What You Wanna Know about Where to Stay in Chicago Downtown Loop

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Are you planning a trip to Chicago and you’re not sure where the hell you should stay or what things to do?  Well, you’re in the right place!  I will be discussing the city of Chicago in a series of articles geared towards the first time visitor.  However, if you’ve been to Chicago before…stick around anyway!  You might learn something new.

For the first time visitor, staying downtown Chicago is your best option.  But where downtown Chicago is the best area to stay?

The downtown area is big and made up of 6 different communities.

In this article, I’ll be discussing where to stay in the Chicago downtown neighborhood of the Loop. And I also discuss:

  • how to experience Chicago Downtown Loop
  • top 10 things to do in Chicago downtown
  • 4 things you could skip doing if you’re short on time

Chicago Loop

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

Where is the loop in Chicago?

The Loop’s rough boundaries are from Lake Michigan to the North, Chicago River to the West and North (it curves around the Loop from North to West) and Roosevelt Road to the South.

Think of the Loop area of downtown as a square with four quadrants.  Madison (E/W) and State (N/S) is the dividing line.


Where to stay in Chicago Downtown Loop

With amazing choices for accommodations, whether it be either hotels or Airbnb, you will love every bit of this Chicago downtown neighborhood.

Chicago Palmer House

The Palmer House (17 East Monroe) says “Chicago” with its Old-School charm with quiet, understated elegance.  This hotel is breath-taking.  If you’re a history buff or architectural geek, you will want to wander through every nook and cranny of this hotel.

There’s a ballroom, for God-sake!  Baby, they don’t make ’em like this anymore.


where to stay in chicago downtown



The Palmer House location makes it perfect for exploring the Loop area of downtown.  It screams EXCITEMENT…ELEGANCE…COMFORT!  You will be smack dabbed in the middle of all the action and walking distance to a lot of attractions and museums.

  • a block away from Michigan Avenue
  • shopping on State Street
  • restaurants
  • Millennium Park
  • Theater District
  • Art Institute of Chicago


To take a look at Booking.com hotel rates and reviews for the Palmer House, click here.

Staying at an Airbnb in the Loop 

This is prime A1 real estate, people!  Score an awesome Airbnb in this area and be ready to be captivated and amazed!  Click here to explore Airbnb accommodations in the Loop.

Airbnb Tip:  Filtering your search to Super Host will give you great choices but will most likely cost more.  If you’re not too picky, you can find a bunch of bargains with Airbnb in the Loop.

For more information on where to stay in Chicago (includes all downtown neighborhoods and the surrounding area), click here.


How to experience the Loop downtown Chicago

The city’s business is conducted in the Loop.  Just looking at that statement, you might be thinking that sounds like an area of downtown I want to avoid.

During the day hours, the Loop is vibrant.  Tons of commuters from all over the city and suburbs flowing into the downtown area like a river. The commuter pedestrian AM/PM rush can be a little overwhelming for the visitor who’s caught in the flow.

After business hours, the area of the loop near the Chicago Board of Trade (financial district – centered around LaSalle Street)  becomes quiet.  However, you will find that the rest of the Loop area is still booming with activity once the sun goes down.

Why Should I Visit Chicago?

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 in downtown Chicago if you’re interested in the following:

  • The Theatre Experience
  • Chicago’s History through Architecture
  • Museum Lovers
  • Food Lovers Experience

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 History through its 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 exhibits 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 6 different eateries in the Loop area.

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

where to stay in chicago downtown

Not sure what to do? Top 10 things to do in Downtown Chicago Loop

Don’t worry.  Regardless of whether you have an air-tight itinerary or you’re winging it – you’re going to have a good time.

Recommendation:  Even after 30 years of living in Chicago, my favorite way to get around the downtown area (pretending to be a tourist) 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 popular sites if you don’t sure how to plan your itinerary.

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 things to do in Chicago while staying in the downtown Loop area.  Some of these things are not just in the Loop area, but I feel you shouldn’t skip the experience.

1.  Architectural River Cruise – if you don’t do the one mentioned in this article, do ONE of them.  You will not be disappointed, and it’s a unique way to see Chicago.

2.  Millennium Park – ice skate during the winter or splash in the fountains during the summer.  Have a drink at the Park Grill.  Take a pic of the Bean (Cloud Gate). Check out Movie in the Park (Tuesdays, June – August).

3. Even if you hate art, be sure to get a selfie in front of the Lions of the Art Institute of Chicago

4.  Harold’s Chicken at 612 South Wabash – a local chain but this one is my favorite downtown location.  Don’t forget the mild sauce.  It’s a Chicago thing.

5.  Pizza at Lou Malnati – it will change your life, and you will never want pizza from anyplace else.

6. Drinks at the Signature Lounge on the 95th floor of the Handcock Building (now called the 875 North Michigan Avenue Building).  Go during sunset.

7.  An evening stroll (or jog) along the Lake Front

8.  A selfie in front of Buckingham Fountain.  Go back at night and watch the light show.

9.  Lunch and wine at the Walnut Room in the old Marshall Fields Building – now Macy’s at 111 North State. Check out the huge Christmas Tree at during the holiday season

10.  Baseball Game at Wrigley Field (if in season) – one of the last great old ballparks.  Even if you hate baseball, you will love the neighborly vibe of the neighborhood of Lakeview.  After the game slip into one of the many taverns in the Wrigleyville/Lakeview area for a beer and great local baseball commentary.



Four things you could skip if you’re not the touristy type traveler

You know who I’m talking about. The traveler who wants the real, authentic travel experience and don’t want to stand in line and spend a shit load of money on trinkets and refrigerator magnets.

And never shops for souvenirs for friends or family or stupid t-shirts – don’t even ask!  Here are my picks for tourist attractions that you might want to skip

1.  Navy Pier – if you eat or shop here be prepared to spend a lot of money.  An extra amusement tax is added on top of every, every purchase.  Don’t eat at McDonald’s; don’t even buy a soda because it will cost you double.  If you want, check out the Ferris wheel if you’re not afraid of heights. (I am, by the way).

Instead, check out the events (some of them are free) that are held at Navy Pier year-round.  Click here for more information on events and venues.

2.  Willis Tower – I know, right?! Willis Tower’s Skydeck 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.  Enjoy the view once you finally get to the top.  Then let it go – trust me you’re not going to wanna go through it again in this lifetime.

Oh, and check out the Ledge 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 line to purchase tickets. There is no fast pass to the top.

3.  Avoid the Magnificent Mile if you’re not shopping.  This part of Michigan Avenue is impassable just about most of the day due to tons of people walking…very slow.

4.  Deep Dish Pizza – Chicagoans don’t eat deep dish pizza. It’s costly, and you can only eat one slice. And it’s impossible to warm up later because it’s so huge.   Maybe every blue moon we might eat this, but we never take the leftovers home for later.  I recommend trying it just once to say you had it.  Go to either Gino’s East, Lou Malnati or Giordiono for the best.  After that always order thin crust pizza.



Getting to Chicago



2 airports service the Chicagoland area; O’hare Airport (ORD) and Midway Airport (MDW).  You are going to have plenty of ground transportation options once you land. However, the fastest and cheapest way to get downtown is by public transportation. Both airports are easily accessible by public transit; the Chicago ‘L’ trains.

Traffic from the airports is horrible unless you fly in very early or late (after 7 PM).  Unless you love sitting in mind-numbing traffic, I recommend taking the ‘L.’  During rush hour (6 AM- 10 AM and 2 PM – 6:30-7 PM), it can take up to 2 hours to reach downtown from either airport (even though MDW is a lot closer to downtown).


Union Station (225 South Canal)Click the link for more information on Amtrak.


Greyhound Bus Station (630 West Harrison St) or Megabus (Van Buren St between South Canal and Clinton St)


Three expressways run through the Chicagoland area: Interstate 90/94, Interstate 55, Interstate 290.


Getting around the Loop

Traffic is crazy.  And unless you have a robust constitution or a death wish, I recommend not renting a car while staying downtown.  Besides, the price of parking is outrageous, and most hotels don’t have free parking.

The best way to experience downtown Chicago is by walking.  Uber, taxi or public transportation are also great options.

The exception to this rule is if your travel itinerary includes traveling outside of the downtown area and even then I would only rent a vehicle on the days your travel plans take you elsewhere.

As a visitor, staying in the middle of downtown Chicago will give you a taste of what it’s like to live in the city. Everything is convenient and right at your fingertips.

And as far as safety, a visitor should treat this city like any other metropolitan oasis – with some common sense.  That being said downtown Chicago is patrolled by the men and women of the Chicago Police, Chicago Transit Police, University Police/security force (in some neighborhoods) and a host of other law enforcement entities.

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