10 Things to do in Chicago

Chicago's SkylineFrom Jazz Festivals to Medieval dinners and jousting tournaments, Chicago’s got a little something for everyone, regardless of your budget. To prove it, we’ve come up with a list of 10 things to do in Chicago which we think should keep everybody happy.


1. Check out the city at 1,000ft from the John Hancock Center

John Hancock Building ChicagoUnless you’re terrified of heights, there really is no better way to view the city than the observation deck at the top of the John Hancock Observatory.

Standing at more than 1,000ft in height, the imposing tower is one of Chicago’s most well-known buildings and was designed to withstand winds in excess of 60 miles per hour, which is pretty handy given Chicago’s reputation for blowing a gale!

Inside, the complex is vast and contains its own post office, apartments, shops, a hotel, ice rink and restaurants including the famous Signature Room on the 95th and 96th floors.

However, it’s the views from the observation deck that people come to see and you can rest assured that these are well worth the occasionally lengthy queues and ticket price of $17.50.

Top Tip: Head up the Observatory for the best views in town of the Navy Pier Fireworks, which take place during the summer months. Make sure you arrive early though to avoid missing out!

2.  Eat like a king on a Progressive Dining Tour

Chicago PizzaThere is no shortage of decent places to eat in Chicago but if you’re after something a little bit different from your dining experience, then a Progressive Dining Tour with Chicago Dine-Around is it.

The tour takes you on a culinary adventure which sees you stop off for courses at some of Chicago’s finest restaurants. Your very own chauffeur in a luxury coach drives you between three restaurants – for Hors D’oeuvres, Main Course and Dessert.

The tour is an exciting way to experience Chicago dining and to get to see a bit of the city, but it doesn’t come cheap at $85 per head. So, if you’re on a tight budget, it’s probably not for you. However, it’s ideal if you want a romantic meal or are celebrating a special occasion.

For prices, restaurants and menus go to the Chicago Dine-Around website.

3. Get lost in the Amazing Chicago Funhouse Maze

Located at the East end of Navy Pier, the Amazing Chicago Funhouse Maze sounds like something that should be left to the kids but it’s actually great for people of all ages and not as easy as it looks.

Featuring 4,000 sq. ft of tunnels and mazes, as well as interactive games and informative narration, the Maze will get you in a muddle and at some point you will find yourself twisting, turning and going back on yourself along with everybody else.

As a result, the Maze is guaranteed to keep you entertained for a good couple of hours at the very least or possibly longer if you get stuck.

Don’t believe us? Then you’ll just have to try the Maze for yourself and see how you get on!

Open daily at 10am. Prices start at $9.95; group rates available.

4. Give yourself a fright on a Chicago Ghost House Investigation

We know what many of you must be thinking- there’s no such thing as ghosts. Maybe you’re right, but that doesn’t mean that you shouldn’t have fun trying to locate them. Fictional or otherwise.

Chicago Ghost House Investigation allows you to do just that in some of Chicago’s most haunted locations. Armed with sensors, detectors and cameras that work in the dark you will be taught by your very own Ghostbuster how to use the equipment to locate potential spirit activity.

Your poltergeist expert will also teach you a psychic technique, which will allow you the opportunity to potentially communicate with the spirit of a loved one in the world beyond.

As with any tour of this nature, there’s absolutely no guarantee that you’ll see a ghost or ‘make a connection’ with a spirit, but it’s great fun nonetheless and what you get out of the whole experience depends a lot on how much you let your imagination run away with you.

Tours depart from the Old Water Tower at Chicago and Michigan Avenues. $50 per person, with day time and week day discounts available; group rates available.

5. Go back in time at a Medieval Dinner & Tournament

If you’ve ever seen the film Role Models, where Paul Rudd et al get dressed up to play soldiers in a mythical world of sword craft and honor, then you’ll have some idea of what to expect from the Medieval Times experience.

Guests are taken back to the 11th Century, where King Philippe reigns supreme alongside his daughter-in-law Princess Leonore and is presiding over a four-course feast to which you have been invited.

As part of the entertainment guests are treated to medieval jousting tournaments and occasionally even bloody battles in authentic medieval tournaments.

This, like Ghost hunting, might be a stretch too far for many, but the Medieval Times franchise is increasing in popularity in the United States and Chicago boasts some of the country’s most loyal fans.

With tickets starting at $36, Medieval Times is well worth a visit.

6. Come face-to-face with a T-Rex at the Field Museum

The Field Museum is Chicago’s Natural History Museum and is famous for being home to Sue, the largest Tyrannosaurus Rex skeleton in the world.

It’s only when you get right up to the enormous skeleton that you get a sense of scale of what was once the world’s largest  natural predator.

Getting the opportunity to get up close and personal with a T-Rex is worth the admission money alone, however, the Museum is also home to a great collection of stuffed creatures from around the globe.

Check out the Field Museum website for more details.

7. Shop until you drop on the Chicagoland mile

Chicagoans love shopping as much as the rest of America and thankfully Chicago has the shopping malls, department stores and boutiques necessary to satisfy shoppers of all tastes and budgets.

The City’s primary shopping strip is between Michigan Avenue and Oak Street- an area also known as the Magnificent Mile. Here you’ll find all the big department stores and clothing retailers like Bloomingdales and Ralph Lauren, as well as a number of thrift and discount stores.

The Magnificent Mile also features several shopping malls that have as many as 900 stores, which should keep even the most avid of shoppers happy.

For the indecisive amongst you – book yourself on to a shopping tour and get a personal guide for the day. These tours aren’t cheap but they can help you find the kind of stores and clothes you’re after.

If you are interested in getting yourself some help with the shopping, there are plenty of the shopping tour companies out there including See More Shopping Tours but do shop around before you commit to one.

8. Explore Navy Pier

Navy Pier is an absolute must see when visiting Chicago, as many of the cities primary attractions can be found along this 1.5 mile boardwalk by the Chicago River.

Along the Pier, catch one of Shakespeare’s plays at the Shakespeare Theater or ride a 15-storey Ferris wheel. If you get tired of the Pier, you can hop on one of the many cruises that offer trips around Lake Michigan or on the Chicago River, which can range from a short jaunt to a full dinner cruise.

Navy Pier’s opening hours:
Monday – Thursday, 10am to 8pm.
Friday – Saturday, 10am to 10pm.
Sunday, 10am to 7pm.

Don’t forget to check out the free fireworks on the pier every Wednesday and Friday night during the summer.

9. Take a stroll in Grant Park

Sometimes all you want when visiting a big city is a bit of fresh air and Chicago has no shortage of parks and green space for you to do that.

Grant Park is the biggest and arguably the best. Here you’ll find joggers, walkers and picnickers of all ages enjoying the stunning views, beautiful lake and Buckingham fountain.

During the summer, the park comes alive as the outdoor concerts and festivals come to town, including Taste of Chicago and the city’s annual Blues Festival.

Also home to the Shedd Aquarium and the Field Museum of Natural History, anyone visiting Chicago is bound to end up in Grant Park at some point.

Another park worth checking out is Lincoln Park, which boasts its own zoo, nature museum and outdoor theatre.

10. Check out a festival

Taking in one of the many festivals is an absolute must during your stay in the Windy City. Taste of Chicago Festival

Many of the biggest and most popular festivals are held during the summer months from May through to the end of August. Don’t panic if you’re planning a trip outside of this time period though – there are festivals going on throughout the year.

Taste of Chicago is the biggest and the best known of the city’s festivals. Held in Grant Park each year, the festival is a food tasting extravaganza on an enormous scale, featuring the best food that Chicago has to offer.

Vendors from all over town take part in Taste of Chicago, including the Chicago Chocolate Company and Connie’s Pizza, which gives you the opportunity to taste a slice of one of Chicago’s world-renowned pizzas.

Another of Chicago’s headline festivals is the St. Patrick’s Day Festival, where the city takes to the streets to watch the Chicago River dyed green in honor of the Emerald Isle’s Patron Saint.

For music lovers two other festivals well worth considering are the Blues and Jazz Festivals, which take place in June and late August respectively.

Like what you’ve read? Check out our Chicago hostels on the HostelBookers website.

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Thanks to bryce_edwards, apanopoly, TaraDSturm, tixie21, Dave Rytell, Noodlefish, ghostlly, offonmars, Nate254Ray_from_LA, amber.kennedy, David Paul Ohmer & danperry.com for the Flickr images! Please note, images were held under the Creative Commons Licence at the time of publication.

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