Chicago Travel Guides (Updated July 2026)

Cool Destinations wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Destinations over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

Cool Rewards

• Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

• Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
• Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
• Earned rewards will be available to redeem once they are no longer in a pending state.
• For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
• If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

Redeeming rewards

• To redeem rewards, you must be logged into your Cool Destinations account.
• Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
• You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
• There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
• Rewards are non-transferable and cannot be redeemed for cash.
• If rewards are redeemed against a booking that is canceled or refunded, the rewards will be reissued to your account.

Miscellaneous

• You can check your Cool Destinations account to see the rewards you have collected at any time. You are responsible for ensuring that your rewards balance is correct.
• We reserve the right to modify these Cool Rewards Terms and Conditions at any time, with or without notice, including the rules for earning and redeeming rewards. Any changes will be reflected in the updated Terms and Conditions.
• We reserve the right to terminate the Cool Rewards program and cease issuing any further rewards on future bookings. All pending and available rewards balances will be honored.
• By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.