Chicago is an incredible city full of food, culture, and amazing architecture and while you can’t experience it all in 2 days, you can definitely get to a lot of the good stuff. If you spend your time wisely, experiencing the best of Chi-Town is far more doable than you may think, even if you’ve just got 48 hours. From the deep dish in the city to famous jazz bars, here’s how to best spend 48 hours in Chicago.
After you’ve checked into your hotel, it’s time to get some noms. Depending on when you wake up, Chicago is home to a number of breakfast and lunch spots. Wildberry Pancakes and Cafe often has long waits, but it’s worth it – their signature pancakes are some of the best in the city. While you’re waiting for your table, hop over to Millenium Park for a stroll–Wildberry will call you when you seat is ready. Home of the famous “The Bean,” which you will want to take about 500 pictures of, Millennium Park is also home to Crown Fountain–two 50 foot towers that face each other across a shallow reflecting pool. During the warmer months, the screens show various faces of the people of Chicago. Lurie Gardens and the Boeing Galleries (an outdoor sculpture walk) are also located in Millenium Park. All that said, if you’re not in the mood to wait, Eggy’s is a local diner with massive portions tucked inside the River West Neighborhood.
If you prefer to sleep in or don’t care much for breakfast, there is no shortage of lunch cafes. And of course, no trip to Chi-Town is complete without trying Chicago deep dish pizza, and Lou Malnati’s is known as the oldest family name in Chicago pizza. For a quick, delicious, and affordable meal, visit Oasis Cafe, which is known for their mouthwatering Mediterranean food. Nestled in the back of a jewelry store on Wabash, Oasis Cafe is a hidden gem that is known for their falafels. If you’re having trouble deciding on what type of cuisine you want, Revival Food Hall houses 15 different food stalls. In the same area, you can also visit Greektown, which is home to some of Chicago’s best Mediterranean restaurants, including Athena and Artopolis Bakery.
Once you’re all fueled up, head over to the Art Institute of Chicago. Be sure to enter through the Michigan Avenue entrance so that you can say hello to the iconic lions who guard the museum. Once you’ve entered the museum, download the Art Institute of Chicago mobile app, which will help you plan out your tour as well as listen to free audio tours. The “must-see” exhibits often include Grant Wood’s American Gothic, George Seurat’s A Sunday on La Grande Jatte, Edward Hopper’s Nighthawks, Pablo Picasso’s The Old Guitarist, Vincent Van Gogh’s The Bedroom, and Buddha Shakyamuni Seated in Meditation (Dhyanamudra).
Chicago is known for its unique architecture, and the best way to see it is aboard an architecture river cruise. During a river cruise, you’ll learn about the history of some of Chicago’s most famous landmarks, including Willis Tower, the Wrigley Building, and the Merchandise Market. There are a large number of cruises to pick from, but we recommend boarding Chicago First Lady Cruises since your guide will be a docent from the Chicago Architecture Center. They also offer an evening cruise where you can see Chicago’s famous buildings during sunset. Wendella Sightseeing Co. also offers a wider variety of river cruises, including tours catered to specific parts of Chicago and specialty cruises such as the wine & cheese cruise. While there are some river cruises in the winter, we recommend going on this adventure during late spring or summer.
When it comes to finding a restaurant for dinner, the choices are endless. Chicago’s pseudo “restaurant district” is the West Loop, where you’ll find casual cafes alongside fine dining. Winner of Bravo’s Top Chef, Stephanie Izard has three restaurants in the West Loop (Fulton Market) area, two of which are open for dinner. Girl & The Goat serves a variety of tapas such as a goat cheese board and chickpea fritters, while Duck Duck Goat serves Chinese food. Avec is a Chicago staple that fuses American and Mediterranean cuisine. The West Loop is also home to a number of upscale Japanese restaurants, including Michelen starred Omakase Yume if you’re in the mood for a 16 course meal.
Before you head in for the night, stop by The Green Mill. What was once one of Al Capone’s hangouts, The Green Mill has live music every night (usually jazz) and holds dance nights on Tuesdays and Thursdays. Do note that The Green Mill accepts cash only.
Start your day with a stroll through Grant Park, where at the heart of it you will find Buckingham Fountain. Much like “The Bean,” Buckingham Fountain is selfie worthy, and during the summer, the jets within the fountain put on their own choreographed show. Grant Park is close to a number of museums, but before exploring them you will want to get a bite to eat. Either hop on the subway or go for a walk to Portillo’s, where you can try a Chicago-style hot dog or Italian beef.
Museum Campus consists of the Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium. If you’re up for it, you can easily visit all three of these attractions, since they are all within walking distance of each other. However, each museum does offer their own unique exhibits. The Field Museum is home to more than 20 million specimens as well as the largest and most preserved t-rex fossil to ever be discovered. Shedd Aquarium houses a number of ocean critters, including dolphins, beluga whales, sea otters, sharks, turtles, and even an amphibian exhibit dedicated to frogs. The Adler Planetarium is a great educational experience that has two full-size planetarium theaters.
If you live for science, skip museum campus and instead head to Hyde Park and visit the Museum of Science and Industry, where you can tour the real U-505 submarine, which is the only German submarine in the states; tour possible inventions of the future; examine the complexities of your body, and learn about the physics of storms. Since the Museum of Science and Industry is a bit outside of the Loop, you should explore some of Hyde Park’s dining scene. Virtue specializes in Southern American cuisine, while Medici on 57th is known for their burgers, not their pizza.
Before heading out for a night out on the town, head over to Logan Square/Avondale to try the scrumptious chicken at Honey Butter Fried Chicken. Lula Cafe serves a variety of contemporary American dishes, and for some upscale Greek food, head over to Andros Taverna.
If you want to check out the “hip” nightlife in Logan Square, visit Emporium Arcade Bar. Home to the largest collection of games in the city, Emporium has pool tables, foosball, air hockey, and classic arcade games.
Have extra time to spare? Add a brewery visit to your list. Here are the Best Breweries in Chicago.