An Insider’s Guide To Where to Stay in Chicago

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where to stay in chicago

Are you planning a trip to Chicago, but you’re unsure where to stay in Chicago?

Here’s the thing…Chicago has 77 communities with over 200 neighborhoods and hundreds of hotels.  Choosing where to stay is going to be an essential decision.  And probably the most significant part of your travel expense.

You don’t want to toss a coin and give that kind of decision up to chance.

So, what can you do about it?  Blind-fold yourself, throw a dart at a board containing the names of each neighborhood, and hope that it lands on the best choice?


I got something better than that for you.  Here’s my insider’s guide to where to stay in Chicago for the first time. This article is your introduction to Chicago neighborhoods.


Drop your name and email below and receive a cheat sheet of the 10 Best Areas to Stay in Chicago




Why you’re going to love Chicago

5.8 million people visited Chicago in 2018.  Conde Nast Traveler’s readers named Chicago the number one “Best Big City” for 2019.  And there is a reason for that distinction.  Chicago is known for its:

  • Amazing food scene
  • beautiful architecture
  • home to a number of professional sport teams
  • museums, theater district and shopping
  • friendly and clean
  • beautiful views of Lake Michigan

Where to stay in Chicago (especially if this is your first time)

If this will be your first time visiting Chicago, I recommend staying in the downtown area.  Staying downtown puts you within walking distance of Chicago’s most popular attractions such as the Willis Tower, Millennium Park, the Art Institute of Chicago and lots more!

To book your hotel stay through, click here.


where to stay in Chicago

Best areas to stay in downtown Chicago

The downtown area is a mixed business and residential community.   You will find the best hotels in downtown Chicago located in these areas.  Any of the following neighborhoods in the downtown Chicago area will be ideal:

  • Loop
  • South Loop
  • West Loop
  • River North
  • Streeterville
  • Gold Coast

Below is a brief description of each neighborhood and what makes it special.


Be ready to be wowed.

The Loop

The Loop area of downtown Chicago includes the business (financial) and theater district.

Michigan Avenue and State Street are where you will find a great deal of the Loop’s activity.  Willis Tower, Millennium Park, Buckingham Fountain, Art Institue of Chicago are all located in the Loop.

The financial district is centered around LaSalle Street near the Chicago Board of Trade.  This part of downtown is very active during business hours but settles down once downtown workers leave at the end of the day.

The Theater District of the Loop is located along Randolph and Lake Street – west of State Street. The theaters located in this area are:

  • Chicago Theater
  • Cadillac Theater
  • Nederlander Theater (use to be Oriental Theater)
  • Goodman Theater

CIBC Theater and University Theater are located south of the Theater District – for more information on the Theater District, click here.

What’s hot in the Loop: Printer’s Row, Millennium Park, the Bean, Willis Tower

Where to stay in the Loop

Whether it be either hotel, Airbnb or hostel, you will have amazing choices when it comes to accommodations. Even though the Loop is the business district, it is highly residential. In other words, staying at an Airbnb in the Loop would be an awesome alternative to staying at a hotel.

To begin your search for the perfect Airbnb spot, click here.

The Loop is one of the best areas to stay in Chicago.

Recommended best hotels to stay in the Chicago Loop


For more information about Airbnb in the Loop, click here.


To read more about things to do in the Chicago Loop, click here.


South Loop

This area of downtown is mainly residential.  It quiets down after work hours, but there are lots of cute eating places and bars.  The South Loop is an excellent area to stay if you’re thinking about Airbnb.

It is the closest downtown neighborhood to Soldier’s Field.

Field Museum of Natural History, Shedd Aquarium, and Planetarium (all part of the Museum Campus) are located in the South Loop.

Hot spots: Dearborn Park, Burnham Place, and Central Station

Where to stay in the South Loop

Whether it be either hotel, Airbnb or hostel, you will have amazing choices when it comes to accommodations. The South Loop is primarily residential.  It is a lovely area with plenty of high-rise apartments townhomes and condos.  Airbnb is a great alternative.  To begin your search for the perfect Airbnb spot, click here.

Recommended Best Hotels to Stay in Chicago South Loop 

For more information about Airbnb in the Loop, click here.


To read more about things to do in the South Loop, click here.

West Loop

West Loop – has become the area for good eating with Restaurant Row on Randolph Street. Greektown is also located in the West Loop (plenty of great eating here as well…Opa!). The West Loop area isn’t exactly close to the majority of top places to visit in Chicago (however, the Willis Tower is just across the River).

However, West Loop’s appeal is the hipness factor and a sheer number of cool points.  Several cool bars and wineries have sprung up in this neighborhood, making it a great area to hang out.

Check out my favorite European inspired food court at the French Market (131 North Clinton St at the Metra Station) for a quick bite or lunch.

Hot spot: Home to Chicago’s version of the meatpacking districtFulton Market District.

Where to stay in the West Loop

Whether it be either hotel, Airbnb or hostel, you will have amazing choices when it comes to accommodations. The West Loop is primarily mixed-use residential/commercial properties. Airbnb is a great alternative.

For more information on Airbnb in the West Loop, click here.


Recommended Best Hotels to Stay in Chicago West Loop 


River North

Chicago River North – another area of downtown known for its eateries and nightlife.  This neighborhood is where the Merchandise Mart and House of Blues are located.  Plenty of art galleries to stroll in and out of (if you are looking to buy some art).

The River North neighborhood borders the Magnificent Mile on the east and the Chicago Riverwalk to the south.

Hot spots: Ohio and Grand Avenue

River North Hotels


Streeterville – Home to Navy Pier and the Magnificent Mile. The Museum of Contemporary Art and Hancock Building (currently called 875 North Michigan building) is also located in Streeterville.

The biggest Starbucks just opened on Michigan Avenue in Streeterville.

Ohio Street Beach is part of this neighborhood.

Hot spot – Magnificent Mile

Streeterville Hotels


Gold Coast

Gold Coast – Very posh residential neighborhood (hence the name “Gold Coast).  High-end restaurants and shopping on Rush Street.

Oak Street Beach located here.

Quiet neighborhood that features beautiful stately homes. Hugh Hefner lived in this neighborhood. The first Playboy Club was located at 116 East Walton.

Hot spot – Rush Street

Gold Coast Hotels

Is the downtown area safe?

Even as a long-time resident, it’s very easy to forget that the downtown area has its fair share of crime. However, it’s not the wild, wild west either.

For the most part, downtown Chicago is safe.  The Chicago Police Department is excellent (and helpful – should you find yourself lost) at keeping downtown safe.

But you still need to do your part by not making yourself a target for crime.  Later in this article, I discuss tips on staying safe while visiting Chicago.

Airbnb or Hostel?  Cheap places to stay in Chicago

Where is the best place to stay in Chicago if you’re trying to save money?  One excellent option for affordable accommodations, whether downtown or in one the neighborhoods in and around Chicago, is Airbnb.  Here are some reasons why staying at an Airbnb is a good idea:

  • more affordable than a hotel room
  • great opportunity to get to the know Chicago and its neighborhoods
  • a great way to show love by supporting the local economy


If you are looking for cheap but excellent accommodations, a great option would be staying at one of Chicago hostels located downtown.

I recommend HI Chicago Hostel in the Chicago Loop area – a great location!

Click here for more information on other hostels located in Chicago from Hostel World.


Tips on staying safe in Chicago

Yes, parts of Chicago can be dangerous.  But don’t most cities (both U.S. and abroad) have elements that are considered not safe? With a little street-savvy and awareness of how you’re presenting yourself, you will be fine.

  • Just like any city that you visit, always be aware of your environment.
  • Try not to appear touristy.
  •  If you’re like me and love carrying huge-ass purses, make sure the bag has a shoulder strap that you can wear across your body.
  • Never leave your purse on the back of your chair.  Especially if you are enjoying a meal at one of Chicago’s many sidewalk cafes/restaurants.
  • Do not take shortcuts through alleys.  No matter how tempting.
  • When going out at night, stick to well-lit sidewalks, main streets, and parks.  The lakefront is gorgeous at night.  Full of good people with neighborly and friendly mid-western values.  Join them and enjoy the amazingly beautiful city that is Chicago.  I never get tired of the welcoming energy of my city.
  • Enjoy yourself.


This guide to where to stay in Chicago will take the stress out of making the most critical decision when it comes to planning a trip to Chicago.

Chicago has over 200 neighborhoods within 77 communities.  For the first time visitor, I recommend staying in downtown Chicago.

If you’re interested in exploring communities outside of the downtown area, I discuss in this article 5 great communities you will love to get to know.

Lastly, Chicago is amazingly beautiful.  It is possible to have a safe experience while visiting by staying mindful of your surroundings.

And now you’re ready to start planning!




For more information on Chicago, check out the following articles:


Drop your name and email below and receive a 10 Best Areas to Stay in Chicago Cheat Sheet

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