Best of 18 restaurants in Old Town
Old Town, a cherished historic district, is a popular destination offering a unique dining experience. Discover the charm of "restaurants in Old Town," where a delightful blend of rich history and exquisite cuisine creates unforgettable memories. Whether you're seeking cozy eateries or upscale dining, Old Town's restaurants cater to various tastes and preferences. Immerse yourself in the vibrant atmosphere and savor the flavors at these exceptional "restaurants in Old Town."
- 1. The VIG
- 2. Topo Gigio Ristorante in Old Town
- 3. Old Town Pour House (Old Town - Chicago)
- 4. Twin Anchors Restaurant & Tavern in Old Town
- 5. Orso's
- 6. Broken English Taco Pub
- 7. Gussie's Handmade Italian
- 8. The Glunz Tavern
- 9. Nookies on Wells
- 10. Old Jerusalem Restaurant
- 11. Woodie's Flat in Old Town
- 12. Kamehachi
- 13. LG's Bar & Kitchen
- 14. Old Town Pub
- 15. 1959 Kitchen & Bar
- 16. Adobo Grill
- 17. Boka
- 18. Gallucci Pizzeria Napoletana
1. The VIG
Historic location, live music on weekends

The service is a major highlight of the guest experience, with many praising it as stupendous, kind, and attentive. Servers are particularly singled out for their amazing energy and outstanding service.
Guests are impressed with the quality of the food and the venue. The overall consensus is that it is great. Many guests also express their intention to return, highlighting their satisfaction with their experience.
TOPICS
- Italian Cuisine
- Mid-Range
- Downtown Spots
- Vegetarian Options
2. Topo Gigio Ristorante in Old Town
Authentic Italian experience since 1989, extensive wine list

The service at this establishment is highly regarded by users, who describe it as friendly, quick, attentive, helpful, and impeccable. The food offerings are varied and include well-prepared, fresh options such as pasta dishes, grilled calamari, veal, and chicken. Although some reviewers mention the high prices, the food is generally highly recommended.
A recent visitor raved about their experience at the restaurant, advising future patrons to arrive hungry due to the generously-sized portions. The reviewer specifically praised the Italian food and noted that the restaurant was busy, but tables were not crowded together, which was appreciated in the current pandemic context. The restaurant is spacious with both indoor and outdoor seating areas. The wait staff were attentive and friendly, contributing to the positive experience of the reviewer.
TOPICS
- Italian Cuisine
- Downtown Spots
- Mid-Range
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3. Old Town Pour House (Old Town - Chicago)
Features over 90 craft beers on tap and a rooftop bar

Old Town Pour House is a spacious sports bar located in the Old Town area of Chicago, known for its high ceilings, large TVs, and upscale atmosphere. The bar offers an extensive selection of beers on tap and serves quality food, including sandwiches, burgers, and other hearty fare.
Making reservations is a breeze, and the interior design is striking, making it an excellent choice for a group dinner. The prices are reasonable considering the location and portion sizes. The fish tacos are a popular menu item, known for their delicious taste. Whether you're looking to catch a game or enjoy a meal with friends, Old Town Pour House is an excellent choice.
TOPICS
- Happy Hours
- Social Gatherings
- Downtown Spots
4. Twin Anchors Restaurant & Tavern in Old Town
Family-owned and operated since 1932, cash-only establishment

The service at this establishment is generally regarded as fast, friendly, and efficient. However, there are some reviews that mention less than satisfactory service experiences. It is important to note that long wait times are to be expected, particularly on weekends. To accommodate guests, the bar area is open for seating while they wait. The staff is known to be friendly and attentive, which helps to create a positive atmosphere despite potential delays.
In summary, the service at this establishment is mostly seen as good, with a few exceptions. The wait times can be lengthy, but the friendly and accommodating staff make the experience more enjoyable. The bar area is open for seating while guests wait, allowing them to relax and enjoy themselves before being seated.
TOPICS
- American Cuisine
- Mid-Range
- Downtown Spots
- Dinner
5. Orso's
Established in 1975, Orso's is a classic Italian restaurant with live music on weekends.

The service provided at the event was highly praised by reviewers. They described it as perfect, friendly, and efficient. The staff went above and beyond to ensure that guests were comfortable and satisfied. One aspect of the service that stood out was how attentive and accommodating the staff was when it came to drinks.
Guests were served drinks before and after the ceremony, with a champagne toast provided. The staff made sure that drinks never went empty, constantly checking on guests and topping them off. Their proactive approach to ensuring guests had enough to drink was greatly appreciated and contributed to the overall positive atmosphere of the event.
TOPICS
- Italian Cuisine
- Social Gatherings
- Budget-Friendly Eats
- Downtown Spots
6. Broken English Taco Pub
Cool interior design, extensive tequila list, late-night happy hour

Broken English is a restaurant that offers a welcoming atmosphere with good vibes, delicious drinks, and food. The service is exceptional, with servers who are dedicated to ensuring customers have a great dining experience. One such server, Lyssie, stands out for her outstanding service.
During a walk through Lincoln Park and Old Town on Wells, a group of people decided to have lunch at Broken English, which opened at 12 noon. The guests entered the restaurant just as it opened and ordered guacamole with chips, chicken tacos, and fried guac tacos. The food was excellent, and the service was top-notch, making for an enjoyable lunch experience.
TOPICS
- Mexican Cuisine
- Vegetarian Options
- Budget-Friendly Eats
7. Gussie's Handmade Italian
Family-owned restaurant with a traditional Italian menu

Gussie'handmade Italian, located on North Avenue, is a hidden gem that offers an unexpected culinary experience inspired by family and the diverse kitchens across Italy. Driving by, it may be easy to miss, but for those who discover it, they are in for a treat. The establishment is a neighborhood place that takes you on a delightful journey across the ocean, thanks to its menu filled with homemade dishes that are sure to impress.
From the moment you step inside Gussie's, you are greeted with a warm and inviting atmosphere that makes you feel right at home. The menu is filled with an array of homemade dishes that are inspired by the diverse kitchens across Italy. Each item is prepared with love and care, and it's easy to see why this place has become a local favorite. From the pasta to the sauces and everything in between, everything is made in-house, ensuring a truly authentic Italian dining experience. Whether you're looking for a cozy spot for a date night or a place to catch up with friends, Gussie's Handmade Italian is the perfect spot.
TOPICS
- Italian Cuisine
- Downtown Spots
- Dinner
8. The Glunz Tavern
Historic location since 1879, Extensive wine list, German-American cuisine

The service at this establishment is highly regarded by guests, who describe it as stupendous, kind, attentive, and outstanding. The servers are a particular highlight, with guests praising their amazing attitudes and great energy. Overall, the service is described as friendly, quick, helpful, and impeccable.
The food at this restaurant is highly recommended, with reviewers raving about the delicious flavors and fresh ingredients. There is a wide variety of options on the menu, including pasta dishes, grilled calamari, veal, and chicken. Although some reviewers mention the high prices, the fresh and perfectly prepared food makes it worth the cost.
TOPICS
- Social Gatherings
- Italian Cuisine
- Vegetarian Options
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9. Nookies on Wells
Offers alcohol-infused cookie shots

Nookies on Wells is a restaurant that stands out with its exceptional service and delicious food. Customers can expect to be well taken care of, with a focus on providing love and warmth through their meals.
The restaurant is known for its super fast service, ensuring that customers don't have to wait long to enjoy their delicious food. The menu features standout items such as blueberry pancakes, which are widely regarded as the best around, and satisfying omelets that have received high praise from young diners.
TOPICS
- Italian Cuisine
- Mid-Range
- Downtown Spots
- Vegetarian Options
10. Old Jerusalem Restaurant
Family-owned restaurant operating since 1977, featuring halal menu options

The portions of the food served at this establishment are generous, providing good value for the money spent. The service received by customers is generally positive, with staff described as friendly, efficient, and quick. However, there are some reviews that mention the service can be slow at times.
This restaurant specializes in Middle Eastern cuisine, offering a variety of dishes that cater to different tastes. Popular options include chicken, gyros, baba ghannouch, falafel, hummus, and many more. The menu provides a wide range of choices for customers to explore and enjoy the rich flavors of Middle Eastern food.
TOPICS
- Social Gatherings
- Italian Cuisine
- Mid-Range
- Downtown Spots
11. Woodie's Flat in Old Town
Features a rooftop deck, live music, and pool tables.

Woodie's Flat is a casual restaurant in Old Town known for its great atmosphere and exceptional wings. It's an excellent place to enjoy a relaxed evening while watching a sports game. The wings are one of the highlights of the menu, perfectly smoked to the point of falling off the bone. There is a wide variety of sauces to choose from, making each wing experience unique.
If you're in the mood for some delicious wings and a casual night out, Woodie's Flat is the place to be. Located in Old Town, this restaurant offers a great atmosphere and an extensive selection of sauces to go with their amazing wings. Whether you're watching basketball or just looking for a place to grab a bite, Woodie's Flat is sure to impress with its perfectly smoked wings and diverse sauce options.
TOPICS
- American Cuisine
- Affordable Nightlife
- Downtown Spots
12. Kamehachi
Established in 1973, one of the first sushi restaurants in Chicago

The food offered at this establishment is consistently described as delicious by reviewers. Two popular items mentioned are sushi and gyoza. While some visitors had less than satisfactory service experiences, others rated it as accommodating and friendly.
Service seems to be a hit-or-miss experience for visitors. A few reviewers describe the service as slow, while others found it to be friendly and spotty. However, there are also some who had wonderful encounters with the service staff.
TOPICS
- Asian Cuisine
- Downtown Spots
13. LG's Bar & Kitchen
Live music on weekends, dog-friendly patio, and happy hour specials

The food at this establishment is truly delicious, with a diverse and interesting menu that is sure to impress. The atmosphere is warm and inviting, making it a great place to gather with friends and family.
The drinks selection is equally impressive, with a variety of options that are sure to please even the most discerning of palates. Customers rave about the quality and taste of the beverages, making it a popular spot for socializing and unwinding. Whether you're in the mood for something fruity, bold, or refreshing, this establishment has got you covered.
TOPICS
- American Cuisine
- Affordable Nightlife
- Downtown Spots
14. Old Town Pub
Offers a happy hour with discounted drinks and food.

The cozy bar, a staple in the neighborhood for years, features beautiful holiday lighting and real garlands as part of its decor. Inside, the bar is small but offers a welcoming atmosphere with good music, a friendly bartender, and enjoyable conversations with other patrons. The option to sit outside is also available, providing a nice space for conversation.
During a recent visit with a friend, we had the opportunity to experience both the outdoor and indoor seating. The indoor bar area is compact but conducive to having conversations. The menu includes pizza, which I am looking forward to trying on my next visit. Overall, the welcoming ambiance and friendly service make this bar a place I would like to return to.
TOPICS
- Social Gatherings
- American Cuisine
- Mid-Range
- Downtown Spots
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15. 1959 Kitchen & Bar
Impressive city view, Cozy outdoor seating, Great cocktails and wine list

This establishment is an excellent choice for a pre-show drink, situated near popular venues like Second City and Zanies. The staff is known for their accommodating service and the drinks are reasonably priced. On Friday night, we opted to have dinner here before our show. However, we found the menu to be quite limited.
I ordered the crab cake, which was the only dining option that caught my interest. Unfortunately, the serving size was smaller than expected; I received only one small cake. While the taste was enjoyable, I've previously only encountered crab cake orders that included at least two pieces. The size of the portion was not what I had in mind, considering the limited options on the menu.
TOPICS
- American Cuisine
- Downtown Spots
- Dinner
- Late Night
16. Adobo Grill
Live Latin music, extensive tequila selection, freshly made salsas

Adobo Grill is a well-known restaurant in Chicago that specializes in authentic Mexican cuisine. The restaurant offers a diverse menu that showcases the rich flavors and spices of Mexico. Guests can enjoy a variety of dishes, including tacos, enchiladas, and tamales, all made with fresh ingredients and traditional cooking techniques.
The restaurant is also known for its vibrant atmosphere, which adds to the overall dining experience. Adobo Grill's lively atmosphere is complemented by its decor, which features bright colors and traditional Mexican art. The restaurant's staff are friendly and attentive, providing excellent service to guests. Overall, Adobo Grill is a great destination for anyone looking to experience authentic Mexican cuisine in a welcoming and energetic environment.
TOPICS
- Mexican Cuisine
- Vegan Options
- Mid-Range
- Downtown Spots
17. Boka
All-you-can-eat option available, High-quality meat selection, On-site BBQ grills

TOPICS
- American Cuisine
- High-End
- Downtown Spots
18. Gallucci Pizzeria Napoletana
Wood-fired oven, imported Italian ingredients

TOPICS
- Italian Cuisine
- Mid-Range
- Downtown Spots