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Architecture Boat Tour — one of the best ways to experience the rich architectural landscape of the city is by boat, cruising on the Chicago River. This is a must-do in Chicago as tourists and locals alike can be found aboard these vessels to learn about the city and admire the stunning views. There are several tour companies and each offer different types of cruises like to see the sunset, fireworks, or focus on a specific geography or topic. Most tours are led by very knowledgeable guides who will share history, fun trivia, and point out the best photo ops. Food Tours — one way to eat your way through the Windy City is by joining a food tour.

Although there are many that take place downtown targeted at tourists, venture to one of the neighborhoods for a more authentic flavor.

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Check out tours in places like Pilsen, Chinatown , and Little Italy for local eats and restaurants that are off the beaten path. These are an ideal way to discover a new part of the city while filling your belly with tasty eats. Walking, Biking, Bus Tours — there are so many ways to roam around while discovering hidden gems. Chicago is a very pedestrian-friendly city, so walking tours are very common and sometimes the best way to sightsee at your own pace.

If cruising on two wheels is more your style, bike tours are the way to go. Like many other cities, the big red double-decker buses are always an option. West Randolph — often referred to as restaurant row, this stretch of Randolph just west of the expressway is a foodie mecca boasting some of the hottest new restaurants and bars. Beware that some of these spots can book up months in advance, yet sometimes you can snag an open table during non-peak hours.

Food Trucks — the food truck craze has finally made its way to Chicago. If you ever miss one, remember that most have brick-and-mortar locations you can visit, too.

Even carnivores will be floored by the meat-free Radical Reuben and the award-winning vegan milkshake to wash it down. Boystown — the gayborhood is better known for dance floors and disco balls than a killer food scene. From brunch to craft cocktails, Wood is named after its wood-fired oven offering American small plates. A popular no-frills hangout is DS Tequila Co. Lakeview — these honorable mentions are just a short walk from the main Boystwon strip in the Lakeview neighborhood.

One of the first vegetarian and vegan-friendly restaurants in the city, Pick Me Up Cafe is ideal for lunch or a late night bite with a cozy and eclectic atmosphere. Cocktails, wine, and jazz sum up SIP , a tavern and lounge featuring global American plates with an extensive bar list. Satiate your sweet tooth at Bobtail Ice Cream, an old-school ice cream parlor scooping up homemade ice cream, sundaes, shakes, and coffee.

Start with brunch at m. Additionally, the menu has tasty gluten-free, vegetarian, and vegan options. Housed in a vintage art deco building, Tweet is another popular brunch and lunch spot with an artsy flair.


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American comfort food takes on gluten-free and plant-based variations at this cash-only gem. Sip a glass of wine and savor cheeses and artisan breads at Appellation. This bistro serves up rustic dishes made from gourmet Pastoral ingredients. This spacious video bar has numerous bar areas and spots to chat and mingle.

Themed nights often feature drag shows and music videos on the enormous screens. Enjoy carefully crafter drinks like a signature martini and weekly specials at this trendy cocktail bar. It really has the best of both worlds.


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  • Check their calendar for regular drag shows and special events. Peruse a martini and cocktail list of over items while savoring upscale contemporary cuisine at this entertainment hot spot.

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    Second Story Bar — one of the few gay bars downtown, this is an unpretentious, old-school bar with a disco ball. The divey digs draw a mixed crowd of travelers and locals looking for a libation in a comfortable and friendly atmosphere. Scarlet — vintage-inspired bar and lounge with a club atmosphere, themed nights, and special events. The DJs and drink specials attract a something crowd ready to dance the night away.

    Splash — modern styled space with two side bars and a dance floor touting yet another bar all with attractive bartenders. Hydrate is in the heart of Boystown and has a contemporary vibe featuring a lineup of DJs and themed nights. Berlin is a no-attitude nightclub featuring alternative electronic music that draws an eclectic crowd. Try to head over earlier in the night to avoid long lines at the door. Usually landing on the second weekend of June, enjoy two days and three nights of live music, delicious food, and activities for all ages.

    Festivities are on Clark Street stretching from Foster to Catalpa, and residents and local businesses make this a very inclusive and friendly atmosphere for all. Chicago Pride — the main event is the pride parade that usually takes place on the last Sunday of June with a route stretching from Montrose to Diversey on the northside.

    The Saturday morning before is the annual Proud to Run 10k run and 5k walk benefiting several community organizations. However, festivities really begin the weekend before the parade as the pride street festival kicks off the week-long celebration. Pride-related events can be found throughout the city during the entire month of June. Even downtown and in the financial district businesses and large institutions proudly fly the rainbow flag. Lollapalooza Music Festival — an annual four-day music festival, fans come out to see almost performing artists.

    It takes place in Grant Park the first week of August to delight throngs of music fanatics. Although there are countless smaller music festivals throughout the summer, this is by far the largest with the best-known headliners.

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    Tickets are tough to get and your best bet is to buy through a reseller. Northhalsted Market Days — this is the largest outdoor street festival in the Midwest with attendance of over , It covers six block of North Halsted right in the center of boystown with five stages and a non-stop lineup of live music, food, and craft vendors. Think of this as an unofficial pride part II on one of the first weekends of August.

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    Lake Geneva, WI — about a two-hour drive northwest of the city is one of the most popular getaways for urban dwellers. Stroll up and down the quaint main street boutiques and stop for a bite at a restaurant or cafe. Chill out on the beach or get out on the lake for boating and water sports. Take a cruise to marvel at the stunning lakefront mansions or check into a spa for some pampering.

    From spring to fall, this town will give you all the vacation vibes without the jet lag. Oak Park, IL — not only is Chicago an architectural gem, but the nearby suburb of Oak Park has one of the largest concentrations of Frank Lloyd Wright homes in the country. The state park is for the outdoorsman who enjoys camping and hiking. Although most of the midwest is flat grasslands, here you can explore waterfalls and unique rock formations. One of the best times to visit is in the autumn when the foliage lights up in colorful hues of yellow, orange, and red.

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