All Chicago, expedition cruises, self guided adventures and vacation packages. Find the best guided and expert planned vacation and holiday packages. Read more about Chicago
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Chicago Tours & Travel Packages 2025/2026
19 Chicago trips. Compare tour itineraries from 10 tour companies. 0 reviews.
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The Windy City as it's known colloquially, Chicago is one of the most popular cities to visit in the US. Boasting spectacular food and drink options, famous blues bars, a renowned theater scene, and extensive bike paths along enormous Lake Michigan, it's a great family or couples destination. Don't miss taking the architecture ferry tour!
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Traveling to Chicago, an FAQ
1. Does Travelstride have all the tour operators?
Travelstride has the widest selection of tours and tour companies. All the largest companies are on the site and most smaller local operators though we are adding new operators daily. Unlike other websites and agencies, we show you all the options, regardless of whether or not we are paid by the company.
2. How does the Member Savings program save me money?
Travelstride membership is absolutely free. You receive special benefits including saving up to $700 on select tours with top tour operators. The main requirement is to write a review after your trip to access the savings.
3. Can I trust the tour operator and trip reviews on Travelstride?
Yes. Travelstride has both expert reviews, written by Travelstride staff and local experts as well as traveler reviews written by people like you who have used the company and traveled to that destination.
4. What does ‘Stride Preferred’ mean?
Stride Preferred and Stride Premier are status categories to help you sort quickly through known and reliable travel companies. Since there are thousands of tour operators around the globe, Preferred or Premier badges are awarded to companies that Travelstride has determined meet the highest standards of professionalism, customer satisfaction, and quality.