Things to do in Chicago

Insider tips: Explore Chicago like a local

Megan & Aram is a travel blog that focuses mostly on travel in the Nordics and Eastern Europe with the occasional trip beyond those regions. We love coffee, promoting small businesses, and sports.

What should I do on my first trip to Chicago?

Chicago is the third largest city in the United States and there is an endless number of things to do for every type of visitor. If you're visiting Chicago for the first time, start your day at Milennium Park and The Bean - which has, over time, become a symbol of the city. If you're lucky, you may even get to experience a free concert or gathering there during your trip! Don't leave the area before heading out onto Navy Pier for a few photos.

You can't visit Chicago as a first-timer without heading to The Skydeck at Willis Tower. What was previously known as the Sears Tower is now the Willis Tower and is one of the tallest buildings in the Americas! You can step out onto the glass-bottom Skydeck for an epic view of the city and since you'll be 1,353 into the air, you will be able to see everything!

Some museums worth checking out are the Art Institute of Chicago and the Museum of Science and Industry.

If you need an escape from the city, there are plenty of day trips from Chicago that will give you the downtime you need.

What are some hidden gems to see in Chicago?

Chicago is teeming with hidden gems and one of the best places to visit to experience one of the city's most underrated places is the 606 - a park and trail system that has been transformed from its days as an old railroad line. The 2.7-mile trail goes through the city connecting various neighborhoods. Another hidden gem is Promontory Point which is located in Burnham Park. This man-made peninsula offers some of the top views in the city - and you can see the skyline and Lake Michigan while sitting in a relaxing spot. Chicago also has some of the coolest neighborhoods and districts of any US city! And, many of these neighborhoods have large concentrations of different ethnic groups, making it like a trip around the globe without ever leaving the Midwest city.

How much time should I spend in Chicago?

You can see the best of Chicago on a long weekend trip, but a week is an ideal amount of time if you're really wanting to explore the city deeper. You can see the main highlights on a long weekend trip, though. To maximize your time, sign up for city tours and utilize the 'L', or metro system.

What food is Chicago known for?

It would be remiss of me to mention the food of Chicago and not start off with deep-dish pizza! Originating at Pizzeria Uno in 1943, this style of pizza is beloved by residents of the Windy City and it has become Chicago's most iconic dish! Some other foods to try when visiting are Chicago style hot dogs (made famous during the Great Depression), Italian beef, and Chicago BBQ. You can also dive into the city's Eastern European history with some tasty perogies and potato pancakes.

What is the best way to get around Chicago?

While renting a car may be the most ideal option for those looking to take day trips, Chicago is a very well-connected city that lends itself to walking and public transportation!

You will find plenty of taxis, public buses, and bike sharing options within Chicago. The city is also home to the L-train, or the city's metro operated by the Chicago Transit Authority. The L-train stands for 'elevated train' and it serves over 140 stations on its 8 train lines.

What are the best months to visit Chicago?

Winter can be brutally cold in Chicago (and snowy), making the best time to visit the city summer (or the shoulder season). The summers in Chicago are never exceptionally hot and the greenery makes the area pleasant and inviting. Lake Michigan also offers plenty of opportunities during the summer months, as well. You can swim on its beaches or take a boat out into the lake.

What are the best neighborhoods to visit in Chicago?

Chicago has some of the most dynamic neighborhoods of any city I have ever been in! Every one has something interesting and unique to offer! Some of the most popular neighborhoods are Wicker Park (lots of cool bars and cafes), Logan Square (young professionals and hip establishments), Andersonville (known for its Swedish history and Midsommarfest), Pilsen (known for its art scene), Ukrainian Village (lots of Ukrainian history, art museums, and businesses), Lincoln Square (German history with many Bavarian bakeries, etc), and more.

What are the best neighborhoods for food?

Lincoln Park is a favorite Chicago district for food lovers! One thing that the neighborhood is famous for is its brunch options! You can find many international restaurants here - but brunch is a big deal in Lincoln Park and you can find everything from vegetarian brunch options to French toast flights and DIY mimosas!

Another area of the city known for its trend-setting food options is the West Loop. The West Loop is located in the former meatpacking district and now has so much to offer food lovers - from fine dining restaurants to celebrity chefs opening up new concepts to Chicago residents.

If you love Mexican food - head to Pilsen and indulge in some of the city's best Mexican restaurants.

What are the best neighborhoods for shopping?

Chicago is a shopper's paradise and you will find delightful shopping everywhere! Michigan Avenue is the city's most famous shopping thoroughfare - with shops lining the streets and mega malls located along one of the city's busiest streets. The Shops at North Bridge and the 900 North Michigan Shops are some of the places to check out when there. Beyond Michigan Avenue, you can find great shopping on Armitage Avenue in Lincoln Park and cool vintage finds on Belmont Avenue at The Belmont Army. There are also many other second-hand shops and indie stores if you head east on Belmont.

What neighborhood should I stay in when I visit Chicago?

If you're a first-time visitor to Chicago, you will want to stay downtown and near many of the main sights and museums. Other good and safe options are Lakeview, The Loop, and Lincoln Park. All are well connected by public transportation. However, if you're looking for a more 'local' experience, check out hotel options in Logan Square, Lincoln Square, and Wicker Park. There are plenty of food options and hip bars and hang out in!

What's are 4 best tips for a person traveling to Chicago?

1) Don't let yourself get overwhelmed. This is the US' third most populous city and it is a lot to take in! Plan your trip ahead and then try to stay in one area and explore it deeply. You can save additional sights and areas for a future trip.

2) Heading to Chicago in winter? Bundle up! They don't call it the Windy City for nothing! It is cold, windy, and snowy! But, you will still find plenty to do in the city during the winter months that it is always worth a visit!

3) If you're visiting different neighborhoods, research the history of the place and find pieces of those history throughout. For example, if you're visiting Andersonville, you will quickly realize that it has extensive Swedish history. Stop into Swedish bakeries and shops and see how this culture has meshed together with Chicago's throughout the years. It truly is one of the things that makes the Midwest city so unique!

4) Take the L-train! This transport option is cheap, efficient, and the best way to get around the city. You can save so much money by avoiding driving around and parking and just taking the L around.

What should people avoid doing in Chicago?

Avoid thinking that this city is similar to Los Angeles and New York. Chicago retains that Midwestern 'down-to-earth' charm that can get lost a bit on the coasts. The city is sports-centric and bars are super social and friendly. Be sure to go in ready to meet people and make some new friends along the way!

Another thing to avoid is eating at the chain restaurants. While these places are predictable and offer a 'secure' experience - Chicago has some insanely good food options and there is no better way to learn about the city than through its food!

What are your top 5 favourite GetYourGuide experiences in Chicago?

1) Chicago River: 1.5-Hour Guided Architecture Cruise

2) Chicago: Willis Tower Skydeck and The Ledge Ticket

3) Chicago: Gangsters and Ghosts 2-Hour Walking Tour

4) Chicago Lakefront: Seadog Speedboat Ride

5) Chicago: Favorite Foods Guided Walking Tour

What is one thing that surprised you about Chicago?

I have been to Chicago more times than I can count, but the one thing that always surprises me is how friendly everyone is! Big cities tend to be a little unfriendly but Chicago is the absolute opposite. Every time I head there, I meet new people and make new connections and it is difficult to leave. I wouldn't be surprised if I ended up moving there one day and calling the Windy City my home.

What are the best annual events in Chicago?

Chicago has several events annually and one of the city's most popular is the Taste of Chicago, the largest food festival in the world! You'll find a lot of live music, food, and more! It is a must-visit summer festival in Chicago. The city also has several music festivals not only dedicated to popular bands, but also different genres of music. You can head to the Chicago Jazz Festival or the Chicago Blues Festival and see how both styles of music have made an impact on Illinois' largest city.