Where to Stay

Chicago’s layout forces visitors to think about location more than they might in other major cities. The downtown core sits between Lake Michigan and the river, while many food, music, and cultural hubs sit several miles away in neighborhoods like Logan Square, Pilsen, and Andersonville. Travel times add up quickly, so choosing a hotel near the areas you plan to explore can make your trip run far smoother. The CTA’s trains and buses reach most parts of the city, and both airports connect directly to the “L”. Divvy bikes and scooters help with short hops, especially along the lakefront trail and with those options, you can skip a rental car — but you still benefit from staying near the neighborhoods you intend to visit. Here are some of our favorite places to stay across the city.
 

The best hotels in Chicago

Hotel Chicago West Loop — Hotel Chicago is close enough to downtown to be a great base for exploring, but far enough away to help you save a nice chunk of your budget for restaurants, theater tickets, or whatever else. Hotel Chicago is close to the United Center and fantastic dining in the West Loop. The nearby Green, Pink, and Blue Line trains will easily get you anywhere else you need to go.

Hotel Chicago West Loop: 1622 W Jackson Blvd, Chicago, IL 60612

LondonHouse Chicago — LondonHouse Chicago sits in a 1920s high-rise at the start of the Magnificent Mile, directly overlooking the Chicago River. The central location is unbeatable, as are the rooftop bars with skyline views. The hotel has two restaurants — LH Rooftop and LH on 21 — both offering modern American cuisine with small plates, burgers, cocktails, and full-service dining options. You’re also within a short walk of Lake Michigan, the riverwalk, the Loop, and the John Hancock Center, putting much of downtown Chicago within easy reach.

LondonHouse Chicago: 85 E Wacker Dr, Chicago, IL 60601

River Hotel — Much like LondonHouse, River Hotel has about as good a location as you could ask for, right along the Chicago River between Michigan Avenue and State Street. This is the perfect choice for travelers who want a downtown stay with all the amenities but aren’t quite ready to pay that full luxury price. Free coffee, water bottle fills, and self-service laundry help save money and set it apart from nearby hotels that seem to charge extra for everything. Rooms range from compact singles to larger suites, with some offering river views or small kitchenettes.

River Hotel: 75 E Wacker Dr, Chicago, IL 60601

Staypineapple Chicago — Chicago is the birthplace of the skyscraper, and the 1895 Reliance Building is one of the most striking early examples. Staypineapple occupies this National Historic Landmark at 1 W. Washington Street, retrofitted with modern luxuries and amenities to create one of Chicago’s most beautiful and fun hotels. It’s also under a minute away from Millennium Park, making it possibly the single best hotel from which to explore downtown Chicago. Many of the rooms have large windows that look out toward the Loop or the river — adding even more appeal to the already prime location.

Staypineapple Chicago: 1 W Washington St, Chicago, IL 60602

The Ivy — The Ivy is one of Chicago’s smallest boutique hotels, and one of its best. The 16-story building in Streeterville has 63 rooms and suites. It could have more, but the rooms are large — many are nearly double the size of a typical Chicago hotel room. While the rooms feel more like a private residence, the property includes Sky Terrace — a seasonal rooftop lounge with drinks and light bites — plus a separate indoor bar. Its location in Streeterville is just a short walk from the Magnificent Mile, putting shopping, restaurants, and nightlife within easy reach. Several room categories include suites with separate living and sleeping areas — useful for those traveling with young kids.

The Ivy: 233 E Ontario St, Chicago, IL 60611

The Langham — The Chicago River by Wabash Avenue is one of the city’s most scenic spots, and it’s exactly where The Langham is located. The Langham offers a standard of quality and luxury that will impress any traveler. Aside from the views, the location is a perfect base for exploring downtown, the Magnificent Mile, or getting out into the neighborhoods. The setting in a high-rise designed by the legendary Chicago architect Ludwig Mies van der Rohe only adds to the local charm, and many guest rooms offer direct river views or skyline panoramas.

The Langham: 330 N Wabash Ave, Chicago, IL 60611

The Robey — The Robey is a boutique hotel housed in a 1929 Art Deco tower at the intersection of Wicker Park and Bucktown, two of Chicago’s liveliest neighborhoods. From here you’ll have access to winding streets of vintage shops, street-art alleys, and and plenty of food and nightlife spots. On-site, the hotel has a seasonal rooftop pool bar on the sixth floor. There’s also a separate cocktail lounge on the thirteenth floor with panoramic views. Guest rooms are split between the historic tower and an adjoining loft-style annex, offering a choice between classic high-rise layouts and more open, industrial-inspired spaces.

The Robey: 2018 W North Ave, Chicago, IL 60647

Thompson Chicago — Thompson Chicago is set in the Gold Coast, just off Bellevue and close to Michigan Avenue’s restaurants, bars, and shopping. The hotel has 247 rooms, many with floor-to-ceiling windows, and the higher floors offer partial lake views. The on-site restaurant is run by Chicago chef Paul Kahan, who serves a menu centered on Italian seafood and pasta, and it’s popular enough that booking ahead is a good idea. If you want a comfortable stay in a neighborhood setting rather than the middle of downtown, this is a super place to base yourself.

Thompson Chicago: 21 E Bellevue Pl, Chicago, IL 60611

Hostels

Freehand Chicago — Freehand is a hostel set in a three-star hotel, and you’re sure to be in a beautiful space no matter if you go for a private room or a dorm. The River North location is always jumping, and the Red Line train is just steps away. The Broken Shaker cocktail lounge in the lobby does great food and drinks, and the Monday to Friday happy hour from 4:00 PM to 6:00 PM has some of the best deals you’ll find in the city. Many rooms feature private bathrooms and the building dates to 1927 — placing it in the midst of River North’s historic-meets-modern streets.

Freehand Chicago: 19 E Ohio St, Chicago, IL 60611

Getaway Hostel — Getaway Hostel has a great location for a summer visit to the city. It’s a short walk through the lovely Lincoln Park neighborhood to lakefront parks and beaches. The area has plenty of bars and restaurants, and nearby DePaul University gives the neighborhood a college town feel. The hostel is clean, comfortable, and modern, and has convenient bus routes nearby as well as the Red Line train a 10-minute walk away.

Getaway Hostel: 616 West Arlington Place, Chicago, IL 60614

HI Chicago — HI Chicago is the local outpost of Hostelling International and one of the city’s original hostels. If your main goal is to explore the downtown sights, HI is the perfect place to stash your bag and lay your head. It’s a short walk to Millennium Park and all of the Loop train stations. The hostel has safe and comfortable rooms, as well as stylish common areas for lounging, meeting new friends, and playing pool or ping pong. Shared kitchen space and a game room with a billiards table and table-tennis setup round out the amenities — and private rooms are also available if you don’t want a full dorm experience.

HI Chicago: 24 Ida B Wells Drive, Chicago, IL 60605

Airbnbs

Bright and beautiful Airbnb in Chicago Loop — This Guest Favorite Airbnb offers a bright, comfortable base with an open layout connecting the living area and kitchen. It’s got everything you’d want from a city rental — comfortable beds, a lounge area — and it’s a top 10 percent Airbnb, making it one of the best in Chicago. The location is also a winner, being close to Millennium Park, Cloud Gate, Michigan Avenue, and nearby theaters.

Rock-n-Roll themed Airbnb — Sitting above a busy River North restaurant, this rock-n-roll-themed apartment comes filled with music memorabilia that gives it a personality you won’t find in most downtown rentals. The layout includes a large living room and kitchen, two bedrooms, and two bathrooms, along with high ceilings and a carved canopy bed as a centerpiece. You’re only a few blocks from the Mag Mile and the Loop, and the Brown Line station across the street makes it easy to reach spots like Millennium Park or even Wrigley Field. Free parking is included, and the River North art galleries, dining, and shops are all a short walk away.

Trendy apartment with shared pool — For those who want downtown convenience and a few resort-style perks, this Loop apartment offers both a pool deck and easy access to Chicago’s top sites. The unit is arranged for a couple but can sleep up to four more guests in the living area, and the kitchen has quartz counters and stainless-steel appliances if you plan to cook. This rental is right in the center of the Loop, close to train lines, Millennium Park, and the riverwalk, and the building’s amenities — pool, gym, and lounge spaces — give the stay a hotel-like convenience.

Check out Matador‘s full selection of Airbnbs in Chicago