Best Restaurants for People Watching in Old Town
Price
- $30 and under
- $31 to $50
- $50 and over
Cuisine
Regions
Neighborhoods
Top Rated
Dining Options
Seating Options
Award-winning
Accessibility
41 restaurants available nearby
Price: Moderate
• Pizzeria • River North (Chicago)
Booked 32 times today
Price: Expensive
• Steakhouse • Gold Coast / Streeterville
Booked 110 times today
Booked 64 times today
Price: Expensive
• Steak • Gold Coast / Streeterville
Booked 23 times today
Booked 31 times today
Booked 18 times today
Booked 93 times today
Booked 34 times today
See what locals rave about
From verified diners like you
From verified diners like you
- SSuhailChicago / Illinois •1 review5.0Dined 1 day agoGreat service and portions. Really appreciated the great seating as well! Can't wait to return :)More infoGibsons Bar & Steakhouse - ChicagoPrice: Expensive• Steakhouse• Gold Coast / Streeterville•4.7
- MMarkVIPPhoenix / Arizona •11 reviews5.0Dined 1 day agoThis is one of the best experiences in Chicago steakhouses. Forget the big brands names. The service is outstanding. The best skirt steak I’ve ever have —flat out. They have a seared tuna appetizer ,also the best! This is like being at home. No rush— relaxed and true personal experience. Don’t miss this Gem. You will absolutely be thrilled you did its old school charm.More infoRosebud Steakhouse - ChicagoPrice: Expensive• Steak• Gold Coast / Streeterville•4.7
- BBethVIPOrlando / Central Florida East •27 reviews5.0Dined 2 days agoWe had a big group and the team did a great job! The holiday vibe and fun cocktails were awesome!More infoHappy Camper Pizza - Old TownPrice: Moderate• Pizzeria• River North (Chicago)•4.8
- LlynetteVIPChicago / Illinois •16 reviews5.0Dined 2 days agoFood is good. Outdoor space is a bit too noisy but the view is great thoughMore infoCabra - ChicagoPrice: Expensive• Peruvian• West Loop•4.7
- CCaitlinVIPChicago / Illinois •3 reviews5.0Dined 4 days agoThis is our favorite place in the city for many reasons. The drinks, the food, the look and feel of it, but the number one reason we keep coming back is the people who work at RL. It was a wildly busy evening this last time we came in and while many would have folded, the team went out of their way to take care of us. And that’s what sets this place apart. You’re cared for here. We were listened to and made comfortable. It ended up being a wonderful evening all thanks to obviously the food and drink, but mainly each employee we came in contact with. Come for the lush martinis, the perfect dover sole, the rich wood and dim lights but keep coming back for the people.More infoRL RestaurantPrice: Expensive• American• Gold Coast / Streeterville•4.9