Chicago. The city that has been my home for most of my life. It is a place that fills me with energy and a place of endless discoveries. Every time I am in the city, I grow to love it more and more. Chicago is a place with so much to see and do and I want to share with you all that I love about my great city!
If you already live here and need some inspiration or if you are visiting (or re-visting!) Chicago, I have put together my go-to guide of all my favorite places to head to in the city. Whether you are looking for a bite to eat, a place to stay or ideas for what to do, then read on!
Getting Here and Around
Without a doubt, the best times to visit Chicago are in the summer and fall. The lakefront is a key part of what makes this city so great! Those who live here, get through the harsh winters knowing that having summer and autumn in Chicago, is exactly why we choose to live here in the first place. If you are planning a trip here, I highly recommend aiming to come around those seasons.
Chicago is air travel accessible via two airports, Midway and O’Hare. Both are equally as close and equipped with public transportation (the “L”) into the city.
By the “L”
The elevated train, known as the “L” is the main public transportation to get you around the city. It is cheap, convenient and can get you close to just about any place in Chicago.
I highly recommend not renting a car. Parking is expensive and traffic can be a nightmare. If you are not going to use public transportation, then hop in an uber or cab instead. If you are aiming to explore the suburbs, Chicago has two main train stations that will get you out to them.
With station locations throughout the city, utilizing Chicago’s bike share system, Divvy is a fun option for exploring the city, especially the expansive lakefront.
Exploring Chicago on foot is one of the best ways to see the city! Pack a comfortable pair of shoes for getting around because Chicago is made for walking!
What to Do and Explore
Every time I turn around, there always seems to be something new to see and do in Chicago! Personally, I recommend being outdoors as much as possible when exploring the city but you also cannot ignore some of the great museums Chicago has to offer.
Architectural Boat Tour. Chicago’s architectural boat tour was recently named the most popular tour in AMERICA by TripAdvisor! That means it beat out touring the State of Liberty in New York and Alcatraz in San Francisco! There are multiple companies that offer these tours filled with gorgeous Chicago views and fascinating Chicago history. Most of these tours leave from the intersection of Michigan Avenue and Wacker Drive so head there and hop on one!
Bobby’s Bike Hike. One of my favorite ways to see the city and explore the lakefront is on bike! With multiple tour options and points of interest, Bobby’s Bike Hike is a safe, easy and fun way to see and learn about Chicago.
Chicago Riverwalk. A recently expanded park along the Chicago River that has turned the shores of our lake into a bustling hub of activity. The riverwalk offers a variety of places to eat, drink and take in all the action happening along the waterfront.
The 606. With about 8-10 points of entry, the 606 is a 2.7 mile walking trail (one way) that connects six Chicago neighborhoods. You can do (walk/run) or bring just about anything on there such as strollers, bikes and rollerblades. The landscaping along the way is beautiful and there are lots of pretty homes and art installations to take in.
Wrigley Field. There is no better time to head to a Cubs game at Wrigley Field then now! Home to the 2016 World Series Champions (not many of us thought we would ever be saying that!), Wrigley Field is a Chicago landmark and an experience not to be missed. Whether you head to a game, concert or experience the lively neighborhood surrounding the stadium, make sure to add this stop to your Chicago itinerary!
Chicago Museums. No great city is complete without great museums, and Chicago does not fall short in this category. The Museum of Science and Industry, The Field Museum and the Art Institute of Chicago are some of the most popular but my personal favorites include the National Museum of Mexican Art and the Museum of Contemporary Art, the latter which is currently featuring a fantastic, collaborative exhibit on Japanese artist Takashi Murakami.
Chicago Neighborhoods. The Chicago neighborhoods are what make this city so unique and culturally appealing! For good reason, the Gold Coast, Wrigleyville and Lincoln Park attract the most tourists but areas like West Town and Pilsen give this city the vibe and character I have grown to love! To read more about these two special areas head here and here.
Eataly. I could spend a whole day exploring, eating and drinking my way through this Italian marketplace. What’s not to love about being able to sip Bellini’s in one moment, to eating fresh pasta in the next to ending it all with Nutella crepes and a shot of espresso. This is all possible under one roof (and so much more) as you meander through the various walk-up eateries and dining experiences offered at this next best place to Italy itself.
Millennium Park. Home to the famous “Bean” and the outdoor concert venue, the Jay Pritzker Pavillion, Millennium Park is the perfect place to listen to music, watch a movie, have a picnic, stroll through gardens and take in some of the sights and sounds of Chicago.
Where to Eat and Drink
It is impossible to go hungry, thirsty or fall short of finding a place to rest your weary head and feet because Chicago offers some of the best hospitality options in the world! (*denotes favorites)
Best for Breakfast/Brunch
Best for Lunch
Best for Dinner
The Cabana Club (at the Robey Hotel)
Hotel Palomar* (favorite for family)
So there you have it! My go-to guide for Chicago. I am always on the search for new places to explore or try-out in the city so please do not hesitate to reach out with your favorite spots in Chicago!
Photos by Jules Kennedy
Thanks for stopping by!