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Best Southwest American Restaurants in Old Town

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334 restaurants available nearby

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A photo of Benchmark restaurant
4.5
Awesome(5)
Price: Moderate
• Mexican • 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 Utopian Tailgate restaurant
3.9
Excellent(190)
Price: Expensive
• Mexican • Lincoln Park
Booked 5 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 Woodie's Flat restaurant
5.0
Exceptional(1)
Price: Moderate
• Mexican • Old Town
Woodie’s Flat is where sports, wings, and good beers come together in the heart of Old Town. Known for our award-winning wings, we’re the place to watch the big game, or grab a beer with friends.Every inch of our bar is built for fun—massive TVs for all the action, a dog-friendly patio, and a second floor where the energy never dies. Whether it’s college football, NHL, NBA, WNBA, or a random Wednesday night out, you’re gonna want to spend it with Woodie’s and team. And let’s talk about the food—our wings are legendary, and 3x People's Choice award winners at Chicago's Wing Out Festival. As our fearless leader and GM Shawn says, he’ll literally pay for them if you don’t think they’re the best wings you’ve ever had. A sizable beer list and we've even got those trendy non-alcoholic THC seltzers. From 22oz frosty fatpour mugs of beer to late-night bites, Woodie’s is the MVP of your weekend lineup.
A photo of Black Barrel Lounge - OLD TOWN restaurant
4.3
Awesome(110)
Price: Moderate
• Mexican • Old Town
Updated Americana Fare From Scratch!The Black Barrel LIVE is an updated Americana & Brunch fare tavern and LIVE music venue with a sport friendly attitude with an incredible patio. It is a meeting place for patrons of Chicago and those visiting, all are welcome! With our long list of speciality cocktails and craft beer, there is an option for everyone. Live entertainment happens all the time, including Karaoke, Dueling Pianos, Full bands, Singer / Songwriter Jams, Acoustic Brunch.Grab some delicious food and drink and enjoy the LIVE entertainment!Winner 2020 Chicago Hamburger HopIncredible Outdoor Patio, LIVE MUSIC, Happy hour, Specialty Cocktails, Private Barrel Programs, delicious Fare!
A photo of Corcoran’s Grill & Pub restaurant
4.1
Excellent(164)
Price: Moderate
• Mexican • Old Town
Booked 3 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 3 Arts Club Cafe at RH Chicago restaurant
4.8
Exceptional(3750)
Price: Expensive
• Mexican • Gold Coast / Streeterville
Booked 181 times today
The 3 Arts Club Café resides in the grand central garden courtyard of RH Chicago, the Gallery at the Historic Three Arts Club, a 70,000-square-foot design gallery in Chicago's famed Gold Coast neighborhood. We invite you to enjoy our menu of timeless classics for brunch and dinner, and a selection of wines from esteemed vintners in the United States and Europe. RH Chicago also features the 3 Arts Club Wine Vault.For group dining inquiries, please email: chicagohospitality@rh.com
A photo of Summer House - Chicago restaurant
4.7
Exceptional(8125)
Price: Moderate
• Mexican • Lincoln Park
Booked 345 times today
Summer House in Chicago's Lincoln Park offers an authentic taste of Californian cuisine, transporting diners straight to the West Coast with its beach house decor and retractable glass ceiling. Chef Ben Goodnick’s menu brims with seasonal specialties, including market-driven pasta and artisan pizzas that capture the essence of California's fresh, vibrant flavors. Guests rave about the "delicious food and cocktails," with the prickly pear cocktail and oversized cookies receiving special praise. The restaurant’s sunny ambiance and friendly service make it a "wonderful environment" for any dining occasion. Whether brunch or dinner, Summer House provides an exceptional Californian dining experience.
A photo of Café Ba-Ba-Reeba restaurant
4.8
Exceptional(9475)
Price: Moderate
• Mexican • Lincoln Park
Booked 184 times today
Café Ba-Ba-Reeba! in Lincoln Park, Chicago, is a must-visit for those craving authentic American cuisine with a delightful twist. This vibrant restaurant is renowned for its delicious tapas and energetic ambiance, making it "one of the all-time favorites" for locals and visitors alike. The "amazing food, drinks, and service" consistently receive high praise, with many highlighting the delectable seafood paella and flavorful sangria. The lively atmosphere paired with attentive service ensures a memorable dining experience. Café Ba-Ba-Reeba! effortlessly combines traditional American flavors with a contemporary flair, making it a standout choice for any occasion.
A photo of Gibsons Bar & Steakhouse - Chicago restaurant
4.8
Exceptional(9214)
Price: Expensive
• Mexican • Gold Coast / Streeterville
Booked 150 times today
Gibsons Bar & Steakhouse in Chicago’s vibrant Gold Coast is a testament to classic American cuisine at its finest. Renowned for serving "the best steak I’ve ever had," Gibsons offers an unparalleled dining experience that combines premium Gibsons Prime Angus Beef with impeccable service. From the lively ambiance to the expertly crafted cocktails, every visit is a celebration of authentic American dining. Diners rave about the "wonderfully cozy feel" and "outstanding" food, making it a top choice for both locals and visitors alike. With a reputation for excellence, Gibsons is undoubtedly a must-visit destination for lovers of quality American cuisine.
A photo of Girl & the Goat restaurant
4.7
Exceptional(15176)
Price: Moderate
• Mexican • West Loop
Booked 179 times today
Girl & the Goat, nestled in Chicago's vibrant West Loop, is a must-visit for tapas enthusiasts seeking a truly memorable dining experience. Known for its bold and inventive small plates, the restaurant celebrates locally sourced, seasonal ingredients with flair and creativity. Diners rave about standout dishes like the "goat empanadas with their perfectly flaky crust and savory filling" and the "crispy, flavorful chickpea fritters." The lively atmosphere and friendly service only enhance the experience, making it an excellent choice for groups or adventurous foodies. With each dish designed to share, every visit promises a delightful culinary adventure.

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See what locals rave about

From verified diners like you
From verified diners like you
  • AshleyVIP
    Chicago / Illinois •18 reviews
    5.0
    Dined 1 day ago
    Parking is awful around the restaurant looked 20 minutes to park the car.
    More info
    Pilsen YardsPrice: Moderate• Latin American• Pilsen
    4.8
  • JavierVIP
    Chicago / Illinois •23 reviews
    5.0
    Dined 2 days ago
    Very well done and flavorful dishes. We went for breakfast and we really liked it. Portions were just the right amount. Delicious mocktail and they were accommodating with requests.
    More info
    CeibaPrice: Moderate• Contemporary Mexican• Lincoln Park
    4.7
  • Alina
    Chicago / Illinois •5 reviews
    5.0
    Dined 2 days ago
    Great place! Got the pitcher of Margarita with prickly pear and nachos. It was amazing!
    More info
    Big Star Wicker ParkPrice: Moderate• Mexican• Bucktown / Wicker Park
    4.6
  • SinéadVIP
    San Francisco Bay Area •4 reviews
    5.0
    Dined 4 days ago
    i like the mango margarita with tajin on the rim or mango fresca for n/a and my favorite tacos are the carne asada, brisket and ay papasito. 3 very different options. carne is the classic tiny pieces of steak with a generous amount of onion and cilantro on corn. the brisket comes on a flour tortilla with pickled onion, carrot and a jalapeño slice or two. the ay papasito is a fried purple potato small taco and pickled cabbage topped with cheese
    More info
    Broken English Taco Pub - Lake StreetPrice: Expensive• Mexican• Downtown / Loop
    4.7
  • NicoletteVIP
    Chicago / Illinois •9 reviews
    5.0
    Dined on Mar 30, 2025
    We’ve been here several times and it’s always great! We’ve never had a time where the food taste different or not the same, this place is consistent. It’s is a bit pricey, but the quality is great. The drinks are average, more on the sugary side but not mad. Like you have to have a marg at some point! Service is quick and friendly. It’s a bit loud in there between the music and people, but when it’s almost 70 degrees in March then hey if you can’t beat em, join em.
    More info
    Cafe El TapatioPrice: Expensive• Mexican• Lakeview / East Lakeview
    4.8

Discover best Mexican / Southwestern restaurants in Old Town

Discover the vibrant flavors of Mexico in the heart of Old Town, Chicago with a selection of top Mexican restaurants catering to every taste. From authentic tacos to innovative Mexican-inspired dishes, these eateries boast a mix of traditional and modern culinary offerings. Enjoy a diverse menu featuring everything from rich guacamoles to savory enchiladas and refreshing margaritas. Each location prides itself on a warm atmosphere, excellent service, and a commitment to quality ingredients, ensuring a memorable dining experience. Old Town, Chicago is known for its lively dining scene, blending historic charm with contemporary flair, making it a prime destination for both locals and tourists seeking a unique meal. Whether you're in the mood for a casual bite or a sophisticated dinner, the Mexican restaurants in Old Town offer an array of options to satisfy your cravings. Dive into the heart of Mexican cuisine in Chicago and enjoy a blend of taste and culture at every turn.

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