The Best Trails in Chicago, Illinois (United States)

806 trails

Photo of Catherine Chevalier Woods Forest Preserve | Chicago Photo of Cycling - Chicago Lakefront Trail Photo of Bike Lake View Chicago
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  • Cycling - Chicago Lakefront Trail

    Road Bike
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    Author
    ant1606
    Distance
    31.21mi
    Elevation +
    1726f
    TrailRank
    26
    Photo ofCycling - Chicago Lakefront Trail Photo ofCycling - Chicago Lakefront Trail Photo ofCycling - Chicago Lakefront Trail

    Cycling - Experiencing the Lakefront Trail with perfect weather and a great occasion to meet a fellow VirtualTourist local member.

  • Bike Lake View Chicago

    Hiking
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    Author
    Raider_CR506
    Distance
    1.56mi
    Elevation +
    10f
    TrailRank
    24
    Photo ofBike Lake View Chicago

    Lake View Community area Community Area 6 - Lake View Looking across Belmont Harbor toward Lake View Looking across Belmont Harbor toward Lake View Location within the city of Chicago Location within the city of Ch...

  • Chicago to the Indiana dunes

    Road Bike
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    Author
    Adam E 1537
    Distance
    63.85mi
    Elevation +
    223f
    TrailRank
    23

    I could have found a better route around Hammond - see discussion here: https://www.reddit.com/r/chibike/comments/ifalxm/chicago_to_the_indiana_dunes/ Also, rather than hopping off of the Prarie Dunland trail so early...

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  • La Salle Chicago Marathon

    Running
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    Author
    KrisBisg
    Distance
    27.77mi
    Elevation +
    13491f
    TrailRank
    22

    Original track on http://gpsrunning.nicolajsen.nl/?script=viewRoute&id=7. Please note that the times shown in the file are made up.

  • Chicago Lakeshore trail

    Bicycle Touring
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    Author
    VilmaPro
    Distance
    17.23mi
    Elevation +
    1030f
    TrailRank
    22
    Photo ofChicago Lakeshore trail Photo ofChicago Lakeshore trail Photo ofChicago Lakeshore trail

    Real must do. Any level of biking.... this track gives you the best inspiring views of lake Michigan and Chicago. Flat and signaled, the track is just to take it easy and enjoy. Pictures speak for themselves. I did this ...

  • Humboldt Park Lagoon and Beach loop

    Hiking
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    Author
    jaylamble
    Distance
    2.39mi
    Elevation +
    20f
    TrailRank
    17
    Photo ofHumboldt Park Lagoon and Beach loop Photo ofHumboldt Park Lagoon and Beach loop

    Humboldt Park Lagoon and Beach loop from All Trails. Temperature about 30 degrees but with a stiff breeze making it feel colder when in the more exposed parts. Humboldt Park has a nice lagoon (frozen) that used to rent b...

  • Canales Chicago

    Motorboat
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    Author
    juanignaciosalvador
    with crisnavarrete María uxia Gilles Cols
    Distance
    8.54mi
    Elevation +
    3839f
    TrailRank
    62
    Photo ofCanales Chicago Photo ofCanales Chicago Photo ofCanales Chicago

    Precioso paseo en barco eléctrico priado por los canales de Chicago. Resulta muy interesante y relajado, aunque la compañia que de alquiler debería habernos facilitado más información sobre los edificios singulares

  • Endinsem-nos a Chicago

    Walking
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    Author
    mariaponscoll
    Distance
    12.19mi
    Elevation +
    906f
    TrailRank
    56
    Photo ofEndinsem-nos a Chicago Photo ofEndinsem-nos a Chicago Photo ofEndinsem-nos a Chicago

    La ciutat dels gratacels és famosa per la música jazz, blues i soul, els diferents equips com els Cubs, els Bulls, els Blackhawks i pel Llac Michigan. També anomenada Windy City o Second City és la tercera ciutat amb més...

  • Warren Park Loop trail

    Walking
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    Author
    jaylamble
    Distance
    1.29mi
    Elevation +
    16f
    TrailRank
    9

    Snowy but pavement well cleared. Temp 17 degrees. About 10 other walkers total and one runner. Sun was beautiful on the snow

  • Trip to chicago

    Car
    Save to a List
    Author
    Iñaki Ozcáriz Raventós
    Distance
    62.55mi
    Elevation +
    545f
    TrailRank
    30
    Photo ofTrip to chicago Photo ofTrip to chicago Photo ofTrip to chicago

    Aquesta és la sortida des del petit poble de Sandwich fins la megapolis de Chicago. Passant per els barris suburbans i el "Loop" del centre històric i de negocis. Si podeu ampliar el track és fantàstic poder seguir la ru...

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