Chicago

Carousel Images

• Chicago skyline reflected in water

• Chicago River with water taxi

• Chicago cityscape at night

• Aerial view of Chicago lakefront

• Chicago skyline from Lake Michigan

Best areas to stay

• River North

  The best all-around base for first-time visitors. Central, walkable, and packed with dining and nightlife options, River North offers an ideal mix of accessibility and authentic Chicago energy.

• Gold Coast / Near North

  An upscale, quieter neighborhood close to the lakefront with excellent luxury hotel options on or near Michigan Avenue. Perfect for travelers seeking refined elegance.

• Magnificent Mile / Streeterville

  The iconic shopping corridor lined with classic Chicago hotels. Easy access to the Riverwalk and Navy Pier corridor makes this area ideal for sightseeing-focused stays.

• West Loop / Fulton Market

  Chicago's "food capital" with a trend-forward restaurant scene. Home to James Beard Award winners and upscale boutique stays for the culinary-minded traveler.

• The Loop

  Best for museums, architecture, and daytime sightseeing. The historic downtown core offers cultural attractions but can feel quieter after business hours.

• Lincoln Park

  Leafy, classic neighborhoods alongside parks and the free Lincoln Park Zoo. Ideal for travelers seeking a more residential, refined atmosphere away from downtown bustle.

Food neighborhoods

• West Loop / Fulton Market

  High concentration of destination restaurants from Michelin-starred establishments to trendy newcomers.

• River North

  Classic steakhouses, sophisticated cocktail lounges, and buzzy dining destinations.

• Logan Square

  Chef-driven, trend-forward restaurants with a creative, neighborhood feel.

• Pilsen

  Authentic Mexican food and a vibrant arts scene in one of Chicago's most colorful neighborhoods.

• Chinatown

  Excellent value and authentic cuisine—a must-visit for food tourism enthusiasts.

Standout restaurants

• Alinea

  The iconic three-Michelin-star tasting-menu experience. A splurge-worthy culinary journey that redefined American fine dining.

  Lincoln Park

• Smyth

  Two Michelin stars showcasing hyper-seasonal, farm-driven cuisine with ingredients from their own farm in a refined, intimate setting.

  West Loop

• Oriole

  Two Michelin stars in a hidden speakeasy-style space. An extraordinary tasting menu featuring Japanese-influenced American cuisine.

  West Loop

• Ever

  Chef Curtis Duffy's two-Michelin-star restaurant offering an ambitious, artful tasting menu experience.

  West Loop

• Boka

  High-end yet approachable fine dining. A refined neighborhood gem that consistently delivers creative, seasonal American cuisine.

  Lincoln Park

• Girl & the Goat

  A West Loop staple from Top Chef winner Stephanie Izard. Bold, globally-inspired dishes in a lively, energetic atmosphere.

  West Loop

• Monteverde

  Frequently cited as Chicago's best Italian restaurant. Handmade pastas and refined Italian dishes in a warm, welcoming space.

  West Loop

• Au Cheval

  The classic Chicago burger stop. Expect waits for their legendary double cheeseburger—widely considered one of America's best.

  West Loop

• Piccolo Sogno

  Rustic Italian excellence with a beautiful garden patio. A neighborhood favorite for refined, approachable Italian fare.

  River North

• Beatnik on the River

  Mediterranean-inspired cuisine with stunning Riverwalk views. A stylish spot for waterfront dining and craft cocktails.

  River North

Things to do

• Millennium Park / Cloud Gate ("The Bean")

  The iconic reflective sculpture is a must-see centerpiece of this beloved downtown park, offering photo opportunities and people-watching year-round.

• Chicago Riverwalk

  Stroll along the river, stop for drinks or a meal, and soak in the city's unique waterfront energy. A quintessential Chicago experience.

• Architecture Cruise

  The single best "Chicago is different" activity. A narrated boat tour showcasing the city's legendary architectural heritage from the water.

• Art Institute of Chicago

  One of the world's great art museums, home to iconic works including Seurat's A Sunday on La Grande Jatte and Hopper's Nighthawks.

• Museum of Science and Industry

  A massive, interactive museum perfect for curious minds of all ages. Highlights include a captured German U-boat and a working coal mine exhibit.

• Shedd Aquarium

  World-class aquarium on the lakefront featuring marine life from around the globe, including beluga whales and a Caribbean reef exhibit.

• Adler Planetarium

  America's first planetarium offers stunning sky shows and one of the best skyline views in the city from its lakefront location.

• Observation Deck / Skyline Views

  Choose between Skydeck Chicago (Willis Tower) or 360 Chicago (Hancock Center) based on location and timing—both offer spectacular panoramas.

• Cubs or Sox Game

  Catch a baseball game at historic Wrigley Field (Cubs) or Guaranteed Rate Field (Sox) for an authentic Chicago sports experience. Seasonal.

• Comedy + Jazz/Blues

  A classic Chicago night out. The city is home to legendary comedy clubs like Second City and iconic jazz and blues venues.

Practical considerations

Getting Around

Getting Around

Chicago is very doable without a car for most visitors. The city's public transit system is efficient and covers all major areas. The CTA "L" trains and buses form the core of Chicago's public transit network. Use Ventra (available as a physical card or mobile app) to pay—simply tap to ride. Rideshare services and taxis are readily available for late nights or when hopping between neighborhoods. For a comprehensive orientation to the transit system, the RTA rider guide provides helpful explainers for first-time visitors. Most downtown hotels are within walking distance of major attractions, and the Riverwalk offers a scenic pedestrian route through the heart of the city.

When To Visit

When to Visit

Chicago is a seasonal city—choose your timing based on your tolerance for crowds versus weather. **Spring + Fall:** Milder weather with fewer crowds makes these excellent "luxury value" windows. April–May and September–October offer pleasant temperatures and lower hotel rates. **Summer:** Festival season brings lakefront energy, outdoor concerts, and rooftop bar culture. This is also the busiest and most expensive time to visit, so book accommodations well in advance. **Winter:** Holiday charm abounds with festive markets and seasonal attractions. Hotel deals are plentiful, but the cold and famous Chicago wind are real factors—come prepared with proper layers.

Practical Tips

Practical Considerations

• Winter can be well below freezing with strong lake wind; plan layers and proper outerwear including a wind-resistant jacket.

• Stick to well-traveled areas, use rideshare late at night, and be mindful of your surroundings—especially after dark. Standard city travel common sense applies.

• Check the official Chicago festival and event guide to avoid surprise crowd weekends and plan trips around signature events.

• Major events like Taste of Chicago, Lollapalooza, and marathon weekends can significantly impact hotel availability and pricing—dates are posted publicly but shift year-to-year.

• Many top restaurants require reservations, particularly Michelin-starred establishments and popular brunch spots on weekends.

• The lakefront is stunning but can be significantly colder and windier than neighborhoods a few blocks inland—dress accordingly.

Exceptional Stays

• The Peninsula Chicago

  Located just off the Magnificent Mile, The Peninsula Chicago consistently ranks among the city's finest luxury hotels. Known for its spacious rooms, meticulous service, and world-class wellness facilities, the hotel features a Forbes Five-Star spa, a half-Olympic indoor pool with skyline views, and the stylish Z Bar rooftop lounge. With acclaimed dining venues like Shanghai Terrace and an address steps from Chicago's premier shopping district, The Peninsula delivers one of the most refined five-star hotel experiences in Chicago.

• Four Seasons Hotel Chicago

  Perched above North Michigan Avenue with sweeping views of Lake Michigan, Four Seasons Hotel Chicago offers a polished and residential-style luxury stay. Following an extensive renovation, the hotel features redesigned guest rooms, an elegant lobby lounge, and the signature restaurant Adorn, known for its seasonal American cuisine. With its tranquil spa, indoor pool, and prime location near the Magnificent Mile, the property remains one of the most established luxury hotels in downtown Chicago.

• The Langham, Chicago

  Occupying the first 13 floors of the former IBM Building, a modernist landmark designed by Ludwig Mies van der Rohe, The Langham blends architectural history with contemporary luxury. Overlooking the Chicago River, the hotel features spacious rooms with floor-to-ceiling windows, the serene Chuan Spa, and the acclaimed restaurant Travelle, known for seasonal global cuisine. Its riverfront setting places guests within walking distance of the Magnificent Mile, Millennium Park, and the Loop.

• Waldorf Astoria Chicago

  Tucked into Chicago's elegant Gold Coast neighborhood, Waldorf Astoria Chicago evokes the feel of a Parisian residence with its limestone façade and quiet courtyard entrance. The hotel is known for its unusually spacious suites—many with private terraces and fireplaces—along with a tranquil spa and the Julien Farel salon. Just steps from Oak Street boutiques and the Magnificent Mile, it offers one of the most residential-style luxury stays in Chicago.

• Park Hyatt Chicago

  Located steps from the Magnificent Mile, Park Hyatt Chicago offers refined contemporary design and views of Lake Michigan. The hotel is known for its understated luxury and residential-style guest rooms.

• The St. Regis Chicago

  Rising above the Chicago River in Jeanne Gang's striking sculptural skyscraper, The St. Regis Chicago is one of the city's newest ultra-luxury hotels. The property features expansive rooms with floor-to-ceiling windows, sweeping views of Lake Michigan and the skyline, and refined dining including Miru, a Japanese-inspired restaurant overlooking the river. With its serene spa and dramatic architecture, the hotel offers one of the most distinctive luxury stays in downtown Chicago.

• The Ritz-Carlton, Chicago

  Situated atop Water Tower Place, this well-established luxury hotel offers spacious rooms and sweeping views of the city and Lake Michigan. It has long been known for its attentive service and central location.

• Pendry Chicago

  Pendry Chicago occupies the iconic Carbide & Carbon Building, one of the city's most recognizable Art Deco landmarks. Inside, the historic architecture is paired with sleek modern interiors, creating a stylish boutique hotel in the heart of the Loop. Guests gather at the rooftop bar Chateau Carbide and dine at Chez Maggy, the French brasserie from celebrity chef Dominique Crenn. Its central location places visitors within walking distance of Millennium Park, the Chicago Riverwalk, and Michigan Avenue.

• LondonHouse Chicago

  Set in a historic landmark building at the intersection of the Chicago River and Michigan Avenue, LondonHouse combines classical architecture with a modern glass tower addition. The hotel is known for its expansive river views and its tri-level rooftop bar overlooking the skyline.

• Sofitel Chicago, Magnificent Mile

  Designed by French architect Jean-Paul Viguier, this striking glass tower stands out for its modern architectural design. The hotel combines French-inspired style with a location just steps from the Magnificent Mile.

• Viceroy Chicago

  Located in Chicago's stylish Gold Coast, Viceroy Chicago pairs a restored 1920s façade of the historic Cedar Hotel with a sleek modern tower. The hotel features contemporary rooms with views of Lake Michigan, a rooftop pool and lounge, and Somerset, a lively restaurant known for seasonal Midwestern cuisine. With its location near Oak Street shopping and the lakefront, the Viceroy offers one of the city's most stylish boutique hotel stays in the Gold Coast.

• Thompson Chicago

  Located in Chicago's vibrant Gold Coast, Thompson Chicago is a design-forward boutique hotel known for its sleek interiors and lively atmosphere. The hotel is home to Nico Osteria, a celebrated Italian seafood restaurant that draws both locals and visitors. With its location just a few blocks from Oak Street Beach, Lake Michigan, and the Magnificent Mile, Thompson offers a stylish base for exploring the city.

• Kimpton Gray Hotel

  Set in a historic 1920s building in Chicago's Loop, the Kimpton Gray combines Art Deco architecture with modern boutique design. The hotel is known for its stylish interiors and popular rooftop bar.

• The Gwen

  Part of Marriott's Luxury Collection, The Gwen occupies a landmark 1930s Art Deco building along the Magnificent Mile. Named after sculptor Gwen Lux, whose artwork still appears in the building's façade, the hotel blends historic architecture with contemporary interiors. Guests are drawn to the hotel's expansive rooftop terrace, which offers skyline views and outdoor dining just steps from Chicago's premier shopping district.

• Hotel EMC2

  Hotel EMC2 brings a playful concept to Chicago's Streeterville neighborhood, celebrating the intersection of art and science through its design and programming. Guest rooms feature modern furnishings alongside creative details like robot assistants that deliver room service, while rotating art installations and a lively lobby bar keep the atmosphere energetic. Located just steps from the Magnificent Mile and Lake Michigan, the hotel offers one of the city's most distinctive boutique stays.

• The Robey

  Located in the historic Art Deco Northwest Tower in Wicker Park, The Robey is a design-forward boutique hotel known for its rooftop pool and views of Chicago's northwest neighborhoods.