Where to Stay in Chicago

One  of the most common questions asked by visitors to Chicago is: where should I stay? The answer, of course, depends on several factors.

  • Do you plan to spend most of your time downtown or are you coming in for a specific event, like a business meeting near the airport or a Cubs game at Wrigley Field that you need to stay closer to?
  • Will you be traveling with a car (parking downtown is very expensive) or relying on public transport?
  • Is price a bigger concern than location?
  • Are you celebrating a special occasion, traveling with kids, or visiting with a large group?

Here are some considerations, pros and cons, for each area of the city.

Near O’Hare and Midway Airports

If you’re coming in for business and plan to spend most of your time near one of the airports, it makes sense to stay near O’Hare or Midway. Hotels in the area are just a few moments from each airport, and if you do find yourself with some free time to sightsee, you can be downtown in 30-45 minutes. But if you’re coming in as a tourist, don’t stay near the airports. You’ll miss out on so much of the Chicago experience, and spend so much time in transit that it’s not worth it to stay outside of the city.

>> Find hotels near O’Hare
>> Find hotels near Midway

Near Wrigley Field

This decision isn’t as cut and dry as whether to stay near the airport. If it’s your first time to Chicago, and/or you plan on spending a lot of time downtown, you’ll probably get more out of the experience if you stay in the more touristy areas. Wrigley is only about 20 minutes from downtown, right up the Red Line, so it’s easy to get to on game day. There are lots of restaurants, bars and shops in the area, which has a true neighborhood feel, but if it’s your first visit to the city, you’ll want to spend more of your time downtown, immersed in the city.

On the other hand, if you have visited Chicago before and want to see another side of the city, or if you are just coming in for the game, it makes sense to stay closer to the Field. There are a few hotels in Lakeview and some just a few blocks south in Lincoln Park. They are all within walking distance (less than 10 minutes) or just 1-2 stops away on the Red Line.

>> Find hotels near Wrigley Field

The Loop

The Loop is roughly defined as the area south of the Chicago River, north of Congress, west of the Lake and east of the River. Confusing? A little, but that’s because the River takes a hard left, turning 90 degrees before flowing south. Take a look at the map and it becomes a little more clear. The central business district of Chicago, the Loop is so named for the “loop” made around it by the el tracks. There are several great hotels in the area and it’s one of the most popular places to stay in the city. Hotels here are close to the major attractions of downtown, very close to public transportation (buses and a variety of el lines) and offer easy access to dining and drinking, shopping, and theaters.

But  the Loop does have one major drawback: as it’s predominantly a business area, it can get pretty dead at night and on weekends. While it’s close to dining and drinking, there’s not much actually in the Loop (but rather a short cab or el ride or 10-15 minute walk away) and what’s there is much more touristy. There are plenty of quick lunch options and a few happy hour spots that cater to workers, but after 6pm, there’s not much going on. So, if you’re going to Chicago and don’t need to be in the heart of the action, or don’t mind putting in a bit of effort to get to where the action is, it’s a great places to stay.

The South Loop, the area just off Grant Park between Congress and Roosevelt is equally nice (and equally quiet) with several hotels that offer excellent proximity to the Museum Campus.

The Magnificent Mile

When you think of Chicago – glittering skycrapers towering overhead, bustling streets, larger than life window displays in luxury boutiques – that image you’re seeing is of the Magnificent Mile, the stretch of Michigan Avenue that runs from the Chicago River to Oak Street, from the historic stone Wrigley and Tribune Buildings, past the iconic steel Hancock Tower and dozens of famous name designer shops. The sidewalks here are always clogged with tourists laden with bags from Hershey’s and American Girl Place, street performers, office workers, and locals all trying to get through.

Luxury high-rise hotels like the Peninsula and the Ritz Cartlon line the Mile and the side streets that connect to it. If you want to have that fabulous Chicago experience you’ve been dreaming of, Michigan Avenue is the place to stay. Staying here puts you close to lots of great (though pricey) restaurants, excellent shopping, and easy access to the museums and landmarks like the Hancock Building and Millennium Park. To head north to Lincoln Park, you can catch a bus or walk to the Red Line, the Loop and River North are each a short walk away, and downtown serves as a hub to get you anywhere else easily. The downside: hotels here can be a bit more expensive.

>> Find hotels on the Magnificent Mile

River North

The area north of the river (clever, eh?) and west of Michigan Avenue, roughly between State and Orleans, is known as River North. Home to great restaurants, unique shopping, independent art galleries, and some of the city’s trendiest nightclubs, it also offers several excellent value lodging options, like the eco-friendly Hotel Felix. Here you’ll find some of Chicago’s most iconic restaurants, like Gene and Georgetti’s, Lou Malnati’s, and Portillo’s.

You’re a bit removed from the action of Michigan Avenue here, but there’s more happening at night here than in the loop, so it’s a great compromise. You’ll never be too far from a Red or Brown Line stop in this area, and it’s an easy walk to the Magnificent Mile or Loop, so it’s easy to get around to the rest of Chicago as well.

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