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Chicago is one of America’s greatest cities and definitely a destination to add to your North American travel list. When you think of Chicago, the city’s bold architecture and world-class museums might come to mind first. While the city is well known for arts and culture, its vast array of tours and attractions, festivals, events, dining, shopping, and sports are likely to ensure an unforgettable and enjoyable visit, regardless of interests and hobbies.

What To Do in Chicago

Start your day downtown with a stroll through Millennium Park. Experience 25 acres of greenspace and don’t forget to capture some fun photos in front of the iconic Bean, one of Chicago’s favorite landmarks. Next, take a short walk over to the Art Institute of Chicago (AIOT), voted #1 museum in the World.

Millenium Park/ Photo by Shannon O'Toole via Flickr CC
Millenium Park/ Photo by Shannon O’Toole via Flickr CC

After taking in the arts at the AIOT, enjoy some time at Navy Pier, Chicago’s 50 acre playground which offers entertainment, dining, shopping, and more – don’t leave Chicago without taking a ride on the 150-foot Ferris wheel which will give you stunning views of the city as you soar above Lake Michigan.

For a magnificent aerial view of the city, head to the Willis Tower, still commonly referred to as Sears Tower. More than 1 million people visit its observation deck each year, making it one of Chicago’s most popular tourist attractions. If paying a hefty price of $22/person isn’t within your budget, consider visiting one of these 15 Chicago Restaurants With Top Views of the Windy City instead.

Sears Tower. Photo by Aquistbe via Flickr CC
Sears Tower. Photo by Aquistbe via Flickr CC

Don’t miss a chance to admire Chicago’s rich history, famous architecture, and awesome skyline on one of Chicago’s classic lake and river tours. Hop aboard Chicago’s First Lady Cruises for the Chicago Architecture Foundation River Cruise, voted as one of the Top 10 Tours in the U.S. by TripAdvisor, or opt for a Capture Chicago Photography Cruise that sails only during the summer on Saturdays and Sundays at 9 a.m.

Enjoy dinner in Lincoln Park, home to some of the city’s best restaurants, followed by a visit to a Blues Club.

Lincoln Park. Photo by hey tiffany! via Flickr CC
Lincoln Park. Photo by hey tiffany! via Flickr CC

If you’re visiting Chicago during baseball season, be sure to catch a game at Wrigley Field, home to the Chicago Cubs. A combination of history and nostalgia makes Wrigley Field the number one MLB stadium in America. However, if you’re looking to watch a game from a whole new perspective, consider visiting Wrigley’s Rooftops for a unique rooftop experience.

If you’re looking for other ways to experience Chicago like a local then check out Business Insider’s article “The Real Best Things to do in Chicago

Want other ideas of things to do? Visit Choose Chicago to start planning your Chicago getaway!

Best Time to Visit Chicago

The best time to visit Chi-town is autumn which boasts mostly sunny days and mild temperatures. While the weather in Chicago is enjoyable from late spring through early fall, you might base your time to travel on additional factors such as budget, entertainment, and crowds.

If you are looking for good weather along with affordable hotel rates, then April, May, and September are the best months to visit. Although average temperatures in spring are comfortable, the season is rainy, short, and often unpredictable – Chicago has been known to get snow as late as April. The summer months are hot and humid, making July and August Chicago’s busiest months for tourism. Along with higher hotel rates in the summer months, crowds also influence the city’s most popular tourist attractions.

Chicago Blues Festival. Photo by tomanouc via Flickr CC
Chicago Blues Festival. Photo by tomanouc via Flickr CC

Summer is known for a number of popular events and festivals including the Chicago Blues Festival, the Air and Water Show, and Taste of Chicago. Fall also hosts a number of not-to-be-missed festivals such as Oktoberfest Chicago, the Hyde Park Jazz Festival, and the Chicago International Film Festival.

Where to Eat and Drink in Chicago

Chicago is well known for its epic restaurant scene and is home to some of the best restaurants in the country, and even the world. During my visit to Chi-town I was incredibly lucky to visit Michelin star restaurant Alinea, which has made the top-list of best restaurants in the country for several years. Although this one-time dining experience probably isn’t on most people’s travel itinerary (there is a several month-long wait and an equal amount of time necessary to save up for the meal), I recommend visiting chef  Grant Achatz’s high-concept cocktail lounge Aviary, a much more affordable option yet still a unique dining experience.

For something much more affordable and arguably more iconic, don’t miss a chance to sample Chicago’s legendary deep-dish pizzaLou Malnati’s Pizzeria and Giordano’s Pizza are Chicago’s biggest pizza chains specializing in this stuffed deliciousness, but they are not your only options.

Deep-dish at Lou Malnati's. Photo by Sara B. via Flickr CC
Deep-dish at Lou Malnati’s. Photo by Sara B. via Flickr CC

While these are just a few of the hot spots in the city, Chicago is also well known for lots of other affordable but still delicious restaurants. For the best of the best, check out Time Out’s Guide to Best Restaurants in Chicago

You can also visit the articles below to find out which restaurants and bars people are talking about right now!  

Where to Stay in Chicago

When planning your trip to Chicago, choosing where to stay is one of the biggest decisions to make. Most travelers choose an option in the Loop District in Downtown Chicago, close to the city’s major sights and attractions. Choosing a hotel in this area means you are walking distance to Millennium Park, the Art Institute of Chicago, and the Sears Tower.

If you are looking for a quiet and quaint area to stay, then consider Lincoln Park. This neighborhood is nestled along the city’s lakefront and is well known for being a live-music hub, with several blues clubs and music venues worth checking out. The area is home to some of the best restaurants in the country, and the must-see Lincoln Park Zoo.

Chicago Skyline from Lincoln Park Zoo. Photo by Andrew Seaman via Flickr CC
Chicago Skyline from Lincoln Park Zoo. Photo by Andrew Seaman via Flickr CC

For the perfect place to stay, choose one of CN Traveler’s Top 15 Hotels in Chicago or find your own sweet deal by searching through some great options on Booking.com

If you’ve always dreamed of sleeping inside of a painting, then the bedroom of Vincent Van Gogh might be for you – and is available on Airbnb. Availability is limited so if you can’t score a stay in this room then check out over 300 other options on Airbnb.

Don’t have an Airbnb account yet? Sign up now and receive USD $35 to put towards your first Airbnb stay!

How Much Time Do you Need in Chicago

Chicago is the perfect getaway for a long weekend and is easily accessible from major cities in the northeast including Toronto, New York, and Boston.  You can explore the city in a few short days, but will probably want to visit again to experience the city at a different time of year and/or for a different reason.

Check out the following reads to learn how you can make the most of your time in Chicago:

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What to do in Chicago, when to go, where to stay, where to eat and more tips for visiting the Windy City.

Have you ever visited Chicago? What would you suggest to first-time visitors to the Windy City?

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