Weekend in Chicago: The Ultimate Guide

Chicago’s charm can be enjoyed year-round, but your experience will differ depending on the season. 

Summer brings street festivals, outdoor dining, and the bustling energy of the lakeshore. Spring and fall offer a more relaxed vibe, with fewer crowds and pleasant weather perfect for walking tours. Winter, though cold, has its own magic with festive lights, ice skating, and cozy indoor activities. 

No matter the season, there’s always something happening in Chicago.

When you’re in Chicago, a few landmarks are non-negotiable:

• The Bean in Millennium Park: a perfect spot for photos and people-watching.

• Willis Tower: for panoramic views of the city from the Skydeck.

• The Art Institute of Chicago: a must-see for art lovers, with collections spanning centuries.

• Magnificent Mile: a shopping mecca with everything from luxury boutiques to popular department stores.

• Navy Pier: a scenic spot with attractions, eateries, and beautiful lake views.

Wicker Park and Pilsen: explore these vibrant neighborhoods for art, food, and culture off the beaten path.

If you’re only staying in Chicago for two days, start your first day with a morning walk along the lakefront, perhaps with a stop at Navy Pier. After taking in the views, head over to Millennium Park to snap a picture with the Bean, followed by a visit to the Art Institute. 

For lunch, Chicago’s deep-dish pizza is a must—try a local spot like Lou Malnati’s or Giordano’s. In the afternoon, take a river architecture tour to admire the city’s renowned buildings, or shop along the Magnificent Mile. 

Wrap up your evening with a rooftop bar overlooking the skyline or some live jazz in the West Loop.

On your second day, head to Lincoln Park for a morning walk and visit the zoo—it’s free and offers a peaceful break from the city’s hustle. From there, explore the diverse neighborhoods of Chicago, each with its own character. 

Wicker Park is perfect for brunch and boutique shopping, while Pilsen showcases incredible street art and Mexican cuisine. In the evening, catch a show at the Chicago Theatre or grab dinner in Chinatown for a truly local flavor. 

To make your stay more convenient, choose one of Accor's hotels such as Fairmont Chicago - Millennium Park, Swissôtel Chicago or Sofitel Chicago Magnificent Mile. These options put you right in the heart of the city's best neighborhoods and make exploring easier.

Chicago’s neighborhoods each offer something special. Don’t miss:

• Wicker Park: a trendy area full of art galleries, vintage shops, and cafes.

• Pilsen: known for its Mexican heritage, street art, and vibrant food scene.

• Lincoln Park: a charming mix of green spaces, boutique shops, and laid-back bars.

• South Loop: home to museums, parks, and a relaxed vibe with easy access to the lakefront.

Chicago offers a variety of dining experiences that reflect the city's diverse culture and culinary history. For a true taste of Chicago, start with a deep-dish pizza at Lou Malnati's, where the buttery crust and rich toppings are legendary. 

If you're craving something with a little more flair, The Purple Pig offers Mediterranean-inspired dishes with a focus on shared plates and an exceptional wine list. For an elevated dining experience, head to The Aviary, a rooftop bar serving creative cocktails paired with breathtaking views of the skyline. 

Each of these spots brings something unique to the table, making your Chicago getaway a true culinary adventure.

You don’t need to break the bank to enjoy Chicago. Here are a few affordable options:

• Visit the Lincoln Park Zoo: free admission and plenty to explore.

• Walk the 606: an elevated park and trail system that offers great views of the city.

• Explore the Art Institute's free collection: you can enjoy many exhibits without paying the entry fee.

Take a stroll along Lake Michigan: walk along the shore, take in the views, and enjoy the fresh air.

You can find unique activities and events happening in Chicago this weekend throughout various neighborhoods and cultural hubs. For example, explore Millennium Park for outdoor concerts, visit the Art Institute for special exhibits, or check out local theaters like the Chicago Theatre for live performances.

To make the most of a long weekend in Chicago, staying in a central location can really help. Consider booking a spot in neighborhoods like the Loop or River North, where you're close to attractions like Millennium Park and Navy Pier. Hotels like Fairmont Chicago - Millennium Park, Swissôtel Chicago, or 21c Museum Hotel Chicago offer a convenient base for exploring the city’s best spots, with plenty of hidden gems nearby to discover along the way.

For a change of scenery, Chicago’s surroundings offer some fantastic weekend escapes. Head to nearby destinations like the lakeside town of Michigan City or the charming towns of the Indiana Dunes for a relaxing retreat, or explore the scenic landscapes of Starved Rock State Park for a dose of nature just outside the city.

Make your weekend in Chicago even more unforgettable with Accor hotels. Whether you’re staying at the luxurious Fairmont Chicago or the modern Sofitel, you'll be close to the best attractions and experiences. Plus, with the ALL fidelity program, you’ll unlock exclusive benefits to enhance your stay, making your trip even more enjoyable.

Make the most of your trip with us by your side!