A towering skyline that reflects along the waves of Lake Michigan is the first thing you will notice upon arrival. A closer inspection will reveal ornate architecture, fine dining, and designer store fronts that dot the city’s sacred streets. And the rustling wind flows along the river as it drowns out the honks of taxi cabs or the chattering “L Train”. Chicago is arguably the crown jewel of the Midwest.

Chicago is the third largest city in the United States, spanning across 228 square miles that wind between glistening towers and plush beaches right along the lake. The comfortable duality between urban and lakefront settings naturally nourishes two types of lifestyles.

For those visiting any destination for the first time, there are a lot of elements to consider. Where to stay, what to eat, and what to see are all on the top of one’s mind. Here is a breakdown guide to Chicago for first time visitors looking to venture to some of Chicago’s top attractions and most popular sights.

WHERE TO STAY

Chicago is a modern and industrial city that is home to a variety of luxury hotels. Many hotels boast a unique, innovative architectural style since Chicago is a center for architectural experimentation. Whether guests prefer to lodge along the tranquil Lake Michigan, or sit nestled among the booming skyscrapers, 5-star stays are not hard to find. Discover a home-away-from home within these exclusive retreats.

 Viceroy 

Voted by Travel + Leisure as the #1 hotel in Chicago, Viceroy is located right near Magnificent Mile. The hotel is in a 120-year-old re-imagined and updated building, which combines historic and modern amenities to present a luxurious stay. The 180 guest rooms and suites radiate a retro-chic feel, as floor to ceiling windows let in wonderous views of Lake Michigan. As for dining, guests can venture up to the 18th floor to Devereaux. This seasonal terrace is host to craft cocktails, light snacks, and a swimming pool. Somerset is the hotel’s main dining location. Chef Stephen Gillanders serves seasonal American food with fresh and local ingredients. The restaurant’s interior was inspired by a “new-fashion take on American country club culture”. Viceroy is a centrally located, luxurious hotel that is perfect for first time or returning visitors to Chicago.

Nobu Chicago

Nobu Chicago is located near Willis Tower and Fulton Market—a few of Chicago’s top attractions—placing the hotel right in the center of all the adventurous action. 115 guest rooms and suites were designed and inspired by a blend of old-world Japanese influence and culture, complete with a modern touch. The tranquil, serene rooms boast high ceilings and spa-like bathrooms; perfect for guests searching for peace within this fast-paced city. Located on the 11th floor of the hotel is The Rooftop. The Rooftop has both an indoor lounge and outdoor terrace to accommodate for those chilly Chicago evenings or welcoming spring afternoons. Guests may also opt to dine at the signature Nobu Restaurant which is situated on the ground floor. A fitness center and indoor pool top of the luxurious amenities within the Nobu hotel.

Waldorf Astoria Chicago 

The Waldorf Astoria Chicago is in the Gold Coast Neighborhood. The “chateau-style” inspired architecture and design brings a dash of Paris into Chicago. A total of 215 rooms and suites make up the exclusive hotel. The bright and open rooms are complete with modern furnishings and neutral accents such as grays, blacks, and whites. Views of downtown Chicago or Lake Michigan present a piece of the city right into these luxurious accommodations. For dining, the Waldorf Astoria Chicago is host to The Brasserie. This sophisticated, yet lively restaurant utilizes locally sourced ingredients and infuses a bit of Chicago flare into their dishes. Gold and brown accents emphasize the rich, mysterious interior. Guests will also find a relaxing spa and tranquil indoor lap pool within the Waldorf Astoria.

WHERE TO EAT

Chicago serves more than just their iconic deep-dish pizza and Chicago-style hot dog. Throughout the city, one may discover classic Mid-Western American cuisine, combined with a flare of European inspiration. The diverse selections tie together flavors from all over the world and present them in one central hub.

Moody Tongue 

Moody Tongue is in Chicago’s South Loop. 10-time Michelin star chef, Jared Wentworth, presents a hyper-seasonal tasting menu.  Beer pairings conducted by Brew master Jared Rouben include a selection of 16 draft beers and a variety of specialty bottle options. From perennial beers, to limited release offerings, The Bar within Moody Tongue has a wide array of selections. Warmth, historic, and charm might be a few words that come to mind when describing Moody Tongue’s setting. The restaurant’s interior features mid-century modern touches including a fireplace and preservations from the building’s original interior features. This space is very intimate, with only 28 seats offered in the dining room.

Chicago Cut Steakhouse 

Chicago Cut Steakhouse is placed right alongside the Chicago River. A wall made up entirely of floor to ceiling windows let in rushing views of the river. The large dining space is complete with high ceilings and deep, red plush seating. Chicago Cut Steakhouse is most known for their USDA Prime steaks and the dry aging rooms which are located right on sight. Steaks such as Bone-in Rib Eye and Porterhouse are some of their most popular options. And although the restaurant is well-regarded for the steaks, they also offer an array of other choices such as the Chilean Sea Bass, Grilled Branzino, or Chicken Parmigiana. The ever-expanding wine menu and daily selections of desserts wind out this unforgettable dining experience.

Goosefoot

Goosefoot can be found in Lincoln Square. Chris and Nina Nugent are the chefs and owners of this Michelin star restaurant. The multi-course tasting menu is curated with small artisan farm products and is a combination of French technique with a modern flare that is prominent in every bite. Although the menu changes frequently and is curated to be a surprise, the twelve courses are carefully designed to appease a variety of taste buds. The interior of the restaurant was intended to reflect the cuisine. Nina Nugent describes it as “modern, smart, elegant, and approachable”. From the modern China to the locally crafted banquettes, every aspect enhances the experience.

WHAT TO SEE

Everyone’s travel itinerary might look different while exploring a new city. Some may prefer to indulge in the art of a historic museum, while others might desire to venture out on the waters of Lake Michigan. Chicago offers many sights and destinations for any type of traveller, due to its central geographical location and rich history.

Chicago River Sunset Cruise

The Chicago Sunset Cruise is a wondrous way to witness Chicago in a new light. The cruise departs at Wendella’s Michigan Avenue Docks near the DuSable Bridge. Wendella’s world class tour boats guide passengers along a beautiful and peaceful cruise that is perfect for couples, families, or groups. Views of Chicago’s iconic skyline and Lake Michigan are visible throughout the entire duration of this majestic waterway experience. The boat will navigate through the Chicago Lock and out to the open lake. Some stand out sights include the John Hancock Center, Willis Tower, and the Aqua Tower.

Shopping Along Magnificent Mile

Magnificent Mile is an 0.8-mile strip of Michigan Avenue between the Chicago River at the South end, and Oak Street at the North. Luxury designer stores, pet boutiques, athletic shops, and children’s shopping are right at your fingertips along Magnificent Mile. This shopping area also includes larger shopping centers such as 900 Shops, The Shops at North Bridge, and Water Tower Place. Whether one is simply window shopping or indulging on a shopping spree, Magnificent Mile is home to a variety of shops and luxury stores.

The Art Institute of Chicago 

Founded in 1879, the Art Institute of Chicago located in Grant Park is one of the world’s major museums. Guests can step away from modern day Chicago and enter a portal to the past through the immersive and historic exhibits. There is a wide array of galleries that are dedicated to pieces from ancient Greece, Japan, Africa, and the Americas. One can also discover their displays of Impressionist and Post-Impressionist works. Contemporary and recent art is also on display in the Modern Wing. Families, art lovers, and general visitors alike will admire this world-famous, historic museum.  

Willis Tower

Some may say it’s not worth it, but the views from this building are simply unbeatable. Willis Tower is right in the heart of downtown Chicago. The 110-story building was once the tallest building in the world and is now the second tallest in the Northern Hemisphere. Willis Tower was designed by the architectural firm Skidmore, Owings and Merrill, and opened in 1973. One stand-out feature that this building hosts is the Skydeck and the Ledge. Every year, more than 1.7 million visitors take the 103-story journey upward to The Ledge—the highest observation deck in the United States. Guests can “walk off” the building in a laminated glass unit, as they digest the best views in Chicago. On clear days, up to 50 miles of scenery can be viewed, including four states: Illinois, Indiana, Wisconsin, and Michigan.

Chicago is full of popular attractions and fine dining choices. And one perk to being one of the largest cities in America is that there truly is something for every visitor and type of traveler. Whether one is taking an excursion on a river cruise or venturing over 1,000 feet up the Willis Tower, Chicago always has something down the avenue of adventure. The Windy City is not one you want to miss.