan Avenue, and the menu runs from pita with white miso hummus and shawarma dumplings to miso cod and a 40-ounce tomahawk with za'atar butter. Book through SevenRooms.
At street level, Hugo's Frog Bar & Fish House (1024 N Rush St) is the busy fish house for stone crab claws, oysters and a slice of Muddy Bottom Pie. For a bigger dinner, Maple & Ash (8 W Maple St) cooks dry-aged steaks over a wood-fired hearth.
Red Line and Michigan Avenue Garages
Take the CTA Red Line to Clark/Division or Chicago and walk east to Oak Street and Michigan Avenue. CTA buses run up Michigan Avenue to Oak Street. If you drive, the garages on Michigan Avenue, including the one at 900 North Michigan, are a short walk away. On Nov 21, expect closures around Oak and Michigan from 3pm.
