10 Coolest Neighborhoods To Stay In Chicago, Illinois, USA - Updated 2024

1. Boystown (from USD 119)

Boystown in Lake View attracts the young and trendy crowd with its party scene, a perfect choice for the young and young at heart. Just a short distance away is the Lincoln Park Zoo, Second City comedy theatre, and the Steppenwolf Theatre. Popular concert venues like the Aragon Ballroom and Vic Theatre are nearby. Lakeview is a perfect choice or those interested in museums, food, and restaurants. When you are there, do consider staying at The Majestic Hotel. Built in the 1920s, the wood-burning fireplace, as well as charming decor, is reminiscent of yesteryears. Guests can enjoy 24-hour cookie and tea, coffee services, as well as free daily breakfast.

2. Magnificent Mile (from USD 132)

The Magnificent Mile, as its name suggests, is a commercial district with big-name luxury brands as its shop tenants. A great neighbourhood to stay for those who want to shop. Many tourist attractions are here, such as the historic Wrigley Building, John Hancock centre, and shopping districts. The Chicago theatre district is also within the vicinity. Cambria Hotel is just five minutes walk from Navy Pier. There is a rooftop bar, but guests can also enjoy the views from their rooms, as every room features large windows with city views. The hotel has a 24-hour fitness centre and tour desk, perfect for midnight travellers.

3. Logan Square (from USD 220)

Logan Square, located within Wicker Park is a place that draws the hipster music lovers, with its trendy, hip music clubs and quirky shops. The United Centre, home of the Chicago Bulls, is a 14-minute drive away from the heart of Wicker Park, which is in Logan Square. Stay in the heart of Chicago’s Wicker Park neighbourhood. Every room at The Robey has hardwood floors, luxurious sheets, and large, open spaces. A TV and a Bluetooth-enabled sound system round up the amenities. Free Wifi is available throughout the property. The Robey is 4.8 km (6 miles) away from shopping, dining, and entertainment on the Magnificent Mile.

4. Uptown (from USD 108)

Uptown is a laid-back residential neighbourhood known for its jazz bars and trendy cafes. Lincoln Park Zoo is about 3.8 miles (6 km) from here, while 360 Chicago is 5.4 miles (8.6 km) away. The nearest airport is Chicago O'Hare International Airport, approximately 13.4 miles (21.5 km) from the area. Uptown Gem is very new and was just built in 2016. The property has a living room with a flat-screen TV, a seating area, and a fully equipped kitchen for your cooking needs. Each room has an air conditioner, balcony and free Wifi.

5. The Loop (from USD 149)

The Loop is a vibrant area with eclectic eateries, shops, theatres and parks. An urban neighbourhood with high-rise buildings, it is home to the Art Institute of Chicago and Millennium Park. For art lovers, The Loop is a great place to stay. Remember to visit the “Cloud Gate” sculpture in Millennium Park. Stay here in The Central Loop Hotel. All guests rooms here have comfortable beds and custom-designed furnishings. If you stay in The Loop, you stay in the middle of all activity. A perfect choice for those who prefer to walk to the attractions.

6. Chinatown (from USD 95)

If you need Asian food or just want to be in the vibe of Chinatown, then pick Chicago’s Chinatown. The Cermak-Chinatown subway serves the neighbourhood, and attractions here include the Chinese American Museum of Chicago and the outdoor mall Chinatown Square. If you want to stay in the area, check out Chinatown Hotel, which is near the subway stop. Restaurants and shops are located nearby, and each guestroom has cable TV, air conditioning and Wifi access.

7. Bridgeport (from USD 479)

Bridgeport is a peaceful residential neighbourhood lined with shops and restaurants. One of the city’s most diverse neighbourhoods, it has a reputation for a multinational variety of cuisines. McCormick Place and the Illinois Institute of Technology is in the vicinity. The Polo Inn is a bed and breakfast that you can consider staying in; each suite has a flat-screen cable TV, free Wifi access and a full-size fridge. The home of White Sox (baseball) is at the U.S. Cellular Field, just three minutes’ drive from this hotel.

8. Roscoe Village (from USD 390)

Another laidback neighbourhood, Roscoe Village is on the north side of Chicago and is a collection of pubs, taverns, independent shops and brunch restaurants. A suburban area, staying here feels like you are staying right amongst the locals! Lincoln Park Zoo is 3 miles (5 km) away, while United Center is 5 miles (8 km) from the borough. The nearest airport is Midway International Airport, which is 14.9 miles (23 km) away. Roscoe Village Guesthouse is set in the Roscoe Village of Chicago, and all units have a fully equipped kitchen with a dining area. Guests will also appreciate the bath and shower facilities with free toiletries. Free Wifi is available throughout the property.

9. Lincoln Park (from USD 159)

Lincoln Park is situated along Lake Michigan, which makes it literally the coolest neighbourhood for the windy breezes. It keeps you feeling refreshed throughout the day. It is home to many tourist attractions such as nature reserves, harbours, beaches and, of course, recreational areas. The recreational facilities that you have access to are basketball courts, soccer fields, target archery fields, a driving range, a skate park, boating facilities and much more.

If you like Victorian-style furnishings, then the ‘Inn at Lincoln Park’ with its old-world charm should be your best pick.

10. Wicker Park (from USD 27)

Wicker Park with its eclectic shop offerings is a great choice for those who prefer to stay off-the-beaten-track. Bars, cool restaurants, trendy pubs line the streets here. The Willis (Sears) Tower and the Chicago city centre are a 20 minutes’ train ride away from Division Street, the heart of the Wicker Park neighbourhood. Holiday Jones Chicago Hostel on Division Street is a chic hotel to stay in, with each room featuring artwork created local Chicago artists. The hotel’s onsite restaurant provides for your dining needs, or visitors can relax at the lounge.

Chicago, 'The Great City' - a landscape of architectural wonders

Chicago has many nicknames, amongst them is the nickname ‘The Great City.’ Indeed, this city at the heart of USA’s transportation network is a great place to start if you’re visiting the United States. Whether you are in the state to watch its many sporting games, or just here to explore its architectural landscape, the hotels above would be sure to provide you with a comfortable stay.