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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.
Consider a stay at the Thompson Chicago to explore the city’s Northside and enjoy sleek sophistication when you return to your hotel at the end of the day. This popular boutique hotel in Chicago is near Michigan Avenue, Oak Street Beach, and lots of great restaurants. You can enjoy beautiful views of Lake Michigan from the rooms here, and the on-site restaurant Nico Osteria specializes in delicious Italian and seafood cuisine.
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.
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.