Chicago is an often-overlooked city, but in reality it’s a thriving metropolis with a distinctive personality that boasts world-class art, dining, entertainment, and culture. Our city guide gets to the heart of this midwestern urban gem.

What to do in Chicago

Chicago is a city with a lot of character if you know where to look. It’s downtown center, known as “The Loop,” is world-class, with historic architecture and awe-inducing skyscrapers housing amazing restaurants, high-end shopping, top theaters, and cultural institutions. Outside of downtown, Chicago’s vibrant neighborhoods each boast their own distinctive flavor worth exploring.

There are endless sights and activities to add to your itinerary – below you’ll find the top things to do and see during your stay in Chi-town.


Millenium Park and Grant Park

Of the many things that make Chicago unique is it’s glorious lakefront. Nestled between the shores of Lake Michigan and the edge of the urban grid, Chicago’s expansive stretch of lakefront is reserved exclusively for public space, characterized by green public parks, beaches, and walking/biking paths.

The downtown lakefront is comprised of both Millenium Park and Grant Park, two beautiful green spaces that also offer outdoor art, gardens, and community space. Millenium Park, on the north end of the stretch, includes attractions like Prtizker Pavilion for live outdoor music; the interactive Crown Fountain, where two tall pillar sculptures broadcast changing video screens of faces spitting out streams of water; and the Lurie Garden.

If you head south, you’ll enter Grant Park, where Buckingham Fountain sits as a majestic centerpiece and beautiful open garden spaces are perfect spots for picnics or enjoying the cityscape views. The parks are connected by walking paths and scenic bridgeways.

Cloud Gate, a.k.a The Bean

Perhaps the most iconic part of Millenium Park is the Cloud Gate sculpture, otherwise known to locals as The Bean. Situated at the main entrance to the park, Cloud Gate is a large, stainless steel kidney-bean-like sculpture that reflects the surrounding buildings. It’s free to explore, and makes for great photo ops.


Art Institute of Chicago

Located in Chicago’s downtown area and nestled in scenic Grant Park near the lakefront, The Art Institute of Chicago is home to over 300,000 works of art, with notable permanent collections of Impressionist and Post-Impressionist art. In addition to housing famous classics such as Seurat’s Sunday on La Grande Jatte and Van Gogh’s The Bedroom and Self Portrait, the museum hosts collections spanning American, Ancient and Byzantine, African, and European paintings, sculptures, and more. It also hosts rotating exhibitions from across the world.

The museum’s modern wing displays contemporary works, photography, and architecture and design shows.

It’s a cultural gem in the heart of the city that’s great for spending a few hours exploring while spending a day downtown – it was even voted the #1 museum in the world in 2014 by TripAdvisor. General admission is $25 USD and operating hours are 10:30am-5:00pm daily.


Architectural Tour

Chicago is home to exquisite architecture and some of the most iconic buildings in the world. What’s the best way to fully experience the city’s architectural history? A river cruise architectural tour. Because the Chicago River runs through the heart of downtown, visitors can book a seat on the Chicago Architecture Foundation’s double decker river boat and enjoy a unique 90 minute tour revealing the history of the city and more than 50 of it’s most important architectural contributions.




Food Tour

Chicago is known for many things, but when it comes to food, the city is home to two original staples: deep dish pizza and Chicago-style hot dogs. The former, the famous thick-crust pizza virtually swimming in chunky marinara sauce layered on top of copious amounts of cheese, was originally developed by local Chicago restauranteurs in the 40’s and is worth trying at least once in your life. You might need a nap afterward, but it’s a truly distinctive Chicago experience. The latter is an all-beef hot dog couched in a poppy seed bun with a very specific set of toppings: onion, tomato, green relish, pickle, sport peppers, mustard, and celery salt. Sounds weird? Maybe, but it’s delicious, and addictive. But, don’t even think about ordering ketchup on a hot dog in Chicago – you might as well write tourist on your forehead!

Sample the local cuisine on your own, or consider a food tour. Check out Chicago Food Planet Food Tours, which offers walking tours of select neighborhoods and an insider’s look at the best local establishments. Or book with Tastebud Tours, which will give you your fill of both deep dish pizza and Chicago dogs.


All that being said, Chicago has much more to offer in the way of innovative, gourmet cuisine – home to Michelin-rated hot spots, fine dining restaurants, and everything in between, the city is brimming with options for every taste.

Willis Tower Skydeck

Willis Tower (formerly the Sears Tower – or perhaps still, to some locals) is the second-tallest building in America and the 13th tallest structure in the entire world, towering over Chicago at 108 stories.

The Willis Tower Skydeck, located on the 103rd floor, lets you hang out over the edge of the building in a clear glass box, 1,353 feet in the sky. Possibly not for the faint of heart or those with serious height fears, but those adventurous enough to try will get an unparalleled view of the cityscape and a heart-racing experience to remember. Plus, a great photo!



Don’t be surprised if some locals still refer to the skyscraper as the Sears Tower – it’s such a cultural institution that many still use the name it’s long-time former owner out of habit, or perhaps denial of the change (it’s a Chicago thing).

Tour Chicago Neighborhoods

Chicago is a city of neighborhoods, and venturing outside of the more touristy downtown area is well worth it, and relatively easy with the decent public transit. Most of Chicago’s neighborhoods can be reached via the Chicago Transit Authority (CTA) trains, which form a loop in the downtown area and then branch out north, northwest, west, and south. The bus system can also take you where you’re looking to go, and both the trains and the buses use the same fare card, and a flat $2.25 USD will take you anywhere one-way.


Chicagoans have a deep love and pride for their city, and this is most apparent in it’s local hoods. Here’s a quick breakdown of what you can expect in just a few of Chicago’s popular neighborhoods:

  • Wicker Park and Logan Square are the equivalent of New York City’s Williamsburg – visit this area on Chicago’s northwest side for the young, arty hipster crowd and great restaurants, cafes, bars, art galleries, trendy boutiques, and live music. Take the blue line train to Damen to explore Six Corners, the mecca of all things hip in the area.
  • River North, located on Chicago’s near north side, has a well-established restaurant, club, and bar scene, and is often a favorite area for nightlife among young professionals after work hours. The area is hopping on the weekends, when many of Chicago’s top clubs see lines out the door. River North is also considered the Gallery District, with a large concentration of art galleries to peruse.
  • Lincoln Park and Lakeview make up a large part of Chicago’s north side, and are home to the Chicago Cubs and Wrigley Field, as well as Loyola and DePaul universities. Along with the college crowd, the neighborhood includes many young professionals and families, offering a diverse mix of bars, restaurants, and boutiques. It’s also the location of Lincoln Park Zoo, which is free to the public and great for adults and kids alike.
  • West Loop is an up and coming mecca of hot foodie restaurants and bars, located straight west of Chicago’s downtown. Popular with many professionals working in or near the area, the West Loop is hopping on most week nights and especially on the weekends, where many top chef-owned and critically acclaimed restaurants are located.


Navy Pier

Navy Pier may be the most touristy place in all of Chicago, but it can still be worth a visit. Jutting out into Lake Michigan from the downtown area, the pier provides gorgeous views of the lake and the Chicago skyline, especially from the top of it’s famous ferris wheel. The pier is also home to restaurants, shopping centers, and movie theaters, as well as the world-renowned Chicago Shakespeare Theater. Plus, enjoy fireworks displays twice a week from Memorial Day through Labor Day.



Comedy Clubs and Theaters

Chicago has one of the most (if not the most) robust comedy and stand up scenes in the U.S. Many famous comedians and actors got their start in Chicago’s clubs and theaters, including Tina Fey, Bill Murray, and Robin Williams

Experience the city’s rich scene by attending a comedy show at the legendary Second City, The Comedy Bar, Laugh Factory, or Zanies. Or, watch a play at The Chicago Theater, Steppenwolf, the Cadillac Palace, or the Goodman, which are located in the downtown Theater District and offer everything from broadway to musicals to comedy to contemporary shows.


Water Taxi to China Town

If you want to do like the locals do, hop on a bright black and yellow water taxi and cruise south on the Chicago river to Chinatown to explore the ethnic neighborhood and eat an amazing meal. Taxis traverse the river most of the year save for some of the winter months, and offer great city views during the ride before dropping guests off at a grassy park right outside Chinatown. You’ll be within walking distance to the amazing Chinese restaurants in the main dining square, as well as the main strip of ethnic stores and boutiques.

Chicago Lakefront Trail and Beaches

Running 18 miles along the shores of Lake Michigan is Chicago’s Lakefront Trail, a span of parks running from the south end to the near north end of the lake and featuring a wide, paved path for walking and cycling. The Lakefront trail also runs along open green spaces with baseball diamonds, playgrounds, tennis courts, and soccer fields.

Chicago City Guide | Map&Compass

In addition the trail runs along many of Chicago’s numerous beaches, which feature wide sandy beaches and shallow waters perfect for swimming, plus volleyball courts and areas for grilling. North Avenue Beach is a large and popular beach during the beautiful summertime, as well as Belmont Harbor and Montrose Beach, and Oak Street Beach in the south loop. Beach season is Chicago runs from May through September.

Museums and Culture

In addition to the Art Institute, Chicago is home to many other cultural institutions worth visiting. The south end of Grant Park encompasses The Field Museum, a natural history museum; The Adler Planetarium, dedicated to astronomy and astrophysics; and the Museum of Science and Industry, the largest science museum in the western hemisphere.

Lesser known but equally intriguing museums include the National Museum of Mexican Art in Chicago’s Pilsen neighborhood, and the Hyde Park Art Center, located south of the city in Hyde Park.

Live Music

Chicago is also legendary in the world of music, largely renowned for it’s Blues music scene (created by celebrated blues legends and Chicago natives like Muddy Waters and Buddy Guy) and many nationally-known music venues.

For real local live music experiences, visit the Green Mill, which hosts acts from spoken word poetry slams to varied musical jazz acts from well-known artists to late-night local jam sessions, or grab a blues show at Buddy Guy’s LegendsKingston Mines, or Rosa’s Lounge 

Some of Chicago’s amazing concert halls include the more well-known House of Blues, Lincoln Hall and the Double Door, to the lesser-known Empty Bottle, Schuba’s, and Reggie’s.

Time Out Chicago is a great reference for all things nightlife, live music, and concerts, including upcoming shows and ticketing.


Photo credits: Nimesh Madhavan / Guiseppe Milo / Kevin Dooley / Jeffrey Zeldman / Navin75 / Jaime McCaffrey / Spiterman /  Roman Boed / Dustin Gaffke / Maggie