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Best Restaurants with a Happy Hour in Old Town

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295 restaurants available nearby

A photo of Kayao restaurant
1. Kayao
4.6
Exceptional(188)
Price: Expensive
• Peruvian • Old Town
Booked 23 times today
At Kayao, we aim to showcase the dynamic flavors, techniques, and ingredients that unite Peruvian and Asian culinary traditions. Kayao is a melting pot of cultures and cuisines, where guests are invited to embark on a culinary journey that transcends borders and opens hearts. Through our commitment to authenticity, creativity, Kayao seeks to create intrigue while also pushing the boundaries of culinary innovation.
A photo of Benchmark restaurant
2. Benchmark
4.5
Awesome(4)
Price: Moderate
• American • Old Town
Booked 1 time 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 LG's Bar & Kitchen restaurant
3. LG's Bar & Kitchen
4.3
Awesome(136)
Price: Moderate
• American • Old Town
Booked 3 times today
LG's is a modern Irish American Bar & Kitchen in the heart of Old Town, Chicago. Offering evening meals, weekend brunch, and a variety of daily food and drink specials, LG’s Bar & Kitchen is the premier hotspot on Wells Street. Carrying a diverse selection of craft beers and cocktails, we pay particular attention to our Irish roots and love of Irish whiskeys. Diners can enjoy a variety of globally influenced dishes that are approachable, yet delicious. With an expansive TV selection, guests are welcomed into the best gameday location in Old Town. When the lights go down, LG’s features the best DJs in town, spinning all your favorite tunes. In the warmer months, LG’s has a full pet-friendly patio. We at LG’s like to say, “come for the food and stay for the party!”Our weekly events include:- Bingo Night on Wednesday at 7pm- Trivia Thursday from 7-9pm- All Day Happy Hour on Friday 12pm-7pm- Brunch on Saturdays & Sundays from 11am-3pm
A photo of Corcoran’s Grill & Pub restaurant
4. Corcoran’s Grill & Pub
4.5
Awesome(164)
Price: Moderate
• Irish • Old Town
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 Mercadito - River North restaurant
5. Mercadito - River North
4.6
Exceptional(6346)
Price: Expensive
• Mexican • River North (Chicago)
Booked 81 times today
We are the city’s top Mexican restaurant for authentic modern cuisine, specialty tequila and mezcal cocktails, located in the heart of River North. Our culinary team features popular Mexican dishes, including our signature tacos, as well as fresh salsa and guacamole, ceviche, esquites and more.Mercadito's lounge is nestled in the lower level of Mercadito. It offers a speakeasy-style experience with a chic and exclusive ambiance. The space features banquet-style booths and dim lighting that enhances the elegant wood furniture, creating an inviting and intimate atmosphere. Once inside, guests can enjoy the full Mercadito menu, with the same delectable cuisine and beverages that our restaurant is known for.
A photo of Bar Siena - West Loop restaurant
6. Bar Siena - West Loop
4.5
Awesome(3312)
Price: Moderate
• Italian • West Loop
Booked 60 times today
Perfectly Centralized In Chicago's West Loop 'Restaurant Row', The Two-Story, 8,000-Square-Foot Restaurant Is The Sibling Of DineAmic Hospitality'S River North Staple Eatery, Siena Tavern. Bar Siena Offers Diners The Perfect & Approachable Setting To Enjoy Lunch, Dinner, Late Night, And Weekend Brunch. The Menu Features An Expansive Italian Street Food And Pizza Bar Selection, All Served Within The Streets Of Fulton Market. Our Team Of Hospitality Professionals Are Thrilled And Dedicated To Host Your Next Dining Experience, Private Event Or Catering Function!
A photo of Tre Dita restaurant
7. Tre Dita
4.8
Exceptional(942)
Price: Very Expensive
• Italian • River North (Chicago)
Booked 103 times today
Led by Chef Evan Funke, Tre Dita, Italian for "three fingers", pays homage to the precise measurement of bistecca Fiorentina. If booking in the dining room at Tre Dita, you will enjoy a menu of antipasti, handmade pastas, signature entrees and steaks. If booking in the Bar Tre Dita, you will enjoy a smaller menu of stuzzi, antipasti, handmade pastas and entrees. The full cocktail, wine list and dessert menu is available in both locations.Please note that Tre Dita only accepts reservations 7 days in advance.
A photo of Happy Camper Pizza - Old Town restaurant
8. Happy Camper Pizza - Old Town
4.8
Exceptional(614)
Price: Moderate
• Pizzeria • River North (Chicago)
Booked 31 times today
Minors must be accompanied by parent or guardian for entry. A valid ID is required for guests age 21+.A chic, outdoorsy pizza haven located in Old Town. Happy Camper boasts a décor that includes Airstream trailers, neon renditions of the Great Lakes, warm wooden accents, and tire swing seating around the bar. A wide variety of colorful pizzas and delicious appetizers await you.F*ckin' Charity Bingo on Sundays at 1:30pm is sat on a first come first serve basis. All reservations will be sat in the non-bingo area.We cannot guarantee inside or outside seating.Neighborhood ordinances require our patio to close by 12am. Your table is weather permitting. If there is inclement weather, Happy Camper reserves the right to cancel your reservation. If you are dining when inclement weather occurs your food will be packed and given your bill. You are more than welcome to head to the bar afterward.
A photo of Gibsons Bar & Steakhouse - Chicago restaurant
9. Gibsons Bar & Steakhouse - Chicago
4.8
Exceptional(9036)
Price: Expensive
• Steakhouse • Gold Coast / Streeterville
Booked 99 times today
Gibsons Bar & Steakhouse has been a Chicago icon since partners Hugo Ralli and Steve Lombardo opened its doors in May 1989. The classic American steakhouse serves Gibsons Prime Angus Beef and Gibsons Grassfed Australian Beef. Gibsons also features fresh fish, classic cocktails, an extensive wine list and exceptional service. Celebrities, Chicago visitors and loyal neighborhood residents enjoy three distinct locations: Chicago, Rosemont and Oak Brook. Beautiful private dining and events spaces available.
A photo of The Florentine restaurant
10. The Florentine
4.4
Awesome(1314)
Price: Expensive
• Italian • Downtown / Loop
Booked 8 times today
Located in the JW Marriott Chicago, in the city’s bustling Loop Financial district, The Florentine offers an elegant yet accessible interpretation of seasonal Italian cuisine.Characterized by simplicity and paramount ingredients, the menu showcases top imported Italian pastas, cheeses, salts and meats as well as ingredients from local farms.The Florentine offers semi-private and private dining spaces, accommodating anywhere from an intimate dinner for six, to a cocktail reception for 130. Our large private dining room can seat 60, or be divided into two smaller rooms holding 20-30 guests. Semi-private dining for large groups is also available.

See what locals rave about

From verified diners like you
From verified diners like you
  • Gordon
    Chicago / Illinois •1 review
    5.0
    Dined 2 days ago
    I reserved a special from Mercadito called "Amor y Sabor" and boy it did not disappoint. The ambiance was very chill and the music was not too loud. Our waitress was very nice and attentive with us. The food was fantastic it consisted of a 4 course meal. It began with a shot of tiger de leche (Peruvian cuisine). Then we had a choice of camarones ceviche which was super tasty and flavorful. After that, we had queso Birria tacos with the dip and that was also delicious. Next but not least, we had some nice and tender strip steak which was perfectly cooked and was easy to chew. Our night was capped off with some churro desert and a glass of champagne. Overall an awesome and exciting experience and would highly recommend it!
    More info
    Mercadito - River NorthPrice: Expensive• Mexican• River North (Chicago)
    •
    4.6
  • ReinaldoVIP
    Chicago / Illinois •12 reviews
    5.0
    Dined 2 days ago
    Still one of my favorite restaurants. The octopus is one of the best that I had, as well as the oarmegiano claims. The capelini was the least interesting one, but still good. Can't wait to come back!
    More info
    KayaoPrice: Expensive• Peruvian• Old Town
    •
    4.6
  • Alex
    Chicago / Illinois •5 reviews
    4.0
    Dined 2 days ago
    Food was delicious, recommend the black bean burger and the panini
    More info
    LG's Bar & KitchenPrice: Moderate• American• Old Town
    •
    4.3
  • Gabrielle
    St. Louis •2 reviews
    5.0
    Dined on Jan 14, 2025
    Such a fun happy hour with great drinks, delicious food and wonderful service. Really enjoyed the trivia night on Tuesday nights and the gorgeous atmosphere. I would absolutely recommend to anyone looking for a fun night with friends.
    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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