When you visit a one-of-a-kind city like Chicago, it only makes sense to stay in a hotel that reflects the town’s unique character. Rather than paying a premium for an average hotel or rolling the dice on an Airbnb, book one of the very best Chicago hotels and make your next visit extra special. Here are some of the top places to stay with outstanding service, location, and facilities.
Photo: Expedia
10 Outstanding Chicago Hotels Within Walking Distance to Must-See Sights
We hope you love the Chicago hotels we recommend. Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
The Peninsula Chicago
This five-star hotel is half-block from Michigan Avenue shopping and the historic Water Tower and offers 339 luxurious rooms and suites with stunning views of Lake Michigan, the Chicago skyline, and the surrounding area. Depending on your budget you can choose from deluxe rooms, grand deluxe rooms, executive suites, and presidential suites — the latter often being occupied by celebrities or other VIPs. Expect first-class service including an outstanding concierge team that can arrange tickets to sporting games or city tours.
The Peninsula Chicago: 108 East Superior Street, Chicago, IL, 60611
Price per night: $975
The Langham, Chicago
If you have money to spend, it doesn’t get better than The Langham. The downtown five-star location is ideal. It sits on the Chicago River, just north of the Loop, 10 minutes away from Millennium Park and River North restaurants, bars, and nightclubs. The hotel resides in an office building designed by legendary architect Ludwig Mies van der Rohe and feels like a lavish museum with its extensive art collection. Guests can enjoy breathtaking views of the city skyline from the 52-story landmark tower or bask in natural light that streams through the floor-to-ceiling windows. Langham’s destination-worthy dining means booking a table in advance at Travelle Kitchen + Bar a must. And for those looking for something extra special, the hotel also offers exclusive packages such as afternoon teas and romantic occasions — everything and anything is possible at this spectacular hotel.
The Langham, Chicago: 330 North Wabash Avenue, Chicago, IL, 60611
Price per night: $645
Thompson Chicago
Thompson is located in the heart of Chicago’s historic Gold Coast district. With its prime location, guests are just steps away from Michigan Avenue and downtown’s finest dining, swanky nightlife, and designer shops. Its style is casual luxury and the service is polished. There are 247 rooms with floor-to-ceiling windows with city views (throughout) and lake views (in the elevated rooms.) The restaurant and bar are run by the award-winning chef Paul Kahan who serves a menu of rustic Italian seafood and pasta. Again this is another hotel with a destination restaurant, so it’s recommended to book in advance.
Thompson Chicago: 21 East Bellevue, Chicago, IL, 60611
Price per night: $409
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse is housed in a stunning high-rise building that was built in the 1920s and overlooks the beautiful Chicago River. It’s located at the start of the Magnificent Mile, just a five-minute walk from the John Hancock Center and Lake Michigan. There are two restaurants onsite — LH Rooftop Bar & Grill and LH on 21 — serving delicious American cuisine with breathtaking views of the city skyline.
LondonHouse Chicago, Curio Collection by Hilton: 85 East Wacker Drive, Chicago, IL, 60601
Price per night: $400
Hotel Lincoln
Chicago is known for its unpretentious style and simple Midwestern charm. For a hotel that reflects these qualities, look to Hotel Lincoln, the local outpost of boutique hotelier Joie de Vivre. Besides the fantastic location in the heart of Lincoln Park, the hotel offers fun, quirky perks like free bicycles to take out to the nearby Lakefront Trail. As an added bonus, this Chicago boutique hotel is pet-friendly.
Hotel Lincoln: 1816 N Clark Street, Chicago, IL, 60614
Price per night: $299
Kimpton Hotel Monaco Chicago, an IHG Hotel
With its unique architecture and playful design features, Kimpton Hotel Monaco stands out as one of the most beautiful hotels in the city. The hotel offers a range of rooms for all, from standard guestrooms to spacious suites with stunning views of the city skyline. There’s a variety of amenities including an on-site spa offering relaxing treatments and massages, a 24-hour fitness center with state-of-the-art equipment, and a heated indoor pool. Its location is unbeatable. It’s walking distance from all things a tourist and business traveler could want from a stay in Chicago.
Kimpton Hotel Monaco Chicago, an IHG Hotel: 225 N Wabash Ave, Chicago, IL, 60601
Price per night: $259
Ivy Boutique Hotel
If you want to stay near the Magnificent Mile but don’t want the usual big, boring downtown hotel, Ivy Boutique Hotel is the perfect balance of boutique originality and prime location. With only 63 rooms over 16 stories, just steps away from the shopping of Michigan Avenue, Ivy gives you a great base from which to explore the city. At the end of a long day exploring the city, you can unwind with spa services or enjoy a drink with a view from the 16th-story Ivy Sky Terrace.
Ivy Boutique Hotel: 233 E Ontario, Chicago, IL, 60611
Price per night: $218
The Robey, Chicago, a Member of Design Hotels
Towering over the intersection that is the beating heart of Chicago’s trendy Wicker Park neighborhood, The Robey is one of the city’s best boutique hotels. The 89-room hotel is set in a late-1920s Art Deco skyscraper that has been restored in a way that preserves its heritage while introducing modern comforts and convenience. The rooftop terrace with its small but nice pool gives you panoramic views from high above all the surrounding buildings and on to the downtown skyline.
The Robey, Chicago, a Member of Design Hotels: 2018 W. North Ave., Chicago, IL, 60647
Price per night: $207
The Guesthouse Hotel
Chicago is a city of neighborhoods, and to really experience it you need to get out of downtown and into those neighborhoods. The easiest way to do that is to actually stay in one of them in the first place. The Guesthouse is a great hotel located in the Andersonville neighborhood. The rooms here are all suites that have kitchens complete with all the cookware and utensils you could need to feel at home in Chicago. The most Chicago touch of all, though, is the barbeque grills that come standard on the balconies of the rooms. If you’re grilling a brat on the balcony, you’re doing Chicago right.
The Guesthouse Hotel: 4872 N Clark St, Chicago, IL, 60640
Price per night: $165
Freehand Chicago
If we told you that Freehand Chicago has a hostel-style quad room with two separate bunk beds that sleep four people, you would probably assume that it was not actually a hotel. Yet it is — and a very stylish one at that. Freehand has more traditional hotel rooms, as well, and penthouse suites are available for the high rollers. But there is one other thing it borrows from the hostel scene: the idea that travelers can be a part of a community with one another. Don’t worry, though; this is definitely not a flip-flops-needed-in-the-shower kind of accommodation. 
Freehand Chicago: 19 East Ohio Street, Chicago, IL, 60611
Price per night: $125