A Guide to Chicago
Collected by Allison Murray, AFAR Contributor
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!
233 S Wacker Dr, Chicago, IL 60606, USA
Willis Tower—originally known as the Sears Tower—was the world's tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its "bundled...
1060 W Addison St, Chicago, IL 60613, USA
Steeped in history, loved my many, loathed by some, and sorely in need of a championship, Wrigley Field is a true cornerstone of the always controversial sporting world. No trip to Chicago is complete without a visit to this monument to to...
809 W Randolph St, Chicago, IL 60607, USA
3868 N Lincoln Ave, Chicago, IL 60613, USA
Sola is a Hawaiian-inspired brunch spot in Chicago's trendy Lakeview neighborhood, but I don't ever recall having food this good in Hawaii. Try the sour cream pancakes with blueberry, lemon zest and lemon ricotta (my personal favorite, pictured...
1137 W Argyle St, Chicago, IL 60640, USA
I'm a huge fan of Pho soups but I'm picky too—I want a rich broth with light springy noodles and slivers of meat, a contrast of textures and tastes. Pho 888 is not only reasonably priced but offers up some of the best Pho I've had in North...
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...
330 W Webster Ave, Chicago, IL 60614, USA
By the Clark and Webster intersection in Chicago, you'll come across this intriguing art installation: a tribute to all the sister cities of Chicago around the world. Part of a school project that will undoubtedly inspire your kids, a group of...
7705 N Eastlake Terrace, Chicago, IL 60626, USA
The northern-most beach in Rogers Park is a gem year round. It's easy to see why this spot is normally crowded with families during the warm months— lifeguards make it safe to swim and the jetty is perfect for a stroll. Lightly populated during...
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...
2959 N Lincoln Ave, Chicago, IL 60657, USA
Heritage Bicycles General Store is so many things: a coffee shop, a general store, and a place to buy a few key items for your hip closet. Most importantly though, it's a place to grab a cup of joe and watch art being created that you can ride...
737 W Randolph St, Chicago, IL 60661, USA
A visit to Chicago's historic meat-packing district at any time is, in and of itself, a bit of an adventure. The area has certainly seen enough transitions to bring in the hip and happening in recent years. However the best reason to visit,...
825 W Fulton Market, Chicago, IL 60607, USA
A primo sourcing grounds for picnic provisions or a casual cafe meal, Publican Quality Meats is the latest food enterprise by the never-miss restaurant team behind Avec, Publican, and Big Star. Billed as a contemporary American butcher shop, its...
220 E Chicago Ave, Chicago, IL 60611, USA
The interior architecture of Chicago’s MCA building is worth the price of admission. Four floors of exhibit halls branch off the central staircase pictured above, and the East and West facing glass walls have unparalleled views over Lake Michigan...
770 N Halsted St, Chicago, IL 60642, USA
Chicago, home to one of the largest Indian-American populations in the U.S., throws some great bhangra parties—as long as you know how to find them. Their parties rotate venues and events are often held in conjunction with celebrations like Holi,...
3856 N Lincoln Ave, Chicago, IL 60613, USA
I'll be honest, unless you are up on your geography of Great Britain, the name of this store, Isle of Man, may appear a bit puzzling at first. However, upon entering and talking to the shopkeepers, it all immediately makes sense. The owners love...
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...
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...
531 N Wells St, Chicago, IL 60654, USA
GT Fish & Oyster is a standout on Chicago’s seafood scene. Run by Michelin-starred chef Giuseppe Tentori, the restaurant serves elevated versions of many classics, including clam chowder with housemade oyster crackers and beer-battered cod with...
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...
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...
5014 N Broadway, Chicago, IL 60640, USA
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...
2601 N Milwaukee Ave, Chicago, IL 60647, USA
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...
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...
954 N California Ave, Chicago, IL 60622, USA
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...
1551 N Wells St, Chicago, IL 60610, USA
I've been to most of Chicago's well-known wine bars, but this one surpasses the rest. In the fashionable Old Town neighborhood just north of downtown, Flight 1551 pours more than 250 wines by the glass and by the flight. Burger flights, hummus...
469 N Racine Ave, Chicago, IL 60642, USA
I took my wife here for a glassmaking course on her birthday, and it was amazing! We were always interested in doing this and I finally decided to look up studios that offered courses. Sharon Gilbert, the artist that owns Talisman Glass, was very...
5547 N Clark St, Chicago, IL 60640, USA
I wrestled with even posting this highlight, since this is hands down the best sushi joint in Chicago. It's up north, it's BYOB, it plays only music from the 80's, you can get reservations at the drop of a hat, the sushi chefs are personable, they...
McCormick Blvd, Skokie, IL 60076, USA
Located a bit north of downtown Chicago is the Skokie Northshore Sculpture Park. This two-mile stretch of McCormick Boulevard runs north/south between Touhy Avenue and Dempster Street and features over 60 incredible sculptures. The one featured...
1230 W Greenleaf Ave, Chicago, IL 60626, USA
For the most relaxing beach experience, travel a short distance north on Lakeshore Drive and you will find idyllic beaches that you can have almost all to yourself. Here you'll feel free to play, exercise or take a romantic stroll away from the...
875 N Michigan Ave, Chicago, IL 60611, USA
Watch the Chicago city lights come up as the sun goes down at the the Signature Lounge. While the Observatory on the 97th floor is a popular spot, you'll have an even more memorable experience lounging, cocktail in hand, overlooking the same...
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