Best things to do in Chicago: From rock climbing to architecture tours and FREE live music
The Windy City certainly has a different vibe from hotspots like New York and California. Here we reveal the top seven activities and sights to make you know your Bears from your Bulls and your deep dish from your dirty dogs.
1. Look up – all
the way up – at the famous architecture
Chicago is the home of the skyscraper - where high-rises were first dreamt. They aren’t just home to city bankers, the vintage art deco towers or stunning glass blocks are tourist attractions in their own right.
Every Chicago itinerary must include a river tour even if architecture isn't your thing the guides onboard wendella sightseeing boats (www.wendellaboats.com) explain Chicago's history and culture, point out the main sites from city's three river branches, and show you incredible views of some of the most famous buildings in the US (which you will undoubtedly visit).
It’s finished off with a trip just into Lake Michigan for a stunning view of the 26-mile skyline. Head over for sunset to see the city transform.
Of all the skyscrapers in Chicago, the best two to visit are Willis Tower and the John Hancock Center
Formerly known as Sears Tower, Willis Tower has the famous Ledge, where those with a taste for heights can step onto a glass box to see the street below from 1,353 feet up. If you don’t have the nerve, you can still cast your eye over nearby sites including Buckingham Fountain and Lake Michigan from what was, when built, the tallest building in the world.
John Hancock Center gives a completely different aspect of the city -
looking out over the lake, the north shore beach, and for miles into
the flat mid west from the 360 Chicago observatory.
Test your mettle by stepping out onto Tilt where, 94 floors up, the glass wall slowly falls away, tipping you forward to the ground below. It's an experience like none other in the eighth tallest building in the world.
2. Get outdoors
Although Chicago is famous for its skyscrapers this is not a
city which feels claustrophobic. For those who like outdoor fun, Lake
Michigan is always in sight with a path for cyclists, runners and
Millennium Park is boosted by newly developed areas offering fun for all ages.
Maggie Daley Park, within the grounds of Millennium Park, is a hive of activity with a superb children's play area featuring interactive and sensory stimulus (even adults will love the slides), miniature golf, an outdoor rock climbing wall, and a unique skating ribbon. In winter this course is frozen over to become an ice skating path taking skaters through the park on a loop twice the length of a standard lap of a rink.
If you fancy seeing a different side to Chicago head to the 606 trail, a disused train line turned trail for walkers, runners and cyclists above the streets weaving through hipster neighbourhoods and past craft ale bars (You can also grab some authentic fried chicken at Parson’s Chicken and Fish at the end on 2952 W Armitage Avenue)
3. See the magic Bean
you visit the park, this is also a great chance to visit Chicago's
The giant reflective Cloud Gate sculpture by Briton Sir Anish Kapoor is as random as it is captivating, with hundreds of tourists at a time taking photos of the fun and odd reflections similar to those you'd find in a funfair hall of mirrors.
If you're really after the perfect holiday snap, head there at sunrise where you may just be able to get a photo with nobody else there. A rarity, that's for sure.
4. Take in the views
A fun and time-economical way to see the parks and museum grounds is to hire a Segway (ChicagoSegways.com). Your guide will whizz you through an eight mile loop in no time at all, telling you some history of the city, the tourist must-sees and their own favourite spots.
You can catch a glimpse of The Bean from a hang-out popular with ‘those in the know’ called Cindy’s (12 S Michigan Ave). The rooftop bar is within the historical place of fancy called the Chicago Athletic Association, a plush hotel with antique charm and overlooks Millennium Park, the Art Institute and Lake Michigan.
5. Listen to live music – everywhere
Rock, house, jazz, piano, and everything
in between is easy to
be found with the city partying into the small hours on a daily basis.
If you want a singalong in a truly American and raucous way head to a piano bar such as The Redhead (16 W Ontario St) where their in-house musician will play your request and encourage you singing at the top of your lungs.
Many restaurants and bars have live music to accompany your meal, such as the Tortoise Supper Club (350 N State St) which is a classy, low lighting establishment with some of the best steak in town.
If you fancy some free live music, check out the Pritszker pavilion by Maggie Daley Park. Chicago Symphony Orchestra do free concerts on Monday nights, and you can catch them at lunch times rehearsing. On Tuesdays it turns into an outdoor cinema, and Saturdays fitness classes are held. Entertainment here is usually free, so it's a great spot to have a picnic or eat some street food.
6. Shop at America’s finest
Millennium Park is a five minute walk to Macy’s and Saks, the start of the shopping haven on the outskirts of the Magnificent Mile on Michigan Avenue, which is crammed with more than 400 shops.
Expect a good service, the Macy’s building was home to Chicagoans’ beloved Marshall Field, the US’ first department store where the phrases 'the customer is always right' and 'give the lady what she wants' were invented.
7. Eat EVERYTHING
Chicago is proud of its twist on popular
dishes. Deep dish
pizzas at Gino’s East (500 N LaSalle Drive) are legendary, and if you
like Italian food Eataly (43 E Ohio St) is a bumper Mediterranean
LatiniCity (108 N State Street) is another food mecca, with 10 Latin inspired stations in a funky hall with its own bar, brought to customers by world-renowned chef Richard Sandoval. It overlooks a Picasso sculpture in a Daley Plaza which hosts a farmers’ market every Thursday.
As already mentioned, the Tortoise Supper Club is a beautiful special treat with fantastic service and Parson’s Chicken and Fish (2952 W Armitage Avenue) has traditional fried chicken in a casual setting.