15 Fantastic Bars in Chicago, IL
Last updated in October 2024
Chicago’s bar scene is as diverse as the city itself, with spots ranging from intimate cocktail lounges to lively dive bars. Whether you’re in the mood for a classic drink at a nostalgic tavern or craving something a bit edgy and modern, there’s a perfect spot waiting for you. For instance, Osito's Tap offers an inviting speakeasy vibe in Little Village, where craft cocktails and Latin flair come together beautifully. Then again, if you’re feeling cozy and want to enjoy some gin-centric cocktails, Scofflaw in Logan Square has got that laid-back atmosphere just right, complete with the sweetest end-of-night chocolate chip cookies to boot!
Bar Pendry Chicago
Bar Pendry Chicago is a chic bar that perfectly blends the classic ambiance of a traditional Chicago bar with a modern twist. Located in the heart of downtown, it's a go-to spot whether you're after an early cocktail or a late-night aperitif. The space features an inviting decor, highlighted by a double-sided fireplace and stunning artwork, making it a fantastic place to relax. Patrons rave about the stellar cocktail menu and the outstanding service from the staff, making it an unforgettable experience during your time in the city.
What People Love
Inviting and cozy atmosphere with a modern twist.
Exceptional cocktail selection with creatively crafted drinks.
Attentive and friendly staff that enhance the experience.
Delicious light bites and small plates to complement drinks.
Great location for both casual drinks and special occasions.
What People Don't Like
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Drink prices can be on the higher side, typical for the area.
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Service can slow down, especially during busy times.
You Have to Try
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The Old Fashioned - hailed as one of the best by visitors, it's a must for bourbon lovers!
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House-special cocktails like the Aviation and Mull It Over for something unique.
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Delicious small plates, perfect for sharing while sipping on drinks.
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Gourmet fries - a recommended snack that pairs effortlessly with any drink.
Best Intentions
Best Intentions is a lively bar located in the heart of Logan Square, Chicago. This neighborhood gem stands out with its retro dive bar vibe and a fantastic outdoor patio, perfect for those warm summer nights. Known for its inventive cocktails and scrumptious food offerings, including tasty burgers and a variety of bar snacks, it’s a favorite among locals and visitors alike. The atmosphere is laid-back and friendly, making it an inviting spot to hang out with friends or unwind after a long day.
What People Love
Unique and creative cocktails that are well-prepared and delicious.
A great atmosphere that feels cozy and welcoming.
Affordable prices for food and drinks, especially the burgers.
Fantastic outdoor patio that enhances the experience.
Friendly and attentive staff that contribute to a positive vibe.
What People Don't Like
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Service can be slow and overly busy during peak times.
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Some complaints about understaffing or rudeness from a few bartenders.
You Have to Try
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The smash burger, often touted as one of the best in the city.
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Fries paired with the house sauce, which many claim is delicious.
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Unique cocktails like the Wondermint and homemade ginger beer.
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The Reuben sandwich, regarded as one of the best around.
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The outdoor patio experience when the weather is nice.
Delilah's
Delilah's is a punk-inspired bar in Lincoln Park that's been capturing the hearts of locals since 1993. It boasts an extensive selection of over 1000 beers and spirits, making it a haven for whiskey and bourbon enthusiasts. The lively atmosphere is enhanced by a great lineup of DJs spinning everything from rock and roll to ska. Plus, Delilah's hosts various special events, including art openings and film screenings, all within a quirky dive bar setting that feels like home.
What People Love
Incredible selection of whiskey and bourbon, with knowledgeable staff to guide you.
Great atmosphere with a punk rock vibe, perfect for relaxing or socializing.
Friendly and accommodating staff make everyone feel welcome.
Fun events and daily specials keep things lively and engaging.
Excellent jukebox and music variety creates a nostalgic feel.
What People Don't Like
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Occasional service issues, particularly with specific bartenders being dismissive.
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The bathrooms might not meet everyone's taste, reflecting a true dive bar experience.
You Have to Try
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Their extensive whiskey and bourbon menu—it's a whiskey lover's paradise!
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Check out the daily drink specials for fantastic deals on drinks, especially on Mondays.
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Don't miss the opportunity to catch a fun event like beer tastings or themed nights.
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If you're in the mood for games, the upstairs pool table area is a blast.
Desert Hawk
2049 W Division St
Chicago, IL 60622
Desert Hawk is a fresh take on the neighborhood bar scene in Wicker Park, Chicago, blending California desert vibes with an exciting selection of agave spirits and craft cocktails. With its fun atmosphere, delicious street tacos, and standout smashburgers, it’s quickly becoming a favorite spot for locals. Whether you’re looking for a laid-back place to hang out with friends or a lively spot for a date night, this bar has you covered. Plus, don't miss out on their fantastic karaoke nights!
What People Love
Vibrant and inviting atmosphere perfect for a casual night out or date.
Impressive cocktail selection, especially tequila-based drinks.
Friendly and attentive staff that enhance the overall experience.
Delicious food, particularly the smashburgers and tacos.
Fun events like karaoke nights that contribute to a lively vibe.
What People Don't Like
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Ordering food at the bar can feel clunky during busy times.
You Have to Try
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Smashburgers that are large, flavorful, and crowd favorites.
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Delicious tacos with generous portions of meat and flavorful toppings.
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Craft cocktails, especially the spicy margaritas and custom mezcal drinks.
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The loaded fries that are perfect to share with friends.
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Great options for non-alcoholic cocktails that aren’t an afterthought.
Fox Bar
113-125 N Green St
Chicago, IL 60607
Fox Bar is a cozy late-night bar located upstairs in Chicago's Chicken Shop, part of the West Loop's vibrant dining scene. With a charming and intimate setting, it’s an ideal spot for enjoying locally-inspired cocktails and small bites, all while soaking in the sounds from local DJs. The decor is eclectic and inviting, making it a perfect hideaway for those in the know.
What People Love
Charming, intimate atmosphere that's perfect for dates or small gatherings.
Creative and delicious cocktails that are often highlighted as a standout feature.
Excellent and friendly bartenders who really know their craft.
A unique experience with a vintage payphone to order pizzas from Pizza East.
Vibrant music from local DJs keeps the vibe lively and fun.
What People Don't Like
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Service can be slow, especially during peak hours, which may leave you waiting longer than expected.
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The noise level can get excessively loud, making conversation challenging.
You Have to Try
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The Balancing Act cocktail, a crowd favorite that many say is outstanding.
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The cozy saloon room upstairs, which offers a unique ambiance and excellent drink specials.
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Small bites from the bar menu that perfectly complement the cocktails, especially their fries.
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The ability to order pizza via an old payphone, adding a quirky twist to your night out.
Kasey's Tavern
Kasey's Tavern is a beloved neighborhood bar located in the heart of Chicago's South Loop. Known for its vintage charm and cozy vibe, this tavern offers an impressive beer selection with over 130 varieties, appealing to both beer aficionados and casual drinkers alike. The bartenders are friendly and attentive, making it a fantastic spot to relax, catch a game, or simply enjoy good company. Though they primarily serve frozen pizza, you're welcome to bring in your own food, adding a fun and flexible dining element to your experience.
What People Love
Cozy and welcoming atmosphere that's perfect for hanging out with friends.
Extensive beer selection with over 130 options, including local craft beers.
Friendly and attentive staff who go out of their way to make you feel at home.
Affordable prices that make it a great option in downtown Chicago.
A charming vintage vibe that adds to the overall experience.
What People Don't Like
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Some guests have experienced slow service during busy times.
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A few have mentioned not feeling welcomed by certain staff members.
You Have to Try
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Their frozen pizza, especially when topped with hot sauce—it's a local favorite!
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The extensive drink menu featuring local crafts and tasty cocktails is a must-try!
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Enjoying a cold beer on the cozy outdoor patio, perfect for warm summer nights!
Matchbox Bar
Matchbox Bar, known as Chicago's smallest bar, is a delightful corner spot exuding charm and intimacy in every inch. Tucked away in a vintage building, it serves up an impressive selection of premium cocktails, making it a go-to for both locals and visitors. Its friendly bartenders create a welcoming atmosphere, perfect for a cozy date night or a chill evening with friends. With a lovely outdoor patio that's dog-friendly, this bar is not just a place to grab a drink, but a community hub where everyone knows your name.
What People Love
Charming, cozy atmosphere perfect for intimate gatherings or dates.
Friendly and engaging bartenders who know their craft well.
Highly praised signature cocktails, especially the gimlet and margarita.
A vibrant neighborhood feel that makes it a local favorite.
Unique outdoor seating area, which adds to the charm.
What People Don't Like
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Some issues reported with specific cocktails, particularly the espresso martini.
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Inconsistent service experiences, particularly with the bartenders' attitudes.
You Have to Try
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The delicious vodka gimlet, which many consider a must-order.
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Their signature margarita, often highlighted as exceptional.
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The creative drinks like the Gin and Jam and Pineapple Gimlet that impress patrons.
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Special offerings like the sidecar of extra cocktail that comes with certain drinks.
Mother's Ruin
2943 N Milwaukee Ave
Chicago, IL 60618
Mother's Ruin is a welcoming bar in the Avondale neighborhood of Chicago, known for its lively atmosphere and expertly crafted cocktails. Open until late every night, this cozy spot combines the best of a local bar with an elevated food experience, featuring everything from burgers to brussel sprouts. Whether you're dropping in for happy hour or late-night bites, the friendly staff and vibrant vibe make this place a go-to destination for a casual night out.
What People Love
Great cocktails and unique drink specials.
Friendly and hospitable staff.
Tasty food with a solid late-night menu.
Chill atmosphere with fun music.
Excellent waffle fries and burgers.
What People Don't Like
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Service can be hit or miss, with some staff not being attentive enough.
You Have to Try
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The spicy chicken sandwich for its crispy deliciousness.
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Waffle fries seasoned to perfection.
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French onion grilled cheese that has impressed many.
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Unique cocktails like the Oaxacan Old Fashioned and various slushies.
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Nachos, which are a crowd favorite.
Old Town Ale House
Located in the vibrant Old Town neighborhood of Chicago, just a stone's throw from the iconic Second City comedy club, the Old Town Ale House is a beloved dive bar known for its laid-back atmosphere and eclectic artistry. With walls adorned by humorous and provocative paintings, this cash-only establishment provides a unique backdrop for enjoying a great selection of beers and drinks. It's the ideal spot for casual meetups or unwinding after a show, and it truly captures the essence of Chicago's rich bar culture.
What People Love
Unique and quirky atmosphere with interesting artwork adorning the walls.
Great drink prices, especially for a dive bar in Chicago.
Laid-back vibe perfect for casual hangouts or after-show drinks.
Strong connection to the comedy scene; a favorite of Anthony Bourdain.
Friendly staff and patrons create a welcoming environment.
What People Don't Like
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Service can sometimes be hit or miss, with reports of unfriendliness.
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It's cash-only, which can be inconvenient for some.
You Have to Try
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The vast selection of beers, including local favorites.
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The old-school jukebox that sets the perfect vibe for your drinking experience.
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The witty and often politically charged artwork throughout the bar - it's a conversation starter!
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The Old Fashioned, praised for its preparation and taste.
Osito's Tap
Osito's Tap is a charming speakeasy-style bar located in the vibrant Little Village neighborhood of Chicago. Opened in 2019, this local hotspot combines a modern Latin flair with the spirit of classic Chicago cocktail culture. The bar is known for its exceptional craft cocktails and a diverse selection of mezcal and tequila. The welcoming atmosphere and dedicated staff create an inviting space for everything from casual drinks to special celebrations. Plus, the historical backdrop of the building adds a unique character to your experience.
What People Love
Creative and well-crafted cocktails that stand out for their unique flavors and presentation.
A cozy, speakeasy-style atmosphere filled with warm lighting and cultural touches.
Friendly and attentive staff who are knowledgeable about the drink menu.
A terrific selection of mezcal and tequila, making it a go-to spot for these spirits.
Delicious food options, including brunch favorites and flavorful Mexican dishes.
What People Don't Like
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Inconsistent service, with some guests feeling neglected or receiving poor service from certain staff members.
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Food quality can be hit or miss, with some dishes not meeting expectations.
You Have to Try
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The quesaditzin, a standout entrée that’s frequently mentioned as a must-try.
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Unique mezcal cocktails like the Cafe de Olla Martini and La Dama that reflect the establishment's Mexican flair.
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Brunch items such as pozole and chilaquiles, which have received high praise for their flavors.
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The grilled cheese appetizer, which is often recommended as an excellent choice.
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Muerte por cocoa flan for dessert, noted for its rich flavors.
Pleasant House Pub
Located in the vibrant Pilsen neighborhood of Chicago, Pleasant House Pub serves up a delightful menu featuring farm-to-table fare inspired by traditional British pub cuisine. With a focus on savory pies and hearty burgers, this rustic cafe is known for creating an inviting atmosphere perfect for enjoying brunch, drinks, or a cozy dinner. The charming decor, complemented by a rotating selection of beers and cocktails, makes it a fantastic spot to relax with friends or family.
What People Love
Outstanding selection of savory pies, including vegan options that are a hit.
Great local beer selection that complements the food offerings well.
Friendly and welcoming atmosphere reminiscent of a classic British pub.
The burger is often referred to as one of the best in Chicago, with delicious toppings.
Affordable prices given the quality of food and generous portions.
What People Don't Like
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Service can be inconsistent, with some patrons experiencing delays and inattentiveness.
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Some customers wish for more variety in the menu or consider prices slightly high.
You Have to Try
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The Steak and Ale pie is a must-have for any meat lover, especially topped with creamy mashed potatoes.
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Don't miss the Scotch Egg; it's a perfect starter that many rave about.
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Their Chicken Balti pie is another standout, with just the right amount of spice.
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Curry Chips are a popular side that pairs perfectly with their beer selection.
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If you’re there on a Friday, the Fish and Chips special comes highly recommended.
Rossi's
Rossi's is a quintessential dive bar located in downtown Chicago, known for its laid-back vibe and eclectic crowd. With its impressive selection of local craft beers and a friendly atmosphere, it's a great spot to unwind after a long day or to start your night out. The bartenders are often recognized for their warmth and humor, making first-timers feel right at home. And while the bar operates on a cash-only basis, the combination of affordable drinks and a genuine neighborhood feel keeps patrons coming back again and again.
What People Love
Welcoming atmosphere perfect for socializing with locals and visitors alike.
Outstanding selection of local and craft beers, which you can pick from the coolers.
Friendly staff who create a fun vibe, often remembered by name by regulars.
Great prices on drinks which won't break the bank, especially for downtown Chicago.
A true dive bar experience that makes you feel at home, regardless of where you're from.
What People Don't Like
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Service can be hit or miss, with some bartenders being less than friendly on occasion.
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It's cash only, which might be a hassle for some.
You Have to Try
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The selection of craft beers from local breweries in the cooler – it's impressive!
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The unique bar atmosphere, complete with classic tunes on the jukebox that beckon for a sing-along.
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Grab a cold PBR for a true dive experience; it’s a crowd favorite!
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If you’re in the mood for shots, the bartenders serve them up strong!
Scofflaw
Scofflaw is a delightful gem in the Logan Square neighborhood, known for its gin-centric cocktails and cozy, urban-rustic vibes. With a menu that features tasty pub grub and an impressive selection of craft beers, it's a great spot for gatherings with friends or a laid-back date night. Patrons rave about the inviting atmosphere, perfect for relaxing after a long day, and the friendly staff always make you feel welcome. Plus, if you stick around until midnight, they treat you to fresh chocolate chip cookies!
What People Love
Cozy and inviting atmosphere, perfect for socializing.
Exceptional cocktails with a strong focus on gin.
Delicious food that stands out among bar offerings.
Notable Scofflaw burger, often called one of the best in Chicago.
Friendly and attentive staff that enhances the experience.
What People Don't Like
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Some find the menu a bit limited in options.
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Inconsistencies in service at times.
You Have to Try
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The Scofflaw burger, featuring a perfectly cooked double patty and house sauce.
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The charcuterie selection, offering a delightful mix of meats and cheeses.
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Innovative cocktails, especially their gin-focused creations.
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The midnight chocolate chip cookies, a sweet treat just for sticking around.
Skylark
Skylark is a true dive bar in Pilsen that perfectly combines a laid-back vibe with a great selection of craft beers and delicious pub food. Known for its unique retro decor and friendly service, this cash-only bar offers a cozy atmosphere where locals and visitors can enjoy a drink, catch live music, or indulge in food favorites like burgers and tater tots. The space also features a fun photo booth and a pinball machine, making it a nostalgic spot for anyone looking to kick back and enjoy Chicago's dive bar scene.
What People Love
Great craft beer selection at affordable prices.
Delicious pub food including burgers and tater tots.
Friendly and efficient bartenders providing excellent service.
Chill, relaxed atmosphere perfect for hanging out with friends.
Unique features like a photo booth and pinball machine.
What People Don't Like
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The bar is cash-only, which can be inconvenient without access to an ATM.
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Some patrons have expressed concerns over safety and parking in the area.
You Have to Try
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The Skylark burger, often cited as one of the best in Chicago.
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Tater tots, considered a must-try snack, often praised for their quality.
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Buffalo chicken legs when they feature as a special, highly recommended for their flavor.
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Cod po-boy, celebrated for its taste and preparation.
The Red Lion Pub
The Red Lion Pub is a charming English-style pub located in Lincoln Park, Chicago. Known for its cozy atmosphere, it brings a touch of the UK to the city with an impressive selection of British ales and hearty dishes like fish and chips and shepherd's pie. The decor is rich with history, featuring books and military artifacts that create an inviting environment for patrons seeking good food and drinks. A truly welcoming spot, it’s perfect for a casual night out or a cozy weekend meal.
What People Love
Cozy and inviting atmosphere reminiscent of a classic English pub.
Delicious food offerings, especially the fish and chips and shepherd's pie.
Knowledgeable and friendly staff, including the owner who engages patrons.
Unique decor filled with history and charm, creating a warm, library-like vibe.
Great selection of drinks, particularly British ales and whiskies.
What People Don't Like
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Some dishes were deemed overpriced for the portion sizes offered.
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Occasional service issues, such as long waits for food or drinks.
You Have to Try
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The fish and chips, always praised as some of the best in Chicago.
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Scotch eggs that are a must-have for first-time visitors.
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Shepherd's pie, noted for its authenticity and taste.
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Bangers and mash, providing a true British experience.
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Sticky toffee pudding for dessert, perfect for those with a sweet tooth.
