Travel Muse Magazine

Downtown may be an American way to say “city center,” but it’s not really a Chicago thing. Here, people are more specific, defining the particular parts of downtown, as in “The Loop” (the heart of the city) and expanding out to “The Mag Mile” and so forth. Depending on who you ask, you’ll likely get slightly varied answers about exactly which areas are “downtown” Chicago, in addition to “The Loop” (which is defined by the Chicago Loop Alliance as starting at Lake Michigan on the east, the Chicago River on the north and to the west, and Ida B. Wells Drive on the south.) Other parts of “downtown” Chicago are made up of:

• South Loop: Technically, according to the Chicago Loop Alliance, “South Loop” is part of “The Loop,” because the true “southern boundary goes all the way to Roosevelt Road in context of Chicago’s 77 designated Community areas and census demography.”
• Magnificent Mile (aka “Mag Mile” aka North Michigan Avenue): This is pretty much just this famous shopping street, because the areas on both sides of it have their own names. 
• River North: This is the part of downtown immediately north of the Chicago River packed with trendy restaurants, adjacent to Mag Mile.
• Streeterville: On the east of Mag Mile is Streeterville. Busy during the weekday, but can feel like empty canyons on weekends. Most famous here: Navy Pier!
• West Loop: Is not part of “The Loop,” like “South Loop.” It is a completely different area named this because it is west of “The” Loop.  
• Gold Coast: Some people won’t consider the Gold Coast part of “downtown” Chicago. They’ll say, that’s “north” of downtown. But when you’re there, it’ll feel like basically the top of the Mag Mile and Streeterville. It’s the extra fancy part.
• Lakeshore East: This is another area that’s officially part of The Loop, but is sometimes defined as a smaller neighborhood unto itself.

Okay, now that we’ve covered that… I lived in Chicago’s fabulous northside neighborhoods of Wrigleyville and North Halsted and worked “downtown” in Streeterville for several years and my husband hails from Chicago, so people often ask us for advice on what to do there. And while there never seemed to be enough time to do all the things Chicago has to offer, I still enjoy going back and visiting. Here, then, are the top things I tend to recommend people start with when they ask me what they should do “downtown” Chicago for the weekend…

The Art Institute of Chicago

Even if “art” is not your thing, you’ve got to go visit this world-class museum! Among the 300,000 works of art here are several American classics, including Grant Wood’s “American Gothic“ and Edward Hopper’s “Nighthawks“ plus several Georgia O’Keeffe works like “Cow’s Skull with Calico Roses“… all of which you’ve seen and heard of, even if you have no idea of the artists names or the titles of these works. You’ll also find international masterpieces, like Georges Seurat‘s “A Sunday Afternoon on the Island of La Grande Jatte”, van Gogh‘s “The Bedroom,” Picasso‘s “The Old Guitarist” from his blue period… and the list goes on and on. Check out the Art Institute’s “what to see if you’ve only got an hour” suggestions here.

The Bean

On the way to or from the art museum, you’ve got to wonder into Millennium Park to see The Bean. If I told you to go see Anish Kapoor’s world-famous Cloud Gate, would you know it’s the same thing? Probably not. And most people don’t know Cloud Gate is the actual name of the shiny cool silver bean thing that looks like it bends time and space as people gather around for pics. It’s free and it’s a must-see.

TIP: Across Michigan Ave, close to The Bean on your way to the river is a great little coffee shop with a gorgeous setting: Venteux Brasserie, Cafe & Oyster Bar. I can’t speak to their food, but their lattes are worth stopping in for while admiring the lovely art painted on the walls here.

Architectural River Cruise

After a recharge from a coffee and some good river pics from the Michigan Ave. bridge, grab a spot on a classic architectural-themed history cruise on the Chicago River. It’s a relaxing ride along the pretty blue-green water where skyscrapers shoot up everywhere you look. Seeing that the world’s first-ever building to be called a skyscraper is here (the Home Insurance Building), it’s a perfect tour to learn some historical facts, get some good photos, good views and relax from all the walking you’re bound to be doing on your weekend.

The Mag Mile

Next up, time to stroll The Mag Mile. If high-end shopping is your thing, you can blow a whole lotta cash in these few blocks of town. Even if that idea sounds like the opposite of fun, you’ll want to walk down this street to take in a few (free) sights and probably also some food. Your kids will love that the old-but-cool-again films Ferris Bueller’s Day Off and Christmas Vacation both have memorable scenes here. And there’s street art and seasonal decor to enjoy too.

Places to stop at take a look at:

• Tribune Tower – This Neo-Gothic building is decorated with rocks from world landmarks. Look for labeled pieces of the Great Wall of China, the Great Pyramid of Cheops, and the Berlin Wall, among others.
• Historic Water Tower – famous for being one of the few structures to survive the 1871 Great Chicago Fire.
• Hancock Center aka 875 North Michigan Avenue – After the insurance company that gave it the name moved out, this skyscraper known for its famous views at the top changed its name. There’s a bar, the “Tilt,” sky yoga and more to do way up at the top here.

On the food front…

• For burgers on the south end of the mile, visit the Chicago institution Billy Goat Tavern.
• For Chicago-style deep dish pizza head to Gino’s East “Mag-Mile” original location on Superior just a block or so off Michigan.
• If you’re a Starbucks fanatic, you may also want to stop in at the world’s largest Starbucks. The Starbucks Reserve Roastery (at 646 N. Michigan Ave.) is called a “coffee theater” with five stories and 35,000-square-feet of coffee fun.

There’s so much more to do just in this section! You could maybe never fit it all in without dedicated time just to purposefully visit each and every store and eatery packed into this mega-space.

Catch a Live Show

What’s not happening in Chicago could possibly be a shorter list. “Downtown” has so many places to catch a live show. You could do House of Blues or Buddy Guy’s Legends for live music classics. Or head to the Chicago Theatre for live comedy, music and other shows. Or catch Broadway shows at the Nederlander and Cadillac Palace, among others. Check ChicagoPlays.com or BroadwayInChicago.com to find out what’s on and what’s coming.

The Second City is THE place for comedy. It is THE place of comedy legends. And they’re still doing live sketch comedy here, plus classes and so many other funny things. BUT, this is not downtown. It is downtown-adjacent-ish. (Like 2.5-ish miles from Gino’s East by cab.) But look, John Belushi, Bill Murray, Chris Farley, Gilda Radner, Tina Fey, Amy Poehler, Stephen Colbert, Steve Carell, Jordan Peele and Keegan-Michael Key… and so, so many more all have been part of the shows here! Take an Uber to North Ave at North Wells St. You deserve to laugh!