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 to stay in an average chain hotel or rolling the dice on an Airbnb, stay at one of our favorite boutique hotels in Chicago, and make your next visit extra special.
1. The Guesthouse
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.
2. 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.
3. 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.
4. The Robey
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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.
5. Ivy Boutique
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.
6. The Dana
If you’re looking for the ultimate in style in the heart of the bustling River North neighborhood, The Dana Hotel and Spa is the perfect place to stay in Chicago. While the 216 rooms are more than the typical boutique hotel, the industrial style and pure class of this hotel definitely give the feel of a smaller luxury property.
7. The Alise
If you want to stay downtown near Millennium Park, the Theater District, and the shopping while really steeping yourself in classical Chicago, you need to check out The Alise. This boutique hotel is in a restored 1895 building designed by Daniel Burnham — the architect and city planner responsible for a lot of the initiatives that have made Chicago the city it is today. It’s a gorgeous building, and the modern renewal ensures every modern need and comfort is met.
8. Soho House
Soho House is an exclusive private members’ club based in London with locations around the world. Most branches have rooms that members are able to use but that the public can also rent as hotel rooms, and the Chicago Soho House is no exception. Staying in this hotel is like becoming a temporary member of an exclusive club, and it’s a pretty cool club, too. Members are typically artists and creative directors, not lawyers and stock brokers.