Perched on the shores of Lake Michigan, the Windy City has long been a popular destination for travellers from within the United States and beyond. The third-largest metropolis in the country, it’s a thriving sports, culture and foodie hub, with stacks for visitors of all ages to enjoy. Catch a game at Wrigley Field, saunter along the Chicago Riverwalk, admire the Art Institute of Chicago’s spectacular collection, and tuck into delicious deep-dish pizza. Whether you’re travelling solo, as a couple or with family and friends, our selection of top boutique hotels in Chicago is the perfect starting point for planning a trip to remember.
West Loop Show the map
140 rooms 
Wicker Park Show the map
69 rooms 
Old Town Show the map
8 rooms 
The Loop Show the map
122 rooms 
The Loop Show the map
241 rooms 
Uptown Show the map
25 rooms 
Magnificent Mile, River North Show the map
280 rooms 
West Loop Show the map
159 rooms 
Gold coast Show the map
285 rooms 
The Loop Show the map
403 rooms 
Chicago Show the map
400 rooms 
Chicago Show the map
193 rooms 
Chicago Show the map
191 rooms 
Chicago Show the map
164 rooms 
Chicago Show the map
567 rooms 
Chicago Show the map
160 rooms 
Chicago Show the map
365 rooms 
Chicago Show the map
218 rooms 
Chicago Show the map
415 rooms 
Chicago Show the map
139 rooms 
Chicago Show the map
7 rooms 
Chicago Show the map
339 rooms 
West Loop Show the map
100 rooms 
River North Show the map
98 rooms 
Wicker Park Show the map
9 rooms Originally a tiny trading post at the mouth of the Chicago River, Chicago is now a bustling metropolis with a glittering skyline including some of the world’s very first high-rises. Begin your journey at Millennium Park, home to the striking Cloud Gate sculpture, nicknamed ‘the Bean’, and offering sweeping city views. The Chicago Riverwalk, too, promises an unmatched parade of heritage and contemporary architecture. Out on Lake Michigan, the Navy Pier offers family-friendly fun, and boat tours are wonderful.
Delve into Chicago’s cultural history through Frank Lloyd Wright’s home and studio, the fascinating Ernest Hemingway Birthplace Museum, and the street murals of the colourful Pilsen district. The Art Institute of Chicago houses a dazzling collection, with pieces from artists ranging from Grand Wood to George Seurat, whilst the Garfield Park Conservatory stuns with its botanical beauty.
The city’s blues and jazz heritage runs deep, too. Catch live gigs at legendary venues including Kingston Mines and Andy’s Jazz Club for a real sense of Chicago’s soul. Shows at the Steppenwolf Theatre come highly recommended, whilst little compares to the roar of the crowd when the Chicago Cubs play at Wrigley Field.
No visit to Chicago is complete without at least one deep-dish pizza. Lou Malnati’s and Giordano’s top the list when it comes to classic eateries, whilst neighbourhood stands specialise in Chicago-style hot dogs, complete with mustard, relish and peppers; never ketchup! If you’re keen to dress up for dinner, trendy West Loop has a brilliant buzz.
To stay close to major attractions and the famed Chicago Riverwalk, base yourself in the Loop or River North, the city’s bustling downtown district. Expect excellent transport links, upscale hotels and a great evening vibe, too.
For a more laid-back residential feel, consider the tree-lined streets of Lincoln Park. Very well-connected, this neighbourhood is a family favourite. The Chicago Zoo and Lincoln Park will be sure-fire hits with the kids.
Hip and artsy travellers should make a beeline for Wicker Park and Bucktown, with their easygoing atmosphere, independent coffee shops, vintage shopping and live music scene. There are a burgeoning crop of reasonably priced hotels in the neighbourhood, but this area continues to focus on its residents, offering a perfect insight into local Chicago life. Creatives on a budget should also look to the increasingly popular Logan Square.
Lovers of luxury, on the other hand, will find high-end boutiques and grand hotels on the Magnificent Mile. An upscale stretch of Michigan Avenue, this area has long been home to some of the city’s most storied hotels, and continues to be associated with glamour and opulence.
Rebuilt following the infamous 1871 fire, Chicago boasts an abundance of classic Beaux Arts, Art Deco and Gothic Revival buildings, as well as soaring steel-framed skyscrapers. Big, bold and designed to impress, many of the top boutique hotels in Chicago are housed in striking Art Deco towers, dating back over a century. Featuring lavish lobbies and bars, complete with geometric decor, polished metalwork and mosaics, these hotels combine timeless glamour with all the 21st century mod-cons. Expect expansive gyms and soothing spas, gourmet eateries and superb event spaces in larger hotels.
Chicago is a city of distinct neighbourhoods, and most hotels, large or small, are eager to highlight their district through guided walking tours, bicycle rides and hosting regular entertainment. Speak to their teams in advance to find out what’s on during your visit.
