ZipPicks Awards
Best Rooftop Restaurants in Magnificent Mile & Streeterville
Best Late Night Restaurants in Magnificent Mile & Streeterville
Master Critic Review
Terrace 16
8.4
Terrace 16 crowns Trump International Hotel & Tower with a dining room and river-facing terrace serving contemporary American plates, steaks, and brunch dishes. With lobster pastas, composed seafood, and burgers alongside one of the stronger downtown river views, it draws both hotel guests and locals looking for special-occasion rooftop-adjacent dining.
Must-Try Dishes:
Lobster Arrabbiata, Ora King Salmon, Terrace Burger
Scores:
Value: 7.6
Service: 8.3
Consistency: 8.5
Food Quality: 8.7
Atmosphere: 9.1
Cultural Relevance: 8.4
What makes it special: A riverfront terrace sixteen floors up where steak, seafood, and classic brunch dishes come with close-up Chicago River and skyline views.
Who should go: Guests wanting white-tablecloth dishes with serious downtown views.
When to visit: Clear evenings or weekend brunch for maximum river-and-skyline impact.
What to order: Lobster Arrabbiata, Ora King Salmon, Terrace Burger with fries.
Insider tip: Reserve terrace seating and time arrival near sunset to see the river corridor shift from daylight into full night lights.
Logistics & Planning
Parking: Hotel valet at Trump International is available, but rates are premium and can vary by event/time; nearby paid garages are the most reliable option. Street parking in this stretch of River North is scarce and not practical for most visits.
Dress code: Smart casual leaning dressy — jackets, dresses, and polished outfits fit the room; upscale denim is generally acceptable, but athletic wear will feel out of place.
Noise level: Moderate — indoor dining can feel lively during peak dinner and weekend brunch, but two-person conversation is typically manageable; the terrace is quieter earlier in the evening.
Weekend wait: Reservations are strongly recommended; walk-ins may face long or unavailable seating for terrace tables, with limited bar or lounge availability.
Weekday lunch: Usually easier to be seated with a reservation; walk-ins are sometimes accommodated, especially indoors, but terrace seating is not guaranteed.
Dietary Options
Vegetarian options: Yes — salads, pasta, and a few composed plates can be made or ordered vegetarian; ask your server for guidance on substitutions.
Vegan options: Limited — the menu is not vegan-focused, but the kitchen can sometimes adapt salads or vegetable sides upon request; confirm details with staff.
Gluten-free options: Yes — several dishes (especially seafood and steak) can be prepared gluten-free, and staff are accustomed to noting allergies, though a fully separate prep environment is not advertised.
Good to Know
Is this good for a first date? Yes — the river views, terrace seating, and polished service make it feel special and memorable, especially at sunset. It works best for a higher-end first date where conversation and atmosphere matter as much as the food.
Can I get a table without a reservation? Sometimes — indoor bar or lounge seating may open up, but terrace and window tables are rarely available to walk-ins during prime times. If the view is important, book ahead and request outdoor or river-facing seating.
Is it kid-friendly? Occasionally — families do dine here, particularly at brunch, but the vibe skews adult, celebratory, and date-night. It is better suited for older kids or special occasions rather than casual family meals.
Best For
Better for: Special-occasion meals where close-up Chicago River views and a refined, hotel-level experience are the priority — especially sunset cocktails, celebratory dinners, and upscale brunch on the terrace.
Skip if: You want a casual rooftop hangout, budget-friendly pricing, or a loud party-style rooftop scene — or if your plans depend on guaranteed outdoor seating during peak weather hours.