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Chicago may have one the longest and harshest winter seasons in the country, but when spring rolls around and turns into summer, this is a city that should be on every traveler’s bucket list. Chicago has a vibrant theater scene, an exciting sports culture, and is consistently ranked among the top global destinations for foodies.
Chicago is also a city of unique and diverse neighborhoods, so your Chicago experience varies greatly depending on where you decide to stay and spend your time. From Downtown to the Gold Coast, the North Side, the South Side, and everywhere in between, there are lots of great options for accommodations if you aren’t staying with a local friend.
These are some of the most amazing hotels in Chicago to make your stay in the Windy City unforgettable.
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Located on Wabash Avenue along the Chicago River, The Langham is a highly recommended hotel for travelers who want to be in the middle of it all. Located inside a 52-story high-rise, it’s one of the most romantic hotels in Chicago, less than a mile from the Magnificent Mile shopping area and has a large spa, health club, and indoor pool. This is a great pick for first-time visitors to the city and for travelers who want to spend their downtime relaxing in luxury.
Speaking of luxury accommodations, Waldorf Astoria is a popular Hilton hotel in Chicago. It’s located on East Walton in the Gold Coast neighborhood and a favorite among couples looking for a romantic getaway. The Brasserie is the hotel’s onsite restaurant, and there’s a spa here as well where you can book a massage or take a dip in the indoor pool. There are luxury rooms and suites here and over 19 stories for you to enjoy breathtaking views of the city down below.
Thompson Chicago offers a prime Gold Coast location tucked among historic mansions. A top Chicago luxury boutique hotel, it’s ideal for exploring the Northside, with many of its rooms boasting gorgeous views of Lake Michigan while others offer a view over the city. All come with beds with high-thread-count sheets, flat-screen TVs, robes and slippers, and marble bathrooms. Some have soaking tubs and private terraces too. Fine dining can be enjoyed at the Nico Osteria restaurant, which features an open kitchen with a menu of Italian and seafood. Complimentary luxury car service is also provided.
Another famous hotel in Chicago is The Peninsula, which is situated right along all the shops and restaurants you’ll want to see on the Magnificent Mile. This cosmopolitan and ultra-comfortable hotel is well-known for its spa, which has many treatment rooms and fitness facilities to soothe your aching muscles, relax your mind, and stay in shape. Stop by the hotel lobby bar for afternoon tea during your stay, and the Shanghai Terrace Restaurant serves some delicious Cantonese dishes if you’re in the mood for high-end Chinese cuisine.
The Hyatt Regency Chicago is just a short walk from the Magnificent Mile and offers spectacular views of downtown, the Chicago River, and Lake Michigan. Some rooms come with views of the river or the lake (some of the best lake views in the city), and all feature amenities like flat-screen TVs, minibars, and coffeemakers. There’s a modern fitness center on-site with elliptical machines and treadmills that have private LCD screens and headphones along with multiple dining options, from a steak and sushi restaurant to locally sourced farm-to-table cuisine and handcrafted beverages at the American Craft Kitchen & Bar.
The Blackstone, set within a French Beaux-Arts building, opened its doors well over a century ago. It’s had many well-known guests, including the Astors, Vanderbilts, and at least a dozen presidents from Theodore Roosevelt to JFK and Jimmy Carter. Located near Millennium Park on the “Cultural Mile, this Theater District hotel features rooms that offer Lake Michigan views with standard amenities, including flat-screen cable TVs, minifridges, and marble bathrooms. Some of the suites even include fireplaces. There’s also an excellent 24-hour fitness center and a tapas restaurant popular among locals and guests alike.
Overlooking the Magnificent Mile and one of best Marriott hotels you’ll find in Chicago, the Gwen Hotel offers elegant rooms and suites, nearly all with spectacular skyline views. If you want something unique, a glamping experience is even offered on the 16th-floor suite terrace with views over the skyline. All have big windows, huge flat-screen TVs, and Bluetooth speakers, while suites include Keurig coffeemakers and other upscale amenities. There are excellent dining options, including fine dining on pan-Mediterranean fare at Kostali and a rooftop bar for sipping craft cocktails with a view.
Set along North Lake Shore Drive, the W Chicago offers magnificent Lake Michigan views as well as views of Ohio Street Beach, Milton Lee Olive Park, and the Navy Pier. It has an indoor pool and an excellent 24/7 fitness center with high-end cardio and weight training equipment. Personal trainers are available too. Dining can be enjoyed at the Current Restaurant, while unwinding at the Living Room lobby bar is popular among locals and visitors alike. The stylish rooms feature soft feather beds with 350 thread count Egyptian cotton sheets, pillow-top mattresses, and feather beds. Pets are also welcome at W Chicago for a fee.
Another B&B worth checking out is Chicago’s Wicker Park Inn, which is housed in a traditional brownstone building and is perfect for spending time in the city’s trendy Wicker Park neighborhood. It’s located on a lovely tree-lined block and close to the neighborhood’s best shops and eateries. It’s also just a quick walk away from the Bucktown shopping district, which is known for thrift shops, boutique stores, and fun bars. There are guest rooms available and package deals feature in-room massage, romantic champagne with chocolate, and fresh flowers. You can also stay in one of the spacious apartments for more space and privacy. Full continental breakfast with fruit, pastries, and croissant sandwiches is available for a fee.
Another eclectic and fun neighborhood to check out in Chicago is Logan Square, which is locally known as “hipster central.” If you’ve ever wished that you could just go upstairs above the bar to sleep off that last whiskey flight, then Longman & Eagle is your ideal accommodations pick. There’s an inn that is above this restaurant and bar of the same name, each with local art and creative handmade touches. Be aware that you may hear noise from the tavern down below if you’re calling it an early night.
Another Chicago neighborhood popular with locals and tourists alike is Lakeview, and a good place to stay here is the Old Chicago Inn. It’s located in a historic greystone building and just a few blocks from the legendary baseball stadium, Wrigley Field. Driving and parking around the stadium is a nightmare on game days, so this is a great place to stay for sports fans looking to catch a game while they’re in town. You’re also right by the Belmont “El” stop, which will take you to lots of different places around the city. This is another bed & breakfast, and there’s a bar on site that specializes in classic, prohibition-era cocktail recipes. Guests here enjoy complimentary plush robes, free Wi-Fi, membership to a full gym, and continental breakfast served daily.
Although hostel culture is much bigger in Europe (and even New York City, for that matter), there are also a couple of hostels in Chicago to stay at if you’re traveling on a tight budget. The Chicago Getaway Hostel is located in the popular and busy Lincoln Park neighborhood and has free daily social events, such as pub crawls and brewery tours, to get to know other travelers. Guests enjoy free continental breakfast and free Wi-Fi, and you can even rent bikes. Bike culture is huge in Chicago and a great way to see the city up-close and personal. Standard dorm rooms here accommodate from eight to 12 guests, en-suite dorms from six to eight guests, premium dorms for men-only for up to four guests, and private rooms are available too.
Chicago may be more well-known for its hotels than its B&Bs, but there are still some excellent bed and breakfasts around town to enjoy a city experience away from the towering skyscraper scene. The Benedictine Bed & Breakfast is unique because it is on the grounds of an actual urban monastery where real monks welcome travelers from around the world. This B&B is in the city’s Bridgeport neighborhood, which is southwest of downtown and the museum campus. There’s a garden house apartment (two bedrooms) and a loft apartment (three bedrooms) for guests to stay in. Each morning, loft guests get a fresh, hot breakfast prepared by the monks themselves, while garden house guests can enjoy a self-serve breakfast from the stocked refrigerator.