Chicago 5-Day 4-Night Guide — Must-Do Activities 🏙️

Day 1 I wanted to try two different hotels this time, so right after landing, I stayed near Navy Pier for the lake view 🏞️. Went straight for dinner at night—most importantly: drinks, drinks, drinks! 🍺 Then visited the Ferris wheel at night 🎡. Day 2 Started with brunch at the hotel 🥐, then walked over to Navy Pier (super windy 💨!). Came across Bike & Roll and rented an e-bike for the day—$69. Way better than Lyft bikes (those are dirty 😷). We biked along Lake Michigan for 2–3 hours 🚴‍♀️🌊, then headed to Millennium Park—saw the Crown Fountain 👀 and the Bean 🪅. Absolutely stunning! (Highly recommend biking—scenic views and plenty of shirtless runners to keep you smiling 😏) Passed by the Trump Tower 🏢—no need to go out of your way to see it, you’ll likely cross paths anyway. Went up 360 Chicago for skyline views 🌆—booked an evening slot but beware: glass reflections make photos tricky 📸. Wrapped up at the Magnificent Mile—shopper’s paradise 🛍️. Day 3 The Art Institute of Chicago 🖼️ — my favorite part was the miniature Thorne Rooms 😍! Also saw plenty of famous paintings. Lasted 3 hours 🫠—that was my max. In the evening, walked across the Chicago River bridges 🌉 for photos. Day 4 Visited the Chicago Architecture Center near the hotel 🏗️—full of urban planning exhibits. Had to go as an architecture nerd 🤓. Afternoon: went to LondonHouse Rooftop for panoramic river views 🏙️☀️. Took the Architecture Tour by boat 🚢—booked the 5 PM slot. Got to experience daylight, sunset, and night views all in 90 mins! ✨ Checked out the Chicago Theatre neon sign at night 🎭—nice but not mind-blowing. Walked along the river at night—saw the corn towers 🌽, architecture... coming from Seattle, I felt the big-city buzz 🌃. Day 5 Chinatown — Not recommended 👎. Places I skipped (low energy bar ⚡): Willis Tower SkyDeck Light water show 💦 Chicago Magic Lounge 🎩 Urban Kayaks 🚣 World’s Largest Starbucks ☕ Griffin Museum of Industrial History Big Monster Toys 🧸 Rookery Building 🕍 Tip of the day: Don’t rent a car 🚗—parking is expensive and hard to find. Hotel parking was $80/night 😱! #Chicago #LifeInTheUS #ChicagoFood #ChicagoTravel #ChicagoGuide #StudyInChicago 🇺🇸🏙️🍕🎨📸