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See the Windy City from above with tickets to Skydeck Chicago at Willis Tower. Here, panoramic vistas offer a whole new perspective on the city skyline. A more casual, can’t-miss attraction is Cloud Gate, also known as “the Bean,” at Millenium Park. A short walk away, you’ll come across Chicago Union Station, a magnificent Beaux-Arts landmark and train station with active Amtrak routes. Even if you aren’t traveling, you can still check out the shops or grab a snack here.

Explore the Magnificent Mile for upscale shopping along Michigan Avenue, or discover unique finds at smaller boutiques on Halsted and Clark Streets. From here, make your way down to the nearby Navy Pier, and then (possibly the most important stop of your trip) to the Art Institute of Chicago, which is ranked one of the top museums in the world.

The city’s cultural hotspots include the legendary Green Mill, a cash only cocktail lounge that hosts live music, comedy shows, and even poetry readings. If you’re looking to sharpen your cooking skills, sign up for a hands-on class at The Chopping Block, where you'll learn to whip up delicious dishes like a pro.

In the summer, Chicago weather is glorious. Surround yourself with nature at the Garfield Park Conservatory or embark on a kayak adventure along the Chicago River. Alternatively, you can get that heart rate up with a stroll, run, or bike ride along the scenic Bloomingdale Trail. With kids in tow, you may also want to pay a visit to the animals at the Lincoln Park Zoo. A fun and free activity is the Millenium Park Summer Music Series, featuring a wide variety of music from local, national, and international artists at the Pritzker Pavilion. During the wintertime, a seasonal skating rink is constructed for locals and visitors to glide across the ice festively. Admission to the skating rink is free and you might even be able to snag free skating lessons if it’s your first time or if you need a quick refresher.

When it comes to sports in Chicago, you’ll never be bored. Cheer on the Cubs at the historic Wrigley Field (home to the Chicago Cubs since 1914), or catch a game at Soldier Field, the oldest football stadium in the country. Guaranteed Rate Field, formerly known as US Cellular Field, on the South Side of Chicago is where the White Sox play since 1991.

Near the West Side of Chicago, experience the thrill of basketball or hockey at United Center, an indoor arena home to the Chicago Bulls and the Chicago Blackhawks. Here, passionate fans come together to witness action-packed matches or sing-along to their favorite artists’ songs at regular concerts. There are dozens of diverse dining options at United Center including a taqueria by famed Girl & the Goat chef Stephanie Izard. And—of course—burgers, beer, and Chicago dogs abound.

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On the Magnificent Mile, InterContinental Chicago exudes pure luxury in the heart of the Windy City. In a historic 1929 building, the architectural landmark holds stories from nearly a century ago and has preserved its Roaring 20’s charm while also being newly renovated. Pet-friendly and near some of the best places for sightseeing like Navy Pier and Millennium Park, the InterContinental Chicago boasts world-class amenities including a spa, sauna, and a Junior Olympic swimming pool. Enjoy seasonal programming here like the Winter Chalet and Jazz Nights in the lobby every Thursday.

Voted one of the best hotels in the country by US News & World Report, the Four Diamond-rated Kimpton Gray Hotel radiates timeless sophistication in the Loop neighborhood. A short walk to Willis Tower and Union Station, the Gray hosts a nightly social hour in the lobby living room just for guests and even has a Somadome meditation pod in the wellness lounge that guests can book for color light therapy, sound therapy, or just a quiet relaxing break from the world. A chic urban retreat in downtown Chicago, the Gray is pet-friendly, provides guests with access to bikes, and serves coffee from La Colombe, an integrity-driven coffee roaster.

Close to the West Loop, Fulton Market, and Millenium Park, voco Chicago downtown provides guests with a swanky stay in the River North neighborhood, an area known for impeccable art and design. With an indoor pool (it has a glass ceiling!) and gym on the 16th floor, guestrooms with gorgeous city views, and even self-parking that includes in-and-out privileges, the trendy hotel is a centrally-located stylish oasis perfect for exploring the city on foot or by car.

Maybe you’re traveling to Chicago and plan to stay a bit outside the city near family or friends. If so, you might find that flying into Chicago Midway International Airport is the way to go and that a stay at the boutique Hotel Indigo Naperville Riverwalk (just 40 minutes by car from downtown Chicago) is exactly what you’re looking for. Escape the hustle and bustle with a scenic retreat along the Riverwalk, where contemporary comforts meet suburban tranquility. The hotel has a lovely rooftop bar, where you can grab a drink and see the city’s murals from above. While in the area, visit Naper Settlement, an outdoor history museum, or Centennial Beach for swimming and sunbathing. Downtown Naperville is also a fun place to window shop or grab a coffee.

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Step into the world of a basketball legend at Michael Jordan's Steak House at InterContinental Chicago Magnificent Mile. Here, you’ll savor premium steaks and seafood in a classy atmosphere, complemented by an extensive wine selection. Expect the highest quality steaks here, prepared to your liking.

Or experience a culinary trifecta at the Kimpton Gray Hotel with its three wonderful restaurants: Boleo, Vol. 39, and The Fillmore. Boleo offers tasty Latin-inspired cuisine and cocktails on the 15th floor rooftop; on the second floor, Vol. 39 provides a cozy lounge setting for classic cocktails and light bites; and on the lobby level, The Fillmore named after San Francisco’s famously diverse district, serves innovative West Coast and American-Asian fare in a chic dining space.

Heighten your dining experience at Waterview, located on the 15th floor of voco Chicago downtown. With panoramic views of the skyline and Lake Michigan, plus an eclectic menu featuring classic Chicago gastronomy and handcrafted cocktails, Waterview is open for both happy hour and dinner.

Did you know Chicago is home to the second largest Mexican-born immigrant community in the U.S. outside of Los Angeles? It’s no wonder there are incredible and authentic Mexican restaurants that can be found all over town. Pueblo Nuevo is a family-owned favorite and the perfect place to start, with a menu consisting of green pozole, tortas, huaraches, and much more. For over a decade, the restaurant has served mouthwatering adaptations of street food in the Portage Park neighborhood and their customers come from far and wide to experience it.

You can walk into almost any Chicago restaurant and know you’ll have a great meal, but a couple musts, beloved for their very famous dishes, are Lou Malnati's Pizzeria and Portillo’s. Lou Malnati's is a Chicago institution famous for its deep-dish pizza, which features a buttery crust, rich tomato sauce, and ooey-gooey cheese. And then Portillo's has the best classic Chicago-style hot dogs (can’t leave the city without trying one), Italian beef sandwiches, and other delicious comfort foods.

The Publican - A lively gastropub specializing in hearty, rustic fare, including seafood, a pork-heavy menu, and an impressive selection of beer, the Publican is your go-to brunch spot as long as you can get a reservation. Otherwise, expect to wait for a table for hours. Trade the traditional bloody Mary or mimosa for a beer-mosa here (hefeweizen & orange juice) and pair it with the piri piri chicken schnitzel, the shrimp and grits, or the croque madame.

Description: Chicago has an abundance of transportation options and the nice thing is that you can totally get away with not having or renting a car. It might, in fact, be easier to rely on rideshare, the efficiency of the iconic 'L' train system, or the reliability of buses operated by the Chicago Transit Authority (CTA). For shorter distances, walking or biking along the scenic lakefront or through hip neighborhoods offers a chance to soak in the city's rich culture and architecture. Additionally, Chicago's expansive network of bike lanes and bike-sharing program make cycling a convenient and eco-friendly choice. With its accessible and varied transportation infrastructure, navigating the Windy City is both seamless and exhilarating.

Description: When planning a trip to Chicago, be sure to check the weather forecast for your travel dates. In spring and fall, layering is key as temperatures can vary. Bring a mix of lightweight tops, sweaters or jackets, and comfortable jeans or pants. Don't forget a sturdy pair of walking shoes for exploring the city. For summer visits, pack lightweight clothing such as shorts, t-shirts, and sundresses, along with sunglasses, sunscreen, and a hat to protect against the sun. In winter, bundle up with warm coats, hats, gloves, scarves, and insulated boots to stay cozy, of course. Overall, versatility is key, ensuring you're prepared for whatever the Windy City's weather and diverse activities have in store.

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Experience a vibrant and ever-changing cultural calendar in Chicago, where every season brings a new celebration of art, music, and tradition. There’s the Chicago Air and Water Show, where daredevil pilots take to the skies above Lake Michigan, thrilling audiences with aerobatics and gravity-defying stunts. Foodies will want to savor the city’s flavors at Taste of Chicago, one of the globe’s largest food festivals. Here, dishes from Chicago's diverse cultures and neighborhoods take center stage.

Experience the magic of the holiday season at ZooLights, as Lincoln Park Zoo transforms into a winter wonderland adorned with sparkling lights, festive displays, and holiday activities for the whole family. Or embrace the holiday spirit even further at the Christkindlmarket, a beloved tradition that transforms Daley Plaza into a charming European-inspired village, with handcrafted gifts, festive treats, mulled wine, and live entertainment.

Rhythm is going to get you at summer music festivals like Lollapalooza and Pitchfork, where top artists from around the world converge to perform across multiple stages. If visual art is more your cup of tea, you can celebrate the ingenuity of local artists at summer art shows, where galleries and outdoor exhibitions really showcase the talents of Chicago's creative community.

Last, you’ll want to join the sea of green on Saint Patrick's Day as locals and tourists come together to celebrate Irish culture with a lively parade that includes bagpipes, drum corps, Irish dancers, and more. One of the biggest Saint Patty’s Day celebrations in the country, Chicago’s includes dyeing the Chicago River green every March. To view the parade, head to Grant Park and follow the action as it heads north from Balbo Drive and Columbus Drive.