Most locals have at one point taken the Chicago Architectural Foundation River Cruise of downtown’s historic landmarks and loved it. Each certified volunteer docent is brimming with incredible details about the way the city grew from a small outpost into a major national crossroads in a matter of 100 years. The docents enthusiastically guide you down the Chicago River pointing out more than 50 major buildings. Tours begin April 30 and run through October 30 including all major holidays.
Check out the Modern Wing of the Art Institute which opened in 2009. This elegant new home for the museum’s excellent 20th- and 21st- century art collections was designed by Pritzker Prize-winning Architect Renzo Piano.
When winter comes, there is still fun to be had! Ice skating in Millenium Park’s McCormick Tribune Ice Rink begins mid-November and runs through the beginning of March (weather permitting). Skate rental is available for those who don’t bring their own pair, and there is no better place to be as the holidays roll in.
Visit the West Loop for some of the best dining in the city. With such noted restaurants as Girl and the Goat, The Publican, Blackbird, and avec, the West Loop food scene is one of the most exciting spots for the gastronomically inclined.
In the summertime, you’ll want to pack a picnic and head to Movies in The Parks. With over 175 movies in parks across Chicago all summer long, there’s bound to be something to suit your mood/taste/themed dinner. All movies are free and begin at dusk.
The Chicago Green City Market is the city’s year-round sustainable farmers market. Focused on spreading knowledge about local and sustainably grown foods, the bustling market gives shoppers the opportunity to meet the people who grow their food. You’ll even get great recipes from the people who know the food best.
If you’re looking to take in a show, Chicago is lucky to be a stop on almost all touring Broadway plays and musicals. Beautiful theaters are located all over the Loop, and finding out what’s in town is as easy as stopping at the Hot Tix booth at 72 E. Randolph. In addition to theater, you’ll likely find some incredible dance or music at the ultra-modern Harris Theater in Millenium Park and the classic, lavish Auditorium Theater of Roosevelt University.
Speaking of shows, the Second City is one of Chicago’s best known improvised comedy companies known for putting Tina Fey, Gilda Radner, Dan Akroyd, and many other hilarious luminaries on the map. With an ever-changing lineup of current shows, Second City is a great option for a night out for anyone who enjoys a good laugh.
Circus in the Parks is began as a fundraising program for Welles Park in Lincoln Square and has quickly grown into one of the most popular autumnal attractions across the city. Once you find them in a park near you, you’ll be blown away by the talents of these quirky performers. Produced by local company the Midnight Circus, all proceeds benefit the host park district.
Just south of the Andersonville line in Uptown, you’ll find a delightful bar called The Hopleaf with a beer selection that will make your eyes pop. In the front room, you’ll undoubtedly find a bit of a crowd squeezed into booths and standing in corners–just find a spot and get comfortable. The convivial neighborhood vibe is infectious. If you’re hungry, the significantly quieter and less crowded dining room serves up delicious European-style food (try the mussels). It’s 21 and over here, so make sure you bring your ID.