Best Restaurants for People Watching in Downtown / Loop
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44 restaurants available nearby
How are Featured results ranked
Price: Moderate
• Contemporary American • Downtown / Loop
Booked 197 times today
Booked 118 times today
Booked 125 times today
Price: Expensive
• Steakhouse • Gold Coast / Streeterville
Booked 115 times today
Booked 97 times today
Booked 76 times today
Booked 88 times today
Price: Moderate
• American • Gold Coast / Streeterville
Booked 44 times today
See what locals rave about
From verified diners like you
From verified diners like you
- SSusanVIPChicago / Illinois •28 reviews5.0Dined 2 days agoWe had a fantastic meal at Siena Tavern! Everything from start to finish was spot on. We started with the meatball and coccolini appetizers—both were delicious and great for sharing. The standout mains were the brick chicken, which was perfectly cooked and full of flavor, and the margherita pizza with its fresh, simple ingredients done right. Our group had a mix of drinkers and non-drinkers, and the cocktail and mocktail selections were impressive and well-crafted. Service was friendly and attentive, and the ambiance was vibrant without being too loud. Highly recommend for a great night out in Chicago!More infoSiena TavernPrice: Moderate• Italian• River North (Chicago)•4.6
- HHannahAustin •1 review5.0Dined 2 days agoI had my birthday dinner here and it was amazing. The food is delicious and the service is great!More infoGibsons ItaliaPrice: Expensive• Italian• River North (Chicago)•4.9
- FFabiolaOrlando / Central Florida East •1 review5.0Dined 6 days agoUnbelievable experience with amazing views Food is amazing i had a great time would totally come back on my next visit to chicago The variety of Spritz are great choice for this summer :)More infoPizzeria PortofinoPrice: Expensive• Italian• River North (Chicago)•4.8
- PPamelaVIPPhiladelphia County •12 reviews4.0Dined on May 18, 2025The service was outstanding from the time we entered the restaurant and our waiter Randy was attentive to details and very knowledgeable about the food. I would definitely go back.More infoAtwoodPrice: Expensive• American• Downtown / Loop•4.3
- DDietzVIPIowa •18 reviews5.0Dined on Oct 2, 2023We loved the food and great service as always! Thank you for your work!More infoTiny Tapp & Cafe - RiverwalkPrice: Moderate• Contemporary American• Downtown / Loop•4.6