Best hotels in Chicago 2020: top places to stay in the Windy City

Chicago, Illinois is one of America’s biggest cities. Known as the Windy City, due to sitting on the edge of Lake Michigan, Chicago is made up of soaring skyscrapers and a rich cultural and artistic history, with something for everyone. 

From museums to neo-Gothic architecture, this certainly is a city with character, and our hotel guide will advise you on where is best to stay depending on what experience you want from Chicago, and there are plenty to choose from!

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Where to stay in Chicago?

Downtown Chicago is a popular area; the bustling business district with towering skyscrapers and lively nightlife, whereas the Gold Coast provides a much more chilled vibe as it’s by the beach. 

The Thompson is just a two-minute walk from the beach and you’re in a prime location to explore the best of Chicago. Stay here for great shopping, history museums and pretty views. 

Other great shopping areas include the Magnificent Mile and there are plenty of parks for when you want to sit down and chill in the sun. If you want to discover some of Chicago’s hippest bars and restaurants, then River North is home to some of the best craft cocktails, coffee, and delicious food. 

Check out our list below of some of the best hotels in Chicago. From luxurious spa hotels to swanky hotels with rooftop bars; these hotels all have something unique and special about them.

The 9 best hotels in Chicago

With its laid-back style and quirky décor, this building from the 1920s is one of the coolest places to stay in the city, not to mention the friendliest. 

If you’re passing through the windy city solo, then Freehand Chicago is a great place to meet like-minded travellers. Located in Chicago’s River North, a hip part of the city, you can check out some of the coolest bars with crafted cocktails or simply mingle in the hotel’s very own Café Integral – serving up some of the best coffee as well as adult beverages.

Those travelling on a budget or simply wanting hostel vibes can opt for a shared dorm or a private room is still very reasonable. Staff are said to be incredibly friendly and willing to give you tips on exploring the city, and you’re only a short walk away from other popular locations such as the Magnificent Mile.

It’s hard to say whether this hotel should be best for luxury or location. Not only is the building itself stunning, but it is in a prime location, with just a short walk to the beaches and main attractions. During your stay you’ll receive complementary daily newspapers, and access to their 1,000 square ft fitness centre. 

The hotel restaurant is said to offer homemade dishes such as pasta and local seafood, as well as a sophisticated cocktail menu for you to enjoy your evenings in this city. A must for those who want to indulge during their stay.

For scenic views of both Lake Michigan and the skyline, The Gwen is the perfect place to stay. Within 12 minutes reach of the beach by foot, and a rooftop terrace, you can soak up the Chicago atmosphere with cocktails both day and night. 

The rooms are spacious and luxurious; coming equipped with TV, fully stocked mini-fridge and a bathroom full of products. It’s a great place to stay for both business and pleasure, as you’re only a short distance away from Chicago’s theatre district, providing show-stopping entertainment of an evening. Photographers will also love the panoramic views you can get from the roof.

This swanky boutique hotel offers sophisticated rooms, filled with luxury bath products, iPod docking stations and TVs, as well as a stunning rooftop bar serving Latin inspired cocktails. It’s located in the heart of the city, and the hotel itself is a pretty impressive skyscraper. 

The Gray is in a fabulous shopping location for that looking to splash the cash, but what really makes this little boutique so unique is its free bike tours and a complimentary wine hour! What a great way to explore the city and wind down after a busy day.

Who says going away with the kids has to be cheap and cheerful? The Langham Hotel offers pure luxury with a family-friendly atmosphere, good food and easy access to all the best parts of the city. 

Floor-to-ceiling windows provide stunning views, and the hotel restaurants serves up traditional American dishes that the kids will love. If you fancy having a relaxing day, there is a spa where you can treat yourself to a massage while the kids play in the pool. You’ll have so many options here that none of the family will get bored.

When you walk into the Waldorf Astoria, it looks like an art gallery. With high ceilings and marble everywhere, the atmosphere is cool and elegant and it seems like it’d be easy to relax. The rooms are grand, with bathrooms you’ll want to spend more time in than the city itself. 

Plus you’ll get complimentary Nespresso machines and a chauffeur who will take you within a two-mile radius which makes getting around the city easier than ever. The French restaurant offers authentic dishes and an extensive wine list, so if traditional American dining isn’t for you, you’ll find this hotel a nice change of scenery.

If you want to stay in Chicago like a high-flyer, then there’s nowhere more apt than Richard Branson’s Virgin Hotel. Located in The Loop district, this hotel is artsy and quirky, and the “chambers” are plush and luxurious and you’ll find music playing throughout the hotel, making it a fun and lively place to stay. 

It oozes twenties luxury, with a sense of grandeur both inside and out. Sip cocktails on the rooftop or chill out in your suite which has a dressing room and even a bed for your dog should you wish to bring them along for the trip.

If you fancy something a little bit different, then the Peninsula provides a modern hotel with an Asian twist.  The Asian-inspired spa is a great place to relax and unwind, while the hotel serving champagne and chocolates is also a welcome treat after a long day of sight-seeing. 

If you’re sick of pizza and burgers, head down to the Shanghai Terrace for some fantastic authentic Chinese food. This restaurant is voted the “number one Chinese restaurant in Chicago”. The half Olympic swimming pool is impressive just to look at, and the floor-to-ceiling windows make going for a dip a spectacular event.

With 92 floors of sleek and modern steel and rooms bigger than some people’s homes, some may find, like Trump himself, this hotel a little bit OTT. You’ll have a fully equipped kitchen including dishwasher, stove and Nespresso machine, as well as a bathroom complete with Swarovski crystal accents, a TV in the mirror, and floor to ceiling windows with the most epic of views. Would you expect anything less? Certainly not for the price, which starts at around £300 a night for King Room. 

Location is ideal for nightlife, with all the top bars, restaurants and clubs in the surrounding area, or for a more relaxing stay, the hotel comes complete with heated pool, spa and a two-Michelin star restaurant. The Terrace is also great for dining alfresco in the summer months and watching the world go by.

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