Vacation homes in Chicago

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Vacation homes in Chicago

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top neighborhoods in Chicago

The Loop map

The Loop

The Loop electrifies with skyscraper energy and cultural powerhouses that'll make your neck hurt from looking up. Snap selfies with "The Bean" in Millennium Park or lose track of time at the Art Institute's world-class art collection. The Chicago Symphony Orchestra delivers spine-tingling performances while the rumbling "L" trains create the neighborhood's signature urban soundtrack. Getting around couldn't be easier with multiple train and metro stations connecting you to everywhere worth going. Dining options range from quick lunch spots to upscale steakhouses catering to the business crowd. Hotels tend toward the luxurious side, perfect for travelers who appreciate downtown convenience with a side of architectural wow-factor.

River North map

River North

River North buzzes with Chicago's most vibrant nightlife and foodie scene. Art lovers can explore America's largest gallery concentration outside Manhattan, with everything from contemporary pieces to photography exhibits. The Chicago River offers scenic strolls while Merchandise Mart and swanky shops keep retail therapy within reach. You won't lack things to do in this playground for grown-ups. Upscale hotels and boutique properties dominate the accommodation scene, many with rooftop bars and river views. Getting around is a breeze with three metro stations (Merchandise Mart, Chicago, and Grand) connecting you to the whole city. The neighborhood's grid layout makes walking a pleasure despite the bustling crowds.

Magnificent Mile map

Magnificent Mile

Magnificent Mile dazzles with its canyon of glitzy skyscrapers and luxury flagship stores that make window shopping an Olympic sport. The historic Water Tower stands proudly among modern retail palaces, while Chicago's stunning riverfront beckons just steps away. From rooftop cocktail lounges to celebrity chef restaurants, this stretch delivers big-city energy with a side of architectural wonder. Getting around couldn't be easier with frequent buses, nearby train stations, and super-walkable wide sidewalks. High-end hotels dominate the accommodation scene, putting you right in the heart of Chicago's shopping paradise. Expect a polished, international atmosphere where tourists and business travelers mingle amid the retail magic.

West Loop map

West Loop

West Loop has transformed from an industrial zone into Chicago's culinary playground. Former warehouses now house art galleries and design studios, while "Restaurant Row" sizzles with celebrity chef hotspots and craft breweries. Visitors can explore converted lofts, browse boutique shops, or relax in Mary Bartelme Park between food adventures. Getting around is a breeze with three transit stations including Racine and Clinton on the Green Line. Most attractions sit within easy walking distance along wide sidewalks and bike lanes. Accommodation options feature industrial-chic hotels with exposed brick and modern amenities, perfectly matching the neighborhood's creative energy.

Lincoln Park map

Lincoln Park

Lincoln Park is where Chicago shows off its outdoorsy side with a splash of sophistication. The 1,200-acre park offers everything from a free zoo with 1,000 animals to serene lily pools and a tropical plant conservatory. Locals and visitors alike hit the lakefront trails for morning jogs or grab a volleyball game at North Avenue Beach. Tree-lined streets with gorgeous brownstones give you that authentic Chicago neighborhood feel. Restaurants range from upscale bistros to trendy gastropubs, with most spots requiring dinner reservations. Getting around couldn't be easier with three metro stations and plenty of bus routes crisscrossing the area. Shop the boutiques along Armitage Avenue or catch live performances at nearby theaters for the full Lincoln Park experience.

Top landmarks in Chicago

Chicago and related destinations

Gaze up at towering skyscrapers while cruising the Chicago River on an architecture tour. Snap a selfie at 'The Bean' before savoring deep-dish pizza and catching a Cubs game at Wrigley Field.