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Best Southwest American Restaurants in Old Town

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356 restaurants available nearby

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A photo of Utopian Tailgate restaurant
4.2
Awesome(205)
Price: Expensive
• Mexican • Lincoln Park
Booked 22 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
4.4
Awesome(5)
Price: Moderate
• Mexican • Old Town
Booked 14 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
• Mexican • Old Town
Booked 4 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 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 3 Arts Club Cafe at RH Chicago restaurant
4.8
Exceptional(3883)
Price: Expensive
• Mexican • Gold Coast / Streeterville
Booked 205 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(8302)
Price: Moderate
• Mexican • Lincoln Park
Booked 337 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 Gibsons Bar & Steakhouse - Chicago restaurant
4.8
Exceptional(9409)
Price: Expensive
• Mexican • Gold Coast / Streeterville
Booked 160 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 Café Ba-Ba-Reeba restaurant
4.8
Exceptional(9560)
Price: Moderate
• Mexican • Lincoln Park
Booked 164 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 LUXBAR restaurant
4.7
Exceptional(3030)
Price: Moderate
• Mexican • Gold Coast / Streeterville
Booked 98 times today
At LUXBAR in Chicago's vibrant Gold Coast neighborhood, you will discover the pinnacle of Burger cuisine. Known for its delectable burgers, LUXBAR offers a menu that transforms a classic staple into a gourmet delight. Each burger is "perfectly prepared and satisfying," with flavors that truly stand out, making it a must-try for any burger aficionado. The restaurant's commitment to quality is evident, as guests rave about the "royal burger being perfectly cooked" and paired with "amazing fries." LUXBAR's lively atmosphere, coupled with its "top-notch service," ensures an unforgettable dining experience where both the food and ambiance shine.
A photo of Girl & the Goat restaurant
4.7
Exceptional(15399)
Price: Moderate
• Mexican • West Loop
Booked 246 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
  • PiaVIP
    New York City •2 reviews
    5.0
    Dined 2 days ago
    Great food, authentic Mexican soup was a nice welcome. The Mexican tortillas were amazing, The mexican IPA and pilsener were outstanding . The service was great as well as the cocktails. Will def go back.
    More info
    CeibaPrice: Moderate• Contemporary Mexican• Lincoln Park
    4.9
  • Alexander
    Philadelphia County •1 review
    5.0
    Dined 3 days ago
    Great staff and great food . Molly family had a great food experience.
    More info
    Broken English Taco Pub - Lake StreetPrice: Expensive• Mexican• Downtown / Loop
    4.7
  • scott
    Central Kentucky •1 review
    5.0
    Dined 5 days ago
    Outstanding food great service right across the street from heaven Wrigley Field. Definitely a great place to go before a game as well outstanding tequila great bourbon can’t go wrong.
    More info
    Big Star - WrigleyvillePrice: Moderate• Mexican• Wrigleyville
    4.4
  • IanVIP
    Chicago / Illinois •6 reviews
    5.0
    Dined on Jun 5, 2025
    Always great and new food options we amazing. Sitting on patio is always fun.
    More info
    Big Star Wicker ParkPrice: Moderate• Mexican• Bucktown / Wicker Park
    4.4
  • JohnVIP
    Chicago / Illinois •26 reviews
    4.0
    Dined on May 24, 2025
    We are regulars. I’ve been eating at El Tapatio since 1989 not long after I graduated college and moved into the neighborhood. It’s been consistent and fantastic ever since. The only reason I didn’t give a perfect score this time, was in spite of having a reservation for 6:30. We had to wait till 7:00 to be seated. In spite of noticing several other similar sized groups being seated ahead of us. I’m sure it’s due to being a party of 3, but that’s not my problem. We needed to be somewhere be a certain time afterward. Which is the reason for a reservation. In the future, if I make a reservation for a specific time, the polite thing to do is seat us within 10 minutes of that time. Or at least freaking apologize, or buy us a drink while we wait, or acknowledge the screw up. But nothing? Not a damn word. Disappointed. You guys can do better.
    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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