Urban Adventures In Chicago
Madeleine McGuire

Museum Educator

The Doughnut Vault
There is no better place to start a day in Chicago. There's something about waiting in line for delicious, baked breakfast that gets the Midwestern spirit pumping for the day. I love being situated right in the middle of the city, ready for a day of urban adventure. Get there early, they close when they sell out!
Millenium Park
The ultimate tourist and local favorite, Millenium Park is the perfect place to see the city reflected through nature and public sculpture. I always bring my camera with me, there are endless beautiful (and hilarious) photo opportunities.
The Art Institute of Chicago
Right next door to Millenium Park, the Art Institute is one of the city's most treasured locations. The iconic lion statues standing out front are worth the visit alone, and there is tons to see whether you're a seasoned art-goer or just curious to explore. I love to visit the Impressionist Galleries or walk through the new Modern Wing that overlooks Millenium Park and Lake Michigan.
Willis Tower
Don't be deceived: this is the Sears Tower. Best place to see the city. Chicago is so freakin' flat you'll never get a sweeping view of the urban wonderland, so visit one of the sky scrapers to enjoy it's impressive spread along Lake Michigan. I love the view!
State Street
If you need a traditional Chicago fix, State Street is the place to go. Go shopping, visit the old Marshall Field's (now Macy's, the horror), and stop for all the delicious coffee along the way. I love the fast-paced city feel, it's always a great time.
Ann Sather
If you're in Chicago for a day, you've got to eat breakfast for lunch. It's one of those quirky local traditions that you must indulge while you're in town. Ann Sather has the best cinnamon rolls in the entire world, and is located in Chicago's Swedish neighborhood, full of fun shops, mini-museums, and bookshops. I love their diner coffee, and I love an excuse to walk around the neighborhood.
Brown Elephant
This great quality consignment shop is located in an old 1920's theater, and is worth a visit for the amazing architecture. Their proceeds benefit AIDS research and providing medical services within the gay community, making it one of the neatest local shopping venues. I love to go here for one-stop shopping, or browsing their awesome vintage magazines.
Lakefront Path
Bike the lakefront path! Don't let crazy weather hold you back - the landscape is well worth bundling up for the adventure. The summer is stunning with the lake juxtaposed with the city, and in the winter the frozen waves are unforgettable. No bike? Just walk!
Music Box Theatre
Catch a show or just check out the incredible venue. The Music Box is an amazing local theater with a live organ. I love to see silent movies here - the live music makes it so interactive and fun.
John's Place
John's Place is the kind of place where no matter what you order, it will be delicious. I've taken friends, family, dates, and co-workers to this restaurant, and it never fails to impress. Expect incredible dishes in a warm, comforting atmosphere. And right next door is Sweet Mandy B's...
Sweet Mandy B's
Their pastel booths and super retro-feel sometimes crack a few giggles at first glance... but there is nothing funny about their cupcakes. My suggestion? Go classic with vanilla or chocolate.
The Second City
I think this comedy club might be my favorite place in the world. I love their close-knit, table seating, and I leave laughing for hours after the curtains close. The Second City is home to dozens of Saturday Night Live alumni and endless famous actors and actresses. Enjoy a show where stars are being born with delicious cocktails, and prepare to laugh your pants off.
Fountainhead Rooftop
I love this place! Grab a local brew and enjoy the rooftop after a classic Chicago Theater show. Never disappoints. The perfect way to end a day in the windy city.
I would stay at: PUBLIC Chicago
Stay at the Public: they always have great promos, and have a crisp, clean, and cool vibe, not to mention an ideal location.