Gray Line Chicago

Nearby Deals

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  1. 1
    Up to 57% Off Urban Scavenger Race
    Dick's Last Resort
    $80 $39 0.2 miles
  2. 2
    Up to 60% Off Chocolate Tour of Chicago
    $50 $25 0.2 miles
  3. 3
    50% Pub Crawl or Brunch Tour
    The Loop
    $80 $40 0.2 miles
  4. 4
    50% Off Segway Tours for Two
    Multiple Locations
    $138 $69 0.4 miles
  5. 5
    Up to 56% Off Pizza Walking Tour
    Near North Side
    $90 $42 0.4 miles
  6. 6
    Up to Half Off Urban Dare Adventure Race for Two
    Allstars Sports Bar
    $90 $45 0.4 miles
  7. 7
    Up to 44% Off Loop Interior Architecture Tour for Two
    The Loop
    $52 $29 0.5 miles
600 North Clark Street Chicago, IL 60654


The Chicago branch of Gray Line's global sightseeing operation organizes a wide variety of tours and excursions throughout the Windy City, from architectural tours that send passengers coasting on the river and lake for sun-drenched educational cruises to shopping odysseys at Chicago Premium Outlets, where travelers can zip through more than 100 stores and restaurants after being shuttled to the retail utopia. Blues outings treat music lovers to raw licks, soul food, and real tears at celebrated concert venues such as Buddy Guy's Legends and Rosa's Lounge.

Gray Line's cherry-red trolleys transport visitors and residents alike to famous Chicago sites. Just north of the river, the vehicles idle before the Wrigley Building's sparkling white terra cotta façade, which in the 1920s stood as the first major skyscraper outside of The Loop. From there, the trolley may motor north to the John Hancock Center, where elevators to its observatory sweep guests 96 floors in 39 seconds. The trolley could also steer south to the Willis Tower, which lost its maiden name of Sears after being charmed by a passing cumulus cloud.

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