Collected by Brie Madison
Chicago, IL 60601, USA
Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel...
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...
111 S Michigan Ave, Chicago, IL 60603, USA
337 E Randolph St, Chicago, IL 60601, USA
I know, I know, Lollapalooza may be a little overpriced and overrated. But the truth is, it is still one of the best music festivals in the country. Amazing live performances by well-known artists and new talents, worldwide travellers, a quirky...
1521 S Linn White Dr, Chicago, IL 60605, USA
Many people who visit the U.S. immediately think of New York as the quintessential American city. But they are missing out. Chicago is a world-class city with so much to offer. From shopping on Michigan Avenue to renowned chefs/dining to the Bean...
201 E Randolph St, Chicago, IL 60602, USA
Every June hundreds of internationally renowned blues musicians rock Chicago for 3 days and 4 nights in the world's largest free blues festival. Did I mention it’s free? 3 solid days of music for free! Food vendors flock to Millennium Park for...
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...
Old Town, Chicago, IL, USA
Located a short train ride from the Loop, this wrought-iron doorway marks the entrance to Chicago’s Old Town. You'll find plentiful shopping and restaurant options in the neighborhood, as well as St. Michael’s Church, one of the city's oldest...
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...
401 N Franklin St, Chicago, IL 60654, USA
I have two pieces of advice for you regarding the Doughnut Vault: 1. Go early. They open at 8am Tuesday-Friday and 9:30am on Saturdays and if you want a breath of a hope of a chance of getting a doughnut before they sell out, you want to be there...
700 S Wabash Ave, Chicago, IL 60605, USA
Buddy Guy’s Legends is a legendary blues bar in Chicago and Buddy Guy himself is still alive, making music and appearances on his own stage. Legends has been open since 1989 and the stage has seen the eclectic likes of Eric Clapton, Keith...
Magnificent Mile, Chicago, IL 60611, USA
Chicago’s Magnificent Mile runs along Michigan Avenue between the Gold Coast and the Loop. There are 460 retail stores, from high-end designers like Gucci, Cartier, and Louis Vuitton to local boutiques and trendsetting fashion stores. In between...
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...
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...
140 E Walton Pl, Chicago, IL 60611, USA
You know you're somewhere special when your car pulls up in front of the The Drake Hotel, located right off of Michigan Ave. in downtown Chicago. A white gloved bellman opens the door and greets you in the most charming, old school way. As you...
Chicago, IL 60626, USA
Pick up your morning coffee at one of the many local coffee shops, and walk to Rogers Beach (known by locals as Lighthouse Beach). The sunrise over Lake Michigan is stunning! Locals fish off the lighthouse pier in the early morning semi-darkness....
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...
1655 W Cortland St, Chicago, IL 60622, USA
To find the Trap Door Theatre, you walk down a narrow walkway between two white brick walls. A steel door opens onto the kitchen of Jane's Restaurant. A second door leads to a small black box theater. There, for the last 15 plus years, the Trap...
1138 W Bryn Mawr Ave, Chicago, IL 60660, USA
Lovely, Too is a delightful little bakery up in Andersonville. They serve Intelligensia coffee, a Chicago brand, and their pastry case is drool worthy with incredible scones, cookies and cupcakes. It's rarely crowded and there are plenty of tables...
20 N Upper Wacker Dr, Chicago, IL 60606, USA
Pass through the beautiful lobby and enter a world where your senses are immersed in soaring vocal art. The Lyric Opera of Chicago is a world-renowned music establishment that features the most famous voices on the globe. There are two on-site...
15 E Ohio St, Chicago, IL 60611, USA
The Acme is my favorite hotel in Chicago. First off, most of the rooms are suites with tiny kitchenettes, refrigerators, microwaves and separate bedrooms. The “knock and drop” coffee feature means someone will bring you a thermos of hot coffee at...
1400 S Lake Shore Dr, Chicago, IL 60605, USA
Dinosaurs, pyramids, cave paintings, sharks—if you don't like the Field Museum then you must never have been a kid. Home to an extensive assortment of magical displays highlighting all facets of natural history from around the world, the...
141 W Jackson Blvd, Chicago, IL 60604, USA
For their roving, event-based Volume Gallery, Claire Warner and Sam Vintz pluck contemporary American designers like Thaddeus Wolf and Rich Brilliant Willing and set up short-run installations at galleries all over Chicago. One of Chicago’s own,...
1300 S Lake Shore Dr, Chicago, IL 60605, USA
It’s difficult to design a museum suitable for both kids and adults, but Adler makes it look easy. Children will love the area known as Planet Explorers, where they can play astronaut with space rovers and rocket-launch simulators, peer...
5700 S Lake Shore Dr, Chicago, IL 60637, USA
Anyone who's into model trains should visit the Museum of Science and Industry in Chicago. Originally opened in 1941, The Great Train Story was the largest model train of its day. After being briefly shuttered in 2002 for extensive additions, this...
951 Chicago Ave, Oak Park, IL 60302, USA
Frank Lloyd Wright built 700+ houses all over this nation but he lived and worked in Oak Park, just a 45 minute train ride from the city center of Chicago. His house and studio are now a museum with guided tours that let you see the playroom he...
78 E Washington St, Chicago, IL 60602, USA
Chicago's art scene is often overshadowed by the ever-increasing foodie scene but the Windy City offers just as much contemporary and historical art as pizzas and gourmet doughnuts. The Chicago Cultural Center is one of my favorite art-focused...
111 E Upper Wacker Dr, Chicago, IL 60601, USA
The Chicago Architecture Foundation is a must see if you are an architecture fanatic or just love the Chicago skyline. The CAF has a great shop inside the Historic Santa Fe Building in downtown Chicago. They sell informative books about...
1601 N Clark St, Chicago, IL 60614, USA
The Chicago History Museum examines Chicago’s local history as well as its position in the larger scope of American history. The engaging exhibits cover a wide range of subjects such as Abraham Lincoln’s life and presidency, the first locomotive...
600 S Michigan Ave, Chicago, IL 60605, USA
Chicago's Museum of Contemporary Photography occupies a small compact space with gorgeously designed photography exhibits on three floors. The current exhibit, called Dandy Lion, explores black masculine identity in photographs of sharply...
- 1 Where to Go in Fall Made for Walking: Stylish Travel Shoes That Are Actually Comfortable
- 2 Air Travel These North American Airports Rank Best (and Worst) in Passenger Satisfaction
- 3 Food + Drink The Untapped Region Where Italy’s Oldest Culinary Traditions Live On
- 4 History + Culture Europe’s Lesser-Visited UNESCO Sites Are Easier Than Ever to Explore
- 5 Travel News Several High-Speed Train Routes Are Coming to the United States