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Chicago for Solo Travelers

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While Chicago is a city with tremendous history, its contemporary culture, rich arts & music scene, and distinct neighborhoods make it a truly fascinating destination. Sports are also a passion point—catching a game can be a great way to connect with locals!
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900 Michigan Avenue, Chicago, IL 60611, USA
I thought New York was a good shopping city but Chicago has pretty much the same big name shops and they're spaced out. The 900 Shops was probably my favorite space in terms of cleanliness, space and quality of shops. The best J. Crew is here and...
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220 S Michigan Ave, Chicago, IL 60604, USA
Going to the CSO is like visiting another planet where all communication is done through music. The space is dazzling, the crowd is cultured, and once the orchestra begins your heart will soar with each and every perfectly played note. If you are...
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4839 N Western Ave, Chicago, IL 60625, USA
Tucked away behind an unassuming storefront you will find a shop with a misnomer of a name: Ravenswood Used Bookstore (it's located in Lincoln Square, not Ravenswood). Our hero and proprietor, Jim, has gathered such an incredible collection of...
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2519 N Halsted St, Chicago, IL 60657, USA
B.L.U.E.S. is not a big bar, but they play plenty of great blues (and have been voted best blues club on Chicago's North Side). Primarily local artists play in this comfortable, intimate setting. If you want a seat, push way in past the stage and...
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4621 N Lincoln Ave, Chicago, IL 60625, USA
Nestled in Lincoln Square, Fine Wine Brokers will truly cater to your needs. They have one of the more eclectic selections of choice wines anywhere in the city of Chicago. There are tastings on the weekends, and grand gala events every few months...
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5014 North Broadway, Chicago, IL 60640, USA
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Just steps from the colorful Argyle CTA stop in Chicago's Uptown neighborhood, Ba Le Bakery specializes in Vietnamese food—efficient, fast and tasty fusion food. You can’t go wrong with the Bun Thit Nuong ($7.95)—piping-hot grilled pork, cold rice...
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2601 N Milwaukee Ave, Chicago, IL 60647, USA
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Located in Logan Square, and featuring one of the more eclectic wine lists I've seen in a while, Telegraph Wine Bar is the perfect place to swing by for a leisurely bite to eat and drink. The antique fixtures and lights provide a bit of a...
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5491 S Shore Dr, Chicago, IL 60615, USA
With loads of green grass, trees and playgrounds, there is something for everyone at Promontory Point Park. Overlooking the swimmers and sunbathers on the rocks below, one can sit for hours looking at the skyline and Lake Michigan. Locals have...
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5507 N Clark St, Chicago, IL 60640, USA
The goods at Arrin Williams’s year-old Andersonville shop, Haymaker, are mostly handmade by local artisans. Powder-coated-steel side tables by David Greene, hanging plant holders made from reclaimed wood, and coveted leather bags by Chicago-based...
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2391 N Stockton Dr, Chicago, IL 60614, USA
Lincoln Park is a wonderful green area nearing Lake Michigan in Chicago. It has a Zoo free to the public as well as green lawns and flower beds. Near the North end is the multiple room conservator. Like the rest if the park it is open free to the...
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954 N California Ave, Chicago, IL 60622, USA
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Rootstock crafts great drinks and bites with laid-back style and without pretension. Chef Duncan Biddulph pays attention to the details—he focuses on incorporating locally farmed produce whenever possible and produces their wine and beer in small...
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1417 W Fullerton Ave, Chicago, IL 60614, USA
Sprout was a suggestion from dear friends who had just returned to Chicago after years living and eating in NYC. Sprout has a menu that notes tastes not necessarily ingredients. Ask your server to explain what is what. This is not your standard...