What are the best options for Chicago Multi-day & Extended Tours?

According to verified reviews on Cool Destinations and TripAdvisor, the best Chicago Multi-day & Extended Tours are: Chicago and All MidWest Self Guided AI Audio Tours for 7 Days 5-Day Tour of Superior, Huron and Michigan from Chicago Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago Continental US Train Zephyr Adventure CA -CO - Il

What are the best kid-friendly options for Chicago Multi-day & Extended Tours Tours?

According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly Chicago Multi-day & Extended Tours are: 5-Day Tour of Superior, Huron and Michigan from Chicago Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago Continental US Train Zephyr Adventure CA -CO - Il View all kid-friendly Tours →

Which Chicago Multi-day & Extended Tours have Instant Confirmation?

Chicago Multi-day & Extended Tours with Instant Confirmation include: Chicago and All MidWest Self Guided AI Audio Tours for 7 Days Continental US Train Zephyr Adventure CA -CO - Il View all Tours with Instant Confirmation →

Which Chicago Multi-day & Extended Tours have Free Cancellation?

Chicago Multi-day & Extended Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include: Chicago and All MidWest Self Guided AI Audio Tours for 7 Days 5-Day Tour of Superior, Huron and Michigan from Chicago Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago Continental US Train Zephyr Adventure CA -CO - Il Great Smoky Mountains,Gatlinburg 4-Day Tour from Chicago View all Tours with Free Cancellation →

Got any more Chicago trip ideas?

We sure do. Check out our curated lists of hand-picked Chicago Tours. Top 10 Chicago 2026 Senior-friendly tours Chicago The best tours and activities for culture lovers in Chicago Top Day Trips from Chicago Things to do in Chicago this summer View all Chicago Trip Ideas →

What are the most popular styles of Tours and Activities in Chicago?

Based on our sales data over the past year, the most popular styles of tours and activities in Chicago are: Chicago Luxury & Special Occasions Chicago Luxury Tours Chicago Tours & Sightseeing Chicago Cruises, Sailing & Water Tours Chicago Boat Tours View all tour styles in Chicago →

Top Chicago Multi-day & Extended Tours 2026 (w/Prices)

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.
Your account and your rewards balance are shared across all our participating sites, including cooldestinations.com. Rewards earned on any participating site can be redeemed on any other participating site.

Earning rewards

Rewards can be earned by making bookings on Cool Destinations or on any other participating site. You will 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. You can redeem them on Cool Destinations or on any other participating site.
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 switch them off at checkout. 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 rewards balance in your account at any time, on Cool Destinations or on any other participating site. 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.

Interpretation & Definitions

Interpretation
The words of which the initial letter is capitalized have meanings defined under the following conditions.

Definitions
For the purposes of these Terms and Conditions (please note: the following definitions shall have the same meaning regardless of whether they appear in singular or in plural):

Affiliate means an entity that controls, is controlled by or is under common control with a party, where “control” means ownership of 50% or more of the shares, equity interest, or other securities entitled to vote for the election of directors or other managing authority.
Account means a unique account created for You to access our Service or parts of our Service.
Company (referred to as either “the Company”, “We”, “Us” or “Our” in this Agreement) refers to Cool Destinations.
Country refers to: United States of America
Device means any device that can access the Service such as a computer, a cellphone, or a digital tablet.
Feedback means feedback, innovations, or suggestions sent by You regarding the attributes, performance, or features of our Service.
Goods or Services (referred to as either “Goods”, “Services”, “Experiences”, “Activities”, “Excursions” or “Tours” in this Agreement) refer to the items and services offered for sale on the Service.
Orders (referred to as either “Order”, “Booking”, “Ticket” or “Reservation” in this Agreement) mean a request by You to purchase Goods or Services from Us.
Promotions refer to contests, sweepstakes, or other promotions offered through the Service.
Service refers to the Website.
Terms and Conditions (also referred to as “Terms” and “Terms of use”) mean these Terms and Conditions that form the entire agreement between You and the Company regarding the use of the Service.
Third-party Social Media Service means any services or content (including data, information, products, or services) provided by a third-party that may be displayed, included, or made available by the Service.
Website refers to Cool Destinations, accessible from cooldestinations.com.
You means the individual accessing or using the Service, or the company, or other legal entity on behalf of which such individual is accessing or using the Service, as applicable.

Acknowledgement

These are the Terms and Conditions governing the use of this Service and the agreement that operates between You and the Company. These Terms and Conditions set out the rights and obligations of all users regarding the use of the Service.

Your access to and use of the Service is conditioned on Your acceptance of and compliance with these Terms and Conditions. These Terms and Conditions apply to all visitors, users and others who access or use the Service.

By accessing or using the Service You agree to be bound by these Terms and Conditions. If You disagree with any part of these Terms and Conditions then You may not access the Service.

You represent that you are over the age of 18. The Company does not permit those under 18 to use the Service.

Your access to and use of the Service is also conditioned on Your acceptance of and compliance with the Privacy Policy of the Company. Our Privacy Policy describes Our policies and procedures on the collection, use, and disclosure of Your personal information when You use the Application or the Website and tells You about Your privacy rights and how the law protects You. Please read Our Privacy Policy carefully before using Our Service.

Placing Orders for Goods or Services

By placing an Order for Goods or Services through the Service, You warrant that You are legally capable of entering into binding contracts.

Your Information
If You wish to place an Order for Goods or Services available on the Service, You may be asked to supply certain information relevant to Your Order including, without limitation, Your name, Your email, Your phone number, Your credit card number, the expiration date of Your credit card, Your billing address, and if applicable, Your shipping information.

You represent and warrant that: (i) You have the legal right to use any credit or debit card(s) or other payment method(s) in connection with any Order; and that (ii) the information You supply to us is true, correct and complete.

By submitting such information, You grant us the right to provide the information to payment processing third parties for purposes of facilitating the completion of Your Order.

Order Cancellation
We reserve the right to refuse or cancel Your Order at any time for certain reasons including but not limited to:

Goods or Services availability
Errors in the description or prices for Goods or Services
Errors in Your Order

We reserve the right to refuse or cancel Your Order if fraud or an unauthorized or illegal transaction is suspected.

Availability, Errors, and Inaccuracies
We are constantly updating Our offerings of Goods or Services on the Service. The Goods or Services available on Our Service may be mispriced, described inaccurately, or unavailable, and We may experience delays in updating information regarding our Goods or Services on the Service and in Our advertising on other websites.

We cannot and do not guarantee the accuracy or completeness of any information, including prices, product images, specifications, availability, and services. We reserve the right to change or update information and to correct errors, inaccuracies, or omissions at any time without prior notice.

Prices Policy
The Company reserves the right to revise its prices at any time prior to accepting an Order.

Payments
Payment can be made through various payment methods we have available, such as Visa, MasterCard, Discover, and American Express. Payment cards (credit cards or debit cards) are subject to validation checks and authorization by Your card issuer. If we do not receive the required authorization, We will not be liable for any delay of Your Order.

Promotions

Any Promotions made available through the Service may be governed by rules that are separate from these Terms.

If You participate in any Promotions, please review the applicable rules as well as our Privacy policy. If the rules for a Promotion conflict with these Terms, the Promotion rules will apply.

User Accounts

When You create an account with Us, You must provide Us information that is accurate, complete, and current at all times. Failure to do so constitutes a breach of the Terms, which may result in immediate termination of Your account on Our Service.

You are responsible for safeguarding the password that You use to access the Service and for any activities or actions under Your password, whether Your password is with Our Service or a Third-Party Social Media Service.

You agree not to disclose Your password to any third party. You must notify Us immediately upon becoming aware of any breach of security or unauthorized use of Your account.

You may not use as a username the name of another person or entity or that is not lawfully available for use, a name or trademark that is subject to any rights of another person or entity other than You without appropriate authorization, or a name that is otherwise offensive, vulgar or obscene.

Intellectual Property

The Service and its original content (excluding Content provided by You or other users), features, and functionality are and will remain the exclusive property of the Company and its licensors.

The Service is protected by copyright, trademark, and other laws of both the Country and foreign countries.

Our trademarks and trade dress may not be used in connection with any product or service without the prior written consent of the Company.

Your Feedback to Us

You assign all rights, title, and interest in any Feedback You provide the Company. If for any reason such assignment is ineffective, You agree to grant the Company a non-exclusive, perpetual, irrevocable, royalty-free, worldwide right and license to use, reproduce, disclose, sub-license, distribute, modify and exploit such Feedback without restriction.

Links to Other Websites

Our Service may contain links to third-party websites or services that are not owned or controlled by the Company.

The Company has no control over and assumes no responsibility for, the content, privacy policies, or practices of any third-party websites or services. You further acknowledge and agree that the Company shall not be responsible or liable, directly or indirectly, for any damage or loss caused or alleged to be caused by or in connection with the use of or reliance on any such content, goods or services available on or through any such web sites or services.

We strongly advise You to read the terms and conditions and privacy policies of any third-party websites or services that You visit.

Cancellation Policies

Cool Destinations uses three different cancellation policies, depending on your specific Tour or Activity. Please be sure to verify which one applies to your chosen experience before confirming your Booking.

This information can be found on every Experience we offer under the Cancellation Policy section, as well as on the checkout page.

Standard Cancellation Policy — A majority of our activity cancellations are free up to 24 hours before the activity commencement time (based on the local time of the activity).

All Sales Final — If any Goods or Services are designated as ‘All Sales Final’ or with materially similar messaging (which includes but is not limited to all group bookings booked through our Group Bookings Department), it is non-refundable, and it will not be possible to change or cancel it after making a Booking for any reason.

Non-Standard Cancellation Policy — A minority of Goods or Services have other, different cancellation policies. In all circumstances, you must check the cancellation policy contained in the applicable Product listing at the time of your Booking, which is the policy that will apply to and govern the terms of your cancellation and any refunds.

Cancelling Your Reservation

To cancel your Reservation you must contact Cool Destinations as soon as possible.

Cancellation Due To Bad Weather
If your Activity Operator must cancel due to bad weather and cannot accommodate you on another day, you will be issued a refund. Please be aware before issuing a refund, Cool Destinations will confirm if this is the case. Please note, this is only a valid reason if the Tour Operator cancels the tour.

If Tour Operator Cancels Tour or Excursion
If, for some reason, a Tour Operator cancels and cannot accommodate you on another day or at another time, you will be offered a refund and the option to take the trip. In the event of cancellation due to bad weather, Cool Destinations will confirm this before authorizing a refund.

Refunds

No refunds are available once an Experience has commenced, or for any package components that have started to be utilized.
- If your Experience materially differed from its description, please contact us within 7 days. We investigate every report and, where warranted, will provide an appropriate remedy.
- Credit card disputes filed for services delivered as described are contested with full documentation, including redemption records, and this agreement.
Wherever possible, refunds are handled via our automated online system. In some cases, your refund request will require verification from various parties, and that work is done exclusively via email.
Approved refunds will be issued to your original method of payment within thirty (30 days) from the date of the approval.

Adjusting Your Reservation

Contact our office directly to make any adjustments to your reservations. If you call and reach voicemail, please leave a message including time, date, number of guests attending, and the name of the Tour or Excursion.
If you adjust your reservation, a voucher will be issued and applied to your new reservation date. Subsequently, a revised confirmation will be emailed to you.
If the newly adjusted Activity is canceled for any reason, a store credit will be issued. A non-refundable change fee of $25 per adult ticket will be applied at the time of reservation change.

Customer Responsibility

Showing Up Late
If you or a member of your party shows up late and are consequently not able to participate you will still be responsible for the full amount of the Tour, Activity, or Excursion.

No Shows
If you, or a member of your party, do not show up for your Tour, Activity, or Excursion you will be responsible for the full amount of reservation.

Unsatisfactory Activity Experience
If you experience an issue of any sort with a Tour, Activity, or Excursion you have booked via Cool Destinations, immediately bring this to the attention of the Tour, Activity, or Excursion’s operator. Make your concerns and complaints heard with the person in charge so that you may reach an agreeable solution immediately. Do not wait until you return from your vacation. If, for some reason, you feel a partial or full refund is merited, you must make this known on the same day of your Tour or Excursion.

Payment Dispute Policy

If You have any concerns or disputes about the Service, You agree first to try to resolve the dispute informally by contacting the Company.

Termination

We may terminate or suspend Your Account immediately, without prior notice or liability, for any reason whatsoever, including without limitation if You breach these Terms and Conditions.

Upon termination, Your right to use the Service will cease immediately. If You wish to terminate Your Account, You may simply discontinue using the Service.

Limitation of Liability

Notwithstanding any damages that You might incur, the entire liability of the Company and any of its suppliers under any provision of this Terms and Your exclusive remedy for all of the foregoing shall be limited to the amount actually paid by You through the Service or 100 USD if You haven’t purchased anything through the Service.

To the maximum extent permitted by applicable law, in no event shall the Company or its suppliers be liable for any special, incidental, indirect, or consequential damages whatsoever (including, but not limited to, damages for loss of profits, loss of data or other information, for business interruption, for personal injury, loss of privacy arising out of or in any way related to the use of or inability to use the Service, third-party software and/or third-party hardware used with the Service, or otherwise in connection with any provision of this Terms), even if the Company or any supplier has been advised of the possibility of such damages and even if the remedy fails of its essential purpose.

Arrangements set forth in Your Booking are made solely for the convenience of the Ticket Holder and are at Ticket Holder’s risk. The Providers of such Services are independent contractors and are not acting as agents or representatives of Cool Destinations, or their respective affiliates or subsidiaries. In no event shall Cool Destinations be liable for any accident or harm to Ticket Holders, which occurs as a result of any acts, omissions, or negligence of any independent contractors.

Some states do not allow the exclusion of implied warranties or limitation of liability for incidental or consequential damages, which means that some of the above limitations may not apply. In these states, each party’s liability will be limited to the greatest extent permitted by law.

“AS IS” and “AS AVAILABLE” Disclaimer

The Service is provided to You “AS IS” and “AS AVAILABLE” and with all faults and defects without warranty of any kind. To the maximum extent permitted under applicable law, the Company, on its own behalf and on behalf of its Affiliates and its and their respective licensors and service providers, expressly disclaims all warranties, whether express, implied, statutory or otherwise, with respect to the Service, including all implied warranties of merchantability, fitness for a particular purpose, title and non-infringement, and warranties that may arise out of course of dealing, course of performance, usage or trade practice. Without limitation to the foregoing, the Company provides no warranty or undertaking, and makes no representation of any kind that the Service will meet Your requirements, achieve any intended results, be compatible or work with any other software, applications, systems or services, operate without interruption, meet any performance or reliability standards or be error free or that any errors or defects can or will be corrected.

Without limiting the foregoing, neither the Company nor any of the company’s provider makes any representation or warranty of any kind, express or implied: (i) as to the operation or availability of the Service, or the information, content, and materials or products included thereon; (ii) that the Service will be uninterrupted or error-free; (iii) as to the accuracy, reliability, or currency of any information or content provided through the Service; or (iv) that the Service, its servers, the content, or e-mails sent from or on behalf of the Company are free of viruses, scripts, trojan horses, worms, malware, timebombs or other harmful components.

Some jurisdictions do not allow the exclusion of certain types of warranties or limitations on applicable statutory rights of a consumer, so some or all of the above exclusions and limitations may not apply to You. But in such a case the exclusions and limitations set forth in this section shall be applied to the greatest extent enforceable under applicable law.

Governing Law

The laws of the Country, excluding its conflicts of law rules, shall govern this Terms and Your use of the Service. Your use of the Application may also be subject to other local, state, national, or international laws.

For European Union (EU) Users

If You are a European Union consumer, you will benefit from any mandatory provisions of the law of the country in which you are resident in.

United States Federal Government End Use Provisions

If You are a U.S. federal government end user, our Service is a “Commercial Item” as that term is defined at 48 C.F.R. §2.101.

United States Legal Compliance

You represent and warrant that (i) You are not located in a country that is subject to the United States government embargo, or that has been designated by the United States government as a “terrorist supporting” country, and (ii) You are not listed on any United States government list of prohibited or restricted parties.

Severability and Waiver

Severability
If any provision of these Terms is held to be unenforceable or invalid, such provision will be changed and interpreted to accomplish the objectives of such provision to the greatest extent possible under applicable law and the remaining provisions will continue in full force and effect.

Waiver
Except as provided herein, the failure to exercise a right or to require performance of an obligation under this Terms shall not effect a party’s ability to exercise such right or require such performance at any time thereafter nor shall be the waiver of a breach constitute a waiver of any subsequent breach.

Translation Interpretation

These Terms and Conditions may have been translated if We have made them available to You on our Service.

You agree that the original English text shall prevail in the case of a dispute.

Changes to These Terms and Conditions

We reserve the right, at Our sole discretion, to modify or replace these Terms at any time. If a revision is material We will make reasonable efforts to provide at least 30 days’ notice prior to any new terms taking effect. What constitutes a material change will be determined at Our sole discretion.

By continuing to access or use Our Service after those revisions become effective, You agree to be bound by the revised terms. If You do not agree to the new terms, in whole or in part, please stop using the website and the Service.

Top Chicago Multi-day & Extended Tours

Chicago Tours

Attractions

Guides

Calendar

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

5-Day Tour of Superior, Huron and Michigan from Chicago

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Continental US Train Zephyr Adventure CA -CO - Il

Great Smoky Mountains,Gatlinburg 4-Day Tour from Chicago

Frequently Asked Questions

Top Chicago Multi-day & Extended Tours

Chicago Tours

Attractions

Guides

Calendar

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

5-Day Tour of Superior, Huron and Michigan from Chicago

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Continental US Train Zephyr Adventure CA -CO - Il

Great Smoky Mountains,Gatlinburg 4-Day Tour from Chicago

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Interpretation & Definitions

Acknowledgement

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Promotions

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Intellectual Property

Your Feedback to Us

Links to Other Websites

Cancellation Policies

Cancelling Your Reservation

Refunds

Adjusting Your Reservation

Customer Responsibility

Payment Dispute Policy

Termination

Limitation of Liability

“AS IS” and “AS AVAILABLE” Disclaimer

Governing Law

For European Union (EU) Users

United States Federal Government End Use Provisions

United States Legal Compliance

Severability and Waiver

Translation Interpretation

Changes to These Terms and Conditions

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