835 West Washington Boulevard

Chicago, IL

+1 312 404 9188

This unpretentious gallery space exhibits watercolor paintings, sculptures and refined style minus the attitude.

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1035 North Western Avenue

Chicago,IL

+1 773 276 3300

Skinny jeans and art-house style meet their match at this rag-tag Ukrainian Village venue. Chicago's premier experimental and emerging music destination is schooled on indie rock and left-of-center talent.

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5020 South Cornell Avenue

Chicago,IL

+1 773 324 5520

Multi-media exhibits and photography bring an artistic air to President Barack Obama's native stomping grounds.

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2828 North Clark Street

Chicago,IL

+1 773 509 4949

For a landmark Chicago movie experience that involves popcorn, fountain drinks and good taste, we recommend this old-fashioned theater.

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5153 North Ashland Avenue

Chicago,IL

+1 773 878 4557

This theater troupe races to perform 30 mini-plays during a 60 minute show. Sometimes they finish, sometimes they don't; either way, it's always entertaining.

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220 East Chicago

Chicago,IL

+1 312 280 2660

Chef Wolfgang Puck styles the hors d'oeuvres at MCA's "First Friday" evening events, where DJs and art paint the picture.

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1616 North Wells Street

Chicago,IL

+1 312 337 3992

Performances at this Chicago improv mainstay have been both on-the-spot and spot on for the past 50 years.

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1852 West 19th Street

Chicago,IL

+1 312 738 1503

Chicago's Mexican cultural influences beam brightly in the Pilsen neighborhood. See the folk art, textiles and print collections that make them shine.

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4050 North Milwaukee Avenue

Chicago, IL

+1 773 736 4050

View independent and international films at the Silent Film Society of Chicago's refurbished theater. No need to keep quiet about this historic gem.

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119 North Peoria Street, Unit 2D

Chicago,IL

+1 312 432 2972

On Friday nights, this three-level art maze could double for any bustling Chicago bar. Discuss the work over martinis and play the part.

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3111 North Western Avenue

Chicago,IL

+1 773 296 6024

Located directly under a viaduct, this Chicago theater is also known for its under-the-radar playwrights, musicians and events— including an indoor carnival.

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4802 North Broadway Street

Chicago,IL

+1 773 878 5552

A thriving cornerstone of the Chicago jazz and blues genres, this landmark Uptown club swings until the wee hours, serving strong drinks all the while.

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2433 North Lincoln Avenue

Chicago, IL

+1 773 871 3000

Culturally diverse playwrights shine at one of Chicago's landmark theaters. The recent $11.8 million renovation is another victory altogether.

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1850 West Fulton Street

Chicago,IL

+1 312 563 0023

Wake up! That's the smell of a Chicago coffee original brewing. A tour of its Roasting Works earns you a free half-pound of beans, freshly roasted on site.

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Millennium Park

Chicago,IL

Costing $23 million, this sculpture is made from thousands of steel plates-all polished to distorted perfection.

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585 East Illinois

Chicago,IL

+1 312 527 1977

European architectural influences give Chicago visitors a good reason to float along the Chicago River and crane their necks in wonder. They'll learn a few things too.

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1000 Lake Cook Road

Glencoe,IL

+1 847 835 5440

Combine 2.3 million plants with 8,979 types of plants and green thumbs realize that they have struck gold.

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2326 West Devon Avenue

Chicago, IL

Sweet scents of halva and coriander waft over this stretch of Devon Avenue.  Indian and Pakistani families peer into windows filled with colored gowns while basmati rice boils on the back burners. 

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5757 South Woodlawn

Chicago,IL

Prairie-style architecture may have been all the rage 100 years ago, but Wright's designs still flow with easy, Midwest modernity.

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Cermak and Wentworth Avenues

Chicago,IL

The best way to try a Chinatown restaurant is by asking for its secret menu. Most are written in Chinese and pack an authentic punch (think duck feet sous vid).

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300 North Central Park Avenue

Chicago,IL

+1 312 746 5100

Chicago's domed gardens integrate flora and artistry. Glass artist Dale Chihuly exhibited his exquisite glass works here, among Persian lilies.

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1800 North Clybourn Avenue

Chicago,IL

+1 312 915 0071

The city's rampant brewpub explosion is indebted to the pioneering likes of Goose Island. The best time for a brewery tour is Sunday; the time to drink is always.

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1300 South Lakeshore Drive

Chicago,IL

+1 312 443 3600

When the sun sets in the west, shocks of color dazzle the senses in a glass-lined, Art-Deco entryway—all for free.

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230 North Michigan Avenue

Chicago,IL

+1 312 482 8600

Mug shots, leather and chandeliers give this rock lounge a killer, high-end vibe.

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536 West Erie Street

Chicago,IL

+1 312 266 2300

Tucked in a nook of River North, Erie Café's famous strip steaks have been known to make even the most astute businessmen blush.

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1747 North Damen Avenue

Chicago,IL

+1 773 489 1747

This Chicago restaurant and dessert lounge is equally known for Kobe beef and gourmet burgers as it is for warm brioche donuts and artisanal cheeses.

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3324 North California Avenue

Chicago,IL

+1 773 279 9550

Alligator sausage frequents the menu, as well as its famous duck fat fries-served Fridays and Saturdays only. Lines are long but worth the wait.

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1531 North Damen Avenue

Chicago,IL

+1 773 235 4039

Honky-tonk and whiskey meet their match at this Tex-Mex hot spot. Savory a la carte tacos include famous al Pastor and plenty of vegetarian options.

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2005 West Roscoe Street

Chicago,IL

+1 773 248 7372

While patrons sip Hamm's and play Simon Says, they also nosh French Toast Towers and Green Eggs and Ham at this Roscoe Village brunch spot.

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2900 West Belmont Avenue

Chicago, IL

+1 773 604 8769

This Logan Square burger joint is famous for its cast of musical sandwiches, and the tattooed wait staff that serves them with fries and heavy metal attitude.

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2119 South Halsted Street

Chicago,IL

+1 312 526 3385

This Pilsen restaurant got its name for an intimate, earthy charm that's bolstered by wood-grilled duck, Wisconsin trout and handwritten menus.

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Two Mid America Plaza

Oak Brook, IL

+1 630 572 2200

While Da Coach may have few restaurants across the country, there's no more authentic way to experience succulent steaks than in the home of the original super fan.

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1113 West Randolph Street

Chicago,IL

+1 312 929 4787

Behind the backdrop of one of Chicago's best skyline views, singles mingle on the rooftop deck of this West Loop sports bar and restaurant.

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1920 West Division Street

Chicago,IL

+1 773 395 9434

An amazing Grilled Mediterranean Tuna Melt awaits those who join Wicker Park brunch and lunch crowds at this locally revered café.

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806 North Rush Street

Chicago, IL

+1 312 787 5435

See locals, celebrities or a mix of both at this Rush Street-area mainstay. It's a guaranteed good-time Irish pub with an equally rousing jukebox.

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1520 North Damen Avenue

Chicago, IL

+1 773 252 1500

The moody lounge crafts high-end cocktails in a covert locale and has patrons dressing the part.

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900 North Michigan Avenue

Chicago, IL

+1 312 915 3916

When you are done spending big at the 70-plus national and independent boutiques on the Magnificent Mile, take a short walk to drop off your bags at the nearby Park Hyatt or Hyatt Regency Chicago.

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2210 North Halsted Street

Chicago,IL

+1 773 248 5326

With more than 20 brands of designer denim on tap, this Chicago denim shop serves hard-to-find brands via a long, wooden bar.

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North Milwaukee Avenue and North Damen Avenue

Chicago,IL

Recycled and designer fashion coordinate looks in this booming boutique district. The intersection of North, Milwaukee and Damen Avenues opens even more stylistic doors.

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3316 North Lincoln Avenue

Chicago, IL

+1 773 525 7773

The most acclaimed music store in Chicago also houses the largest collection of new and vintage guitars in the city-hundreds, to be non-exact.

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1747 South Halsted Street

Chicago , IL

+1 312 733 0407

Retro looks by Versace, Gaultier and Moschino fit right into the boisterous vibe of Chicago's Pilsen neighborhood.

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1819 West Grand Avenue

Chicago, IL

+1 312 829 6122

Creativity is king at Post 27, where restored furniture and artful accessories spark inspired looks. Hit this West Town gem for scoping rare, urban finds.

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3856 North Lincoln Avenue

Chicago,IL

+1 773 697 8035

This self-proclaimed Lakeview "man-tique" features fedoras, clothes, vintage racing helmets and bacon-chocolate bars from Vosges.

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1039 West Lake Street

Chicago, IL

+1 312 738 0155

There may be champagne in the dressing rooms and disco balls on the ceiling, but there's also an array of hard-to-find Chicago designers, including Bynum & Bang.

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1564 North Milwaukee Avenue

Chicago,IL

+1 773 862 4882

Rummaging through 80,000 old and used book titles can be daunting-navigating three historic levels of stacks is equally challenging.

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1924 West Division Street

Chicago,IL

+1 773 227 2707

If owl screen prints and stuffed pocket mustaches could have their own store, it would be called Renegade Handmade. 

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1840 West Hubbard Street

Chicago, IL

+1 312 733 0098

Junk gets an urban renewal at this 60,000-square-foot design outpost. Its warehouse is ready-made for restored furniture and fixtures crafted from salvaged materials.

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