Chicago is a city of neighborhoods, each with its own unique charm, and that means you’ve got a decision to make about where to stay when you visit. Like anywhere else, there are some incredible options and some that should be avoided at all costs, and your budget is less a factor in that than you might think. Because the city is so big, if you’re visiting and plan to spend a lot of time in specific neighborhoods, it’s worth trying to find a place to stay near there. The city has good public transit, Uber and Lyft, and e-scooter and bike-sharing programs, so it’s also not too hard to get around. Every day of your visit begins and ends in your accommodation, so it’s worth choosing somewhere you’ll love. Here are some of our favorite places to stay in Chicago.
The Robey — This boutique hotel set in a 1920s Art Deco building sits right at the heart of Wicker Park, one of the city’s most happening neighborhoods. The hotel has two restaurants and a cocktail bar on the roof that also has a small pool and some great views over the city. When staying here it will be hard to decide between those options and exploring the neighborhood that’s packed with great bars, restaurants, and clubs.
Hotel Chicago West Loop — This hotel is near enough to Downtown to make for a great base to explore from, 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 to the fantastic dining in the West Loop. The nearby Green, Pink, and Blue Line trains will easily get you anywhere else you need to go.
River Hotel — 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 hotel for travelers who want a downtown hotel with all the amenities but aren’t quite ready to pay that full luxury price. Free coffee, water bottle fills, Wi-Fi, and self-service laundry also help save you money and set it apart from most other nearby hotels that seem to charge extra for everything.
The Langham — The Chicago River by Wabash Avenue is one of the city’s most scenic spots, and it’s the exact location of this stunning hotel. The Langham is a design-forward hotel with a standard of quality and luxury that’ll impress any traveler. Aside from the views, the location is also a perfect base for exploring Downtown, the Magnificent Mile, or getting out into the neighborhoods. The setting in a high-rise, designed by legendary Chicago architect Ludwig Mies van der Rohe, only adds to the local charm.
The Ivy — The Ivy is one of Chicago’s smallest boutique hotels, and one of its best. The 16-story building in Streeterville has just 63 rooms and suites. It could have more, but the rooms are huge — nearly double the size of an average room in other hotels. While the rooms feel more like a private residence, the rest of the property has everything you’d expect from a luxury hotel. The location in Streeterville just steps away from the Magnificent Mile adds to the draw.
Staypineapple Chicago — Chicago is the birthplace of the skyscraper, and the 1895 Reliance Building is one of the most striking early examples. Staypineapple has retrofitted the vintage space with modern luxuries and amenities to create one of Chicago’s most beautiful and unique hotels. This National Historic Landmark is also located under a minute away from Millennium Park, making it possibly the single best hotel from which to explore downtown Chicago.
Freehand Chicago — Freehand is a hostel set in a three-star hotel, and you’re sure to be in a beautiful, design-centric 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.
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.
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.
Castle on Berwyn — This two-bedroom house is on the National Register of Historic Places and has been delightfully filled with Baroque, French, and Rococo antiques to complement the original stained-glass windows. The setting in the lovely Andersonville neighborhood makes it a great place from which to explore the city, and it’s actually an incredibly affordable option for Chicago accommodations.
Historic greystone home one block from Wrigley Field — If the squad is rolling deep, this five-bedroom house is the perfect place to stay. The classic Chicago home is stylishly appointed and equipped with everything you’ll need for a comfortable and convenient visit. The house has a pool table too, but you might not need it; Wrigleyville is absolutely covered in lively bars and restaurants.
Light filled loft apartment near Downtown Chicago — This converted loft in an old Chicago building will take you back to the city’s industrial past with exposed brick, hardwood floors, and large windows filling the space with plenty of light. The owner has appointed the place with every amenity you could ask for to arrive and feel right at home. The location between Wicker Park and Noble Square is unbeatable for anyone looking to be in a happening Chicago neighborhood, and the Blue Line train just two blocks away runs into the Loop and straight out to O’Hare airport.