Free guide: 25 hikes near Montreal
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Hiking in Chicago & Beyond

The 7 Best Hiking Trails in Chicago & Beyond: our selection

7 ideas. Reasons to pick each one.

Compare 7 hiking ideas in Chicago & Beyond: the duration and the level, then open the trail page for the details.

See the 7 hikes

How to pick the best hiking trails for you?

Three guideposts to compare the ideas in this selection.

The experience

Outings with a good mix of moods and challenges in Chicago & Beyond.

The scenery

Panoramas, forests and remarkable natural settings.

Who it suits

Outings for different levels and moods, from a serious challenge to an easy stroll.

Our 7 hikes in Chicago & Beyond

See all trails in Chicago & Beyond

  1. Des Plaines River Trail

    Chicago & Beyond

    2 hr

    See the trail page

  2. Mallard Lake Trail

    Chicago & Beyond

    2 hr 30 min

    See the trail page
  3. millenium park trail - hiking in Chicago & Beyond

    millenium park

    Chicago & Beyond

    2 hr

    See the trail page

  4. Oak Park, Chicago

    Chicago & Beyond

    2 hr

    See the trail page

  5. Prairie Path

    Chicago & Beyond

    See the trail page
  6. Starved Rock trail - hiking in Chicago & Beyond

    Starved Rock

    Chicago & Beyond

    6 hr

    See the trail page
  7. The Loop - Chicago trail - hiking in Chicago & Beyond

    The Loop - Chicago

    Chicago & Beyond

    4 hr 30 min Hard

    See the trail page

How to choose yours?

The Loop - Chicago trail - hiking in Chicago & Beyond

By season

Fall colours, snowy summits, spring flowers: every season offers a different experience.

Explore all regions

Before you book your day

Access, booking, dogs and weather: check the trail page and the site manager.

See our practical tips

Frequently asked questions

How do I know if a hike suits my level?

Each trail page gives the level (easy, moderate or hard) and, when it is known, the duration. Compare them with your experience, then add time for breaks and the way back.

Do some trails in Chicago & Beyond require a booking?

It depends on the site. Some trails are in parks that charge an access fee or require a booking: the trail page says so when the information is known, and the site manager's own website remains the reference.

Can I bring my dog?

The trail page says whether dogs are allowed, when the information is known. Always check the site's rules, especially about leashes.

Good ideas, ready to go.

Free guide: 25 hikes under 2 hours from Montreal

Distance, elevation, parking and season for each one. The ones we go back to ourselves.

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