Old Town Chicago, with its cobblestone streets and charming architecture, offers a delightful dining experience beyond its picturesque setting. This guide explores 18 of the best restaurants, showcasing diverse cuisines and ambiances to satisfy every palate. Whether you're craving a romantic dinner, a casual meal with friends, or a celebratory feast, Old Town has something to offer. We'll cover everything from classic Chicago-style deep dish to global culinary adventures, ensuring you discover your new favorite Old Town gem. This list of the best Old Town Chicago restaurants caters to varied tastes and budgets.
Classic Chicago Charm
1. Lou Mitchell's: A Chicago institution
Lou Mitchell's is a legendary diner that has served Chicagoans and tourists alike for decades. Their massive portions of classic American breakfast fare are a must-try, especially their famous buttermilk pancakes. The nostalgic atmosphere and friendly service transport you back in time, making it a quintessential Old Town experience.
Why it's great: Iconic Chicago experience, massive portions, affordable prices.
2. The Purple Pig: Mediterranean tapas
This vibrant restaurant offers a fantastic selection of Mediterranean-inspired tapas, perfect for sharing and experiencing a variety of flavors. The lively atmosphere and expertly crafted cocktails make it ideal for a fun night out with friends.
Why it's great: Shared plates, diverse flavors, lively atmosphere, extensive cocktail menu.
3. Rosebud on Rush: Upscale Italian
Rosebud on Rush provides an elegant Italian dining experience in a sophisticated setting. Their menu features classic Italian dishes made with high-quality ingredients. It's perfect for a special occasion or a romantic dinner.
Why it's great: Elegant ambiance, classic Italian dishes, high-quality ingredients, ideal for special occasions.
Global Flavors in Old Town
4. RPM Italian: Modern Italian
RPM Italian is known for its stylish setting and elevated take on Italian cuisine. Their pasta dishes are particularly noteworthy. The restaurant's ambiance is perfect for a celebratory meal or an impressive date night.
Why it's great: Stylish ambiance, modern Italian cuisine, expertly crafted pasta.
5. Bavette's Bar & Boeuf: French-inspired steakhouse
Experience a sophisticated French-inspired steakhouse experience at Bavette's. Their prime cuts of beef are cooked to perfection, and the classic sides complement the rich flavors of the meat.
Why it's great: Prime cuts of beef, classic steakhouse experience, sophisticated ambiance.
6. Sunda: Pan-Asian fusion
Sunda offers a unique Pan-Asian fusion experience, blending various Asian culinary traditions into innovative and delicious dishes. The creative menu is a culinary adventure, and the modern setting is both stylish and welcoming.
Why it's great: Unique Pan-Asian fusion, creative menu, modern and welcoming atmosphere.
Casual & Cozy Spots
7. North Pond: Upscale American
North Pond, with its stunning setting overlooking a pond, offers an upscale American menu with seasonal dishes. Their ambiance is perfect for a relaxed yet refined dining experience.
Why it's great: Beautiful setting, upscale American cuisine, seasonal dishes, relaxed yet refined ambiance.
8. Old Town Social: American gastropub
Old Town Social delivers a lively gastropub experience with a modern twist. Their extensive menu features comfort food with creative enhancements, and their extensive beer selection satisfies any brew lover.
Why it's great: Lively gastropub ambiance, creative comfort food, extensive beer selection.
9. Andros Taverna: Authentic Greek
For authentic Greek cuisine, Andros Taverna is a neighborhood favorite. Their fresh ingredients and traditional recipes provide a taste of Greece right in Old Town.
Why it's great: Authentic Greek cuisine, fresh ingredients, traditional recipes, neighborhood favorite.
Unique Dining Experiences
10. Geja's Cafe: Romantic Italian
Geja's Cafe provides an incredibly romantic Italian dining experience, complete with candlelit tables and live music. Their intimate setting creates a magical ambiance perfect for couples.
Why it's great: Incredibly romantic, candlelit tables, live music, intimate setting.
11. The Dearborn: Modern American
The Dearborn offers a modern American menu with a focus on seasonal and locally sourced ingredients. The stylish interior and creative cocktails complete the modern dining experience.
Why it's great: Modern American cuisine, seasonal and locally sourced ingredients, stylish interior, creative cocktails.
Sweet Treats & More
12. Weber Grill Restaurant: Upscale Steakhouse
A sophisticated steakhouse, Weber Grill offers excellent cuts of meat with elevated sides and a high-quality wine list. It's perfect for a special celebration or a business dinner.
Why it's great: Upscale steakhouse, high-quality ingredients, extensive wine list.
13. Big Star: Taco Joint
Enjoy casual and delicious tacos in a vibrant and lively atmosphere. Big Star is a perfect spot for a quick and tasty meal, and their margaritas are always a hit.
Why it's great: Casual dining, delicious tacos, margaritas, lively atmosphere.
Hidden Gems & Neighborhood Favorites
14. DMK Burger Bar: Gourmet Burgers
If you're in the mood for gourmet burgers, DMK Burger Bar offers a variety of creative and delicious options. Their unique burger combinations will surely impress any burger enthusiast.
Why it's great: Gourmet burgers, creative burger combinations, friendly atmosphere.
15. The Winchester: Gastropub
Known for their wide selection of beers and delicious gastropub food, The Winchester is a great place to unwind with friends. Their cozy atmosphere makes it a neighborhood favorite.
Why it's great: Cozy atmosphere, great selection of beers, tasty gastropub food.
Beyond the Usual
16. Monteverde: Modern Italian
Monteverde brings a modern approach to Italian cuisine. Their pasta is handmade, and they prioritize fresh, seasonal ingredients. The restaurant consistently receives high praise from critics and diners.
Why it's great: Modern Italian cuisine, handmade pasta, fresh and seasonal ingredients.
17. The Kinzie Chop House: Upscale Steakhouse
The Kinzie Chop House provides an unforgettable upscale steakhouse experience. Their premium cuts of meat are prepared to perfection. It's a great choice for a memorable meal.
Why it's great: Upscale steakhouse, premium cuts of meat, impeccable service.
18. Tufano's Vernon Park Tap: Italian-American
This long-standing Italian-American restaurant is known for its family atmosphere and classic dishes. It's a perfect place for a relaxed and casual meal.
Why it's great: Family atmosphere, classic Italian-American dishes, casual dining.
This diverse list provides a great starting point for exploring Old Town Chicago's vibrant culinary scene. Remember to make reservations, especially for popular spots, and enjoy the delicious food and charming atmosphere of this historic neighborhood. Happy dining!
