Chicago: Top 10 Things to Do

Chicago skyline

Chicagoan Molly Loeffler takes an in-depth look at her home city to reveal her Chicago top 10

Frank Sinatra got it right when he said Chicago was “My kind of town”. I have lived here for 20 years and truly love Illinois’ largest city – one that’s big to tackle but easy to manoeuvre thanks to buses, cabs, water taxies, free trolleys, and the infamous L – our elevated rail system. If you’re planning a visit here but aren’t sure where to visit, here’s my Chicago top 10:

1. Michigan Avenue

Busy yes, but here it’s definitely worth fighting the crowds. Michigan Avenue’s northern section is known as the Magnificent Mile (Mag Mile among locals) and is filled with high-end shops, popular department stores and wonderful restaurants. One shopping highlight is Water Tower Place – an eight-story shopping mall that’s home to Foodlife, an ‘eating experience’ featuring legendary Chicago restaurants.

Also at the northern end is the Water Tower – one of the few surviving buildings of the Great Chicago Fire of 1871. Follow the Mag Mile further north and you’ll hit Lake Michigan and Oak Street Beach – in the spring it’s lovely to walk the paths along the lakefront and enjoy the picturesque views. When things hot up in the summer you can lie in the sand, play beach volleyball, and, if the water’s warm enough, take a dip.

> Mosey on down to Michigan Avenue with Chicago Map Guide.

2. Millennium and Grant Park

After a day’s shopping it’s time to visit Michigan Avenue’s southern section and Millennium Park. A major tourist spot it might be, but locals still love it here. Jay Pritzker Pavilion is the first thing you’ll notice en route to Millennium Park – a gorgeous steel band shell with 4,000 fixed seats and a large lawn accommodating 7,000 more. During the spring and summer, the pavilion hosts many concerts, performances and events such as free yoga on the lawn.

Another Millennium Park must is the Cloudgate sculpture, known to Chicagoans as ‘the Bean’. A three-story steel structure with a highly-polished exterior, it gives stunning reflections of the skyline and the Chicago cityscape. Walk down the stairs from the Bean towards McCorkmick Tribune Plaza and the Plaza at Park Grill. In the warmer months you can eat outside on the plaza, while in winter there’s an ice skating rink regarded as among Chicago’s best people-watching spots. When it’s time to get away from the park’s crowds, stroll through Lurie Garden – home to the world’s largest green roof.

Next to the pavilion is the Pedestrian Bridge that crosses over Columbus Drive and ends at Grant Park – the perfect way to walk from Millennium Park to Grant Park, aka ‘Chicago’s front lawn’. This 319-acre park is greener than Millennium Park and hosts many concerts and events, including Taste of Chicago and the Lollapalooza music festival. At Grant Park’s centre is Buckingham Fountain – a Chicago icon and one of the largest fountains in the world.

> Gravitate to Grant Park with Red Maps’ Chicago.

Sears Tower

3. Willis Tower (or Sears Tower, as it’s better known)

Willis Group holdings purchased the naming rights to the Sears Tower in 2009, but away from corporate bigwigs no-one calls it by its official name. This 108-story skyscraper is the tallest building in the US (though it may be surpassed by New York’s One World Trade Center later this year) and a huge Chicago attraction – visitors should take the 60-second lift ride to the Skydeck and bask in the views of Illinois (and on a clear day, Michigan, Wisconsin, and Indiana). A new Skydeck feature is the retractable glass balcony boxes, allowing people to look down 108 stories at the streets of Chicago.

> Walk to Willis Tower with Hello Chicago.

4. Museums

Take your pick! The Art Institute of Chicago is the second-largest art museum in the US with more than 260,000 exhibits, including the likes of Monet, Renoir, Grant Wood, Edward Hopper and Matisse. Also recommended is the Museum Campus – home to the Field Museum of Natural History, Adler Planetarium and the Shedd Aquarium. Here visitors will see everything from Sue, the largest and most complete Tyrannosaurus Rex skeleton, to the stars and planets, and, if they so desire, an exhibition on jelly fish. Another institution worth visiting is the Museum of Science and Industry, where the many interesting and interactive exhibits make for a fun afternoon.

> Meander to the museums with MapEasy’s Chicago.

5. Lincoln Park Zoo

This is a fun (and best of all, free) attraction in the Lincoln Park neighbourhood of Chicago. It is One of the oldest zoos in the US, Lincoln Park is home to a wide variety of animals – and best of all, it doesn’t cost a dime to get in!

> Be led to Lincoln Park Zoo with the National Geographic Chicago map.

6. True Chicago Food

It’s a must for visitors to eat the food Chicago is famous for. Fancy a deep dish pizza? Head to Lou Malnati’s or Gino’s East. For a famous Chicago hot dog, go to Portillos or Superdawg – just don’t ask for ketchup. Want a good Italian beef sandwich? Al’s Beef, which does the best beef sandwich in Chicago, has it covered. If you head to the branch on Taylor Street, cross the street after your sandwich for some Mario’s Italian Lemonade – only open in the spring and summer, this little shack has the best lemon ice in the city./p>

One of Chicago’s most famous food attractions is Garrett’s Popcorn. A line may form outside each of its branches, but the popcorn is definitely worth the wait. You can order cheese, caramel, butter and many other flavours, but the most popular item on the menu is the Chicago Mix – a combination of cheese and caramel flavours.

> Roam to Chicago’s restaurants with the Chicago Eyewitness Guide.

7. Navy Pier

This 1,010 m-long pier alongside Lake Michigan was once a navy training centre, but it’s now home to many attractions, shops and restaurants. Travelling with children? Take them to the award-winning Chicago Children’s Museum right at the pier’s entrance. They’ll also enjoy the Navy Pier Ferris Wheel, which runs year-round, weather permitting. During the summer, Navy Pier hosts a fireworks show every Wednesday and Saturday night – watch them from the pier or a boat on the lake!

> Navigate to Navy Pier with Frommer’s Chicago: Free and Dirt Cheap.

8. Wrigleyville and Lincoln Park

If downtown is a little busy, take the ‘L’ out to one of the outer neighbourhoods. Two of my favourite are Wrigleyville and Lincoln Park – both on the north side. Wrigleyville surrounds the famous Wrigley Field, home of the Chicago Cubs baseball team. In the summer when the Cubs are playing, the streets are packed with people going to the game or to a nearby bar like the famous Cubby Bear to watch. On non-matchdays, Wrigleyville is a fun place at night with lots of bars and clubs.

Lincoln Park is another great neighbourhood and the home of Lincoln Park Zoo. It’s filled with many nice shops and delicious restaurants, as well as a great nightlife scene thanks to the plethora of bars here. If you’re paying a visit, I highly suggest going to CBA: Chicago Bagel Authority for breakfast or lunch. This quirky stop has just about every combination of sandwich toppings on a freshly-steamed bagel.

> Walk to Wrigleyville with Lonely Planet’s Chicago City Guide.

9. Shows and theatres

Chicago is always hosting different musicals and plays as well as concerts and comedians. Heading to an event can make for a very fun night and tickets are fairly easy to purchase. My favourite part is the theatres themselves – Chicago is home to many gorgeous old theatres dating back to the early 20th century. Among my favourite are The Chicago Theatre, Ford Centre for the Performing Arts also known as The Oriental Theatre, Bank of America Theatre, and The Cadillac Palace Theatre. All have gorgeous interiors and make the price of a ticket well worth it.

> See a show with the Chicago Wallpaper City Guide.

10. Second City

To understand the sense of humour of Chicagoans, a show at Second City is the thing to do, with this city specialising in sketch comedy and improv. Many hilarious actors and comedians have been discovered at Second City such as Tina Fey, Chris Farley, Steve Carell, Amy Poehler, Mike Myers, Stephen Colbert, Bonnie Hunt and many others.

> Catch up on Chicagoan culture with Chicago Culture Shock.

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>