The Best Areas to Stay in Chicago, Illinois
The Best Areas to Stay in Chicago, Illinois

Best Areas to Stay in Chicago, Illinois

Where to Stay in Chicago – A Guide to the Windy City

Chicago is the most populated city in Illinois and the third-largest city in the US. Located in the northeast of the state, on Lake Michigan, and nicknamed “Windy City,” Chicago is famous for its impressive skyline and architectural heritage, world-class museums, unique local cuisine, and early-20th-century gangsters. In this post, we will discover the best areas to stay in Chicago, IL.

Google “Chicago-style,” and you will realize the sheer influence this town has had in American culture in a relatively short period of time. From pizza to hot dogs; from Chicago School architecture to Chicago-style jazz and the Chicago Outfit, this city seems to be everywhere, and we wouldn’t have it any other way!

One of the first things that come to mind when people think about Chicago is its skyline, outlined by high-rises of all shapes, colors, heights, and styles. Most of the city’s famous skyscrapers are located downtown, and the tallest ones include the Willis Tower (formerly Sears), St. Regis Chicago, and 875 North Michigan Avenue (John Hancock Center). Some historic Chicago high-rises built before 1950 include the Chicago Board of Trade Building, Chicago Temple Building, Palmolive Building, and the Civic Opera House. See accommodation in Downtown Chicago.

To get a proper view of the breathtaking Chicago skyline, Skydeck Chicago, at 1,353 ft (412 m), on the 103rd floor of the Willis Tower, offers a panoramic observation deck and views extending four states. Check fares and book tickets.

Skyscrapers are nice and all, but Chicago is so much more. This Illinois city is home to world-renowned museums and galleries focusing on everything from art to science, history, culture, and music. Some of the most important museums in Chicago include The Art Institute of Chicago, the Field Museum of Natural History, the Museum of Science and Industry, and the Museum Of Contemporary Art. Many of the big-name Chicago museums are located in the city center and along the lakefront, with a cluster of institutions centered around Museum Campus park.

If you’re traveling with children, the Windy City is arguably America’s most family-friendly destination. Some of the most popular kid-oriented attractions in Chicago include the Chicago Children’s Museum, the Peggy Notebaert Nature Museum, Shedd Aquarium, Adler Planetarium, and Lincoln Park Zoo. Chicago is also renowned for its lovely city parks like Millennium Park, Grant Park, Jackson Park, Lurie Garden, and Maggie Daley Park.

Young people will enjoy Chicago’s uber-trendy, hipster-friendly districts like Logan Square, Andersonville, and Bridgeport. These areas are known for their thrift stores, art galleries, farmers’ markets, and artisanal breweries. Likewise, travelers looking to dive into Chicago’s legendary nightlife should definitely look for accommodation in either River North, Wrigleyville, or Wicker Park, Chicago’s main party districts.

While all of Chicago is very LGBT-friendly, the city’s official gayborhood, appropriately named Boystown, is located in the Lakeview district, north of the city center. See accommodation in Lakeview.

Due to its geographical location on Lake Michigan, Chicago has a hot-summer humid continental climate. This translates to four distinct seasons, constant rainfall and, of course, winds. Winters are very cold and snowy, with temperatures hovering between 18 and 32 ºF (-8 – 0 ºC). Meanwhile, summers are warm and humid, with average temperatures between 68 and 85 ºF (20 – 29 ºC). The best time of the year to visit Chicago is from late-spring to mid-fall (May through October), when temperatures are warm enough to enjoy outdoor activities and sightseeing.

To get to Chicago by air, the city has two airports. Midway International Airport is located 8 miles southwest of downtown Chicago and offers short and mid-haul domestic and North American connections. On the other hand, O’Hare International Airport is a major international hub and one of the world’s busiest airports. From here, you can reach a wide range of over two hundred destinations in the Americas, Europe, Asia, Oceania, and Africa.

Chicago is also well-served by train. Chicago Union Station, located downtown, is the main railway hub in the Midwest. This station provides direct Amtrak services across the US to places like New York, Portland, Seattle, LA, and Texas. It also offers commuter, suburban, and intercity connections in the Midwest. See train routes, schedules & fares.

To move around town, Chicago has a very efficient and well-developed intermodal public transport system consisting of eight ‘L’ train lines, 129 bus routes, and 11 commuter rail lines (Metra). Additionally, Chicago offers water taxi services, regular taxis, mobile apps like Uber and Lyft, and car rental offices.

The best area to stay in Chicago is The Loop. This busy and lively downtown district is home to Chicago’s world-class museums, historic high-rises, extensive park network, shopping centers, nightlife, and some of the best restaurants in town. The Loop is also the best-connected area and offers the widest range of hotels. See accommodation in the Chicago Loop.

If you are visiting Chicago for fine dining, luxury shopping, or to pamper yourself in one of its award-winning international hotels, then the upscale River North District and Chicago’s Magnificent Mile are for you. See accommodation in River North & Magnificent Mile.

Other excellent options to keep in mind when choosing the best location in Chicago, IL, include Old Town Chicago, Lincoln Park, West Town, West Loop, and South Loop.

Keep reading to find out more about the best areas to stay in Chicago, IL.

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The Best Areas to Stay in Chicago, Illinois

Chicago Loop (also known as Downtown Chicago) is considered the financial and commercial district of the city, with large office buildings and stores on State Street that make it a very attractive area for shopping enthusiasts.

It is in this area that you will find Millenium Park, the main vegetable lung of the city, as well as the Theater District, ideal to enjoy the most recent plays of Chicago and get caught up in the culture of this great city.

Similarly, this district has a large number of museums, such as the Art Institute of Chicago, the Cultural Center of Chicago, the Museum of Contemporary Photography and the Museum of American Writers.

Chicago Loop has the best public transport connections in the city, with elevated rail stations such as Quincy, Monroe, and Jackson, to name just a few.

Furthermore, Chicago Loop is one of the best areas to stay in Chicago because of its variety of hotels of all types.

Chicago Loop - Best areas to stay in Chicago
Chicago Loop – Best areas to stay in Chicago
Accommodation in Chicago Loop - Click on the map to see all available accommodation in this area
Accommodation in Chicago Loop – Click on the map to see all available accommodation in this area

Why is this a recommended area to stay in Chicago, Illinois:

  • Central location
  • Great public transport connections
  • Best area to stay without a car
  • Best area for sightseeing

2. River North & Magnificent Mile

The most exclusive area of the city is, undoubtedly, the River North and Magnificent Mile, located north of the Chicago Loop and across the Chicago River.

Magnificent Mile, in particular, is the unofficial name given to Michigan Avenue, an important commercial area of Chicago with stores of globally renowned brands.

On the other hand, River North is one of the best areas to stay in Chicago for foodies, thanks to its high-end restaurants that offer all kinds of international cuisine.

River North and Magnificent Mile also stand out for having luxury-type hotels. As a result, it is not the cheapest area to stay in Chicago.

This area connects with the rest of Chicago through public transport and is also a good area to stay in Chicago for nightlife.

River North & Magnificent Mile - The most exclusive area to stay in Chicago
River North & Magnificent Mile – The most exclusive area to stay in Chicago
Accommodation in River North & Magnificent Mile - Click on the map to see all available accommodation in this area
Accommodation in River North & Magnificent Mile – Click on the map to see all available accommodation in this area

3. Old Town

The Old Town of Chicago is one of those charming neighborhoods that deserve to be explored to discover the history of this great city of Illinois.

Walking through its streets, you can see an interesting contrast of buildings dating from before the Chicago fire of 1871 with shops, restaurants and modern bars.

The Old Town is located north of Downtown Chicago and has outstanding attractions such as The Second City, a comedy club where many important American comedians made their debut.

The Old Town is one of the best areas to stay in Chicago, combining the best of a cosmopolitan city with relevant monuments.

This historic neighborhood, in addition to being very pedestrian-friendly, connects with other areas of Chicago through public transport.

Old Town - Where to stay in Chicago
Old Town – Where to stay in Chicago
Accommodation in Old Town Chicago - Click on the map to see all available accommodation in this area
Accommodation in Old Town Chicago – Click on the map to see all available accommodation in this area

Why is this a recommended area to stay in Chicago, Illinois:

  • Pedestrian-friendly
  • Charming area

4. Lincoln Park

Lincoln Park is one of the greenest neighborhoods in Chicago, thanks to the park that gives its name to the area, where you will find a zoo, a botanical garden, and the Peggy Notebaert Natural History Museum.

This neighborhood, located just north of the Old Town, also stands out for its cafes and gourmet restaurants.

Lincoln Park is also a good place to stay in Chicago to get to know the music scene of the city since it has venues revolving around blues, rock, and indie, among other genres.

When moving to other neighborhoods and attractions, you can take the elevated metro at Fullerton and Armitage stations.

Lincoln Park is also one of the best areas to stay in Chicago because of attractions such as the Chicago History Museum and the Riverpoint Shopping Center.

Best areas to stay in Chicago - Lincoln Park
Best areas to stay in Chicago – Lincoln Park
Accommodation in Lincoln Park - Click on the map to see all available accommodation in this area
Accommodation in Lincoln Park – Click on the map to see all available accommodation in this area

Why is this a recommended area to stay in Chicago, Illinois:

  • Green areas
  • Concerts
  • Great food

5. West Town

The West Town of Chicago is located, as its name indicates, west of the Old Town and is a district full of life and charm, ideal for young travelers.

It is one of Chicago’s hipsters neighborhoods par excellence because it has many vintage and second-hand clothing stores, cafes and bars.

West Town is also home to parks like Eckhart Park, with an indoor pool, as well as areas designated to play baseball.

West Town is one of the best areas to stay in Chicago if you want to know the more alternative side of this metropolis.

Public transport options in West Town include elevated metro (blue line) and buses. Likewise, like most of Chicago, it is a very pedestrian-friendly neighborhood.

West Town - Where to stay in Chicago
West Town – Where to stay in Chicago
Accommodation in West Town - Click on the map to see all available accommodation in this area
Accommodation in West Town – Click on the map to see all available accommodation in this area

Why is this a recommended area to stay in Chicago, IL:

  • Hipster area
  • Best area for vintage shopping
  • Eckhart Park

6. Lakeview & Boystown

Lakeview is located in the northern area of Chicago, west of Lake Michigan, and it is precisely its beautiful views of the lake that give it its name.

Within this great district, you’ll find the Boystown neighborhood, famous for being the gay area of Chicago, with many clubs and LGBT-themed bars that make it one of the best areas to stay in Chicago for nightlife.

Lakeview also contains several commercial arteries such as Belmont and Lincoln Avenue that make it a good place to stay in Chicago for shopping.

In the same way, in the surroundings of Lakeview and Boystown, there are different elevated metro stations that make it easier to move to other places in the city.

Another important attraction of Lakeview is the Wrigley Field baseball stadium, home of the Chicago Cubs.

Lakeview - Accommodation in Chicago
Lakeview – Accommodation in Chicago
Accommodation in Lakeview & Boystown - Click on the map to see all available accommodation in this area
Accommodation in Lakeview & Boystown – Click on the map to see all available accommodation in this area

Why is this a recommended area to stay in Chicago:

  • Gay area
  • Good for shopping
  • Wrigley Field Stadium

7. West Loop

West Loop went from being an industrial area to becoming a neighborhood full of life, thanks, in large part, to its well-known Restaurant Row, where you can taste all kinds of dishes.

This neighborhood, which is located southwest of the Old Town, is also home to the Chicago French Market and Randolph Street Market, which make it one of the best areas to stay in Chicago, as there is always something to see and to do here.

As far as public transport is concerned, West Loop has metro stations such as Morgan and Clinton, in addition to the Ogilvie Transportation Center, from where you can catch commuter trains.

West Loop is also famous for its nightlife, with bars and clubs for all types of audiences.

The accommodation options at Chicago’s West Loop are suitable for all types of budget and include luxury-type hotels, apartments and hostels.

Mary Bartelme Park - West Loop - Best areas to stay in Chicago
Mary Bartelme Park – West Loop – Best areas to stay in Chicago
Accommodation in West Loop - Click on the map to see all available accommodation in this area
Accommodation in West Loop – Click on the map to see all available accommodation in this area

Why is this a recommended area to stay in Chicago, Illinois:

  • Restaurant Row
  • Wide variety of hotels
  • Ogilvie Transportation Center

8. South Loop

South Loop is one of the best areas to stay in Chicago if you are looking for a quiet place to stay, but without sacrificing a good location, as this mostly residential area is near the Chicago Loop or Downtown area.

Furthermore, the South Loop has many iconic attractions such as the Adler Planetarium, where events and astronomy exhibitions are held, constantly.

Another place to visit in Chicago’s South Loop is the Field Museum of Natural History, with exhibitions dedicated to Aztec and Egyptian culture, dinosaurs, and more.

South Loop connects to the rest of Chicago through metro stations such as Roosevelt and LaSalle Street.

As in most of the city, the accommodation options in South Loop are varied, so choosing a hotel in this area of Chicago will depend on the budget, taste and reason for your trip.

South Loop - Where to stay in Chicago
South Loop – Where to stay in Chicago
Accommodation in South Loop - Click on the map to see all available accommodation in this area
Accommodation in South Loop – Click on the map to see all available accommodation in this area

Why is this a recommended area to stay in Chicago, IL:

  • Peaceful area
  • Field Museum of Natural History
  • Adler Planetarium

9. Chicago-O’Hare International Airport

O’Hare International Airport in Chicago (ORD) is one of the most important air terminals in the United States, in addition to the main hub of United Airlines.

This airport is the main gateway to Chicago and, besides connecting it to other US cities, it also has flights to various international destinations.

Staying in the O’Hare International Airport area of Chicago is ideal for travelers in transit who stop in the city or for those planning a short stay.

Also, going from the airport to other areas of Chicago is easy, because it has its own metro station (blue line), buses and other means of transport.

The surroundings of O’Hare International Airport in Chicago are one of the best areas to stay in Chicago if you have an early flight to another destination.

Best areas to stay in Chicago - Near O'Hare International Airport
Best areas to stay in Chicago – Near O’Hare International Airport
Accommodation near O'Hare International Airport - Click on the map to see all available accommodation in this area
Accommodation near O’Hare International Airport – Click on the map to see all available accommodation in this area

Why is this a recommended area to stay in Chicago, Illinois:

  • Best area for a stopover
  • Connected by public transport
  • Great area for short stays

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