48 Hours in Chicago – Travel Guide

Head to Chicago and explore all the excitement this city has to offer!

The "Windy City" is located on the shores of Lake Michigan. The city's amazing architecture, deep-rooted history, and exciting culture combine to create a unique place for any traveller. You’ll be able to find all types of attractions while visiting Chicago, whether it’s to see the famous landmarks of Chicago, discover the city’s hidden treasures, or plan out a great trip. In only 48 hours, you’ll find out all that Chicago has to offer. So, what should you do while in Chicago? Read on to begin your amazing adventure!

Start your day at Wildberry Pancakes & Cafe, located in Downtown Chicago. They have creative stacks of pancakes, including Signature Berry Bliss Pancakes with Mascarpone Cheese, Fresh Berries, and Vanilla Cream; Oreo S'mores Pancakes topped with Marshmallows and Chocolate; Cinnamon Roll Pancakes with Cream Cheese Icing; Chocolate Chip Banana Pancakes made with Melting Chocolate and Bananas; and Blueberry Danish Pancakes with Cheesecake Filling and Crumbled Streusel on top. At the Little Goat Diner, breakfast is full of flavorful, fun dishes that reflect the diner’s retro roots.

The Fat Elvis Waffles are piled high with peanut butter and maple syrup, bananas, and bacon, while the Bull’s Eye French Toast consists of layers of brioche, pastry cream, fresh strawberries, and crispy oat streusel. The Okonomiyaki is a Japanese-inspired savory pancake filled with cabbage, pork belly, and a fried egg. The Breakfast Burrito is another beloved classic made with eggs, chorizo sausage, black beans, and salsa, all wrapped in a gigantic tortilla. Lastly, there is the Paratha Egg Sandwich, which consists of 2 pieces of flaky Indian flatbread filled with eggs and spiced potatoes.

The Wild Mile is the world's first floating eco-park atop the North Branch Canal of the Chicago River. The Wild Mile, which was created by a nonprofit restoration group called Urban Rivers, is trying to restore the wetland ecosystems of Chicagoland that existed before urban development. The Wild Mile provides an area for individuals to find peace and reflect. Urban Rivers also holds community events such as yoga classes and fishing. The area can be explored on foot or by boat. Kayaks can be rented at several different points along the Wild Mile.

If you want to experience some Midwest nature within city limits, head to Burnham Park, where you can stroll along the 100-acre wildlife corridor of the city of Chicago on the edge of Lake Michigan and along Lake Shore Drive. There are three main zones: The Burnham Centennial Prairie, the Burnham Nature Sanctuary, and the McCormick Bird Sanctuary, all of which are tucked away so that you can enjoy a sense of wilderness. Birdwatchers should bring binoculars because they may see numerous migratory birds as they pass through on their way south for the winter!

Northalsted Market Days is a colorful festival and one of the largest LGBTQ+ festivals celebrating community, hosted in Chicago’s Northalsted neighborhood (also known as Boystown), making for one of the best Chicago festivals. Take the CTA Red, Brown, or Purple Line, as it gets crowded and fills up quickly. This week-long celebration takes over the streets, offering endless art and craft booths to browse, top DJs to dance to, delicious food trucks, and unique cocktail options, all to enjoy in the warmth of the summer sun. Dress brightly, stay hydrated, put on sunscreen, and get ready to mingle with a crowd of 150,000 participants filling the streets. There is a small entry donation to support the community.

The Shedd Aquarium has been a Chicago landmark since 1930, and it is certainly a visual treat. Your child will identify various animal exhibits, including piranhas, frogs, turtles, sharks, penguins, sea lions, and otters, as you walk through the exhibit hallways organized by geography. You will also have the opportunity to experience immersive activities such as 4D movies and animal encounters with stingrays, sturgeons, and sea stars.

Beckoning beer lovers is Ravenswood on Tap, located in the picturesque neighborhood of Ravenswood. This festival takes place on "Malt Row," a street lined with independent breweries, and spans two days, paired with local restaurants, artisans, and musicians. Walk under the shady, tree-lined street while enjoying all types of delicious beers, from refreshing ales to rich stouts, with friends. In June of every year, Ravenswood on Tap is quickly expanding, now with craft distilleries joining the local breweries. Make sure to bring cash as no cards are allowed, although drink tickets can be purchased beforehand.

The new Museum of Ice Cream Chicago offers a fun and colorful experience in a style similar to the enchanted world of Willy Wonka. Guests will check in and be given an ice cream-themed name: "BaChoc Obama," "Oprah Winfreeze," or "Mintdonna" before being treated to a pink replica of an El train car that takes them on to an experience in many different types of interactive rooms, including a science-based ice cream laboratory, a display of the history of local ice cream manufacturing, mini-golf, and finally, the famous sprinkle pool.

Located against the stunning skyline of Grant Park, this iconic festival transforms downtown Chicago into a music heaven every August for four days of music festivities. Lollapalooza draws crowds of more than 400,000 attendees and features a stellar lineup of artists from around the world spanning all genres, from EDM to reggae, rock to metal, and more. Lollapalooza also provides for a cultural experience featuring vibrant art installations and an array of gourmet vendors. For those who prefer a little less crowd, there are cabanas available for purchase. After an epic day, hop on public transportation or get a ride-share to safely maneuver the crowds.

ndy's Jazz Club has attracted large crowds to experience live music and satisfy their appetites with great Cajun food and creative cocktails. Andy's Jazz Club is guaranteed to be buzzing with activity every day of the week. Meanwhile, Constellation is an innovative theatre utilizing the art of improvisation and contemporary methods of staging. At Constellation, two intimate venues are combined with a full-service bar, small enough to allow everyone in attendance to be part of the performance on some level.
The Green Mill Cocktail Lounge has been at the center of the Chicago jazz scene for over 100 years. It was once a speakeasy for Al Capone during Prohibition and retains all of its vintage elegance as it features live music every night, ranging from traditional jazz to progressive sounds that go until the wee hours of the morning.
Hungry Brain has been a place for new jazz musicians to be creative and experimental since the venue opened in 1996 and has become a community-driven venue offering all types of different styles, from early jazz to improvisational music performance.

Breakfast at Lou Mitchell’s is served in the nostalgic ambiance of this historic Route 66 diner. When you walk through the front door, you’re greeted with the scent of fresh-baked goods and Lou’s famous donut holes. The fluffy omelettes are large and very filling, with the Mediterranean Omelette packed with feta cheese and fresh vegetables being one of the most popular. The Swedish Pancakes are also popular due to their lightness and the addition of lingonberry sauce on top. The Farmer’s Scramble is a staple among Lou Mitchell’s regulars, consisting of eggs, sausage, peppers, and potatoes. The Buttermilk Pancakes are thick, golden brown, and incredibly light, usually served with delicious maple syrup, whereas Biscuits and Gravy provide an overpowering flavour from the creamy sausage gravy slathered over top of these warm, flaky biscuits.

Originally opening before 1893, during the World’s Columbian Exposition, this beautiful park, located between two lagoons on Wooded Island in Jackson Park, served as a symbol and was physically important to the relationship between the US and Japan. Their legacy is still evident with both the renovated pavilion and Japanese-inspired landscape, both of which can be appreciated each spring when the cherry trees bloom.

During the summer months, the Pitchfork Music Festival beckons indie music fans to Chicago. With a curated selection of more than 40 acts, Pitchfork Music Festival provides great music, with local food vendors, interesting pop-up craft stands, and non-profit booths. The event is hosted at Union Park's large front lawn every year. So, bring a blanket or chair to lounge on and catch a break between music sets. Ride a bike to get to this festival in Chicago.

An iconic Lincoln Square spot, Winnemac Park has provided approximately 40 acres of green space for Chicagoans since its opening in 1910. The park has three acres of native prairie plants running through it. Flowering plants are abundant and diverse in the prairie and provide essential habitat for many birds and butterflies. Visitors can take a peaceful walk along the paths that meander through the park or relax on a bench and enjoy the serenity of the natural surroundings.

Ribfest is all about food, pulling together thousands of BBQ enthusiasts in the festive Irving Park neighborhood of Chicago. With over 60 local pitmasters firing up their grills with smoky, saucy, and savory creations, this is one of the best Chicago attractions. Ribfest is held every June, pairing award-winning ribs with live entertainment featuring local and national acts, carnival games, a craft zone, and a playground. You can also vote for the coveted "People's Choice Awards" for "Best Ribs." After a long day, take a relaxing walk through the nearby Horner Park along the Chicago River.

Avondale Park is just 1.24 acres on the drive-by on the Kennedy Expressway. But despite its size, there is a plethora of recreational opportunities at this park (including swimming, soccer, and volleyball). Stop at Joong Boo Market to pick up picnic supplies and then relax and enjoy your time at the park.

Milton Lee Olive Park is located just off Ohio Street Beach, near the Art Institute's South Garden. The park was created on a man-made peninsula within the Chicago River, bordered to the south by a row of honey locust trees covering the walkway at Lake Michigan and providing spectacular views of the lake. Sit on one of the park's black granite benches for a few moments or string up your hammock between the trees, and relax for hours!

Embrace art and community at Bucktown Arts Fest, which was first organized by four dedicated artists in the 1980s. Free to the public, the arts fest gives back to the Bucktown and Wicker Park communities through art education. From unique ceramics to colorful mosaics and family-friendly “make-and-take” art experiences, there are various activities here. The atmosphere is enhanced by the various local food trucks, beer tents, community booths, and local musicians from the neighborhood.

Jazz Showcase has been captivating audiences since it opened its doors in the 1940s, creating a rich history and tradition within the venue for both performers and audiences alike. Performers such as Ira Sullivan, Count Basie, Richie Cole, and Dizzy Gillespie, among a number of others, have performed on the stage at Jazz Showcase and have been a part of the evolving lineup of performers. Live performances are held at the Jazz Showcase seven nights per week, with special Sunday matinee performances that invite families to experience the space together with their children (kids receive free admission). Located in the South Loop, M Lounge is known as a candlelit bar featuring live jazz music in an intimate ambiance. The low-light atmosphere allows for comfortable seating within the lounge; bars with plush couches and chairs create the perfect place to sit back and enjoy the performance. Performances by local artists feature jazz, blues, and R&B and are offered free to customers every Tuesday and Wednesday, adding diversity to M Lounge's retro ambiance.

From museums to iconic attractions, explore Chicago with ease from Chicago South Loop Hotel—reserve your stay now.