In the summer months Chicago is another famous city that’s perfect for a quick weekend trip. With much to see and enjoy planning an itinerary can be quite overwhelming. Lucky for you, here is a WKNDTRP generate itinerary that selects the best venues and places to see in the city. Ensuring your trip is filled with lasting memories.

Day 1: Arrival and Exploration

Morning: Arrival and Check-In

Choosing the right accommdation is a vital aspect to any trip plan. The feeling you get when you’ve checked into your hotel is ideally how you will start your trip. Therefore feeling relaxed, comfortable and excited are great ways to ensure your trip will be enjoyable. In a city as large as Chicago there’s many hotel options to choose from. If you’re looking to indulge in luxury here is an option.

The Langham, Chicago: offers luxurious rooms with floor-to-ceiling windows providing stunning city views. The hotel features an elegant Chuan Spa, a 67-foot swimming pool, and an upscale restaurant, Travelle Kitchen + Bar.

For a more intimate or boutique stay, The Robey, located in the vibrant Wicker Park neighborhood offers modern rooms with Art Deco flair. The hotel features a rooftop lounge with panoramic views, a trendy café, and easy access to nearby boutiques and restaurants.

Late Morning at Millennium Park to see the iconic Cloud Gate (The Bean), a highly reflective sculpture perfect for photos. Enjoy the interactive Crown Fountain and the serene Lurie Garden. The park often hosts events and exhibitions, offering a lively atmosphere.

Enjoy upscale American fare with a contemporary twist at The Gage, located near Millennium Park. The menu features hearty dishes like fish and chips, burgers, and an extensive beer and wine list, all served in a stylish gastropub setting.

In the afternoon explore the renowned Art Institute of Chicago, home to a vast collection of artwork from around the world. Key highlights include Grant Wood's "American Gothic," Edward Hopper's "Nighthawks," and Georges Seurat's "A Sunday on La Grande Jatte." The museum's modern wing offers stunning architecture and contemporary pieces.

Start your evening at Alinea, a three-Michelin-star restaurant known for its innovative and artistic approach to cuisine. Each dish is a masterpiece, combining unusual ingredients and creative presentations. Dining at Alinea is a multi-course experience that requires reservations well in advance.

Head to The Aviary for a night out in the West Loop for avant-garde cocktails in a sophisticated setting. The Aviary is known for its creative and theatrical drinks, often served with unique presentations and unexpected flavor combinations.

Day 2: Culture and Shopping

In the morning take a Chicago Architecture Foundation Center River Cruise to learn about the city’s architectural history and admire the skyline from the water. The 90-minute tour covers over 50 buildings along the Chicago River and provides fascinating insights into the city's development and design.

Enjoy Chicago's famous deep-dish pizza at Lou Malnati’s, a local favorite known for its buttery crust, thick layers of cheese, and rich tomato sauce. The pizzeria offers a cozy atmosphere and friendly service, perfect for a satisfying lunch.

After lunch spend the afternoon exploring interactive exhibits at the Museum of Science and Industry, one of the largest science museums in the world. Highlights include the U-505 Submarine, a replica of a coal mine, and a vast model railroad. The museum offers hands-on experiences that are fun for all ages.

Do some shopping along Michigan Avenue’s Magnificent Mile, home to high-end boutiques, department stores, and luxury brands. Key destinations include Water Tower Place, a multi-story mall with numerous shops and dining options, and the historic Chicago Water Tower.

Kick of your evening at Dine at Girl & the Goat, a trendy restaurant in the West Loop known for its inventive small plates and vibrant atmosphere. Chef Stephanie Izard’s menu features globally inspired dishes, such as roasted pig face, goat empanadas, and wood oven-roasted oysters. Reservations are recommended due to its popularity.

End the night at the historic Green Mill Cocktail Lounge, enjoying live jazz music in a venue with a speakeasy vibe. The Green Mill has been a Chicago institution since the 1900s and offers a cozy, vintage atmosphere with excellent acoustics for its nightly jazz performances.

Day 3: Neighborhoods and Farewell

Start your day with brunch at Cindy’s Rooftop, offering panoramic views of Millennium Park and Lake Michigan. The menu features farm-to-table dishes, including hearty brunch staples like avocado toast, eggs benedict, and craft cocktails. The open-air terrace provides a relaxed, scenic setting.

Explore Lincoln Park, including the Lincoln Park Zoo, one of the oldest free zoos in the country. The zoo houses a diverse range of animals and offers beautiful walking paths. Nearby, the Lincoln Park Conservatory showcases exotic plants and flowers in a lush, glass-enclosed space.

Stop for lunch at The Chicago Diner, famous for its comfort food with a healthy twist. Popular dishes include the Radical Reuben, vegan shakes, and hearty salads. The diner’s casual and welcoming atmosphere makes it a great spot for a relaxing meal.

In the afternoon wander through the Wicker Park and Bucktown neighborhoods, known for their trendy boutiques, vintage shops, and artistic vibe. Visit Myopic Books for a vast selection of used books and Una Mae’s for unique clothing and accessories. The neighborhoods also offer vibrant street art and cozy cafes.

Head to the 360 Chicago Observation Deck at the John Hancock Center for breathtaking views of the city and Lake Michigan. The observation deck offers a thrilling experience with its TILT attraction, where visitors can lean out over the edge of the building for an exhilarating perspective.

Have a final dinner at RPM Italian, a chic restaurant offering modern Italian cuisine and an extensive wine list. The menu includes handmade pastas, prime steaks, and seafood dishes, all served in a stylish, contemporary setting. The restaurant is known for its elegant ambiance and excellent service.

End your trip with drinks at the LondonHouse Rooftop Bar, enjoying the stunning views of the Chicago River and skyline. The rooftop bar offers a sophisticated atmosphere, craft cocktails, and a picturesque setting to reflect on your Chicago adventure.

A trip to Chicago is now super easy to plan with the Trip planner on the app. Create an itinerary with all your favourite venues in just a few minutes. Striving to make travel easy and enjoyable the app offers seamless functionality to ensure you plan the best weekend trips.