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Top 5 Tips for Chicago

Planning a trip to Chicago? Here are 5 essential travel tips to help you experience the best of the Windy City.

Between the lake views, amazing food, and world-class attractions, thereโ€™s so much to see in Chicago but also a few things to know before you go. Here are my top 5 tips to help make your visit to Chicago smoother.

1. Dress for the Weather

Chicago is nicknamed โ€œThe Windy Cityโ€ for a reason! It often feels colder than the temperature, especially near Lake Michigan. Bring layers and a windproof jacket in spring and fall, and bundle up in winter. Summers can be hot and humid, but youโ€™ll still want a light jacket for indoor AC, breezy evenings or sudden rain.

2. Book Major Attractions in Advance

Tickets for popular spots like the Willis Tower Skydeck, Art Institute, and architecture boat tours often sell out. Booking ahead saves time and helps you get your preferred time slot.

3. Stay Near Downtown

If itโ€™s your first visit, choose accommodation around The Loop, River North, or Streeterville. Youโ€™ll be within walking distance of top sights like Millennium Park, the Riverwalk, and the Art Institute.

4. Try the Local Food Classics

Chicago has world-class fine dining options like Alinea, but make sure to also try the cityโ€™s staples: deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches.

5. Watch the Fireworks at Navy Pier

Navy Pier hosts free fireworks every Wednesday and Saturday night in summer, plus special holiday shows throughout the year. Theyโ€™re visible from the pier, beaches, and many spots along the lake.

Looking for things to do in Chicago? Here are the top 5 things we loved most from our visit!


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