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Best Restaurants for People Watching in Old Town

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42 restaurants available nearby

A photo of Happy Camper Pizza - Old Town restaurant
4.8
Exceptional(605)
Price: Moderate
• Pizzeria • River North (Chicago)
Booked 60 times today
Minors must be accompanied by parent or guardian for entry. A valid ID is required for guests age 21+.A chic, outdoorsy pizza haven located in Old Town. Happy Camper boasts a décor that includes Airstream trailers, neon renditions of the Great Lakes, warm wooden accents, and tire swing seating around the bar. A wide variety of colorful pizzas and delicious appetizers await you.F*ckin' Charity Bingo on Sundays at 1:30pm is sat on a first come first serve basis. All reservations will be sat in the non-bingo area.We cannot guarantee inside or outside seating.Neighborhood ordinances require our patio to close by 12am. Your table is weather permitting. If there is inclement weather, Happy Camper reserves the right to cancel your reservation. If you are dining when inclement weather occurs your food will be packed and given your bill. You are more than welcome to head to the bar afterward.
A photo of Gibsons Bar & Steakhouse - Chicago restaurant
4.7
Exceptional(8950)
Price: Expensive
• Steakhouse • Gold Coast / Streeterville
Booked 105 times today
Gibsons Bar & Steakhouse has been a Chicago icon since partners Hugo Ralli and Steve Lombardo opened its doors in May 1989. The classic American steakhouse serves Gibsons Prime Angus Beef and Gibsons Grassfed Australian Beef. Gibsons also features fresh fish, classic cocktails, an extensive wine list and exceptional service. Celebrities, Chicago visitors and loyal neighborhood residents enjoy three distinct locations: Chicago, Rosemont and Oak Brook. Beautiful private dining and events spaces available.
A photo of RL Restaurant restaurant
4.9
Exceptional(7300)
Price: Expensive
• American • Gold Coast / Streeterville
Booked 74 times today
If you do not find availability online, please call the restaurant directly at 312-475-1100.Located adjacent to the Ralph Lauren Chicago flagship store on Michigan Avenue, RL Restaurant features the vision and décor of Ralph Lauren in a modern club atmosphere. RL Restaurant offers classic American cuisine inspired by Ralph Lauren’s personal favorites. Seasonal dishes range from a chopped vegetable salad to a lobster roll sandwich, grilled fish of the day and steaks. On the cocktail list, guests can choose from classic drinks and a diverse selection of wines and other fine spirits.
A photo of Rosebud Steakhouse - Chicago restaurant
4.7
Exceptional(3517)
Price: Expensive
• Steak • Gold Coast / Streeterville
Booked 35 times today
*Rosebud Steakhouse is a special occasion restaurant, with an UPSCALE BUSINESS CASUAL Dress Code Policy. For clarification please review the policy at https://rosebudsteak.com/dress-code/ and we thank you for your courtesy. Welcome to a rare steakhouse, well done! Rosebud Steakhouse knows a thing or two about the fine art of cooking. Located on Walton Street, a stone's throw from Michigan Avenue, this relaxing hideout is the perfect place to enjoy an unforgettable meal paired with a glass of wine from our impressive wine list. The extensive menu features prime steaks by Meats by Linz, fresh seafood and Italian specialties. The beloved hamburger, voted number one in the city of Chicago by the Chicago Tribune, graces our dinner menu. Rosebud Steakhouse invites you to enjoy an unforgettable fine dining experience in a romantic setting. Rosebud Steakhouse is a Creative Hospitality Concepts restaurant. Visit our second location, coming soon to, Munster, Indiana.
A photo of RPM Italian - Chicago restaurant
4.6
Exceptional(12262)
Price: Expensive
• Italian • River North (Chicago)
Booked 157 times today
Located in Chicago’s River North neighborhood, RPM Italian is modern in approach and Italian in spirit, featuring a contemporary menu with dishes meant to be shared. The sister restaurant to RPM Steak and RPM Seafood, RPM Italian marks the first collaboration between partners RJ, Jerrod and Molly Melman of Lettuce Entertain You Enterprises and celebrity couple Giuliana & Bill Rancic.
A photo of Cabra - Chicago restaurant
4.7
Exceptional(3048)
Price: Expensive
• Peruvian • West Loop
Booked 77 times today
Perched atop the Hoxton Hotel in the heart of Chicago’s Fulton Market, Cabra Chicago is a lively rooftop escape, inspired by the bold and vibrant flavors of Peruvian cuisine. Led by James Beard Award and Top Chef winner Stephanie Izard, alongside longtime partners Rob Katz and Kevin Boehm of Boka Restaurant Group, Cabra serves up crave-worthy dishes in a colorful and energetic setting. The restaurant’s airy, plant-filled ambiance, paired with its open kitchen and sweeping city views, creates a dynamic dining experience. Guests can savor a variety of shareable plates, from ceviches to savory meats, all bursting with the rich, fresh flavors of Peru.
A photo of Legal Sea Foods - Chicago restaurant
4.0
Excellent(250)
Price: Expensive
• Seafood • River North (Chicago)
Booked 44 times today
Legal Sea Foods Chicago is now open along the vibrant Riverwalk in the bustling River North neighborhood at the famous Marina Towers. Legal's first Midwest location features two floors of upscale casual New England vibes with sweeping riverfront views and an outdoor space. The brand-new restaurant features a large main dining room, bar area, private event space, and outdoor terraces. Serving New England specialties such as Boston's best Clam Chowder and Half Pound Lobster Rolls, as well as new signature dishes and local favorites. Legal Sea Foods combines New England's coastal fishing traditions with modern culinary flair. A taste of New England in the Mid-West.
A photo of Jake Melnick's Corner Tap restaurant
4.5
Awesome(316)
Price: Moderate
• American • Gold Coast / Streeterville
Booked 62 times today
Come for the wings, stay for the party! Jake Melnick's Corner Tap has been a neighborhood favorite since opening its doors in 2002. The menu features mouth-watering BBQ dishes, classic American pub-fare and world-famous chicken wings – named the “Top Chicken Wings in the U.S.” by the Today Show. Relax and sip on local craft beers while you catch the game or enjoy a casual night out. The cozy indoor dining room and picturesque patio make it the perfect choice any time of year.
A photo of The Evie restaurant
4.8
Exceptional(787)
Price: Expensive
• American • River North (Chicago)
Booked 72 times today
Led by a team of lifelong Chicago restaurant figures, The Evie is a locally-owned upscale dining destination located at the heart of the Magnificent Mile. Led by Partner George Archos (Wildberry Café), Chef-Partner Nick Nitti (Forno Rosso, Lucia Rose, Cucina 3 Italian), and Executive Chef Phil Rubino (Spiaggia, L2O, Cicchetti), the restaurant provides city locals and visitors a place to unwind and indulge while overlooking iconic Michigan Avenue. Named after George’s mother and daughter, the concept puts family at the forefront, with an emphasis on warm, Midwestern hospitality. Evie offers full lunch/dinner and weekend brunch, presenting a menu of reimagined American classics and city favorites, spotlighting dishes like chef-crafted sushi rolls, freshly baked breads, Chicago-style Wagyu hotdogs, and USDA prime steaks. Complementing the menu, our dynamic beverage program weaves together seasonality and elegance, featuring an array of classic and craft cocktails, sake, beer & wine.
A photo of LAUREL restaurant
4.3
Awesome(19)
Price: Expensive
• American • River North (Chicago)
Booked 3 times today
LAUREL, nestled in Chicago's iconic Talbott Hotel, blends New American creativity with Mediterranean flavors, sourcing local and seasonal ingredients. Experience Mediterranean warmth paired with cosmopolitan flair in our full-service yet casual setting, offering a culinary journey for any occasion. Our design pays homage to the Mediterranean's diverse landscapes and artistic influences, creating a modern ambiance. Welcome to LAUREL, where craftsmanship meets creativity, and every meal celebrates flavor, community, and the art of living well.

See what locals rave about

From verified diners like you
From verified diners like you
  • JonVIP
    Chicago / Illinois •40 reviews
    5.0
    Dined 1 day ago
    I have been going to RL since they first opened. Always lovely, comfortable, clubby, excellent. It is a joy to be there. It is hard not to have the Dover sole. My favorite. And tonight. Joseph was our waiter. He was superb. Attentive but not too much. Classy. Friendly. But not too much. Works on the west side of the restaurant. I would ask for him. Can’t wait to go back.
    More info
    RL RestaurantPrice: Expensive• American• Gold Coast / Streeterville
    4.9
  • Peggy
    Chicago / Illinois •36 reviews
    5.0
    Dined 1 day ago
    This was my first time dining at RPM and it will not be my last!! The food, the service, the ambiance, all 10s!!!! But the food!!! OMG! What I like about this outstanding restaurant is they give you good portions of absolutely delicious food! And an elegant, first class dining ambiance with VIP service. I think my server’s name was Matty. Good date place, great place to dine w friends or a special occasion. Highly recommend! My only big complaint….the bar area was filled with gorgeous women!!! NEED MORE MEN PLEASE!! @RPM how about adding a cigar bar to attract the fellas??
    More info
    RPM Italian - ChicagoPrice: Expensive• Italian• River North (Chicago)
    4.6
  • JuneVIP
    Chicago / Illinois •50 reviews
    5.0
    Dined 2 days ago
    LOVE THIS PLACE! It is always my SPECIAL TREAT go to. Food is always outstanding, service is not only impeccable, but warm, thoughtful, and personable. The ambiance is warm and inviting. We made a reservation mid-afternoon so my friend, who is challenged when there is too much noise. could enjoy the very best first experience at Rosebud. The Rosebud staff definitely won her heart. Thank you for great service Tatiana! :-)
    More info
    Rosebud Steakhouse - ChicagoPrice: Expensive• Steak• Gold Coast / Streeterville
    4.7
  • Rene
    Phoenix / Arizona •5 reviews
    5.0
    Dined 5 days ago
    Gibson's is one of my favorite restaurants of all times. We live in San Antonio but make it a point to make reservations when in Chicago, Because of the holidays, I scheduled reservations 3 months in advance. Service was superb, as always. I ordered the W.R.'s Chicago Cut and was very disappointed. The steak was cold and did not appear anywhere close to 22 oz. My son ordered a 7 oz Filet Mignon, and he was disappointed as it was very dry and overcooked. I know I could have said something at the table, but I didn't want to ruin the moment as we were having such a great time being together. The service was outstanding, and hope that next time it will be the same Gibson's experience.
    More info
    Gibsons Bar & Steakhouse - ChicagoPrice: Expensive• Steakhouse• Gold Coast / Streeterville
    4.7
  • MichaelVIP
    Minneapolis - St. Paul •3 reviews
    5.0
    Dined 5 days ago
    Excellent evening great service. Pizza was excellent!
    More info
    Happy Camper Pizza - Old TownPrice: Moderate• Pizzeria• River North (Chicago)
    4.8
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