Collected by Rachel
875 N Michigan Ave, Chicago, IL 60611, USA
Skip the ticketed admission to the John Hancock Observatory on the 97th floor and take the elevator to the “Signature Lounge at the 96th” floor of the John Hancock Tower at no charge. The Chicago skyline glitters at night, but sorry...
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...
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...
2391 N Stockton Dr, Chicago, IL 60614, USA
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...
220 E Chicago Ave, Chicago, IL 60611, USA
Not only does the Museum of Contemporary Art have great exhibitions on local and renowned artists, but the interior architecture of the museum itself is also an attraction. They also provide unusual events and tours—curator-led tours, musicians on...
7705 N Eastlake Terrace, 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....
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...
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...
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...
1 Great America Parkway, Gurnee, IL 60031, USA
Roller coasters, oh yeah! Six Flags is a classic theme park with roller coasters, carnival rides, hot dogs and funnel cakes on the midway and evening shows with gunfights and singing contests. But Six Flags also has a 10,000 square foot water park...
108 E Superior St, Chicago, IL 60611, USA
If you fancy an epic place to stay while visiting the Windy City, The Peninsula, located in the heart of downtown, can cater to your every desire. If it's fancy digs you require, any room that you request will be top notch. For unwinding and...
835 Michigan Avenue, Chicago, IL 60611, USA
Treat your favorite little girl to afternoon tea at the American Girl Place Cafe. You’ll first have to brave the store, as the restaurant is hidden in the back of the top floor, but once you've arrived even dolls get their own chairs and...
1850 W Fulton St, Chicago, IL 60612, USA
In 2004 Intelligentsia decided to focus more on teas and as a result they now offer many different kinds of white, green, black and jasmine teas all brewed from high quality loose leaf tea leaves. Many of the teas offered by the cup in their cafes...
3700 N Western Ave, Chicago, IL 60618, USA
There’s bowling and then there’s cosmic bowling. Regular bowling is pedestrian, under bright fluorescent lights where everyone can judge your bowling skills. Cosmic bowling is infinitely cooler and better because it’s dark with...
2548 N Halsted St, Chicago, IL 60614, USA
I always look forward to visiting Chicago, especially when it's work related and I'm encouraged to take customers out for dinner. A highlight of my last visit in November was dinner at Trattoria no. 10 on Dearborn. Holy Baby Cow Batman, that was...
1035 N Western Ave, Chicago, IL 60622, USA
The Empty Bottle in Ukrainian Village offers great music in a small venue with an angled stage so the views are pretty good from anywhere in the house. The drinks are reasonably priced with friendly bartenders and the location is a bit divey but...
3216 N Sheffield Ave, Chicago, IL 60657, USA
Yeah, you know you want to sing karaoke. And you know why you want to do it at Trader Todd’s? Because they’re also a tiki bar. For people who have a little bit of stage fright (like me) and don’t love singing in front of people (also me) but when...
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...
1501 N Kingsbury St, Chicago, IL 60642, USA
Chicago has a lot of improvised comedy shows with 195 listings on Yelp, the most famous of which is Second City and some of the funniest of which are hosted by the iO theatre. Where else but the iO theatre can you see improv done in iambic...
5153 N Ashland Ave, Chicago, IL 60640, USA
At 10:30pm every Friday and Saturday a line of people form at the corner of Ashland and Foster waiting for entrance into the 11:30pm Neo-Futurist show, a different play every week. For 25 years the Neo-Futurists performed a show that made...
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