Where should I go and what should I do in Chicago?
Private skyline moments: Book an architecture cruise on the Chicago River and see the city in its most glamorous light.
Iconic luxury shopping: The Magnificent Mile and Gold Coast deliver designer labels, flagship stores, and polished hotel access.
World-class dining: Chicago’s Michelin-starred restaurants and tasting menus in Fulton Market make every dinner feel like an event.
Hidden-gem culture: The Arts Club of Chicago and the Smart Museum offer a quieter, more refined cultural experience.
Elegant off-the-radar escapes: The Garfield Park Conservatory and a cocktail stop at a tucked-away speakeasy give the city a softer, more intimate side.
When should I go to Chicago?
May to June: Mild weather, early patio season, and a very walkable city vibe.
September to October: Crisp air, beautiful skyline views, and one of the prettiest times for a luxury city getaway.
December: Great for festive shopping, fine dining, and a cozy urban holiday mood.
July to August: Best for lakefront energy, rooftop dining, and long summer evenings.
What do I need to know for a trip to Chicago?
Bring comfortable walking shoes: Chicago is best enjoyed on foot, especially in the downtown, River North, and Gold Coast areas.
Choose a central hotel: For luxury travelers, stay in the Loop, River North, Gold Coast, or Magnificent Mile for easy access to dining and sightseeing.
Plan around the weather: Winters can be very cold and windy, while summers can feel hot and humid.
Reserve popular restaurants early: Top dining spots fill fast, especially on weekends.
Use rideshares or taxis at night: They’re a convenient way to move between neighborhoods after dinner or events.
Know the airport options: O’Hare is the main international gateway, while Midway can be easier for some domestic flights.
Budget for taxes and tips: Sales tax, hotel taxes, and gratuities can add noticeably to the final cost.
Build in a mix of icons and hidden gems: Pair the big-ticket experiences with a few quieter finds so the trip feels more personal and elevated.
Set within the iconic 1929 Art Deco Carbide & Carbon Building in Chicago’s Loop neighborhood, Pendry Chicago is a modern-day luxury hotel that pays homage to both the past and the present with contemporary, comfortable interiors, signature culinary and cocktail concepts, and inspired gathering spaces throughout that embody the spirit of Chicago.
Named one of the Best Hotels in Chicago 2016 by Travel + Leisure, The Gwen, a Luxury Collection Hotel is located on the Magnificent Mile in the landmark McGraw-Hill Building within walking distance to many of Chicago attractions and the Loop.
With echoes of billiard balls, poker chips, and clinking glasses frozen within its walls, this 1890’s Venetian Gothic landmark in the Chicago Loop springs back to life as an incomparable historic downtown Chicago hotel—where the spirit of play reigns supreme...
An icon in the city, offering majestic views of the skyline, Chicago River, and Lake Michigan, The Langham, Chicago's 316 luxurious guestrooms occupy the first 13 floors of a 52-story building designed by renowned architect Mies van der Rohe.
The Waldorf Astoria Chicago is elegantly appointed, ravishing, yet simple, revitalizing the standards of luxury hospitality in the center of downtown Chicago...
The beautiful 32-story Sofitel Chicago Water Tower boasts a sleek architectural design with equally modern interiors, and stands centrally located in downtown Chicago.
4th Night Free + breakfast + $100
Valid for travel through Dec 31, 2026. Blackout dates may apply.
Take in the fabulous sights, breathe in the crisp air flowing off of Lake Michigan, immerse yourself in the vibrant atmosphere, and discover all the wonders of Chicago at the famed and luxurious Park Hyatt Chicago...
Set in the heart of downtown Chicago, Sports Illustrated Resorts Chicago combines contemporary accommodations with easy access to the city's iconic attractions, sports venues, and cultural landmarks. Currently undergoing a phased transformation into a full Sports Illustrated–branded destination, the hotel offers modern guest rooms, city views, and a prime location near Millennium Park and the Chicago Riverwalk, making it an energetic base for exploring the best of Chicago.
Discover the electrifying atmosphere of the Windy City at Hyatt Regency Chicago. Steps from Navy Pier, our newly-renovated downtown hotel offers contemporary rooms and suites
Featuring stylish design-forward accommodations, rooftop social spaces, and immediate access to Chicago’s acclaimed dining and cultural scene, the hotel offers a sophisticated urban stay rooted in creativity and contemporary style.
River North’s uber-chic, go-to art hotel beckons both couples and corporate travelers looking to explore, eat, drink, shop, indulge and impress in the city from dawn to dusk
Located in the heart of one of the nation's most beautiful cities, Eurostars Magnificent Mileis is a hip boutique haven with a philosophy of pleasure in fabulous Chicago
The Royal Sonesta Chicago River North, is luxury lifestyle hotel in downtown Chicago, central to the city's most exciting shops, culture and nightlife. It is re surrounded by enticements, and make its own distinct impression.
Expect the unexpected in the Windy City. Located just steps from the famous Magnificent Mile, Millennium Park, and renowned museums in downtown Chicago, contemporary art surrounds and inspires you at 21c Museum Hotel Chicago.
A landmark destination in the heart of downtown Chicago, The Whitehall hotel offers a luxurious sense of grace and grandeur between Michigan Avenue and Rush...
Chicago is a city that rewards travelers who like their city breaks polished, design-forward, and full of personality. Spend your days admiring the skyline from a private architecture cruise on the river, wandering the galleries and boutiques of the Gold Coast, or settling into a table at one of the city’s celebrated Michelin-starred restaurants. For a more elevated pace, pair a lakefront stroll with a stay at a refined downtown hotel where the service is as memorable as the view.
Beyond the classic attractions, Chicago has plenty of experiences for travelers who like discovering a city’s quieter luxuries. Explore the hidden speakeasy scene, book a behind-the-scenes art or architecture experience, or slip into the historic charm of the Smart Museum and the nearby university district for a more contemplative afternoon. The Chicago Athletic Association, the Arts Club of Chicago, and the quiet elegance of the Garfield Park Conservatory are all excellent picks for guests who want something a little less obvious, but every bit as memorable.
For a luxe Chicago escape, the best approach is to mix iconic with unexpected: a rooftop cocktail at sunset, a private tasting in Fulton Market, a leisurely morning at the Magnificent Mile, and an evening in an intimate jazz room or chef-led dining experience. Chicago shines when you let it be both grand and intimate at once.