Hotels in Chicago, IL

Best places to stay in Chicago

Some of the tallest buildings in North America, the starting point of the historic Route 66, the home of the Chicago Cubs (Wrigley Field), a Broadway in Chicago show, or simply to take a selfie with The Bean—no matter why you come to visit and what you want to see and do, Chicago promises to be a trip like none other. It is by no means a small city, however. In fact, the United States Census Bureau ranks it the third largest city in the U.S. housing more than 2.5 million residents. Chicago has branched out into 77 separate community areas and spans more than 200 square miles. On your visit to what is popularly known as the “Windy City”, you will find it useful to be aware of the essential six “sides” and then decide on the perfect place to stay.

North Side

The North Side is the most popular for newcomers to the city. This part of Chicago has the River North region, trendy restaurants and clubs, and an upscale area for nightlife. It is also home to the LGBTQ community and the Lincoln Park neighborhood. Hotels on the North Side worth considering include Loews Chicago Hotel, Kimpton Hotel Palomar, and the AC hotel by Marriott Chicago Downtown.

South Side

The South Side is the adopted home of former US president, Barack Obama. It is also home to the Chicago White Sox baseball team, the historic areas of Chicago’s downtown, and colorful Chinatown. Here you find more upscale hotels, including Hyatt Regency McCormick Place and the Chicago South Loop Hotel.

West Side

Wicker Park is technically part of the West Side, but some North Side residents claim ownership too. Also, the infamous Humboldt Park and the Puerto Rican neighborhoods reside on the West Side. Within walking distance, you have the Garfield Park Conservatory, and you can easily walk to the Green Line L. However, most tourists tend to avoid staying on the West Side; instead, they prefer to visit during the day.

Far South Side

The Far South Side is another unique neighborhood that has the Historic Pullman Foundation. The area is known for being a utopian workers’ community, but still has some areas that are not recommended for tourists. Therefore, as a tourist, you are unlikely to find too many suitable hotels here. You are better off staying on the outskirts at hotels like The Wheeler Mansion or the Best Western Grant Park Hotel.

Northwest and Southwest Sides

These areas are predominantly residential, but you can tour the neighborhood to see beautiful, historic brick homes built in the early 1900s. The neighborhoods are a melting pot of ethnic backgrounds and home to some excellent eateries. Hotels on the Northwest side include Renaissance Chicago O’Hare Suites by Marriott Hotel, Hilton Chicago O’Hare Airport, Chicago Marriott O’Hare, Best Western Plus Hawthorne Terrace Hotel, and The Guesthouse Hotel. On the Southwest Side, you can find hotels sprinkled along the route to and from the airport, including Quality Inn Midway Airport, Hyatt Place Chicago Midway Airport, and Holiday Inn Express & Suites Chicago-Midway Airport.

Cheap hotels in Chicago

Budget-friendly hotels are throughout downtown and the outskirts. When looking for the best place to stay in Chicago that will not cost too much, there are a few options available for under $100 per night. Raffaello Hotel is an upscale 4-star hotel, but extremely affordable. Also, the Hotel Felix is a chic, budget-friendly stay at a unique structure with reclaimed wood and metal used in the construction. Congress Plaza Hotel offers a comfortable stay and is conveniently located downtown.