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Stay in the Heart of Lakeview a.k.a. Boystown for a Very Good Time
Villa Toscana Guest House In Brief: Built in 1892, this charming Victorian-style bed and breakfast is situated in the heart of the Boystown district of the Lakeview community on the North Side of Chicago. It's surrounded by some of the city's liveliest bars and restaurants, which means that guests can pretty much walk to most destinations.
The property is completely renovated, offering eight European-style rooms that range in decor from Art Deco to Moroccan. There is a seasonally landscaped front yard and garden for guests to relax or enjoy breakfast on the outdoors deck.
Amenities: Free wireless internet, self-serve continental breakfast (6-11 a.m. every morning), digital cable television, community kitchen and living room
Room Rates: March 16-Nov. 30 ($129-$159); Dec. 1-March 15 ($119-$149)
Parking: Villa Toscana offers free overnight parking permits. Pay parking is also available along North Halsted Street and there are pay parking lots both north and south of the property.
Address: 3447 N. Halsted St., 800-404-2643Continue to 2 of 20 below.
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Villa Toscana Guest House's Community Kitchen
There's self-serve continental breakfast served daily in Villa Toscana Guest House's cheery community kitchen. Guests are also welcome to use the refrigerator, pantry, etc.
Address: 3447 N. Halsted St., 800-404-2643Continue to 3 of 20 below.
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Villa Toscana Guest House's English Room
Located on the first level of the inn, Villa Toscana Guest House's English Room is at the very back of the house. It's ideal for those looking for quiet time because the Halsted strip can get very noisy on weekends and during high season in the summer. It contains a private bath, antique prints and English Baronial furnishings. It snugly accommodates up to two guests.
Address: 3447 N. Halsted St., 800-404-2643Continue to 4 of 20 below.
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Details: After about an hour into brunch at Angelina Ristorante, its most popular offering, you’ll notice diners getting a little loopy at surrounding tables. That's because the weekly champagne brunch--held on Saturday and Sunday--includes one Italian-inspired entrée and bottomless bubbly or Mimosas. It's $21 per person (cash only) and reservations are highly recommended. It's only a few blocks from Villa Toscana Guest House.
Address: 3561 N. Broadway, 773-935-5933Continue to 5 of 20 below.
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Details: The Athenaeum Theatre is Chicago’s oldest continuously operating theater outside of the downtown theater scene. The venue is only a five-minute drive from Villa Toscana Guest House, and it offers parking at a small cost. Athenaeum features a main-stage theater as well as three smaller studios that are home to a number of boutique theater groups, improv collectives, bands and dance troupes. Most productions are original.
Address: 2936 N. Southport Ave., 773-935-6875Continue to 6 of 20 below.
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Details: This new American cuisine-focused eatery showcases artisan wines and cheese. Bar Pastoral is very neighborhood focused and serves brunch, weekend lunch and dinner. It's about a five-minute stroll from Villa Toscana Guest House, so there should be plenty of people watching along the way.
Address: 2947 N. Broadway, 773-472-4781Continue to 7 of 20 below.
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Blue Man Group
Details: There's no need to go all the way to Vegas to see the Blue Man Group. The long-running show has been in Chicago since the late 1990s, and it features an exciting experience that changes often. It's only a few blocks from Villa Toscana Guest House.
Address: Briar Street Theater, 3133 N. Halsted St., 773-348-4000Continue to 8 of 20 below.
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The Center on Halsted
Details: Chicago boasts one of the biggest and best LGBT centers in the world with The Center on Halsted, and no trip would be complete without a visit to this amazing community gathering space. Whole Foods Market leases out a portion of the space on the first floor, and visitors may grab some food and eat in the adjacent cafe. There also are art exhibitions, basketball and volleyball, support groups, performances, classes, counseling and more. It's located two blocks north of Villa Toscana Guest House.
Address: 3656 N. Halsted St., 773-472-6469Continue to 9 of 20 below.
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Details: One of the city's most popular vegetarian eateries is only a few doors down from Villa Toscana Guest House. Chicago Diner has been around for more than 30 years. There’s a vegan option for every item on this all-vegetarian menu, which is unusual, and it doesn’t cost extra. The wheat-based meat substitute seitan gets a lot of play and it comes in every style imaginable: BBQ, Buffalo, hickory smoked, grilled and fried. A full-service bar includes biodynamic wines, organic spirits and regional craft beers.
Address: 3411 N. Halsted St., 773-935-6696Continue to 10 of 20 below.
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Details: The seafood-focused restaurant is from the guys behind mEAT and minibar. Everything's nautically and island-inspired at this narrow establishment cranking out oldies but goodies as a soundtrack. Faves include seared tuna nachos, Cajun mac 'n' cheese (with shrimp and crawfish), and signature BoomBoom shrimp that's tossed in a spicy, creamy sauce. The tiki-inspired cocktails range from a classic Rum Runner to Walking The Plank, made with mango rum, Cajun-spiced rum, apricot liqueur, orange juice, lime juice and flaming rum float. The bar, in fact, offers approximately 150 different rums. It's only a couple doors down from Villa Toscana Guest House.
Address: 3445 N. Halsted St., 773-770-4681Continue to 11 of 20 below.
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Duke of Perth
Details: Created to resemble an authentic Scottish pub, Duke of Perth has been around since the late 1980s. It showcases standard British fare such as shepherd's pie, fish and chips and black pudding. It's a few minutes walk from Villa Toscana Guest House.
Address: 2913 N. Clark St., 773-477-1741Continue to 12 of 20 below.
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Details: Craft beers, local artwork and seasonal gourmet pub grub. That's the vibe at DryHop Brewers, which is a brief walk from Villa Toscana Guest House. The focus is on hop-centric ales, and each dish is inspired by them. Think green curry mussels, burgers and bone-in pork chops. What's neat is that you can only get DryHop's brews right here, so fans should be prepared to take a growler home.
Address: 3155 N. Broadway, 773-857-3155Continue to 13 of 20 below.
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Details: Pretty boys. “Fashionistos.” Or whatever you’d prefer to call the trend-obsessed barflies frequenting this well-intended watering hole on the legendary Halsted strip. You’ll find an extensive list of classic cocktails as well as signature, updated versions such as the Nutty Old Fashioned made with bourbon, walnut syrup and walnut bitters. It's across the street from Villa Toscana Guest House.
Address: 3452 N. Halsted St., 773-975-9244Continue to 14 of 20 below.
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DS Tequila Co.
Details: While not technically a lesbian lounge, the lively venue attracts an overwhelming share of attractive young revelers who come for a boozy good time. DS Tequila operates as a contemporary Tex-Mex restaurant and late-night hang. It's only a block away from Villa Toscana Guest House.
Address: 3352 N. Halsted St., 773-697-9127Continue to 15 of 20 below.
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Details: Occupying the site of the long-running (and infamously raucous) Manhole club, the somewhat more eclectic, but still quite "cruisy" Hydrate dance club has earned a loyal following for its imaginative theme nights (such as the "Hydrag Revue" on Wednesday nights). Mostly, though, it's just a pounding and pulsing place to dance to some of the best music in the neighborhood and check out hot and shirtless patrons. It's across the street from Villa Toscana Guest House.
Address: 3458 N. Halsted St., 773-975-9244Continue to 16 of 20 below.
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Kit Kat Lounge & Supper Club
Details: Years before RuPaul’s “Drag Show” emerged with its cast of sassy characters, the Kit Kat “divas” were sashaying through the dining room like it was a sequined stage. They’re decked out looking like everyone from Lady Gaga to Patti LaBelle and every diva in between. Cocktails and cuisine are typically themed based. It's a few blocks north of Villa Toscana Guest House.
Address: 3700 N. Halsted St., 773-525-1111Continue to 17 of 20 below.
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Details: Local neighborhood chain Nookies is famous for its hot cakes, which arrive topped with fresh, seasonal fruits, nuts and more. It serves breakfast all day, including omelets and frittatas, plus diners may B.Y.O.B. The Lakeview location is open 24 hours every weekend--for all the late-night owls. It's a block down from Villa Toscana Guest House.
Address: 3334 N. Halsted St., 773-248-9888Continue to 18 of 20 below.
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Revolucion Mexican Steakhouse
Details: This Mexican-inspired steakhouse takes its concept seriously and is more than a colorful atmosphere and classic Latin fare. It introduces diners to a new way of enjoying authentic Mexican cuisine. You won't find any other steakhouse in the city with such crave-worthy sides like grilled cactus salad, caramelized fried plantains or guajillo-cotija fries. It's a few minutes walk from Villa Toscana Guest House.
Address: 3443 North Broadway, 773-661-9893Continue to 19 of 20 below.
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Details: If the idea of a “video bar” sounds very 1980s to you, it’s totally by design. Sidetrack opened in 1982 during the dawn of the New Wave scene. While you’ll occasionally get a taste of the likes of Duran Duran and The Go Go’s, the music is mostly contemporary and so is the crowd. It's a block away from Villa Toscana Guest House.
Address: 3349 N. Halsted St., 773-477-9189Continue to 20 of 20 below.
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Details: A former Alinea chef helms the kitchen at this contemporary American restaurant offering a casual setting and seasonal dishes made with local ingredients. A strong craft cocktail program complements the chef-driven menu. It's a block away from Villa Toscana Guest House.
Address: 3335 N. Halsted St., 773-935-9663