What to book in advance

Question

I am visiting Chicago for four days in late August. Do I need to book any activities in advance? I am not sure if things sell out/fill up during this time. Here are the activities I'm considering:

360 Chicago

History and Architecture Walking Tour (Get Your Guide)

Chicago Architecture Center River Cruise

Iconic Foods of Chicago Walking Tour

Thank you!

Answer

For your upcoming visit to Chicago in late August, it’s a good idea to plan ahead and book some activities in advance. Late August is a popular time to visit Chicago, especially with the summer festivals, so certain tours and attractions can sell out or fill up quickly. Here’s a breakdown of the activities you’re considering and whether it’s recommended to book in advance:

360 Chicago: This is one of the city's most popular attractions, offering stunning views from the John Hancock Center. While it’s generally less likely to sell out, booking in advance can save you time and potentially offer better pricing or special skip-the-line access. It's especially worth booking if you want to visit at sunset or during peak hours to avoid long waits.
History and Architecture Walking Tour (Get Your Guide): Walking tours, especially those focused on Chicago’s iconic architecture and history, tend to fill up quickly during peak seasons. It’s a good idea to book this in advance, particularly if you have a specific tour or time in mind. Booking early ensures you won’t miss out, as these tours are popular and can sometimes have limited availability.
Chicago Architecture Center River Cruise: The river cruise is one of the best ways to see the city, and it’s very popular, especially during summer and fall months. It’s highly recommended to book this tour in advance to secure your spot, especially since tours can fill up, and you may have a hard time getting tickets on the day of. If you’re looking for a specific time or want to avoid sold-out cruises, it’s best to book as soon as you finalize your plans.
Iconic Foods of Chicago Walking Tour: Food tours in Chicago, especially those that focus on iconic dishes like deep-dish pizza and Chicago-style hot dogs, are often in high demand. Given that these tours are limited in size and can sell out, it’s a good idea to book this in advance. If you have a specific tour guide or time that works for you, booking ahead will ensure you don’t miss out.

Overall, I recommend booking the History and Architecture Walking Tour, Chicago Architecture Center River Cruise, and the Iconic Foods of Chicago Walking Tour in advance to guarantee your spots. For 360 Chicago, you can book in advance if you want to lock in a specific time, but it’s generally less of a concern.

Booking tours in advance also helps you avoid long lines and ensures a smoother, more organized experience, especially during the busy summer months. Enjoy your time in Chicago!

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