5-Day Chicago Trip: Top Attractions, Food Experiences and Travel Tips

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Advisor - Michelle Malter
Curated By

Michelle Malter

  • Chicago

  • Arts & Culture

  • City Travel

  • History

  • Architecture

  • Insta-Worthy

5-Day Chicago Trip: Top Attractions, Food Experiences and Travel Tips
Curator’s statement

Chicago holds a special place in my heart, having grown up in Illinois until I was 25. The city's blend of rich history and modern vibrancy feels like home to me. The immersive History Museum, diverse and delicious Chicago food scene, and iconic landmarks like the lively Bean made my trip truly unforgettable. Despite the parking challenges, the luxurious and relaxed atmosphere of my Chicago hotel added to the wonderful experience.

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My recent five-day trip to Chicago was a fantastic blend of history and modern city life. A highlight was visiting the Chicago History Museum, where each room felt like stepping into a different era. This spot is perfect for history buffs, a unique date night, or a family outing. Walking through the bustling downtown mall and visiting the iconic Bean added to the city's charm.


Chicago's food scene truly stands out. Growing up in Illinois until I was 25, I've always appreciated good food, but Chicago's culinary diversity is exceptional. From deep-dish pizza at Lou Malnati’s to hot dogs at Portillo's, the options are endless. For anyone visiting, exploring the local food scene is a must!

A group of people looking at their reflections in front of a reflective sculpture

Getting around the city, I found that using public transportation or walking was the best approach. Parking can be challenging and often comes with high fees, so these alternatives made my trip smoother. Despite the parking challenges, my stay at a luxurious hotel added to the overall comfort of my visit. The hotel's atmosphere and breakfast offerings were top-notch, making it an excellent choice for travelers.

Chicago is a city that demands multiple visits to fully appreciate its rich history, delicious food, and vibrant culture. I can't wait to return and explore even more!

Chicago is a city that truly comes alive through its local experiences and vibrant neighborhoods. Visiting neighborhoods like Wicker Park and Lincoln Park offers a taste of Chicago's eclectic charm. For art lovers, the Art Institute of Chicago is a must-see with its impressive collection. Additionally, a river cruise provides a unique perspective on the city's stunning architecture. Whether you're strolling through Millennium Park or enjoying the nightlife, Chicago's dynamic energy makes every visit memorable. and of course, enjoy! Reach out to book with me :)

Need to know

This trip report is part of our ongoing series on travel to Chicago. In need of further inspiration? Check out Danielle Thomas’s guide, Free Ways to Explore Chicago: Your Budget-Friendly Guide to "The Windy City".

Advisor - Michelle Malter

Travel Advisor

Michelle Malter

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