- Nobu Hotel ChicagoNobu Hotel Chicago, North Peoria Street, Chicago, IL, USA
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- Doughnut VaultDoughnut Vault, North Franklin Street, Chicago, IL, USA
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- Architectural cruise (Shoreline)10:00 AMShoreline Sightseeing, North Michigan Avenue, Chicago, IL, USA
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- Stroll along the Chicago RiverwalkChicago Riverwalk, Chicago, IL, USA
- Deep dish pizza @ Lou Malnati'sLou Malnati's Pizzeria, North Michigan Avenue, Chicago, IL, USA
- Stroll along Michigan Avenue ('the Magnificent Mile')Magnificent Mile, Chicago, IL, USA
- Museum of Contemporary ArtMuseum Of Contemporary Art Chicago, East Chicago Avenue, Chicago, IL, USA
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- Oak Street BeachOak Street Beach, Illinois, USA
- ART on the MARTArt on The Mart, West Merchandise Mart Plaza, Chicago, IL, USA
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- Baseball (Cubs), basketball (Bulls) or Football (Bears) game
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- Nobu Hotel Chicago
- Ride the loopWashington/Wabash, Chicago, IL, USA
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- The Art Institute of ChicagoThe Art Institute of Chicago, South Michigan Avenue, Chicago, IL, USA
- Brunch @ Revival Food HallRevival Food Hall, South Clark Street, Chicago, IL, USA
- Millennium ParkMillennium Park, Chicago, IL, USA
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- Pick up Divvy bicycleChicago Yacht Club, East Monroe Street, Chicago, IL, USA
- Cycle along the Lakefront Trail (Chicago Yacht Club → North Avenue Beach Pier)North Avenue Beach Pier, Unnamed Road, Chicago, IL, USA
- Skyline views from North Avenue Beach PierNorth Avenue Beach Pier, Unnamed Road, Chicago, IL, USA
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- Cycle North Avenue Beach Pier → The Bloomingdale Trail - East Trailhead. Follow trail.The Bloomingdale Trail - East Trailhead - Ashland Ave - 1600 W, North Ashland Avenue, Chicago, IL, USA
- Coffee @ Ipsento 606Ipsento 606, North Milwaukee Avenue, Chicago, IL, USA
- Deep dish pizza @ PequodsPequod's Pizza, North Clybourn Avenue, Chicago, IL, USA
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- Return Divvy bike
- LH Rooftop (city views)LH Rooftop, East Wacker Drive, Chicago, IL, USA