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Downtown Chicago Neighborhood Guide

Cloudgate The Bean

So, Downtown Chicago isn’t so much a neighborhood, but the place where we gather to celebrate, to unwind, to work, and to simply stand in awe of this remarkable city.

Lounge in the sun in Grant Park, or wander through the sea of humanity along Michigan Avenue or Upper Wacker Drive.

Get off the El at Jackson and you’ll be looking through the cavern of the street at the fringes of Frank Gehry’s awesome Pritzker Pavilion. Get off at Monroe and stare down the lions at the steps of the Art Institute of Chicago.

There is no shortage of sights, of shopping, or food here. But a word to the wise - you won’t get it all in in one day, or even one visit. If you have one day, pick your top two or three destinations to hit, leaving a little room for serendipity.

If you have a couple of days to spend down here, expand your list. But know that even with more time, you’ll leave stones unturned.

Here’s a quick list of some of the top attractions awaiting you in Downtown Chicago - but be warned, this list will just keep getting longer!

Downtown Chicago Attractions

Maggie Daley Park and Ice Ribbon:  This new park at the north end of Millennium Park is a children’s paradise come summer, and the new ice ribbon that meanders through the park has wowed visitors since opening in December of 2014.

Millennium Park:  Where to begin - the gardens, the fountains, The Bean, or the Pritzker Pavillion? The park is no one thing, but a combination of art, nature, music, and people that leaves millions in awe every year.

Marshall Fields:  OK, it’s technically a Macy’s store now, but to Chicagoans, it will always be Fields.

The Bean (Cloudgate):  Technically it’s named Cloudgate, but everyone calls it The Bean. Only 10 years old, the sculpture is now as synonymous with Chicago as the Sears Tower, Wrigley Field, and Michael Jordan.

Art Institute of Chicago:  One of the handful of greatest art collections in the world.

Field Museum:  Just north of Soldier Field, The Field Museum was founded in 1893 as the Columbian Museum of Chicago and has spent more than 120 years in the pursuit of scientific knowledge about the world around us.

Soldier Field:  Originally built to honor WWI veterans, the field is home to the Chicago Bears and a host of concerts and events each summer on the lakeshore.

Pritzker Pavillion:  This striking outdoor amphitheatre designed by famed architect Frank Gehry hosts free concerts from acclaimed musicians every Monday night from mid-June through July.

Adler Planetarium:  One of the nation’s premier observatories, and a great spot to look back on the skyline for a unique view.

Shedd Aquarium:  Situated in Grant Park in downtown Chicago, Shedd is home to 32,000 aquatic animals representing more than 1,500 species of fishes, reptiles, amphibians, invertebrates, birds and mammals from waters around the world.

Northerly Island:  Once an airstrip, this man-made island south of Soldier Field is now a place to hike, cross-country ski, and come summertime - one of the great concert venues in the city.

Grant Park Skate Park:  Proudly referred to as Chicago's "front yard," Grant Park is a public park, 319 acres located in Chicago’s central business district in the Loop Community area.

Chicago Architectural Foundation:  The home to the celebrators of the world’s greatest architectural marvels features an amazing scale model of the city’s downtown skyline. You’ll also find special exhibits and a one-of-a-kind gift shop.

Aqua:  If there’s a hotter architect in the world than Jeanne Gang, the mastermind behind this spell-binding tower, we haven’t heard of her.

Crown Fountain:  Faces of Chicago spew water into a shallow wading pool at the entrance to Millennium Park. If you have kids, they’ll love it, and if you have a kid in you, you’ll love it too.

Buckingham Fountain:  Yup, another photo op, for the more traditional fountain enthusiast. In the heart of Grant Park. Go at night when it’s lit up!

Navy Pier:  Yes, it’s a tourist trap and we locals would never admit visiting, but that Ferris Wheel really is something to see!

State Street:  Where to shop in the downtown area, with the biggest names and grandest outlets.

Trump Tower:  The second tallest building in the city, Trump gleams from its perch on the river. It’s also home to a Michelin-starred restaurant, 16.

Pritzker Pavillon, Millennium Park, Chicago

Performance and Theater

Gene Siskel Film Center:  Named for the late film critic, the center hosts forums and showings of many films you won’t find elsewhere or for the first time.

Goodman Theatre:  For 90 years, the home of some of the best theater in the city and America.

Chicago Theater:  Maybe the grandest of all Chicago live music venues, you’ll want to visit, if only to take a picture in front of the famous marquee.

Oriental Theatre:  Broadway in Chicago, where the grand marquee makes you feel like you’re in New York City in the heart of the Windy City’s theatre district.

Lyric Opera:  Where the awe-inspiring building is matched only by incredible performance.

Bars and Restaurants

The Berghoff:  The famed German restaurant on Adams street is a pure Chicago experience.

Walnut Room:  For many, a trip to the Walnut Room inside of Marshall Field’s Macy’s is a holiday tradition. It’s worth a visit, if only for the lobster bisque!

Billy Goat Tavern:  Made famous by Saturday Night Live, you can still get your cheezeboigers here, once you finally hunt the place down below Michigan Ave.


Public transit in Chicago is excellent, and although the systems are easy to use, using the CTA website or Google Maps for trip planning is always a good idea. Google Maps is very accurate for Chicago Public Transit - it’s what we use.  

A one-way train or bus fare is $2.25 per person. If you intend to use public transit multiple times throughout your trip, consider an unlimited 3 day or 7 day pass.  These are available at any CVS Pharmacy or Walgreens.

On the CTA Red Line Get off at (transfer to the Brown Line at Belmont or Fullerton):

  • Chicago: The Gold Coast, Water Tower Place, Hancock, and the Magnificent Mile.

  • Grand:  for Navy Pier, Magnificent Mile, Riverwalk, Chicago Riverboat Architecture Tours

  • Monroe, Jackson:  for Art Institute of Chicago and Grant Park

  • Harrison, Jackson, Roosevelt: Grant Park

  • Roosevelt:  Museum Campus, including the Shedd Aquarium, Field Museum, Adler Planetarium, Soldier Field

  • Monroe:  Millenium Park, The Bean, Pritzker Pavillion

  • Cermak/ Chinatown:  Chinatown

  • Fullerton:  Lincoln Park, DePaul, Transfer to Brown Line

  • Sox/ 35th:  U.S. Cellular Field

CTA Busses

Busses can be used to access a multitude of the Chicagoland area’s attractions, including Michigan Avenue. Google Maps has accurate directions for using the bus system.


You can usually flag down a cab quickly, but we also love Uber, a simple mobile app you can use to have a cab come right to your door. The app has clear pricing and allows you to split your fare with other riders.


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