Top Chicago Outdoor Activities

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  • Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate
    Likely to Sell Out

    Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate

    48

    When you arrive at the Chicago Lincoln Park indoor skydiving location, get started by putting on your provided gear and going through a specialized training...
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     1 hour 15 minutes  Instant Confirmation
    from
    $98.09
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    from
    $98.09
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  • Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate
    Likely to Sell Out

    Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

    21

    Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Chicago in Rosemont, a premier indoor skydiving facility powered...
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     1 hour 15 minutes  Instant Confirmation
    from
    $92.69
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    from
    $92.69
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  • Chicago Shoreline Adventure Boat Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Chicago Shoreline Adventure Boat Tour

    36

    This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $90
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    from
    $90
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  • Chicago Highlights Running Tour
    Likely to Sell Out

    Chicago Highlights Running Tour

    New To The Site!

    Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list”...
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     1 hour 15 minutes  Free Cancellation  Instant Confirmation
    from
    $44
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    $44
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  • Skip-the-Line Field Museum Natural History Semi-Private Guided Tour (8ppl Max)

    Skip-the-Line Field Museum Natural History Semi-Private Guided Tour (8ppl Max)

    New To The Site!

    125 years in the making, this collection now exceeds 40 million artifacts. On this 2.5 hour semi-private (8 guests max.) guided museum tour, your guide...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $115.54
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    from
    $115.54
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Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Chicago Outdoor Activities?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best Chicago Outdoor Activities are:

Q: What are the best kid-friendly options for Chicago Outdoor Activities Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly Chicago Outdoor Activities are:

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Q: Which Chicago Outdoor Activities have Instant Confirmation?

A: Chicago Outdoor Activities with Instant Confirmation include:

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Q: Which Chicago Outdoor Activities have Free Cancellation?

A: Chicago Outdoor Activities with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

Q: Got any more Chicago trip ideas?

A: We sure do. Check out our curated lists of hand-picked Chicago Tours.

View all Chicago Trip Ideas →

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

A: Based on our sales data over the past year, the most popular styles of tours and activities in Chicago are:

View all tour styles in Chicago →