Where to stay in Chicago: 4 Key Areas in 2024

Figuring out where to stay in Chicago can be tricky for first-time visitors. I recently had this problem after booking a very last-minute trip to the Windy City and knowing only a little about the city, mostly that it is home to the Chicago Deep Dish Pizza and sits on the shores of Lake Michigan. Other than that, I had very little knowledge of where to stay in Chicago. 

One of my favorite things to do when organizing a vacation is to not only scour the internet for a list of ideas of what to do but also where to stay. By the time I actually arrive at the destination I know about the immediate area and what can be found nearby. The great thing about major cities in the US is that they are well-served with local transportation systems, restaurants, and stores.

Deciding where to stay in Chicago is relatively easy, and the city is compact enough to easily walk from each major site. We only took public transportation once (we took the Metra to the Museum of Science and Industry), and loved walking around the city of Chicago. You can check out how to spend 3 perfect days in Chicago here.

Chicago is one of the most beautiful cities I’ve visited in the United States. The skyscraper was born in the city in the late 19th century by architects Burnham & Root. And as you gaze around the city, you’ll catch your breath with each skyscraper that pops into view. It’s a dazzling spectacle and you simply have to do an architecture boat tour on the Chicago River to gain a better understanding of the city and its buildings. 

Where to stay in Chicago the first time

There are a few locations that whether you are visiting Chicago for the first time or a repeat visitor that you should consider when deciding where to stay in Chicago. 

  • The Loop
  • Magnificent Mile
  • River North
  • Gold Coast

Over the next couple of paragraphs, I’ll go over what each area of Chicago has to offer and why it might be appealing to stay in that area for your visit to the city. 

The Loop

The area known as the Loop features some of Chicago’s most visited attractions. A stay in the Loop means you are located within the Theater District of Chicago, close to Millennium Park which is home to the iconic ‘Bean’ and the tallest building in Chicago – Willis Tower.

If you decided this is where to stay in Chicago for the first time, you can rest assured that you are in an excellent location for exploration, shopping, and sightseeing

One of the downsides to staying in this area of Chicago is that there are a number of fast-food restaurants and nothing really top-end. The areas underneath the L Train can be a little bit grim and dimly lit, but it’s always busy with people. 

The Chicago Pedway is a series of underground walkways that make it easy to get around during the summer and winter months when the weather is unfavorable above ground. You’ll find stores, fast-food restaurants, and underground trains that can be accessed via the Chicago Pedway. 

The shopping in this area is superb, with stores like Macy’s and Primark on Wabash and North State Streets, as well as firm favorites Anthropologie, Target & Uniqlo.

Stay at The Loop for:

  • Shopping
  • Willis Tower (Tallest building in Chicago and home to ‘The Ledge’)
  • Theatres (Chicago Theatre, Nederlander..)
  • The Bean
  • Millennium Park
  • Art Institute of Chicago
  • The Riverwalk
  • Museum Campus (Adler Planetarium, Shedd Aquarium, Field Natural History Museum)

Hotels on The Loop

Hyatt Centric The Loop Chicago ($$$$)

Renaissance Chicago Downtown Hotel ($$$$)

The Palmer House Hilton ($$$)

Magnificent Mile

If there was only one place where to stay in Chicago the first time it would have to be Magnificent Mile. It’s a shopper’s paradise, and the wide street of Michigan Avenue is arrestingly beautiful. You’ll also find some of the top names in the hotel industry have their flagship hotels on this stretch of Chicago. 

Magnificent Mile is a fantastic place to base your stay in Chicago if you want everything on your doorstep. You’ll also find alongside top-tier hotels such as the Intercontinental & The Drake some budget-friendly hotels such as the Allerton & St Clair Hotel. 

Being based on the Magnificent Mile means that many excellent restaurants and bars are just on your doorstep too. After a long day shopping in Nordstrom or Saks 5th Avenue, you can head to the Purple Pig for a delectable meal. Visit the John Hancock Tower and experience 360 Chicago and the TILT ‘ride’.

TILT at 360 Chicago on Magnificent Mile

A few blocks away from the Magnificent Mile is the wonderful Navy Pier. This is the gateway to Lake Michigan and a perfect afternoon to take a tour of this enormous lake. Navy Pier has attractions such as the Centennial Wheel and a carousel which makes a perfect afternoon or evening out. 

Stay at Magnificent Mile for:

  • Shopping (Nordstrom, Saks 5th Avenue, Neiman Marcus, Bloomingdales)
  • Eating (Lou Malnati’s, Purple Pig)
  • Wendella Boat Tours
  • Apple Store
  • Starbucks Reserve Roastery
  • Navy Pier
  • 360 Chicago

Hotels on Magnificent Mile

Intercontinental Chicago Magnificent Mile ($$$$$)

Loews Chicago Hotel ($$$$)

Hotel Saint Clair Magnificent Mile ($$)

River North

Staying in River North is staying in Chicago with everything that you could possibly need or want. You’ll find some of the best restaurants in the city in River North, it’s a short walk to the Chicago River & its impressive skyline, and there is a wide range of excellent bars here too. 

Consider staying at River North if you are wondering where to stay in Chicago without a car as everything is on your doorstop and you won’t need to travel very far to get what you need. This is also a good base for someone who is on a business trip and likes to have the convenience of a selection of restaurants and bars closeby. 

Stay at River North for:

  • Skyscrapers
  • The best restaurants in the Chicago
  • Excellent bars
  • No car needed

Hotels in River North

Trump International Hotel & Tower Chicago ($$$$$)

The Westin Chicago River North ($$$$)

Moxy Chicago Downtown ($$$)

Gold Coast

I decided to include the Gold Coast as a location of where to stay in Chicago for those looking to be in the city, but a little bit removed from the chaos of a major city. The Gold Coast has a village-type feel to it. A very bougie village. You can tell walking around this area of Chicago that it’s a lot higher-end than some other parts of the city. 

The Gold Coast is where prime-real estate meets the edges of the city. You can walk to the Magnificent Mile in less than 10 minutes from the Gold Coast, and there is a fantastic selection of restaurants and bars here. 

The shopping in Gold Coast is a lot more higher-end with a focus on luxury brands such as Jimmy Choo, Harry Winston Diamonds & Hermès just to name a few. The Gold Coast is located at the tail end of Magnificent Mile and has a fantastic stretch of beach (Oak Street Beach) that during the summer time is the perfect place to cool off at. 

I would recommend the Gold Coast as where to stay in Chicago if you have your own car or rental as it will make it easier to get around. It’s also very easy to get around by subway too, as there are nearby subway stations such as the Red, Brown & Purple Lines that have stops a few blocks away. 

Stay at the Gold Coast for:

  • Luxury shopping
  • High-end hotels
  • Great city beach
  • Village-like feel

Hotels in Gold Coast Chicago

Waldorf Astoria Chicago ($$$$$)

Four Seasons Chicago ($$$$$)

The Viceroy Chicago ($$$$$)

Once you’ve figured out where to stay in Chicago make sure to check out my perfect 3-day itinerary for exploring the Windy City. Let me know where you end up staying in the comments below and what you thought of the city!

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