Welcome to the Windy City where historical art deco buildings, the Chicago River, and Lake Michigan provide for a cityscape unlike any other. The river runs straight through the center of the city, creating a delightful view of multiple bridges and water taxis. The bridges in themselves are a fun sight to see as they open up to let larger boats pass by underneath. Be sure to check out the history of the bridges (such as the DuSable Bridge) as you stop by for an unique photo opportunity. Also, I found Chicago to be very public transportation-friendly so no worries if you don't have a car to get around. Even the airport is connected via trains, and the buses seemed to run efficiently according to their app.
WHAT TO DO
Chicago Architecture Foundation River Cruise (Various Locations) – The Architecture River Cruise is often my first stop when visiting. Take a leisurely cruise down the river and learn details about the beautiful buildings flanking each side, as well as about the history of Chicago and the river itself. Tours are offered seasonally so check boat schedules before you go and grab a seat on the top deck for maximum visibility.
Grant Park and Buckingham Fountain (337 East Randolph Street) – Grant Park is often referred to as “Chicago’s front yard” and is a meticulously managed urban park located in the heart of downtown. Be sure to check out the choreographed displays with lights and music at Buckingham Fountain, one of the largest fountains in the world. You’ll find that Grant Park is at the center of Chicago’s social calendar, with festivals and events throughout the year, and an ice rink during the winter months. Grant Park is home to many of Chicago’s other must-see stops, such as the Art Institute, Millennium Park, and the Field Museum.
Millennium Park (201 East Randolph Street) – No visit to Chicago is complete without a stop at “The Bean” - a 110-ton bean shaped sculpture titled Cloud Gate. The Bean reflects the Chicago skyline perfectly and is an impressive sight both day or night. You’ll also find the Crown Fountain at Millennium Park with its tall towers and LED screen projections. Millennium Park is part of Grant Park and is perfect for a picnic on a nice day or taking in one of the concerts offered seasonally. Extra points for visiting in the winter months when the Christmas tree is lit up, and the ice skating rink sparkles!
The Art Institute of Chicago (111 South Michigan Avenue) – One of the great art museums and a must-see for anyone visiting Chicago. The permanent collections are impressive with everything from medieval to impressionist to modern and beyond. In particular, the Art Institute houses the largest collection of impressionist and post-impressionist paintings outside of Paris. The schedule for the temporary exhibits is, of course, also worth checking out with big names and famous works stopping by regularly. Other than paintings and drawings, also look for the ancient artifacts, including mosaics, pottery, coins, and jewelry.
Magnificent Mile (201 East Randolph Street) – Looking to do some shopping? You need to stop by the famous Magnificent Mile. Here, you’ll find huge flagship stores of your favorite brands and fancy high-end boutiques, rivaling those on New York’s Fifth Avenue. Also, be sure to look up! Magnificent Mile has some of the best architectural sights in Chicago, from the Historical Water Tower that survived the Great Chicago Fire to the Wrigley Building and the Tribune Tower.
Starbucks Reserve Roastery (646 North Michigan Avenue) – After a day of shopping on the Magnificent Mile, stop by the Chicago Roastery for a cup of coffee. The largest Starbucks in the world, this massive store serves up coffee, cocktails, and food, in addition to a large merchandise/retail area where you can pick up goods you won't find anywhere else. There is an outdoor rooftop area that is open seasonally, and you can sign up for tours of the Roastery to see where the magic happens.
Promontory Point (5491 South Shore Drive) – Stop by Promontory Point for a scenic view of Lake Michigan. A part of Burnham Park, Promontory Point is a favorite of picnic aficionados and photographers alike, and the numerous rock formations and public art installations create a fun gathering spot for locals and visitors. It is particularly enchanting in the fall when the foliage turns into an autumn wonderland.
Navy Pier (600 East Grand Avenue) – One of the most well-known attractions in Chicago is the Navy Pier. You’ll find the iconic ferris wheel, restaurants, shops, and exhibitions. The top draw, of course, is the unparalleled views of Lake Michigan. During the summer months, there are spectacular fireworks displays that shouldn’t be missed. One caveat - it’s been my experience that everything pretty much shuts down in the winter months (and the wind is bone-chillingly cold) so don’t expect too much in the way of activities during those months.
Christkindlmarket Chicago (50 West Washington Street) – If you happen to be in Chicago during the Christmas season, brave the cold to check out this annual Christmas market. A scene reminiscent of European Christmas markets, you will find food vendors, along with local shops and artisans. Be sure to grab a drink in a boot mug to help warm up!
WHAT TO EAT
Chicago Deep Dish Pizza – Did you even go to Chicago if you didn't eat the deep dish pizza? Locals have their individual favorites and will debate you until blue in the face. Deep dish pies can take a while to prepare so order ahead if you can and expect a wait. Although there are many other fabulous stops as well, a good place to start your pizza journey is at one of the three favorites: Lou Malnati's Pizzeria, Giordano's, or Pequod's Pizza. Lou Malnati's (multiple locations) is a Chicago institution - serving up deep dish pies since 1971. Check out one of their many locations for well-rounded pizzas with a robust sauce. Giordano's (multiple locations) is another favorite chain, and they are known for their cheese-stuffed deep dish pies. Pequod's (two locations) is a favorite among locals and visitors alike. Their crust is doughy perfection and cooked to a caramelized crisp.
J.P. Graziano Grocery (901 West Randolph Street) – If you aren't carbed out yet, stop by J.P. Graziano Grocery for a fantastic sandwich to go. Piles of deli meats are stacked into fresh baked bread to create favorites such as the porchetta, Italian, or the signature Mr. G sandwich. They do close early, and lines can get long so try to call ahead or order online if you want to save time.
Virtue Restaurant (1462 East 53rd Street) – Amidst the Italian fare hotspot that is Chicago, Virtue serves up Southern comfort food in a chic yet welcoming atmosphere. Local favorites include the shrimp and grits, gumbo, and cornbread, but really you can't miss with any of the menu choices. If you're in a hurry or headed elsewhere, the take-out is fantastic as well.
Lula Cafe (2537 North Kedzie Boulevard) – If you love brunch as much as I do, be sure to stop by Lula Cafe for pancakes, french toast, omelettes, and all your other favorites. Located in the Logan Square neighborhood, Lula serves up breakfast, lunch, and dinner at this bustling neighborhood eatery. There will usually be a wait on the weekends for brunch, and they are only open four days a week so check their hours online before heading over.
Au Cheval (800 West Randolph Street) – Beloved by visitors and locals alike, Au Cheval is Chicago's favorite destination for a classic burger. Served in an old-school diner, their top-notch burgers are served up with a myriad of toppings. Favorites are the thick bacon and runny eggs. The garlic aioli crispy fries are also not to be missed. Waits can get lengthy, and they don't accept reservations so try your luck on a weekday or later at night.
Revival Food Hall (125 South Clark Street) – If you find yourself in the Loop and in need of a quick lunch stop, consider Revival - an elevated food court. Here you'll find various types of cuisine, with everything from ramen and poke to tacos and seafood. You'll also find Chicago local favorites such as Smoque BBQ and Mindy's Hot Chocolate, all under one roof. The space itself is beautifully designed and is usually filled with a local lunch crowd. If you find yourself in the West Loop or need a similar option for late night, consider Time Out Market Chicago (916 West Fulton Market) for more options. Either way, these food halls provide so many options, and you can find a little something for everyone.
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