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Best Casual Restaurants in Old Town

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72 restaurants available nearby

How are Featured results ranked

A photo of Utopian Tailgate restaurant
4.0
Excellent(197)
Price: Expensive
• American • Lincoln Park
Booked 25 times today
A place for friends, wanderers, and adventurers. May you have a drink in your hand and a song in your heart. A playground for grownups 21+ With a curated menu of elevated tailgate fare and an extensive bar program, Utopian Tailgate delivers high times, chill vibes, and an unforgettable experience where the party never ends... and neither do the views.Perched high atop Piper's Alley, above world-famous comedy enclave The Second City, Utopian Tailgate is Chicago's best never-ending rooftop party. Super-sized Jenga, drinking games, disco dance party, and a whole lot more mix with elevated eats and whimsical whistle-wetters all year ‘round. Reservations are encouraged, but we always accept walk-ins until we reach capacity. Reservations will be held for 15 minutes. We offer indoor and outdoor table reservations, as well as party booths (with minimum required spend). We're a 21+ venue.
A photo of Benchmark restaurant
4.5
Awesome(5)
Price: Moderate
• American • Old Town
Booked 4 times today
Benchmark, located in the heart of Old Town, is open for lunch, happy hour, and dinner—Tuesday through Friday from 5pm to close, and Saturday and Sunday from 11am to close. Indulge in our delicious new menu, refreshing cocktails, and vibrant atmosphere—perfect for enjoying great food, catching the game, celebrating parties, or just hanging out with friends.
A photo of Corcoran’s Grill & Pub restaurant
4.5
Awesome(164)
Price: Moderate
• Irish • Old Town
Booked 2 times today
Corcoran's Grill & Pub is located in the heart of Old Town neighborhood, across the street from The Second City. 15 Beers on Tap (including craft, Irish imports and domestic selections), signature cocktails and wine. Irish & American cuisine featuring Pub burger, Fish & Chips, Corned Beef Sandwich and much more! Open for lunch, dinner and late night, offering great daily deals. In the spring and summer we offer special hours, an amazing beer garden as well as a front patio.
A photo of LUXBAR restaurant
4.6
Exceptional(3018)
Price: Moderate
• American • Gold Coast / Streeterville
Booked 94 times today
The quintessential American bar, LUXBAR features seasonal and classic cocktails made from freshly pressed juices, premium ice, house made shrubs, and an extensive selection of spirits that runs especially deep in whiskey and bourbon. A "Build Your Own Manhattan" menu, thoughtful, approachable wine list, and beer menu with vintage and local options make the bar a go-to for casual, mid-week drinks and bites with friends, watching weekend sports and post-shopping. Beautiful private dining and events spaces available.
A photo of LAUREL restaurant
4.3
Awesome(52)
Price: Expensive
• American • River North (Chicago)
Booked 4 times today
LAUREL, nestled in The Talbott, 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.
A photo of Tavern on Rush restaurant
4.6
Exceptional(3738)
Price: Expensive
• Steak • Gold Coast / Streeterville
Booked 66 times today
Tavern On Rush is the premier dining destination for steaks & seafood in Chicago. The upscale, contemporary steakhouse features multi-level seating, private dining, a bustling bar, and Chicago's favorite outdoor patio.
A photo of Shore Club restaurant
4.4
Awesome(750)
Price: Expensive
• Global, International • Gold Coast / Streeterville
Booked 118 times today
Inspired by beautiful beaches around the world, the elevated food menu, great service, and unobstructed views of Lake Michigan making it Chicago's go-to summer destination.Outdoor Patio Seating is available for reservations and walk-ins. In the case of inclement weather, our team will do our best to accommodate outdoor patio reservations inside, but indoor seating is not guaranteed. Reservations for The Oasis at Shore Club can be made at https://www.shoreclubchi.com/oasis-shore-clubShore Club Chicago is Credit Card Only. We Accepts All Major Credit Cards & Apple Pay. We Do Not Accept CASH.
A photo of Pandan restaurant
4.7
Exceptional(54)
Price: Moderate
• Cocktail Bar • Gold Coast / Streeterville
Booked 21 times today
Venture to the 18th floor of Viceroy Chicago to discover a seductive world where the sky is your ceiling and gorgeous city views unfold from every angle. Welcome to Pandan, a lush cocktail experience in the heart of the Gold Coast. Bask in what seems like infinite sunshine and starlight as you share baos and buns from the menu of Southeast Asian cuisine. The cocktail menu is as vast as the skyline itself and full of alluring flavors you haven't yet imagined. Sink into a lounge chair surrounded by botanicals and greenery. You'll quickly see: Pandan is a world unto itself -a haven for secluded celebrations, important connections, and whispered secrets. And the undercurrent of exclusivity is undeniable. Pandan is not just a scene. It's a satisfying new perspective. Come up. Elevate.
A photo of The Publican restaurant
4.6
Exceptional(5964)
Price: Expensive
• American • West Loop
Booked 37 times today
An homage to oysters, pork and beer, The Publican's eclectic menu is inspired by simple farmhouse fare in a space evocative of a European beer hall. Chef-Partner Paul Kahan has developed a network of purveyors to supply the restaurant with hand-selected and sustainably-raised fish, seafood and pork.Patio seating is first come, first served. Walk-ins are always welcome!
A photo of Ada Street restaurant
4.8
Exceptional(1106)
Price: Expensive
• American • Bucktown / Wicker Park
Booked 31 times today
Located in the Elston Industrial District--not quite Bucktown, not quite Lincoln Park--Ada Street offers dinner service five days a week.

See what locals rave about

From verified diners like you
From verified diners like you
  • LindaVIP
    Chicago / Illinois •109 reviews
    5.0
    Dined 7 days ago
    Great food, great , friendly service with an energetic ambiance.
    More info
    LUXBARPrice: Moderate• American• Gold Coast / Streeterville
    4.6
  • Tiaa
    Chicago / Illinois •3 reviews
    5.0
    Dined on Jun 3, 2025
    Alyssa was a super dope waitress. Her customer service and attentiveness was excellent.
    More info
    Utopian TailgatePrice: Expensive• American• Lincoln Park
    4
  • Brian
    Philadelphia County •30 reviews
    4.0
    Dined on Jun 2, 2025
    Food and drinks were fine. Service was a little inattentive. Value was not there.
    More info
    LAURELPrice: Expensive• American• River North (Chicago)
    4.3
  • NancyVIP
    Chicago / Illinois •64 reviews
    4.0
    Dined on Feb 12, 2025
    We are old, maybe even qualifying as elderly. We wanted to find a place to eat in Old Town on a very cold, very snowy evening before we headed for a show at Second City. Benchmark looked about right for a quick, burger meal. Now keep in mind that the next day we had lunch at our more regular haunts, Gibson's and then the day after at RL. Both were what we would describe as 5 stars in every category, so keep that in mind. We're giving this four stars since the burgers would good and came as ordered. The waitress was attentive and helpful. It happened to also be Trivia Night, so we had some entertainment, though we didn't participate, but enjoyed the tables around us of young people. We knew nearly every single answer and we shared a few with the neighboring tables. Probably against the rules, but who's going to complain about that nice older couple? I'd say if you're looking for a fairly quiet bar with decent food up on Wells, you might try this spot. Not outstanding, nothing like our usual, but adequate under the circumstances. Would we go again? Yes maybe, but clearly not our jam.....but damn we were good at trivia!
    More info
    BenchmarkPrice: Moderate• American• Old Town
    4.5
  • Lauri
    Grand Rapids / Western Michigan •16 reviews
    5.0
    Dined on Jan 12, 2025
    Great little pub to grab a bite before Second City. Friendly staff and food was delicious. Highly recommend
    More info
    Corcoran’s Grill & PubPrice: Moderate• Irish• Old Town
    4.5
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