Chicago Downtown Loop: Hot Chicago Neighborhoods You Should Visit

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Loop has always been the epicenter or heart of the downtown community.  It is where the city of Chicago conducts its business.

Although the Loop is the “business” hub for the city, it is also the location of several of Chicago’s famous attractions, museums, architecture, cultural activities, and fantastic food choices.  These attractive attributes make Loop one of the best Chicago neighborhoods to visit as a female solo traveler over 50.

The Loop is one of six neighborhoods that make up the Chicago downtown community.

Each downtown Chicago neighborhood has its unique character and charm.  You will find the Loop neighborhood just as charming and unique as the other downtown neighborhoods.

During the day, the Loop is vibrant with tons of commuters on their way to work.  After business hours, the Loop becomes less busy, more settled, and ready for the evening.

Be ready to be amazed!

In this article, I’ll be discussing the Chicago downtown neighborhood of the Loop:  

  • What is the Loop in Chicago
  • Where to stay while visiting the Loop area
  • What to do in the Chicago Loop
  • Where to eat

The Loop’s history: a city of immigrants

Chicago was discovered by Jean-Baptise DuSable in the 1780s in an area we Chicagoans now call the Loop.  The Loop is where Chicago began.

By the time Chicago was incorporated in 1833, it was already a bustling city – full of immigrants. The makeup or characteristics of the people of Chicago are culturally diverse; a melting pot grounded in traditional, hard-working Midwestern values.

Chicago is a city of neighborhoods.  Some of them, even in the era we currently live in, not completely integrated.  However imperfect our diversity is; we are very proud of our immigrant roots.

After the Chicago Fire

Most of the city (downtown) burned to the ground during the Chicago Fire of 1871.  Luckily, the city had already established itself as a major commercial hub so it was just a matter of rebuilding it from the ashes.

And the city did rebuild…quite fast.

In 1885, Chicago built its first skyscraper…and so began the city’s love affair and fascination with architecture.

By the 1890s, Chicago’s population had grown to one million.

What is the Loop in Chicago

In 1893, the elevated train was built to transport workers from Chicago’s neighborhoods to the downtown area.  This elevated train (we call it the L) made a “loop” around downtown, dropping off folks to different stops so they could get to work.  And that’s how the Loop neighborhood got its name.

And perhaps, the city’s motto as well – “The city that works“.

However, as with most major cities in the United States in the age of automobiles, the downtown area faded a bit once people left the city for the suburbs.

But by the 1960s, the Loop and the downtown area of Chicago became hot again with people coming downtown for the shopping.

Where is the loop in Chicago?

The loop’s boundaries are Lake Michigan to the east, Chicago River to the West, Chicago River to the South (the river curves around the loop almost like a parenthesis) and Congress Parkway)to the South.

It is important to take these boundaries with a grain of salt and not get too caught up in exacts. Depending on whom you speak to in Chicago, the Loop’s southern boundary is Roosevelt Road (instead of Congress Parkway).

To provide consistency and clarification across each article on neighborhoods, I will state what I consider the boundaries to be.  However, please forgive me if I also blur the lines, so to speak.

chicago downtown loop

Getting Around the Loop

As you know, Chicago is a big city. In a lot of ways, each interconnected neighborhood is like a little town. Once you’ve conquered and explored downtown Chicago, getting to know the surrounding communities is going to be a snap.

There are several ways to get around downtown Chicago. The ways to get around the Loop that I will be discussing in this article are:

  • Walking
  • Public transportation
  • Hop-on/Hop-off
  • Bicycle
  • Car

Downtown Chicago Loop by foot

The absolute best way to get around Chicago is by walking. Most downtown Chicago attractions will be within walking distance of your hotel or Airbnb accommodation.

The city of Chicago has put a lot of work into making the city pedestrian-friendly. And it shows! Chicago is the 6th most walkable city in America.

So feel free to explore.

Here are some suggestions:

  • Stroll through Millennium Park – be sure to check out Crowne Fountain, Cloud Gate, and Lurie Garden
  • Stroll down Michigan Avenue – stop off at the Art Institute of Chicago, Pritzker Military Museum or Chicago Cultural Center
  • Take a walk on Chicago Riverwalk
  • or continue to Chicago Architecture Center, 111 East Wacker – check out the Chicago City Model Exhibit.  Admission: $12.  For more information, click here. While here grab information on the number of tours offered through CAC.


where to stay in chicago

The Loop by Public Transportation

Chicago has the best public transportation options in the world! 

Okay, I’m biased and overstating it a bit.  But seriously Chicago’s public transportation is one of the best.  

Fare for buses is $2.25, and for the “L” (train), it is $2.50. Buses run every 8-15 minutes depending on the route, day of the week and time of day. Trains run every 8-10 minutes, depending on the time of day.

I recommend Google Maps, which also has a public transportation option. Just type in the address or name of the attraction (for example, Willis Towers), and it will direct you to your destination via buses/trains and walking.   

You can track buses and trains schedules by downloading one of many transit apps from Google Play or Apple store. My favorite is Transit by Transit App, Inc. It is a great app and can be used in most major cities that have decent public transportation.

Hop-On/Hop-off Bus

A great way to get an overview of the downtown area of Chicago is by doing a Hop-On, Hop-Off Bus Tour. It is also a great way to get from one Chicago attraction to the next.

My favorite is the BigBus Hop-On, Hop-off Tour – click here for information on tour prices through  Hop-On and Hop-Off at major Chicago attractions and learn a bit about Chicago’s history in the process.

Getting around the Loop by Bike

Along with being pedestrian-friendly, Chicago is very bike-friendly. Chicago has more than 200 miles of on-street protected, buffered, and shared bike lanes along with many miles of off-street bike paths (such as the Lakefront Trail).

You can rent a bike and set off on your urban adventure! You can check out prices for a full-day rental through Viator, by clicking here. The rental comes with a bike, a lock, helmet, and a detailed city map.  Or click here to go to Divvy’s Bike Share Program to rent a bike for the day.

The city of Chicago has its bike map that you can use to get around. It also gives tips on how to ride Chicago’s streets safely. To download a copy of the map, click here.

The Loop by car

Getting around Chicago by car is my least favorite way to see the city. I’ve always felt that Chicago isn’t very driver-friendly to visitors.

It’s a crazy, aggressively noisy, middle-finger involving anxiety-ridden scene that is exhilarating (once you get the hang of it) but quite intimidating if you’re not used to it.  

 Add to the fact that renting a car comes with added expenses like parking fees (costly), trying to find parking (which isn’t easy), and just a significant pain in the butt.

However, if you decide to drive your car or rent one know this – 

Chicago is easy to navigate.  The streets run on a grid system.  If you remember that the Lake is east, you will never get lost.  

The center or heart of Chicago is at the intersection of State and Madison in the Loop neighborhood.  This intersection is the zero point for the east-west and north-south direction. 

 Even number addresses are on the north and west side of the street; Odd number addresses are on the south and east side of the street.

What to do in Chicago Loop

The Loop is the heart of downtown Chicago. A lot of Chicago’s points of interest and attractions are located in this neighborhood.

It is framed on three sides by water (Lake Michigan and the Chicago River) which makes exploring the Chicago Loop by foot an attractive way to get to know this neighborhood.

If you stick to the outside perimeters of it you can get a lot seen and accomplished. If you take a look at a map of the Loop you can see that most points of interest are located along the boundaries.


Explore by cultural interest

There are plenty of reasons to visit Chicago.  Chicago is known for its history, culture, arts, architecture, and food.  And because it’s impossible to fit everything in –  I recommend focusing on a theme or a cultural interest behind your visit to Chicago.  Here are my picks for what to do while visiting downtown Chicago Loop:

  • Chicago Loop Major Landmarks
  • The Theatre Experience
  • Chicago’s Architecture
  • Museum Lovers
  • Food Lovers Experience

Chicago Loop Major Landmarks

My favorite way to get around the downtown area and check out significant landmarks is Chicago BigBus Hop-on, Hop-off Tour!  It’s a great way (especially if this is a short visit for you) to see Chicago’s most famous sites.

For more information, click here to check out BigBus tour prices through Viator.

Enjoy discount access to five of Chicago’s top attractions. Consider buying the Chicago City Pass. Click here for more information. 

Here’s my list of top places to visit in Chicago


1.  A selfie in front of Buckingham Fountain.  Buckingham Fountain is located in Grant Park and is one of the largest fountains in the world.  It operates between April and October.  At night there is a spectacular light show that is beautiful against the backdrop of Lake Michigan.


2.  Willis Tower’s Skydeck (233 South Wacker Drive) is one of those once-in-a-lifetime bucket-list attractions, so how can you skip it?

Okay, do it.  Suffer through the long, endless lines and the exciting movie that you have to sit through.  But enjoy the view once you get to the top.

Oh, and check out the Ledge (the Skydeck’s glass boxes that extend out 4.3 feet) while you’re up there, of course.  To purchase advance tickets (it’s a bit cheaper) to the Skydeck (so you don’t have to stand in a long line for tickets), click here.

It won’t skip you pass the line to get to the Skydeck, just the path to purchase tickets. There is no fast pass to the top.

3. Even if you hate art, be sure to get a selfie in front of the Lions of the Art Institute of Chicago (111 South Michigan Ave).


4. Take a walk along the Chicago Riverwalk.  It is a 1.5-mile path along the Chicago River that is full of little surprises such as public art, a museum (Bridge Museum), eateries, and a winery.


The Theatre Experience

The theater scene in Chicago is HOT! Several great plays (and named actors) are showcased here.  There are tons of theaters located in the Chicagoland area.  Here are some theaters I recommend checking out while visiting the Loop in Chicago.  Click on each link to be taken directly to their website.

For more information on what playing at which theater go to Broadway in Chicago by clicking here.

Chicago’s Architecture

Chicago is famous for its architecture.  If you’re an architectural buff, like me, you must take a few architectural tours of the downtown area.  Here are some of my favorites:

1.  Chicago Architecture Foundation River Cruise – the original one from back in the day and is still my absolute favorite architectural river cruise (there’s a number of them).  If you don’t do any other tour during your stay, be sure you do the Chicago Architecture Foundation River Cruise.  Click here to research ticket prices.

2.  Chicago Walking Tour: Art Deco Skyscrapers – put on your walking shoes and weave in and out of some of the best examples of 1920s art deco in Chicago.  Tour guides are certified Chicago Architectural Foundation Guides; they know their stuff! Click here to research ticket prices.

3.  If modern architecture is more your thing, then check out Chicago Walking Tour: Modern Architecture that focuses on the Loop’s modern and post-modern additions to the skyline.  Click here to research ticket prices.

Museum Lovers

Oh my God, there are so many museums to see in Chicago.  And most of them you could spend a whole day exploring.  I recommend not rushing;  take your time when visiting my favorites.  I can only get through one a day before I start seeing double.

1.  The Museum Campus (1200 S Lake Shore Drive) – There are three museums located on this campus.

  • Field Museum of Natural History – dinosaurs, mummies, and stuffed polar bears…oh my!
  • Shedd Aquarium – Check out the marine life (and check out Jazzin’ at the Shedd during the summer months – click here for more info).
  • Planetarium – The age of Aquarius, the moon, and the stars are aligned.

2.  The Art Institute of Chicago (111 South Michigan Avenue) – One of my favorite museums.  It is the museum with the two lions out front. The special exhibits are always changing, so it never gets boring, but the main displays don’t get boring either.  Be prepared to spend all day at this one.  For the true art lover.  To research the price of admission, click here.


Enjoy discount access to five of Chicago’s top attractions. Consider buying the Chicago City Pass. Click here for more information. 

Food Lovers Experience

In Chicago, we love pizza, and we love hot dogs.  But there’s so much more to the food scene here.  The best way to sample some of Chicago’s iconic foods is through a tour.

I recommend “Taste of Chicago Food Tour,“; a three-hour walking tour that stops at six different eateries in the Loop area.

For more information, click here to check out tour prices through Viator.

While we are on the subject of food…in the next section, I discuss where you should eat while visiting the Loop.

where to stay in chicago downtown

Where to eat in the Loop

There is a vast food revolution going on in the downtown area of Chicago.  We have Restaurant Row in the West  Loop neighborhood and the dining scene of River North.

The Loop is known for its excellent lunch options.  Most restaurants cater to the taste buds of the worker who only has a limited time for lunch.

Here’s a list of restaurants you should try – some are open for dinner as well!

  1.  The Dearborn (145 North Dearborn) – Traditional American
  2. Fry the Coop (205 West Wacker Drive) – American (Chicken) only open for lunch Monday-Friday
  3. Goddess and The Baker (33 South Wabash) – Cafe/Bakery
  4. Bienmesbe (29 East Adams) – Venezuelan
  5. Brightwok Kitchen (21 East Adams) – Asian fusion


Where to stay in Chicago Loop

Whether it be either hotel, Airbnb, or hostel, you will have amazing choices when it comes to accommodations.


Hotels located on Michigan Ave in the Chicago Loop are the best options due to their proximity to many Loop attractions, restaurants, museums, and cultural experiences.

The following hotels are excellent choices and are located on Michigan Avenue (click on each hotel to research prices on

To check prices on other hotels located in the Loop, click here to be taken to

Hotels near the Financial District (LaSalle Street) are in a quieter area of the Loop – most businesses and restaurants close down in the Financial District after 6 PM.  


Staying at an Airbnb in the Loop 

Staying at an Airbnb located in the Loop is the best way to experience this neighborhood.  Also, it can be a less expensive way to stay downtown.  Hotels rates, even for “budget” accommodations in the downtown area, can be costly.

Score an awesome Airbnb in the Loop area of downtown Chicago and be ready to be captivated, charmed, and amazed!  Click here to explore Airbnb accommodations in the Loop.

Staying at a Hostel Chicago Downtown Loop

Staying at a hostel is the best option If you’re on a strict travel budget.  No accommodations, either hotel or Airbnb, is going to beat the prices offered at the HI Chicago Hostel located at 24 East Ida B Wells Drive in the Loop.

The HI Chicago Hostel has excellent amenities and is located in a great location in the Loop.  You will be near several universities, attractions, museums, and the Auditorium Theater.   To research prices on Hostel World, click here.


The Loop is one of over 200 neighborhoods that make up the city of Chicago.  It is one of 6 neighborhoods that make up the downtown community.

The Loop is the part of downtown where the city of Chicago conducts its business.  Don’t be put off by how boring that sounds.   There’s much more to the Loop neighborhood that makes exploring it exciting.

The Loop is the location of several major Chicago attractions, museums, and cultural experiences.  If you’re looking for a great place to eat lunch, the Loop has excellent options.

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