Chicago is the third most populous city of the United States, nestled on the shores of Lake Michigan. The city of steely skyscrapers, stunning modern urban architecture such as the Frank Gehry’s swooping silver Pritzker Pavilion or the iconic design of Anish Kapoor, the Bean, and the impressive masterpieces of artwork, Chicago reserves some wonderful surprises and encounters for visitors. Some of the avid travelers and sports fanatics visit this city for its Bears football game or baseball match. The city is usually termed as a maniacal sports town. With its diverse population, Chicago is also a foodie haven where you will find tantalizing dishes coming from various cultures, be it Ukrainian traditional dishes or spicy Mexican tacos or Puerto Rican yummy dishes, the list is just too long. To learn how to spend 48 hours in Chicago, scroll down and find out in this article.
Day 1: Afternoon tea at Shokolad Pastry & Cafe
You cannot visit Chicago without feasting on some succulent fine European pastries, cookies, and delicious Ukrainian dishes at the very famous Shokolad Cafe. Start your trip with an afternoon tea at the Shokolad. The cafe is conveniently located at Humboldt Park and Wicker Park which are Ukrainian Village neighborhoods in Chicago. It rapidly became the favorite eating spot since it started. Initially, there were European pastries and cookies on the menu, but over the years, the menu has expanded with the inclusion of some mouth-watering ethnic dishes from Ukraine. There is an eclectic range of specialties available such as torte slices, dainty cookies, plump pierogi with potato and cheese, bacon, yummy crepe sometimes available with spinach and mushrooms, sandwiches like the roast beef panini with caramelized onions, and deserts. The cafe can cater to up to 50 guests. Its interior is cozy with the dimly lit lanterns, wooden furniture, including two-person tables, and the vibrant yellow sunflowers make it an ideal spot to enjoy the food.
Shokolad Pastry & Cafe
Address: 2524 W Chicago Ave, Chicago, IL 60622, USA
Website: Shokolad Pastry & Cafe
Day 1: Evening tour at the Ukrainian Institute of Modern Art and Ukrainian National Museum of Chicago
Stroll along the streets and you might end up finding interesting shops around. Just some 480 meters (0.3 miles) away is the Ukrainian Institute of Modern Art located at the Chicago Avenue. This modern Art Institute is dedicated to contemporary art expressed by Ukrainian artists about their Ukrainian and American experience, but locals also get to present their artwork as well. You can expect to find creative arts through exhibitions, readings, concerts, films, and lectures targeting to serve the cultural needs of the local community and the city. The institute was founded in 1971 through the initiative of art collectors Dr. Achilles and Vera Chreptowsky, and sculptors Konstantin Milonadis and Mychajlo Urban who wanted to bring contemporary art by Ukrainian artists into the limelight.
Get deep into the Ukrainian legacy by visiting the Ukrainian National Museum of Chicago located just a three-minute drive from the Ukrainian Institute of Modern Art. The museum presents the heritage, culture, and people of Ukraine, particularly community present in Chicago. There is a comprehensive collection of artwork by Ukrainian immigrants, artifacts, embroidered folk costumes, musical instruments, household utensils, and souvenir materials from the Soviet Union. Its library section has around 16,320 titles, including rare books, monographs on Émigré Communities, contemporary editions, author-autographed editions, and over 600 periodicals and newspapers.
Ukrainian Institute of Modern Art
Address: 2320 W Chicago Ave, Chicago, IL 60622, USA
Website: Ukrainian Institute of Modern Art
Day 1: Night out at one of the pubs in Humboldt Park
After the enriching museum tour head to the Humboldt Park for a chilled out night where you can slip into one of its pubs. Built in 1869 the Humboldt Park is a 83-hectare (207-acre) park and named after the German naturalist Alexander von Humboldt. The park has a ‘prairie style design’ whereby there is a display of native plants and stone. Its centerpiece is the 1907 Prairie School boathouse and can be full of people during the daytime. The area has a strong influence on the Puerto Rican heritage and hosts the National Museum of Puerto Rican Arts & Culture. Sometimes you might expect some free music concerts or outdoor movie. Just close by you will end by finding lots of restaurants and bars such as the California Clipper which is a peculiar bar featuring live music and most of its drinks are under $10.
Address: 1002 N California Ave, Chicago, IL 60622, USA
Website: California Clipper
Day 2: Morning tour at the Millennium Park and touch the iconic Bean sculpture
If you’re up to try some outdoor activities for free, then head to the Millennium Park which is a popular attraction when visiting Downtown Chicago. In 2004, the park was inaugurated by Mayor Richard M. Daley who had the vision to convert an unsightly industrial wasteland into a 10 hectare (25-acre) park dotted with modern urban sculpture, architecture, and design along with some marvelous flora. If you’re visiting the park in summer then you can find yourself with free night concerts at the Jay Pritzker Pavillion, designed by architect Frank Gehry. You can also find pilates, and yoga classes which take place on Saturday mornings in summer. There is the Family Fun Tent which caters for free kids activities daily in summer.
One of the iconic sculptures is the Bean or Cloud Gate, a centerpiece of AT&T Plaza at Park, designed by Indian-born British artist Anish Kapoor. The artwork is located on the top of Park Grill, between the Chase Promenade and McCormick Tribune Plaza & Ice Rink. This is an ideal spot to take some fantastic shots.
Address: 201 E Randolph St, Chicago, IL 60602, USA
Day 2: Lunch at the newest food hall, Forum 55
Next, to stop your craving for food, find the newest food hall, Forum 55 located within a walking distance of the Millennium Park, right in the heart of Chicago’s Loop. The industrial-chic food hall features breakfast, lunch, and midday noshing. Opened in the fall of 2017, the food hall is created by compass group offering six fast-casual stalls from some of Chicago’s favorite chefs and restaurants. Expect to find some healthy food at its grab-and-go marketplace or at its large salad bars where you can find produce from the Midwestern farmers. Some of the interesting projects of Forum 55 are the Apron Exchange program, a food service incubator designed to help minority female-owned businesses and the Community Garden which is a green area stocked with fresh produce from nearby farmers.
Address: 55 E Monroe St, Chicago, IL 60603, USA
Website: Forum 55
Day 2: Evening leisure walk along the Chicago Riverwalk, and scale 360 Chicago for a panoramic city view
Just a five-minute drive from the Forum 55, find the Chicago Riverwalk, a lush green 2 kms (1.25 miles) of pedestrian stretch located on the south bank of the main branch of the Chicago River. It spans from Lake Shore Drive to Lake Street. The Riverwalk is an ideal place to hang out, chill or even indulge in fun activities. If you’re looking for water-based activities then you can rent a kayak at the Cove also known as the Dearborn to Clark. Or you can relax at the River Theater which is an urban lush oasis adorned with trees growing from the steps, provides shade and a unique respite for city explorers.
Another attraction you cannot miss is located a five-minute drive away from the Chicago Riverwalk. It’s the 360 Chicago and it is an observation deck which lies 1000 feet (304 meters) above the famed Magnificent Mile in the iconic John Hancock Building. Feast your eyes on the 360-degree spectacular views of the city skyline and Lake Michigan.
Address: 875 N Michigan Avenue, 94th Floor, Chicago, IL 60611, United States
Website: 360 Chicago
Day 2: Exciting fireworks at Navy Pier at night
Spend your last night in Chicago by witnessing some stunning fireworks (every Wednesday and Saturday) at the Navy Pier, a very popular attraction which is reputed as being one of the most civic landmarks in the United States, and also featured as one of the most visited leisure and cultural destinations in the world. The attraction consists of carnival rides, along with a 196ft (59.7m) Ferris wheel and an IMAX theater. Taste some refreshing beer at the beer garden and enjoy the cool breezes. For children, there is the Chicago Children’s Museum which is located on the pier itself.
Address: 600 E Grand Ave, Chicago, IL 60611, USA
Website: Navy Pier
Day 3: Last morning tour at the Logan Square Farmers’ Market for brunch and shopping
Logan Square Farmers’ Market is an open-air food market operated by the neighborhood community. The market is a charming little paradise for organic fruits and vegetables and local products. You can find crafts such as candles, homemade cheese, honey, fresh baked bread and pastries, and vibrant flowers. You will be pampered by the variety of lunch options. Additionally, there are live music entertainment and free yoga classes. Enjoy your time shopping at various stalls and choose some pretty souvenirs to take home with you.
Logan Square Farmers’ Market
Address: 2363 N Milwaukee Ave, Chicago, IL 60647, USA
Website: Logan Square Farmers’ Market
The Windy City will blow you away with its popular attractions, delicious food, and awe-inspiring city view. Find out how to spend your next 48 hours in Chicago, Illinois.
Get Trip101 in your inbox
You can buy and claim online, even after you've left home. Travel insurance from WorldNomads.com is available to people from 140 countries. It’s designed for adventurous travellers with cover for overseas medical, evacuation, baggage and a range of adventure sports and activities.
*5% off when you book with our promo code: TRIP101
*For our Canadian and US travellers, unfortunately due to financial services laws, we cannot provide a discount. This promotional code cannot be used with any other discount offer, including World Nomads Members’ discount for travel insurance policy holders.