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Things to Do in Chicago: A Weekend Travel Guide

Canadians are often travelling to the Windy City and it’s no surprise why. There are plenty of fun things to do in Chicago, with some of the best museums in North America, festivals and events year-round, and just about any cuisine you can think of. And with cheap flights leaving from major cities across Canada, Chicago makes for the perfect weekend getaway.

Chicago is one of the best U.S. cities to visit for so many reasons. It is a melting pot of everything: food, art, history, entertainment, sports and culture. But among all of the things to do, it’s easier to see more in a short amount of time. This is because Chicago is easy to navigate through the main Chicago neighbourhoods and manageable on a budget. Furthermore, it is a perfect destination for families, couples, and even solo travellers. So what are you waiting for? Plan your next weekend getaway to the ‘Second City’!

Best Chicago Attractions

Navy Pier

A Chicago landmark, Navy Pier has great dining, shopping and events all year round but especially comes alive with tourists and locals during the summer months. One of the main draws is the pinnacle Centennial Wheel which offers comfort and panoramic city views. For more entertainment, check out the funhouse maze or IMAX Theatre. Even more exciting is the bi-weekly firework shows that take place on Wednesdays and Saturdays from May 27 (Memorial Day) through to September 2 (Labour Day).

Chicago is a very picturesque city due to its location on the water. If you want a relaxed evening with the Chicago skyline in view, you can take a cruise from Navy Pier either on Lake Michigan or the Chicago River. Or for more laid-back vibes, spend a Spring or Summer evening at the Miller Lite Beer Garden for a pint of craft beer and free, live music.

Navy Pier in Chicago
Chicago Travel Guide | Skyscanner Canada

Millennium Park

No trip to Chicago would be complete without strolling or biking through Millennium Park, home to ‘The Bean’ structure. Once you have taken your fair share of selfies, there is still quite a bit to be explored. If you want to do something more active, the warmer months are a perfect time to try your hand at the rock climbing walls in Maggie Daley Park. If you happen to be visiting Chicago during the colder months, rent a pair of skates at McCormick Tribune Plaza for a magical Winter experience.

If you’re a fan of concerts and festivals, then you might want to plan your trip to Chicago around one of the many summer events that take place at Jay Pritzker Pavilion in Millennium Park. Festivals include a Summer Film Series and Summer Music Series, put on by the city of Chicago. Other festivals include the Chicago Blues Festival, Chicago Jazz Festival and the Grant Park Music Festival. Bring your blanket, some snacks (head to the closest Trader Joe’s location and indulge in all the goodness your little Canadian heart might desire) and just enjoy a chilled out, sunny day.

Millennium Park and the Bean
Chicago Travel Guide | Skyscanner Canada

Pilsen neighbourhood

Located in the Lower West Side of the city by Chicago’s ‘South Loop’, Pilsen is an area in Chicago that has historically housed communities of immigrants from Eastern Europe to mostly Latinos today. An artistic Chicago neighbourhood with murals sprawled in front of houses and on the sides of buildings and overpasses, Pilsen is a great place to get lost in and spend the better part of a day exploring. If you are interested in more art, then the National Museum of Mexican Art is not to be missed.

This is also the place to go for authentic Mexican food so once you started feeling hungry from your wandering, head to local establishments such as 5 Rabanitos Restaurante and Taqueria or Taqueria Los Comales.

Mexican food
Chicago Travel Guide | Skyscanner Canada

Skydeck Chicago

Every iconic city needs its views from above, and Chicago is no exception. Willis Tower is home to the Skydeck on the 103rd floor and offers visitors 360-degree views of the city. Film buffs may remember the scene in Ferris Bueller’s Day Off when the main characters leaned their foreheads on the glass panels to look at the city below. If you’re feeling even more fearless, there is now the ledge extension made up of glass boxes to give way to harrowing views beneath your feet.

Insider Tip: Try timing your visit to the Skydeck either early in the morning to avoid the crowds or an hour before sunset for an epic golden hour picture from above.

Chicago at sunset
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Must-See Chicago Museums

Art Institute of Chicago

This majestic museum is definitely worth your time, as it is a world-class leader in the fine arts. With around 330,000 pieces on display at the Art Institute of Chicago to admire, question and ponder over, you will feel extremely cultured after spending an afternoon here. Better than the range of time periods that are represented at this Chicago establishment, is the wide variety of art from all over the world. From European impressionist art to American post-impressionist pieces, to Chinese, contemporary and installation art, there is something at the Art Institute that will pique everyone’s interest.

General admission for adults is $25, $19 for students and children under 14 get free access.

The Field Museum

Have you ever been curious about how extensive and dangerous a Tyrannosaurus rex was? Well, seeing “Sue”, the name of one of the largest and best preserved Tyrannosaurus rex specimens might be as close as you can get to feeling the enormity and perceived threat of these dinosaurs. At Chicago’s Field Museum, you can see Sue and more with the incredible 65,000 exhibits that house 40 million natural wonders and cultural artifacts. Learn more about the planets and other time periods with an afternoon spent here.

Basic admission prices go for $24 (adults), $21 for students and $17 for children between 3-11 years.

the front entrance to the Field Museum in Chicago
Chicago Travel Guide | Skyscanner Canada

Chicago Museum of Science and Industry

One of the largest museums in the world, the Museum of Science and Industry is a unique experience. This is an ideal place to tap into your curiosity as you discover new things here and take part in the interactive aspects. Exhibits at this Chicago museum include learning about technology, submarines, energy, transportation, coal and more. The entrance fee for most exhibits is $21.95 for adults and $12.95 for children. The time will slip right under your fingers here and you’ll leave feeling inspired

Two young boys tapping on a screen in a museum
Chicago Travel Guide | Skyscanner Canada

A Night Out in Chicago

Second City

Chicago is the birthplace of the infamous improv comedy club, the Second City. Several big names of comedy have passed through these doors, including Alan Arkin, Stephen Colbert and Tina Fey. The comedy shows put on here are of high quality and if you are able to score tickets to one of their shows, then you are truly experiencing a Chicago institution. Get ready for a good belly laugh!


If you want to get out on the town but want a more casual, informal setting, than Kibbitznest is the perfect spot for you. Once you step inside, you immediately feel at home, with books lining the shelves, board games packed in corners, and intimate conversations being had by customers. In fact, one of their best features is being a wifi-free zone, in an effort to encourage and celebrate more human connection. So order a glass of wine and be present in your next read or friend that tagged along with you. Your social media updates can wait.

coffee and books on a table
Chicago Travel Guide | Skyscanner Canada

Three Dots and a Dash

This bar is a must for a night out in Chicago. Think tropical tiki bar meets speakeasy. The atmosphere is not lost in this place, it is decorated to make you feel as if you have transported to an island in another time. Their menu features a wide variety of cocktails with the freshest fruit and the best rums, spirits and juices. Not to mention, the quirky and eclectic cups that they fill the drinks in just add to the experience. Three Dots and a Dash is quite popular so get there earlier to get a table. Perfect as a date spot or just a fun night out with friends.

bartender pouring drinks at a bar
Chicago Travel Guide | Skyscanner Canada

Things to Do in Chicago with Kids

Wrigley Field

Take me home to the ball game! Home to the Chicago Cubs, Wrigley Field is a great spot for your weekend in Chicago if you happen to be there during the baseball season and there is a scheduled home game. This is especially a perfect activity to do with the kids and you will undoubtedly have fantastic memories. If you are in Chicago during the off-season, you can still do a tour of Wrigley Field which will still take you up close and personal through this historical sports centre.

the outside of Wrigley Field in Chicago
Chicago Travel Guide | Skyscanner Canada

Chicago Children’s Museum

This is a perfect place dedicated specifically for the kids! Located at Chicago’s Navy Pier, the Children’s Museum is three floors of interactive and educational activities covering a range of subjects such as math, art, science and health. Some of the interactive exhibits allow children to dig for dinosaur bones, play with water pumps and even step into the shoes of a firefighter with a life-size, simulated fire truck. All this and more can be found at this family-friendly museum. Admission for children and adults is $14.95 and children under one can get in for free.

Hop-On Hop-Off Tours

The Hop-On Hop-Off bus tours operating in Chicago, offering 1-day and 2-day packages, are an ideal way to see the city at your own pace within the comfort of a double-decker bus. An experienced guide will take you through past Chicago’s major landmarks and the city’s most vibrant sights. Then you can choose to get off to see something that peaks your interest or simply stay on for the ride. Some buses also have free onboard WiFi. Book your tickets online for last-minute deals on various Hop-On Hop-Off tours in Chicago.

Chicago Eats

When it comes to food, Chicago is probably most well known for their deep dish pizza, so you can’t make a trip without digging into this culinary treat. Beware though as these savoury pizzas are delicious but mighty and will fill you up fast. Opt for sharing if you are with company! Great places for good deep dish in Chicago include Pequod’s Pizza, Lou Malnati’s Pizzeria, and Giordano’s.

deep dish pizza
Chicago Travel Guide | Skyscanner Canada

How to Save Money on Your Chicago Trip

Given that there are several attractions that can quickly eat away at your time and budget, you may want to think about purchasing the Chicago CityPASS. This pass is eligible for nine days and in some cases allows you to skip ticket lines at busy sites. The CityPASS allows you to save up to 50% off on admission fees for included attractions. Three attractions are included on every pass and you can choose two of four other possible options if you are interested in seeing more. The price for adults is $108 and the price for children is $89.

Getting Around Chicago

While its a reasonably large city, getting around Chicago is quite simple and convenient. If you are there during the warmer months, it is a very walkable city. In fact, walking is one of the best ways to truly take in the history and architecture in the downtown area. Additionally, the buses and trains are easy to navigate and will get you to most areas. The above ground train is a great way to see The Loop (the heart of downtown Chicago).

With the Chicago Transit Authority (CTA), visitor passes are the best bank for your buck. You can get unlimited rides with a 1-day pass for $10, a 3-day pass for $20 or a 7-day pass for $28.

train moving through downtown Chicago
Chicago Travel Guide | Skyscanner Canada

Best Places to Stay in Chicago

Here are some of the top-rated hotels in Chicago, from budget-friendly to more high-end.

Now that you are equipped with knowledge of things to do and places to stay in Chicago – are you ready to have an unforgettable experience? Want to get there for cheap? Check out the Skyscanner search engine for deals on flights, hotels, and car rentals. Not sure how we can find you the best travel deals out there? Read the FAQs

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